Nerd Journey: Career Advice for the Technology Professional

When does a body of work reach completion? One answer is to end it by choice. This week in episode 356 you’ll hear the reasons behind our intentional ending of the Nerd Journey Podcast. We’ll rewind the clock and focus on the show’s trajectory and inflection points over time just like we’ve done for guests, share what we learned over the course of an 8-year journey from idea to consistently released show, and discuss our favorite moments. All of our content will remain online and accessible for listeners like you to go back and enjoy. Don’t miss our final call to action in this episode. Just because this body of work is complete, there is still work for all of us to do for our careers. Original Recording Date: 12-20-2025 Topics – A Purposeful Ending, Where We Started, Interview Format and Getting to Launch, The Why Behind the Ending, The Lessons We Learned, Our Favorite Moments, What to Expect from Us Moving Forward, There’s More to Be Done for All of Us. 1:01 – A Purposeful Ending We’ll give you the bottom line up front: this is the last episode of the Nerd Journey podcast. We still love the mission, but the time has come for us to complete this body of work. When we have interviewed guests on the show, we’ve talked through their career timeline and pulled out the lessons learned. Today, we’re going to do it for the show itself. 1:38 – Where We Started John was working as a sales engineer at VMware and was the co-host of the VMware Community Roundtable Podcast. He loved listening to podcasts, enjoyed the medium, and wanted to find a topic for a show. At the same time Nick was in the process of joining VMware, John and Nick were discussing all the things Nick needed to know to transition into sales engineering for a technology vendor. “In that conversation, I said ‘maybe we should start a podcast.’” – John White As Nick remembers it, this happened the weekend before Nick started at VMware in December 2017 (almost exactly 8 years before this episode’s recording). Nick wasn’t sure what he would talk about on a podcast. This suggestion from John started the ideation period, and our launch of the show was in July 2018. John talks about some of the initial ideas for the focus of the show. At that time, VMware podcasts and blogs were a great way to interact with the greater community. Doing something like this was also a way to become what John calls “nerd famous.” By the way, no one else can use that term now (trademarked by John). We initially considered talking about VMware news and our opinions on it since we both were going to be working at VMware. Both John and Nick came from small-to-medium business IT operations and eventually became sales engineers at a technology vendor. One of the things the show could be for is to talk about that journey and help others understand it was a possibility for them as well. John and Nick recorded about 10 episodes before launching to help hit the release cadence. Nick doesn’t remember why they chose a weekly release cadence but remembers the show launched while he was on vacation. John and Nick even recorded a podcast episode while Nick was on that vacation, which started a habit of Nick doing podcast work while on vacation. Because they had recorded so many episodes in advance, they were not going to be timely or points of authority on VMware technology. Both Nick and John’s roles were as technical generalists on the VMware side. “The only evergreen stuff that we had was the career stuff, so that became a little bit more the focus. I think that we were still thinking…we’ll just record more maybe VMware specific stuff later on…as that happens. For right now, here it is.” – John White Early episodes were very prescriptive about resumes and job interview processes at larger tech companies, for example. Nick points out that John had to carry the conversation in these early episodes because he was just learning to think about career focused topics (sort of like being new to lifting weights). But, Nick picked up a lot just from the conversations on the show. 7:50 – Interview Format and Getting to Launch Nick couldn’t remember what made them bring in guests originally, but Episode 13 with Tom Delicati was our very first guest interview on the show. John feels bringing in guests was always back of mind for him, and it was what he saw happen on the VMware Community Roundtable Podcast. “We’re just 2 people and we have our experience. But we can’t represent that as the full breadth of all of experience. That just doesn’t make any sense. So, we need to start exploring what other people’s career journeys have looked like and see if we can extract some knowledge and recommendations from that.” – John White Nick doesn’t remember having a prescriptive plan for interviewing guests but feels like they settled into long-form interviews as a style pretty quickly. John says this was a structure they hit upon in the beginning (talking through someone’s job history). The lessons learned from career inflection points like job transitions emerged from conversations with guests. John and Nick did not know this was going to happen when they began. Nick likes being able to highlight more of one specific guest’s story than otherwise could have been done if each interview was only 30 minutes with a guest. But we fully acknowledge people like different lengths of podcasts. “We wanted to tell interesting stories that had an arc: a beginning and an end and a journey in between. And we were able to find those even chopping people’s long 2-hour conversations up into 2 or even 3 episodes. I think that worked for us. I don’t know if it worked for everybody.” – John White “We probably spent the same time interviewing people as we would have. We just didn’t interview as many as if it had been 1 episode per person.” – Nick Korte We also didn’t want to release a 2-hour interview as one episode. That’s a lot of editing for just one episode release. People might not realize how much time goes into editing and production even after recording an interview. At the beginning, John had to give Nick advice on the kind of microphone to get. Nick started recording with a headset and then bought the same mic as John. They would each later invest in nicer microphones as the show progressed. “I knew nothing about editing and really not that much about how to make a podcast.” – Nick Korte, on beginning as a podcaster There were a lot of things we had to figure out just to make the podcast publicly available. John had researched some of the administrative things. He knew there was a WordPress plugin that could be used to turn MP3 files of released episodes into publicly available audio feed that would be the podcast. John says there were some mental blocks and hurdles he had to get through before launching the show, highlighting the fact that it took 6 months to go from idea to publishing. He was getting overwhelmed trying to figure out the back-end production and publishing process. John thinks it was Nick who kept asking what needed to happen for us to launch, and we went with WordPress and the plugin mentioned but never changed anything…because we had no time to go back. Nick and John learned that once you start a show and get it going, you will never run out of ideas. 13:58 – The Why Behind the Ending We never ran out of ideas. In fact, we still have ideas. So why are we stopping the podcast? We ran out of time. Nick has run out of time to work on editing and production. This has been a weekly show (up until the last couple months of our run), and it takes a large time commitment each week. For guest interview episodes, the intro and outro were not recorded at the same time the interview took place. These had to be recorded before the episode was released. The show notes are not AI-generated. Nick enjoyed writing them and adding in important links and references, feeling like it allowed him to remember the episodes better and internalize the lessons within them. Nick has a teenager now with many extracurricular activities and has had a workload increase at his job. “Probably for the last year I think I’ve been fooling myself at how much of a toll it’s been to just get an episode out each week.” – Nick Korte We even tried changing the release schedule to bi-weekly and have missed that cadence a couple of times. John ran out of time about 4 years ago and hasn’t had much time since to handle podcast related tasks. John experienced a job change and new baby at that time and couldn’t add anything else. He also moved at some point. John and Nick have been advancing in their own careers over time as well, which has added responsibility. John and his wife recently had a second child. He also left his job in June 2025 and has been doing a job search at the same time. Before Nick and John made this decision, Nick listened back to some previous episodes to get advice and perspective. Some of the advice that echoed the loudest came from Amy Lewis in Episode 302 – Ending with Intention: Once a Geek Whisperer with Amy Lewis (2/2). The idea of ending with intention stood out. “Rather than being spotty on our releases and not keeping our promise of how often we say we’re going to get the show out, we wanted to end it with intention and say, ‘ok, this is it.’” – Nick Korte “We haven’t lost the love of this task. We both want this to continue. But realistically, we can’t do it. And rather than sputter and peter out and never be heard from again, we just thought we’ll follow the lessons that we’ve learned from our bettors and do what they did. Let’s be intentional about the end.” – John White 18:02 – The Lessons We Learned John learned how much we can learn from the experience of others. He had ideas and biases about how we should handle specific aspects of our career, but doing the podcast allowed him to pressure test these ideas against the experience of others. John appreciates the breadth of background and experience our collective guests have brought to the show. It made him realize there are so many different ways to do certain things. Nick learned a ton about the mechanics of podcast production. It was around Episode 113 when Nick became the editor because John needed to take a break. If you want to hear more about how this happened, check out this blog post. Nick got hooked into podcast communities and even attended a podcast conference in 2025, meeting many other people who run their own podcast. Nick learned how much salesmanship is involved in getting a guest. You have to sell someone on the idea of being on the show and what they can bring to your listeners. How easy can you make it for them to say yes? John and Nick asked guests for 1.5 – 2 hours for an interview. “If you make it easy for someone to say yes and you build the outline of questions you might ask and you tell them what your show is about and what you want to cover, they’ll say yes. And they might give you more time than that…. I learned so much about different people that I never would have met otherwise. I am thankful for all the learnings of all the people who have been on the show. And I’m thankful for everything I’ve learned from you, John.” – Nick Korte John is grateful for the difference in skills he and Nick have and their ability to learn from one another just by co-hosting together. He likes to apply the idea of making it easy for others to say yes when he’s asking something of someone at work, for example. Nick learned how to beat perfectionism weekly. Something can always be edited more or re-recorded. There was a weekly ship date. “The deadline was always there to keep me honest.” – Nick Korte Seth Godin’s The Practice talks about keeping a promise to the people who follow you. Having a weekly release cadence meant we were promising to ship episodes weekly. “So, whether one person listened or a million people listened, we tried to keep that promise. And it was important to us to keep it, even if it was hard.” – Nick Korte “Having a million people listen to a specific episode or even hit the site in a specific week wasn’t the goal. I think the goal was the breadth of work and making it accessible and having people be able to benefit from it.” – John White We also had to learn how to tell people about the show in a clear, succinct way. When John or Nick would join video calls for work, people would see their microphones and ask if they had a podcast. We also used generative AI in our workflow for production a little bit, even if it was not for show notes. Doing the show has dragged with it some reasons to tinker with generative AI. With John’s help Nick learned how to build a Gemini prompt that would take the handwritten show notes and brainstorm titles, episode descriptions, and even create a prompt for a featured image based on the themes in the episode. John shares that we never wanted to use generative AI to take a transcript and generate an episode outline. We might lose touch with the content that way. John talks about the curse of being an audio editor. It’s impossible to NOT hear issues in other audio. Nick can hear mouth noises on Zoom calls like you wouldn’t believe. John says we can listen to someone else’s podcast and may be able to tell who is and is not the editor based on whether they speak into the microphone or move away from it and keep talking. 25:15 – Our Favorite Moments John says it’s hard to pick just one favorite moment. We got to meet some of our heroes in podcasting and other people who were “nerd famous” about their career stories. We had some great conversations with John Nicholson about how to evaluate a job offer and personal finance. Check out these for reference: Episode 224 – Tech Marketing, Interview Questions, and Executives as Wild Bears with John Nicholson (1/3) Episode 225 – Take Stock of Your Compensation with John Nicholson (2/3) Episode 226 – Negotiating Job Offers and Personal Finance Tips with John Nicholson (3/3) Having a podcast allowed us to have lengthy conversations with people who may not have otherwise had a reason to talk to us. John doesn’t think asking someone out of the blue for 2 hours of time without having a podcast would have worked well. John says he has a strong recency bias, often walking away from an interview with a guest thinking it was the best one yet. Nick’s favorite moments Nick remembers the first time we interviewed Mike Burkhart (in Episode 64 and Episode 65). He was having wifi issues and had to move everything into his living room floor to record the episode. John and Mike were kind enough to stay online and still do the interview. John and Nick live in different parts of the United States and have only been able to record together in person a handful of times. These times were special and rare. Nick remembers the time they recorded at VMware Explore and forgot to hit record…twice in a row! If John had to succumb to recency bias, he would pick the recent interview with Milin Desai. This set of interviews stands alone as the only time we were cold pitched a guest by someone we did not know, and it was a perfect fit. We got over 2 hours with a CEO! Episode 349 – Expand Your Curiosity: Build, Own, and Maintain Relevance with Milin Desai (1/3) Episode 350 – Scope and Upside: The Importance of Contextual Communication with Milin Desai (2/3) Episode 350 – Opt In: A CEO’s Take on Becoming AI Native with Milin Desai (3/3) People being both generous with their time and inciteful has been a pattern with guests. Nick and John got to have conversations with people both on the air and off the air. Nick appreciated having Dale McKay on the show (a mentor of his). You can find those episodes here: Episode 288 – Guardrails for Growth: A Mentor’s Experience with Dale McKay (1/2) Episode 289 – Enhance Your Personal Brand: Feedback as a Catalyst for Change with Dale McKay (2/2) Some other favorites from Nick: He enjoyed all of the conversations about the principal title and principal engineers. See also the principal tag for more of these stories. Nick also really enjoyed hearing the stories about why people went into leadership roles and why they moved away from them. One specific episode Nick highlights as a favorite is Episode 127 – Countdown to Burnout with Tom Hollingsworth (3/3). John mentions we all battle burnout from time to time, and having such great advice to go back to is a gift. Nick says being the editor is also a gift because you’re going to get to listen to the recorded discussion multiple times. Many times, the questions Nick and John asked in guest interviews were things they needed help with in their own careers. Hopefully the answers to those questions helped you as a listener too! John liked the fact that we were able to clip some of the times we messed up on the air and include those sound bites at the very end of an episode for people. To find these episodes, look for the Stinger metadata tag on an episode post. Nick mentions the Barry White intro stinger. It’s actually at the end of Episode 17. There are also some good stingers with guest Chris Williams. 31:05 – What to Expect from Us Moving Forward What are the things that will, won’t, and might happen in the future? The Nerd Journey site will remain online and accessible so our content will not disappear. You can still enjoy past episodes, browse the show notes, and leverage the Layoff Resources Page as well as our Career Uncertainty Action Guide. John and Nick can keep it online in a very cost-effective way just as they have to this point since the podcast was never monetized (not even Amazon affiliate links). John still has a dream of making sure we have transcripts of all the episodes and making these available in addition to the show notes. Maybe that could be extended to an AI chat bot that was trained on the transcripts. There would be some overhead involved in doing it, but John thinks it’s definitely possible. You can still reach out to John or Nick on LinkedIn or send us an e-mail. All current communication channels will remain in place. We are available for questions, if you want to talk, etc. We will definitely NOT restart this show. We have declared it complete. Even if we were going to do a show like this again in the future, we would do it differently. We might choose a different name, a different description, or a different format even. But we don’t have the time to do that right now anyway. We are NOT starting a new show (at least not right now). 34:59 – There’s More to Be Done for All of Us Just because the show is ending, that doesn’t mean your work is complete. None of our work is complete when it comes to career. “The things that we’ve talked about in curating your own career and being intentional about it always apply. We’re not going to be around to remind you of that every week, so I hope that people have learned those lessons and internalized them. But if not, do something to make those things intentional. You need to prioritize your career on a consistent basis.” – John White Here are some specific actions that you should take: Document your work. Generate proof of work. Show your work (similar to generating proof of work). John says this is what we were unconsciously doing when we began the podcast, sharing how we got to where we are and our job transitions so others can follow a similar path if they choose. The purpose of showing your work is so that others can learn from your experience and so you can remind yourself of what you’ve accomplished at a later time. Nick highlights that Episode 66: Three-Month Check-In as a Google Cloud Customer Engineer with John White, Part 1 remains the most downloaded episode in our catalog. Aim for small, iterative improvements. Turn information into knowledge. Some of this is through writing. We spoke several times on the show about writing being thinking, and it was specifically referenced in an episode with Josh Duffney – Episode 156 – Better Notes, Better You with Josh Duffney (1/2). Manage your knowledge in some kind of written form that isn’t in your head. Make it a knowledge management system of some kind. Practice Deep Work. It’s the most important work you can do because the skill of sustained attention will be the thing for which people are paid. Be mindful of technology waves and trends, and consider placing some small bets. Many guests have invested time and effort to become proficient in a newer technology before or as it was catching on. Don’t be afraid to tinker with those newer technologies. Consistently invest in your professional network. One way to do this could be via meetup groups or online communities. Reach out to use if you want to talk about careers, starting a podcast, or other fun topics. Nick can also tell you what it’s like to go through the John White School of Mentoring. We want to say a special thank you to every guest who took the time to be on the podcast and every listener who took the time to listen to an episode. If you’d like to read Nick’s reflection post about the show coming to a close, you can find it here – A Promise Kept: Choosing to Sunset the Nerd Journey Podcast. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

Has organizational change redefined your job role? If it hasn’t yet, it will at some point. Whether acknowledged or ignored, every organizational change at a company impacts you. This is broader than just layoffs and more employees under a single manager. What are the organizational changes we might see, and what can we do to stand out and stay the course? This week in episode 355 we’re joined by guest Ryan Conley. Listen closely as we uncover different patterns of organizational change and provide practical tips to take action when those changes happen. Ryan helps us understand the corporate lifecycle and how to reframe this concept to understand where we are in the career lifecycle. You’ll hear from Ryan’s personal experience why the most resilient (and successful) technologists can identify and fill the gaps left after an organizational change whether that means working for a new boss, joining a different team, or changing job roles. Original Recording Date: 11-13-2025 Topics – Framing Our Focus on Organizational Change, Observations and Patterns, Defining the Career Lifecycle, When Colleagues Leave the Company, Layoff Resources, Working for a New Boss, Becoming Part of a Different Team, Shifting Job Roles or Job Level Changes, Parting Thoughts 2:58 – Framing Our Focus on Organizational Change Ryan Conley is a global field principal with 11p years of technical pre-sales experience. Before this, Ryan accumulated 13 years of systems administration in industries like education, finance, and consulting. In a recent episode of our show, guest Milin Desai compared organizations to living, breathing organisms that change. Nick posits that we don’t always think changes at our company will or can affect us as employees, but they do. Ryan references Aswath Damodaran’s writings about organizational change through the frame of a corporate lifecycle. We can relate by considering where our company might be in that lifecycle. As we experience the impacts of organizational change, Ryan encourages us to consider where we are in our career lifecycle. 4:19 – Observations and Patterns We see organizational change in different ways. What are some of the things Ryan has seen that he would classify as organizational changes? Let’s take a step back, past the current headlines, and look at the wider industry. Companies are growing inorganically (through mergers and acquisitions) or organically through investments in R&D (research and development), for example. Ryan has worked with companies that grew by acquiring 2 new companies each year to give an example. When you’re on the IT side of the acquiring company, there is a lot involved in the process like integrating e-mail systems, networks, and CRM systems. This process also involves getting 2 teams to work together. If one team needs to move from Office 365 to Gmail, it can be a big adjustment to employees’ daily workflow. The acquiring and acquired companies may have the same or very different cultures. In some cases, a company will want to acquire others with similar cultures, while some may not be concerned about the culture and choose to focus on the intellectual property (products or services, knowledge of how to build or manufacture something, etc.) of the company to be acquired. Nick says the experience for people on the side of the acquiring company and that of the company getting acquired can be quite different. Nick worked in IT for a manufacturing company for about 9 years, and over the course of his time there saw the company acquire several other companies. Nick usually had to go assess technology systems of companies that were going to be acquired and figure out how to integrate the systems in a way that would best service the user base. From what Nick has seen, some employees from the acquired company were integrated into the acquiring company, while others were eventually no longer with the company. Anxiety levels about an acquisition may be different depending on whether you work for the acquiring company or the acquired company. “The people are just as much of the intellectual property of the company as, in many cases, the actual assets themselves. And in some cases, that culture just isn’t a fit.” – Ryan Conley Ryan shares the example of someone he knew who left after another company acquired their employer because the culture was not a fit. Losing a key leader or a key subject matter expert after an acquisition could create a retention problem because others may want to follow them or start looking elsewhere. "So how do you protect the culture internally? How do you integrate a different culture in? But also, how do you kind of protect the long-term viability of the team as individuals, first and foremost, but then also the organization long-term? Depending on the intellectual property the acquiring company is after, we don’t usually know the level of due diligence completed to understand the key resources or subject matter experts who must be retained for longer-term success. Ryan encourages to imagine being the CTO or VP of Research and Development at a specific company that is suddenly acquired. People in these roles drive the direction of the technology investment for their company today as well as years to come. After being acquired, these people might be asked to work in lower levels of leadership with different titles, which could result in “title shock” and require some humility to accept. This scenario is a leadership change that happens as a result of an acquisition, but we might see leadership changes outside of acquisitions. Some leadership positions get created because of a specific need, others are eliminated for specific reasons, and some get shifted down or changed. Each of these changes has a downstream impact on individual contributors. Ryan talks about the positive impacts of leadership changes and gives the example of when a former manager was promoted to senior manager and allowed that person to hire a manager underneath him. There isn’t always internal mobility, but leadership changes could create these opportunities for individuals. Nick talks about the potential impact of a change in our direct boss / manager. If a boss who was difficult to work for leaves the company, getting a different boss could make a huge positive impact on our daily work lives. Similarly, we might have a great boss leave the company or take a different role, requiring that we learn to work for someone else who may operate very differently. Ryan tells us he has worked for some amazing leaders and says a leader is not the same as a manager. Ryan cites an example of getting promoted into a role that allowed him to have more strategic conversations about the focus of a team with his boss. We can choose to mentor members of our team so that when opportunities arise from structural change, they are equipped to seize those opportunities. Change can be viewed as an opportunity. A company’s overall priorities may have changed. Shifting priorities may require a company to operate very differently than it has in the past, which can cause changes to people, processes, and technology. Nick references a conversation with Milin Desai on constrained planning from Episode 351. Milin encourages regularly asking the question “is this still how we want to operate?” The way a company or team operated in the past may not be the best way to do it in the future. Changes to operations may or may not create opportunities for our career. Ryan loves this mindset of reassessing, which could apply to the company, a team, a business unit, the technology decision, etc. “I love the mindset of ‘what was best, why did we do it, and why was it best then?’ And then the follow up question is ‘is that still best today?’ And it’s ok if the answer is no because that leads to the next question – ‘how should we be doing it today…and why?’” – Ryan Conley, commenting on Milin Desai’s concept of constrained planning Ryan talks about companies reassessing their core focus. We’ve seen some companies divest out of a particular space, for example. Nick says this reassessment could result in a decision to pursue an emerging market which could lead to the creation of a new business unit and new jobs / opportunities for people. It could also go in the other direction where the company decides to shut down an entire business unit. 15:30 – Defining the Career Lifecycle Going back to the analogy Ryan shared about corporate lifecycle, we can reframe this and look at the career lifecycle. “Where are you at in your individual career journey? Where are you at in that lifecycle?” – Ryan Conley People close to retirement may be laser focused on doing well in their current role and hesitant to make a change. Others earlier in the career may want to do more, go deeper, or be more open to making a change. Ryan recounts speaking to a peer who is working on a master’s degree in AI. “With challenge comes opportunity, so do you want to try something new? And it’s ok if the answer’s no. But if there is an opportunity to try something new and you’re willing to invest in yourself and in your company, I think that’s worth considering.” – Ryan Conley We’ve talked to a number of former guests who got in on a technology wave at just the right time, which led to new opportunities and an entirely new career trajectory. Becoming aware of and developing expertise in emerging technologies can lead to new opportunities within your company (i.e. being able to influence the use of that technology within your company). “I think as technologists, whether you’re a business leader over technology, whether you’re day in / day out in technology as an individual contributor…emerging technology brings new challenges, just with a learning curve…. There’s hard skills that have to be learned. You get beyond the education it’s then also sharing with the peers around you…. So, what was best yesterday? Is it still best today? And tomorrow, we’ll ask the question again.” – Ryan Conley Ryan says this goes back to our analogy. Should we be doing certain things manually now, or is it better to rely on tools that can help automate the process? If we go back for a second to Ryan’s previous mention of integrating the technology stack for different companies, being part of the integration process might enable someone to learn an entire new technology stack. We might have to assess what is best between Google Workspace and Microsoft 365, for example, and develop the transition plan to move from one to the other and perhaps even capture the business case for using both within a company. To Ryan, this is an example of seeing a problem or gap and working to fill it. “If you want to be just a long-standing contributor to the team and your individual organization, I think it’s worth calling out…those who stick around longer and get promoted faster are the ones who see a gap and they plug it.” – Ryan Conley Ryan shares a personal story about a co-worker who attended a Microsoft conference on their own dime. This person worked over a weekend to setup a solution that saved the team significant time doing desktop imaging. But then, Ryan’s colleague took it a step further and trained the team on how to use it. Nick highlights the fact that we should remember to document our accomplishments to keep track of how we’ve changed as a result. We can use this information when searching for new opportunities or even in conversations with our leader. 20:34 – When Colleagues Leave the Company Another form of organizational change we’ve seen is outsourcing specific business functions. Daniel Paluszek spoke about companies outsourcing functions outside of their core business in Episode 338. If IT is outside the core business, a company might decide to outsource it. It doesn’t mean that’s the right decision, but it could be a possibility. Companies may outsource other functions like HR and payroll as well to give other examples. If IT was internal and it gets outsourced, that is an organizational change and will affect some people. Similarly, insourcing a function which was previously outsourced will have an impact. Ryan has learned in the last few years that some people are more adaptable to change than others. “And it’s not just looking at the silver lining. It’s recognizing the change. Maybe there’s a why, and maybe there isn’t a why. Or maybe the why hasn’t been clearly articulated to you. Being able to understand, what does this mean to me…. As an organization do I still believe in them? Do I still believe in the technology as a technologist? Do I still enjoy the people I work with? Those are all questions that come up, but ultimately you have to decide…is this change I want to roll with? Is this change I don’t want to roll with?” – Ryan Conley To illustrate, Ryan gives the example of a peer who left an organization after seeing a change they didn’t like in order to shift the focus of their role from technology operations to more of a site reliability engineering focus. While this type of change that results in a talented individual leaving an organization can be difficult for teammates to accept and for a manager to backfill, these types of changes that are beneficial to someone’s career should be celebrated. When we assess whether the changes made at a company are those we can accept and roll with, we can first make sure we understand what we are to focus on as individuals operating within the organization. We have an opportunity to relay that to other members of our team for the benefit of the overall team culture and to build up those who do not adapt to change well. Understanding organizational changes and what they mean for individuals may take repetition. While Ryan understands that he responds well to change, he remains empathetic to those folks to need to hear the message a few times to fully understand. Nick says we can learn from the circumstances surrounding someone leaving the company. For those we know, what interested them about taking a role at another company? Perhaps they took a role you’ve never thought about for yourself that could be something you pursue in the future. If a member of your team leaves the company, sometimes their role gets backfilled, and other times it may not. If the role is backfilled, you get to learn from a new team member. If not, the responsibilities of the departing team member will likely be divided among other team members. Though it would result in extra work, you could ask to take on the responsibility that would both increase your skill set and make you more valuable to the company. When Ryan worked for a hedge fund, the senior vice president left the company. This person was managing the company’s backups. Ryan had experience in this area from a previous role at a consulting firm and volunteered to do it. Shortly after taking on this responsibility for backups, he found that restoring backups from tape and needing to order new servers posed a huge risk to the company in a disaster scenario (i.e. would take weeks to restore everything). Ryan was able to write up a business plan to address the business continuity risk and got it approved by the COO. “Being able to see a gap and fill it is the central theme, and that came from change.” – Ryan Conley Ryan says if you’re willing to do a little more work, it is worth the effort to see a gap and work to fill it. 27:34 – Layoff Resources We acknowledged some of the byproducts of organizational change like layoffs and flatter organizations in the beginning of our discussion. We are not sidestepping the fact that layoffs happen, but that is not the primary focus of our discussion today. Here are a few things that may help if you find yourself being impacted by a layoff: First, know that you are not alone in experiencing this. “When a layoff hits, it’s important to remember…it’s extremely rare that that’s going to be personal. Once it’s firmly accepted, look for the opportunity in a forced career change. It’s there.” – thought shared with us by Megan Wills Check out our Layoff Resources Page to find some of the most impactful conversations on the topic of layoffs on our show to date. We also have our Career Uncertainty Action Guide with a checklist of the 5 pillars of career resilience as well as reusable AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed. 28:43 – Working for a New Boss Let’s move on to section 2 of our discussion. If you’re still at a company after an organization change has happened, we want to talk through some of the ways you can take control, take action, and succeed. We want to share a thought from former guest Daniel Lemire as we begin this discussion: “Companies are the most complicated machine man has ever built. We build great machines to accomplish as set of goals, objectives, or outputs. The better you can understand the value the company delivers…the faster you can understand where you fit in that equation. If you don’t understand where you contribute to that value, there’s work to be done. That work may be on you, may be on your skills, or perhaps it’s your understanding of where you fit into that equation.” – Daniel Lemire Let’s say that you’re impacted by an organizational change and will be working for a new boss. What can we control, and how to we make a positive impact? Ryan says we can be an asset to the team and support larger business goals by first giving some thought to who the new boss is as a person. Try to get to know them on a personal level. Ryan wants to get to know a new boss and be able to ask them difficult questions. Similarly, he wants a boss to be able to ask him difficult questions. Meeting a new boss face-to-face is ideal if that is possible, but this can be more difficult to arrange if your boss lives a large distance from you. Make sure you understand the larger organization’s mission statement. As individual contributors, we may lose sight of this over time. “If that is important to the team and the culture, I think it’s worth making sure you’re aligned with that. I think it’s worth understanding your direct manager’s alignment toward that and then having that kind of fuel the discussions…. What are you expecting of me? Here are my expectations of you as my manager. Where do you see change in the next 6, 12, 18 months?” – Ryan Conley, on using mission to drive conversations with your manager A manager may not have all the answers to your questions. They could also be inheriting a new team. Ryan encourages us to ask how we can help our manager to develop the working relationship further. This is something he learned from a previous boss who would close every 1-1 with “is there anything else I can do to help?” Nick says a manager may be able to contextualize the organization’s mission statement for the team and its members better than we can do for ourselves. For example, the mission and focus of the team may have changed from what it once was. A new manager should (and likely will) set the tone. Nick would classify Ryan’s suggestions above as seeking to learn and understand how your new manager operates. Back in Episode 84 guest Brad Pinkston talked about the importance of wanting to know how his manager likes to communicate and be communicated with. This is about understanding your manager’s communication preferences and can in some ways help set expectations. A manager may be brief when responding to text messages, for example, because they are in a lot of meetings. But if they tell you this ahead of time, it removes some assumptions about any hidden meanings in the response. Ryan gives the example of an executive who used to respond with Y for yes and N for no to e-mails when answering questions. We can also do research on a new boss in advance. We can look on LinkedIn to understand the person’s background and work history. We can speak to other people inside the company to see what they know about the person. Ideally, get a perspective from someone who has worked for the manager in the past because a former direct report might be able to share some of the context about communication preferences and other lessons learned from working with that specific manager. We can also try to be mindful of how the manager’s position may have changed due to organizational flattening. They may have moved from managing managers to having 15 direct reports who are individual contributors, for example. “Their time might be stretched thinner, and they’re just trying to navigate this new leadership organizational change with you.” – Ryan Conley The manager may or may not have wanted the situation they are currently in. How is your boss measured by their boss, and how can you help them hit those metrics? You may not want to ask this in the first 1-1, but you should ask. Ryan suggests asking your boss what success looks like in their role. You can also ask what success for the team looks like in a year and what it will take to get there. Based on the answer, it might mean less 1-1s but more in depth each time, more independence than you want, or even more responsibility than you wanted or expected. Ultimately, by asking these questions, you’re trying to help the team be more successful. We want our manager to understand that we are a competent member of the team. Understanding what success looks like allows us to communicate with our manager in a way that demonstrates we are doing a good job. Some of the time in our 1-1s with a manager will be spent communicating the things we have completed or on which we are actively working. We need to demonstrate our ability to meet deadlines, for example. Daniel Lemire shared this book recommendation with us – The First 90 Days: Proven Strategies for Getting Up to Speed Faster and Smarter. It’s a great resource for new leaders but also excellent for individual contributors. Ryan tells us to keep track of our wins over the course of any given year (something that was taught to him) so we have it ready for performance reviews. He encourages keeping a journal that we start in January. Keep track not only of what you did but the outcomes your work delivered and the success metrics. For example, if you gave a presentation, note the number of people present. The company culture may have some impact on the language you need to use to word your accomplishments (i.e. using “I” statements). “I didn’t want to be the only person who could do it. I’d rather learn it and then enable 5 other people to do it. And then those 5 people go do it, and that is a much bigger outcome.” – Ryan Conley, on the outcome of efforts at work and being a force multiplier Have a journal of the things you do at work that you update consistently. This could be screenshots, a written description, etc. “What are the metrics that you should be tracking? Mentally think about that because…when you have your annual review, you’re going to miss something. You’re going to miss a detail. You’re going to miss an entire line item versus if you started in January and you just get into the practice of ‘I did this.’ And then when you’re having your first annual review with this brand-new manager, it’s far easier to have a more successful conversation.” – Ryan Conley, on the importance of documenting our work in a journal somewhere Ryan reminds us it is ok to use generative AI tools to check our work. Use multiple different tools to get suggestions on how you might want to phrase the outcomes you delivered and the metrics you tracked. Nick says we should document our accomplishments as Ryan mentioned, but we should make sure we keep a copy of them so that we do not need to rewrite them from nothing in the event we are impacted by a layoff. If the journal containing all of your accomplishments is sitting in the corporate OneDrive or cloud storage, you will lose access to it when you leave the company. Be sure you have a disaster recovery plan for your accomplishments! The new boss is probably going to have team calls of some kind. While what you experience may vary from this, in Nick’s experience the first time a manager hosts a call with their team they will share some career background, how they operate, and give team members some idea of what to expect. This kickoff team call usually happens before 1-1s begin. Listen really carefully when this first team call happens. Write down some questions you can ask the boss in that first 1-1 conversation. The manager will have to lead that first 1-1 conversation a little bit, but coming into it prepared with questions will be far easier than trying to think of questions in the moment. A simple follow up question Ryan suggests is how the manager wants to handle time off. Is there a shared team calendar, a formal process, carte blanche, specific blackout dates to be aware of, etc.? We can handle the simple things about how this new manager operates and what their values are early on in our working relationship. Ryan tells us he learned far too late to ask how managers handle promotion / raise / career growth conversations. One of Ryan’s past managers scheduled a quarterly checkpoint to specifically talk about career growth items. Ryan was in charge of making the agenda in advance, and his manager would come prepared to talk about each agenda item. It’s ok to ask for these regular career discussions. If your manager has a large team, these may be less frequent than otherwise. Ask the manager about the best way for both you and them to come into these discussions prepared. Nick likes the idea of an individual owning the agenda for these conversations. Nick tells us about a manager who sent out 1-1s to team members and provided a menu of options for the types of things that could be discussed during the 1-1 time in the body of the meeting invitation. It helps give people ideas for things to discuss but also lets them know the overall intention of the 1-1s. For the very busy manager, we could ask to use a specific 1-1 to talk about career-related items rather than in a separate meeting (if needed). Nick mentions a recent episode of Unicorns in the Breakroom Podcast in which Amy Lewis talks about using a shared document for 1-1s to hold an employee accountable for bringing agenda items and to document what transpired in previous conversations. Along the lines of trying to be helpful to a new manager, ask how they want to handle team calls when on vacation. Will team calls be cancelled when the manager is on vacation, or are they looking for team member volunteers to host these calls? This may be an opportunity to step up and do more if you want that, especially if you want to gain some leadership experience. Ryan tells us at one point he was a team lead, and part of his responsibility was leading team calls in his manager’s absence. This involved leading the call, taking notes, and taking action on follow up items from the meeting. We should bring up time sensitive items to the boss quickly, especially if something needs attention. Communicate things that have a financial impact to the company (a subscription renewal, drop dead due date to exit a datacenter facility, point at which access to something will be lost, etc.). Do not assume your manager knows if you are unsure! Ryan recounts a story from earlier in his career when a CFO wanted a specific number of users added to the Exchange server. There were several cascading impacts of completing this task that went well beyond the scope of licensing and involved procuring more hardware. Ryan took the time to explain the implications. “This is a simple ask. You want the answer to be yes, but I’m going to give you more context…. There is a deadline. I want to make sure we hit it as a team, but there are some implications to your ask. I want to make sure you’re fully aware.” – Ryan Conley, on giving more context to leadership Share what you have in flight and the priorities of those items. The new manager may want you to change the priority level on some things. 45:21 – Becoming Part of a Different Team You could end up working on a completely different team of peers as a result of organizational change. You might work on the same team as people you already know but might not. You may or may not work for the same boss. Ryan and Nick have experienced very large reorganization events and ended up in different divisions than they were previously. Ryan had a change of manager, change of a peer he worked closely with, and joined a new team of individuals reporting up to the same boss all at once. “A little bit of the tough lesson is you go into a bigger pond…. I think it’s ok to take a moment and pause. For me, I had to kind of reassess and kind of figure out…what are these changes? What are the new best ways to operate within this new division so to speak? …within my team, no one on my prior team was on my team, so it was like this whole new world.” – Ryan Conley After this change, Ryan saw an opportunity to go deeper into technology and chose to take a different role. Ryan worked for a new (to Ryan at least) leader who was very supportive of his career goals. This leader helped Ryan through the change of roles. “If you do good work, even through change…if you’re identifying gaps, you’re filling it, you’re stepping up where the team needs you to step up, you’re aligning with the business direction to stay focused…I think there can still be good outcomes even if in the interim period you’re not 100% happy.” – Ryan Conley If you don’t know anyone on your new team, you have an entire set of people from which you can now learn. Does your job function change as a result of joining this new team? Make sure you understand your role and its delineation from other roles. Maybe you serve larger customers or work on different kinds of projects. Maybe you support the technology needs of a specific business unit rather than what we might deem as working in corporate IT. Maybe you focus on storage and high-level architecture rather than only virtualization. It could be a chance to learn and go deeper in new areas. Did the focus of the overall team change (which can trickle down and impact your job function)? Maybe you’re part of a technology team that primarily manages the outsourced pieces of the technology stack for your company. So instead of working with just employees of your company you now work with consulting firms and external vendors. Ryan says we can still be intentional about relationships and he illustrates the necessary intentionality with the story behind his pursuit of a new role. Ryan was intentional about his desire to join a new team after the reorganization, but it didn’t work out on the timeline he wanted. He remained patient and in constant, transparent communication with a specific leader who would eventually advocate for him with the hiring manager. Just doing our job can be difficult when we’re in a challenging situation like a manager we do not get along with, trying to evolve with a top-level strategy change, etc. This can involve internal politics. Stay the course. Ryan tells us about a lesson he learned when interviewing for a new role he wanted. “Maybe be a little bit more vocal. Pat yourself on the back in a concise way. Again…go back to your journal, know your metrics, and stick by them.” – Ryan Conley, on interviewing and humility Nick says the intentionality behind building relationships applies to your relationship with your boss (a new boss or your current boss that has not changed). This also applies to new teammates! What are the strengths in the people you see around you? Who volunteers to help? Who asks questions when others will not? Ryan shares a story about 2 peers who on the surface seemed to disagree a lot but ended up making each other better (and smarter) by often taking opposing sides on a topic. When one of them left the company, the other person missed getting that perspective and intellectual challenge. Ryan suggests we pay attention to the personalities of team members and the kinds of questions they ask. If a specific teammate tends to do all the talking in meetings, find ways to enable others to speak up who have valuable perspectives but may be quieter. This at its heart is about upleveling others. We can do that when we join a new team, but we can also do this for former teammates by keeping in touch with them over time. This could apply to former teammates who still work at the same company as well as those who have left the company. Ryan tells us a story about when he first made the transition from working in IT operations to getting hired at a technology vendor in a very different role. “It’s very different being face-to-face as a consultant, face-to-face as a vendor. And I had a buddy. He started going back 11 years almost to the day here. We were each other’s lifeline…. He would have a bad day, and he would call me. Most of the time I was just there to listen…. And then the next week it was my turn, and I would call him…. So having a buddy in these change situations I think is a great piece of advice.” – Ryan Conley It can be easy to fall out of touch with people we no longer interact with on a daily or weekly basis. This takes some effort. We’ve met people who try to setup a 1-1 with someone in their professional network once every 1-2 weeks. Ryan has a tremendous amount of empathy for others who have recently had a child, for example. We can buddy up with specific professional or life experience and take the opportunity to learn from them. Ryan refers to building an “alumni network” of people you want to remain close with over time. While this helps build our own set of professional connections, we can do this by mentoring others as well (a chance to give back, which is usually much less of a time commitment than we think). Ryan has mentored a number of new college graduates and managed to keep up with their progress over time. Listen to the way he describes the career progression of his mentees and the long-term relationships it produced. We might be mentoring others (on our own team or beyond). This could act as relatable experience for a future role as a team lead or people manager, but highlighting this experience to your manager is something you should do in those career conversations. In those 1-1s with your manager you are asking how you are doing but also how you can do better. Sometimes that means doing more of something you have done in the past. Ryan reminds us that the journal is a tracking mechanism for specific actions and their impact. Whether it’s mentoring or helping the manager with hiring or candidate evaluation, be sure to track it! There might be a gap in expertise on your team that you can fill (either because you have a specific skill or because you learned a new skill to fill that gap). When joining a new team, do some observing and stay humble before you declare there is a gap and that you are the one to fill it. Ryan says we can raise gaps with our manager. For example, maybe there is only one person on the team who knows how to do something. Could you pair with that person and cover them while they are on vacation? “I think it goes back to recognizing that you cannot learn it all and then revaluating…what do I need to learn? So, there’s certain functions that you have to know how to do, and that’s where your manager’s going to help you set those expectations…. We’re in technology, so as a technologist, what do you want to learn? What do you want to do more of? And that could be a gap that you see, and you have that conversation….” – Ryan Conley If there is not an opportunity at work to learn what you want to learn (i.e. your manager might not support you doing more of specific work, etc.), you can learn it on your own time and then re-evaluate longer term what you want to do. 59:46 – Shifting Job Roles or Job Level Changes We talked about this a little bit earlier. Maybe you stay an individual contributor, move into leadership, or change leadership levels entirely within an organization. Ryan talks about the new expectations when you change your daily role. There are expectations we put on ourselves and those expectations put on us by our leaders. There are both opportunities and challenges. Ryan shares that he has been approached in the past to lead a team, but when this has happened, he took the time to think through what he wanted (his career ladder, his motivations, and his desired focus). “Leading people is not something that I want to currently focus on. I know what I’m motivated by. I’m a technologist at heart. I want to keep learning, and I personally like the technology that I’m focused on right now. And it’s not that leadership would necessarily remove technology entirely…. It’s just it would be a different focus area. And I think in your career journey it’s worth just kind of keeping tabs on where you’re at in your career (the ladder of change that we keep mentioning, that lifecycle)…. Do you want to go up the ladder as part of your lifecycle and get into a management role? I think mentorship can be very fulfilling. I think leading people can be very fulfilling. But in my case, I’ve decided I still want to stay an individual contributor. There’s still aspirations that I have there….It’s ok to say no is really what I’m getting at…. Really think about the job that you’re in at the company that you’re in. What are the opportunities within? What motivates you? And stay true to that.” – Ryan Conley Ryan has said no to being a people leader as well as to technical marketing roles. He had a desire to get through the principal program. He encourages listeners to think about whether they would be happy in 1-2 years if they took a new role before making the final decision. Nick mentions the above is excellent when you have the choice to take a new role. But what if it’s forced on you as the result of an organizational change? We can recognize where we are in the career lifecycle even if an organizational change places us in a new role that was not our choice. Make sure you understand what the new role is, and think about how you can align it with where you are in the career lifecycle (including the goals you have and the things you want). Nick had a manager who encouraged his team to align their overall life purpose to the current job role or assignment. In doing this, it will be easier to prevent intertwining your identity with your job or your company. We may have to put out heads down and just do the work for a while. But maybe there is an opportunity to align with the things you want and the type of work you want to do which is not immediately obvious. In this job market, if you are employed, be thankful and do a great job. Ryan hopes listeners can think back to an unexpected change that happened which led to new opportunities later. “Pause, recollect, align your focus with your new manager, align your focus with either the changing mission statement or the current mission statement…. What is fulfilling you personally (your own internal values)? If they are being conflicted, I think there’s a greater answer to some of your challenges, but they’re not being conflicted how can you be your best self in a company without the company being all of yourself? …The cultural identity of the workplace and the home can sometimes be a little too close, a little to intertwined…. Maybe you’re just way too emotionally invested in your day job and it’s just a good moment to reset…. What is your value system? Why? And then how can you be your best self in your workplace? And I think far too often we want to have our dream job…. ‘A dream job is still a job. There are going to be days when it is just a really difficult day because it’s a really difficult job. It’s still your dream job, but every job is going to have a difficult day.’” – Ryan Conley Every job will be impacted by some kind of organizational change multiple times throughout your career. 1:06:18 – Parting Thoughts Ryan closes with a funny anecdote about a person who worked on the same team as him that he never had the chance to meet in person. In this case, the person invested more in their former team than meeting members of their new team. Maybe a good interview question for those seeking new roles could be something about organizational changes and how often they are happening at the company. Ryan encourages us to lead with empathy in this job market and consider how we can help others in our network who may be seeking new roles. Ryan likes to share job alerts on LinkedIn and mentions it has been great to see the formation of alumni groups. “Share your rolodex. Help people connect the dots. And lead with empathy.” – Ryan Conley To follow up on this conversation with Ryan, contact him on LinkedIn. Mentioned in the Outro A special thanks to former guest Daniel Lemire and listener Megan Wills for sharing thoughts on organizational change that we were able to include in this episode! Ryan told us we can lead with empathy when helping others looking for work in this job market, but Nick thinks it’s empathy at work when we’re asking a new boss or team member how we can help. If you want to bring more empathy to the workplace, check out Episode 278 – Uncovering Empathy: The Greatest Skill of an Inclusive Leader with Marni Coffey (1/3) in which guest Marni Coffey tells us about empathy as her greatest skill. It’s full of excellent examples. If you’re looking for other guest experiences with organizational change, here are some recommended episodes: Episode 210 – A Collection of Ambiguous Experiments with Shailvi Wakhlu (1/2) – Shailvi talks about a forced change of role that was actually an opportunity in disguise Episode 168 – Hired and Acquired with Mike Wood (1/2) – Mike Wood’s company was acquired, and the amount of travel went up soon after to increase his stress. Episode 169 – A Thoughtful Personal Sabbatical with Mike Wood (2/2) – Mike Wood shares another acquisition story that this time ended with him taking a sabbatical. Episode 84 -Management Interviews and Transitions with Brad Pinkston – Brad Pinkston shares what he likes to do when working for a new boss. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

Imagine your work day starting off like any other only to find you’ve been laid off. What would you do next? Dave Stevens lived this reality a couple of years ago and joins us this week in episode 354 to share the lessons from that experience. We’ll take you through how Dave processed the news of being laid off, the warning signs he missed, when he knew it was time to begin searching for a new role, how he thought about what to do next, and the critical importance of his personal and professional network throughout this process. Regardless of your age or the size of your professional network, Dave shares actionable suggestions for building professional connections that we all may be overlooking. Original Recording Date: 10-28-2025 Topics – Background and the Impact of a Layoff Event, Initial Forward Progress and Reliance on a Professional Network, Skills Gaps and Unexpected Positives, Elements of the Personal and Professional Network, Reaching Closure and Reflecting Back on the Lessons 2:27 – Background and the Impact of a Layoff Event Dave Stevens is a Field Solutions Architect at Pure Storage. In this role, Dave is a technical overlay for pre-sales technical personnel at Pure across North America. This is the role Dave took after he was impacted by a layoff. What was Dave’s role before he was impacted by a layoff event? For context, the layoff event we discuss in this episode took place around 2.5 years before this recording. Dave was classified as a systems engineer or pre-sales technical resource at his employer supporting multiple account reps. It was more of a solutions architect type of role, and Dave highlights his entry into this organization and role was via acquisition. Was there an element of technical marketing to the role? Nick mentions that Dave often had to attend trade shows in this role. Dave had a virtualization background and went to a lot of events to discuss how his company’s products integrated with those different technology ecosystems. The day Dave was laid off started as a normal day at his home office. His boss was based in Europe, so most 1-1 calls were usually late in the day his boss’s time (early afternoon for Dave). A meeting popped up that was earlier than usual, but Dave didn’t think anything of it. Right after Dave joined the remote session for the meeting, someone from HR joined followed by Dave’s boss. Dave wasn’t quite sure what to expect and didn’t know what was happening. He didn’t know if it was a layoff coming or some other kind of situation happening at his company. When Dave was laid off, they told him it was not for performance reasons, but there weren’t really any other details provided on why he was being laid off. “So, at that point it was just like, ‘what do I do?’” – Dave Stevens, on receiving layoff news After receiving the news, Dave’s access to company systems like e-mail was quickly cut off. He went downstairs and spent the rest of his day relaxing. Dave did not want to talk about what happened any further that first day. Did Dave struggle with separating his identity from his employer or the job he held at all when this happened? Dave says he did, at least a little bit. Dave wanted to be successful in whatever role he found himself, and the reason he was in the systems engineering role at the time of the layoff event is a result of his drive to be successful in the years leading up to that role. “I also wanted to make sure that…the people that I worked with that I enjoyed working with. If I didn’t enjoy working with them, then there was no reason to continue staying there. So that’s part of my identity on how I interact with work.” – Dave Stevens In the early days of Twitter (now X), Dave defined an identity there. He also created a personal blog. Dave says his identity was often tied to where he worked. “Once this all happened, I just kind of cut that off. And I needed some time to really digest what I just went through that day.” – Dave Stevens Is there something Dave wishes people had done for him when this first happened? Dave says he wishes he would have listened to his wife. Before experiencing the layoff event, a number of colleagues who had entered the company through acquisition like Dave were either leaving or had been laid off (including his boss being laid off). At the time, Dave didn’t think much about these events. Dave’s wife had encouraged him to look for other jobs before the layoff happened, and he feels he should have listened. “It’s much easier finding a job when you have a job. There’s not as much pressure on you. You can take your time and really find the job that you want. That’s the one thing that kind of took me by surprise….” – Dave Stevens Did Dave’s wife also point him in a direction or provide feedback on the type of work he should pursue? We’ve spoken to previous guests who had spouses that provided insight into the type of work that made them happy. Dave feels like there has been an element of this in place since he and his wife got married. When Dave got a job opportunity to relocate to the New Hampshire area, his wife had some interesting feedback. “It’s great that you’re going to make more than you’re making at the job you are currently, but I don’t want you to take a job just because of money. I want you to take a job because it’s something you’re interested in doing and you’re going to be happy at. So, I’ve always kept that in the back of my mind every time I go and look for a job….” – Dave Stevens, quoting his wife’s advice Dave considered this same advice when pursuing his current role at Pure. Because he enjoyed meeting and speaking with people during the interview process, the decision to accept the role was easy. Liking the people he would be working with was more important than a pay increase. 10:53 – Initial Forward Progress and Reliance on a Professional Network How long did Dave need to process before taking the first actions toward a new role? For the first 3 weeks or so, Dave relaxed a little bit. There were a number of projects at home that he needed to do and some that he wanted to do. Working on the projects helped take his mind off what had happened. Dave mentions he was given a severance for about 3 months and wanted to find a new role within that time period if possible. But if he could not find something in that time period, it would not be the end of the world. Dave tells us it was easier to find work when he was laid off than it is currently. Close to the time of this recording, AWS announced job cuts for up to 30,000 people. He made the conscious decision after those first few weeks to spend the first part of the day searching for new jobs and then continued working on different projects in the afternoons. How did Dave know who to reach out to first? Nick argues that most of us likely don’t have a list of who we would call if something like this happened. When Dave came to the New England area, he started working for Dell in tech marketing. Through his work, Dave built a tight bond with many of his co-workers. Dave remembers sending a text message to many of his former co-workers (none of which were still at Dell) asking if they knew of any open opportunities. Dave wanted to understand what former colleagues were working on now and what the culture of their company was like. He started by seeking out people he already enjoyed working with and analyzed whether it made sense to go and work with them again. Was Dave open to different types of roles in his job search, or did that not matter? It had to be interesting work and involve people he wanted to work with or enjoyed working with. Dave says as long as it was something in the tech field, it didn’t matter too much. Dave began his career in systems administration and tech support and had experience in the storage industry, with backups, and with Active Directory to name a few areas. He had also done technical marketing and was open to returning to it. Dave also looked at pre-sales systems engineering or solution architect roles. What about taking roles that moved him deeper into a business unit like product management? Dave says product management is interesting work, but depending on the company, the work may not always have the technical aspects he likes. Many of the product managers at Pure are quite technical, but most of the product management roles he observed at other companies were not as technical as he would like. “It just didn’t interest me. It wasn’t technical enough in nature for me.” – Dave Stevens, on moving into product management It sounds like Dave had done a good job of keeping in touch with people in his professional network over time. “I have always made sure to have a small group of folks that I can just reach out to at any time and…chat about anything…. I’ve always made sure to have that…. I didn’t talk to them all the time, but we all interacted in some way, shape, or form whether it was an e-mail or text messaging…even some stuff on LinkedIn. We all kind of kept in touch…. I had people that I could fall back on and reach out to and get advice from if I needed to. This is the time where I really needed some advice on where to go to next.” – Dave Stevens Dave says he was lucky enough to find a new job before the end of his 3 months of severance pay. Dave’s wife commented that she wasn’t too worried about him. She knew he had a strong professional network. Did anyone in Dave’s professional network ask him what he wanted to do next, or did they just start making recommendations based on what they knew about him? Dave says it was a little bit of both. Some people pointed Dave to specific open roles in the same group where they worked (still in tech, of course), while others directed him to the company job site and offered to act as a referral for him. Dave tells us he’s very willing to give others a referral. “I want to make sure that people that I know and I like to work with come to work with me.” – Dave Stevens Dave says he also turned on the Open to Work banner on LinkedIn. While this did result in many recruiters reaching out to Dave, many of the opportunities they contacted him about were not interesting. Dave is hearing from many in our industry that bots are reaching out to people and trying to take advantage of them. His advice is that we need to be guarded in our interactions on LinkedIn as a result to avoid scams. 19:10 – Skills Gaps and Unexpected Positives What kinds of skills gaps did Dave see when seeking new opportunities? For context, this was roughly 2.5 years ago. Dave says at that time, AI wasn’t as helpful as it is today and was not something that was interesting to him. Dave tells us he uses AI heavily today compared to back then. Dave felt confident in the knowledge and skillset he had built through years of industry experience. Ideally, he would land a new role that overlapped those areas, but if a new role required coming up to speed quickly, he would do what was needed. Dave started looking at public cloud and certifications related to Azure and AWS. “Although it was interesting, it wasn’t really what I wanted to do.” – Dave Stevens, on public cloud technologies compared to the technologies with which he was familiar What were some of the unexpected positive outcomes of getting laid off even though it was difficult in the beginning? One positive, according to Dave, is the amount of people in his network he was able to reach out to on LinkedIn. So many people were open to helping. The only negative Dave thinks is maybe not acting quickly enough in starting his job search. “It’s really about building not only your personal network but your professional network. And my professional network really came to my rescue and helped me understand that…it’s not the end of the world. You’re going to make it. You’re going to do fine. But let me know if there’s any way that I can help you in that journey that you’re on right now.” – Dave Stevens Were there any things Dave and his wife had done (conscious or unconscious) to prepare for the layoff event based on market trends? Dave says his wife is very good at managing their home budget, and since they got married, they intentionally build a financial nest egg they could lean on in the event Dave was out of a job. 22:27 – Elements of the Personal and Professional Network What are some of the things Dave is even more intentional about now with his professional network than he was in the past? Dave received some great advice from a co-worker to reach out to one person in his professional network each week. Many times, Dave will do this on LinkedIn or even via text if he has the person’s number. “Keep that personal connection going. As much as AI is taking over, as much as we do a lot of things on Zoom, I’ve learned over my years of working in the industry that there’s nothing better than the face-to-face interaction…. It’s so much more fun and relaxing to just get out of the office or home office…and just sit down with people and keep that personal connection going.” – Dave Stevens Dave mentions he likes to get together with co-workers in the area every now and then, even if they have the same conversation in person that they would have had on Zoom. It’s different and more relaxing. How can younger listeners who may be trying to break into the industry build a professional network when they might not have a deep contact list or large network like someone in the industry for a long time? Nick and Dave talked about this before hitting record and thought it could be helpful to share during our discussion. Dave has a newfound perspective on this from being around his nephews and nieces. The job market is very different today than when Dave first began his career. “Nowadays, resumes just go into a black hole, and you don’t necessarily know if you’re still in the mix for a current job.” – Dave Stevens Dave has encouraged his nephews and nieces to leverage their personal network to build a professional network. He may know someone who knows someone in the field they want to pursue, for example. “There’s no shame or harm in utilizing all your resources…. Utilize your personal network because you don’t have the professional network built up yet to help you get that foot in the door.” – Dave Stevens Young people could even use their parents as a way to broaden their own network. It’s an opportunity to get introduced to others. Dave uses the example of a chance meeting at a concert that could result in a new connection for someone. Nick would encourage younger listeners to get out to in-person meetup groups on any interesting topic. Go ask people what they are learning, why they work where they work, how they got there, and see if they have advice for you. Dave agrees and has leveraged both local professional groups and meetup groups in the New Hampshire area to meet new people. This is expanding your local professional network as Dave calls it (not to be confused with your global professional network) and is a great thing to do when you move to a new place. You never know when a conversation at a local meetup might help you get a warm lead on a job that will be posted soon. Did the layoff come up in interviews at all? How did Dave handle that? Dave says some people brought it up. In other cases, he brought it up in conversation, wanting people to know he was not let go for doing something wrong. 28:22 – Reaching Closure and Reflecting Back on the Lessons How did Dave know he had reached closure on the layoff situation? Dave thinks he was motivated to take action toward finding a job due to a fear of boredom. He had been working on various projects but knew he would run out of them at some point. Dave had enough time to adjust to not having a job, and he was ready to begin doing some kind of work again. “I didn’t want to get bored. I hate being bored. I hate being bored at work. I hate being bored in general. That’s really what the impetus was for me to go out and start looking…that fear of relaxing for too long and being bored.” – Dave Stevens At this point Dave reached further into his professional network beyond that first group of friends and former colleagues he mentioned earlier. Does taking action in a direction mean we’re ready to move on from what happened? Is it when we have to discuss what happened in an interview, or is it something else? How do we measure this? Dave says it was easier to accept and felt mostly behind him when he was actively looking for a new position. He knew only he could take the actions to move forward. The feeling of what happened before went completely away when Dave accepted a new job at Pure. Dave feels he was very lucky to find a role. Lining up multiple interviews gave Dave momentum and a feeling of positivity. “I feel that people understand that I have the skills for these jobs. Otherwise, I wouldn’t have gotten 5 job interviews as quickly after I really started taking action to look for a job. So, I got lucky.” – Dave Stevens If Dave had to do it all again, what would he do differently? Dave feels he has about 10 more years left working in the tech industry. For now, Dave enjoys the job he has, wants to excel doing it, and wants to continue growing. Dave currently works for the best boss he’s had to date. “He not only pushes me, but he pushes our entire team to just get better….” – Dave Stevens, on his current manager Dave tells us he does not want to be a people manager or a product manager. “I want to continue to excel and expand my depth of knowledge across the virtualization industry and the storage industry.” – Dave Stevens The work at Pure is very interesting to Dave, which is also motivating him to continue learning and excelling. Part of this is using more AI-focused tooling as it becomes available to use. What does Dave think the role of AI tools is in helping with one’s job search? There are a number of tools out there we can leverage to analyze our resume. Dave suggests keeping track of which tool we’ve used to analyze our resume because that could be used to train a model. In addition to this, use AI to research companies. Use them to help you understand what companies are like and what their culture is like. Many people in a sales role within Pure, for example, use an AI tool of some kind to learn more about their customers. Nick reiterates the nuances of acquisitions. Dave worked for a company that was acquired by another company. Over time there was a pattern of people from the company which was acquired being laid off. Perhaps this is a sign we should watch for and prepare. Dave says we need to be looking at and listening for the signs coming toward us. He listens to his wife more intently when she makes a suggestion. Dave continues to check in with people in his professional network and offers advice when they need it. Dave would encourage all of us to use our personal and professional network if we end up in the situation he was in (experiencing a layoff). “Not everybody is going to be able to help you or is willing to reach out and help you, but when someone does…don’t just brush it aside as they want something out of this. They probably genuinely want to help you. So, take advantage….” – Dave Stevens If you want to follow up with Dave on this conversation, Connect with Dave on LinkedIn Check out Dave’s blog site Mentioned in the Outro The three week period Dave took to work on projects may have been what gave him the clarity on the type of work he did and did not want to do once he began his search. Dave mentions getting some great advice from his wife and her emphasis on him pursuing roles that would make him happy and be enjoyable work. This echoes something similar to what Brad Christian shared in Episode 264 – Back to Basics: Technology Bets and Industry Relationships with Brad Christian (2/2) when it came to choosing what to do next after a layoff. If you enjoyed this format and want to hear other stories of people recounting their layoff experience, check out these episodes featuring Jason Gass. He talks about the lost art of supporting others in episode 343, which aligns very well with Dave’s advice on building our personal and professional network. Episode 342 – Planting Seeds: Networking and Maneuvering Unexpected Job Loss with Jason Gass (1/2) Episode 343 – The Lost Art: Marketplace Heartbeat and Finding Closure after a Layoff with Jason Gass (2/2) Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

How can we help recruiters advocate for us in a tough job market? According to people industry veteran Christy Honeycutt, our guest in episode 353, it starts with being kind and translating your experience into something a recruiter can understand. And even more importantly, it takes practice. In part 2 of our discussion with Christy, she translates deep experience in talent acquisition and recruitment that gives us insight into the current job market. You’ll hear more details about the nuances of RPOs (recruitment process outsourcers), the difference between job hugging and job abandonment, and the importance of personal branding and differentiation. Stay until the end when Christy shares her reasons for turning down C-suite positions and how clarity on her long-term goals is carrying her forward into what’s next. Now that you’ve heard someone model it for you, how will you translate your own experience? If you missed part 1 of our discussion with Christy, check out Episode 352 – People First: Systematizing Go-to-Market for Your Role with Christy Honeycutt (1/2). Original Recording Date: 09-30-2025 Topics – A Deeper Look at Recruitment Process Outsourcing (RPO), Translating Your Experience with 3 Wins, Bad Actors and Leadership in the People Industry, Today’s Job Market and Life Outside the C-Suite 2:56 – A Deeper Look at Recruitment Process Outsourcing (RPO) When it comes to RPO (recruitment process outsourcing), is this a one-size-fits-all approach, or does it show up differently depending on what a company needs? In Christy’s experience, most RPO organizations offer services like executive search, but they may offer full RPO, which usually involves hiring more than 500 people per year. Normally an RPO brings a mix of skills to the table. A client may want the RPO to take only talent acquisition or may want to control offer management, but they may want the RPO to take everything (attracting new talent, offer management, coordinating with HR for new employee onboarding). “If a company wants it a certain way, they can stop it at a certain point…. But most RPOs, full RPOs, is attraction to offer accepted and then it tees over to the HR team.” – Christy Honeycutt John has worked for companies where the recruitment or talent acquisition personnel were marked as contractors in the internal global address book but had company e-mail addresses. Would this mean the personnel are contracting directly with a company or working through an RPO? Christy says it could be either scenario. When she managed an RPO earlier in her career, they were most successful when the client encouraged the RPO to brand as the company. Someone might indicate they do recruitment for a specific company on LinkedIn but be an employee of an RPO. Christy tells us how important it is for the RPO to understand an organization’s mission, vision, benefits, and culture because the RPO is often attracting talent and selling people on why they should apply and interview. “When you think about recruitment and talent acquisition, regardless, it’s a lot of marketing because you’ve got a really cool position and you’ve got to find the perfect fit.” – Christy Honeycutt 5:55 – Translating Your Experience with 3 Wins Right now, recruiters and talent acquisition professionals have a distinct challenge. Many resumes look the same because candidates are using AI tools. “What people think is helping set them apart is actually making them look more similar. So now you’ve got recruiters and talent acquisition; they don’t know if these are fake resumes. They don’t know if they’re real. And they’re getting on the call with these people and finding out they are fake; they don’t have any of this requirement.” – Christy Honeycutt Christy shares a little secret about learning recruitment. She gives the example of a recruiter needing to recruit for an executive level role in technology. Recruiters are encouraged to seek out and find the C-players to practice asking them questions, understand nuance, and grasp the terminology. This is a training exercise. Following this process, a recruiter would then have more credibility once they speak to the A-players they actually want to hire. “What I would encourage is if you are a C-player, you’re not going to know it. Just be kind and know that the person you’re talking to has never held a technical role (probably, most likely)…and might not understand half the stuff that you guys do. The acronyms aren’t going to be the same. Just be gracious with them because the more you can help them translate your experience, the better you’re going to be positioned to get you over the line…. They don’t want to talk to 10 people to get 1 hire. They want to talk to 3 people to get a hire…. And remember that the TA, HR, recruiters, whatever you want to call them…there’s a pretty good chance that they want to help you and that they’re doing the job because they like people. And I think they get a bad rap.” – Christy Honeycutt Christy tells us about something called a slate (a group of 3-5 individuals who apply for a job that a recruiter will go and interview). Recruiters are using AI to help filter through applications. “The biggest thing I can tell you is be your own person. Be your own, authentic person. Have your stories of how you’ve shown up and shown out…. I tell everybody for every job that you’ve worked at, you need to have 3 wins…. Figure out…your top things that you accomplished at each role and have that and be ready to speak to it. And then…ask questions. Interview them too…. Make sure it’s a culture fit for you.” – Christy Honeycutt Christy says things like the great resignation and quiet quitting are just behaviors that get repeated over time. Right now, there is a fearful state of job hugging. “We’re job hugging. No one is hugging a job. People are trying to stay employed in the market. That’s all it is.” – Christy Honeycutt Christy says if you are staying somewhere because you have a job and are not happy, figure out how to make yourself happy by determining it is not a fit, understanding your passions, and beginning your exit plan. “Companies are not our families. They are going to let us go. It’s going to come down to the business.” – Christy Honeycutt It’s important to keep the human element in mind if we are seeking a new role (the human element on both sides). Christy tells the story of a senior recruiter who called her about a conversation with a job candidate, and Christy knew the person was burned out, bored, and curious. “High performers are always open minded and curious, but if you fall in that category, figure it out sooner than later so you’re not burning yourself out because then you’re in a very dangerous situation. That job hugging is going to be job abandonment. You’re going to get to boot. It’s not going to be the other way around. It’s just kind of level setting with your psyche.” – Christy Honeycutt 11:28 – Bad Actors and Leadership in the People Industry Going back to recruiters getting practice and experience from interviewing candidates, Nick looks at this from the lens that everyone needs at bats to gain experience. Though it may be batting practice for a recruiter, it is also practice for the candidate. We don’t practice interviewing very often. Christy agrees it is practice on both sides and emphasizes that kindness is key. She’s had multiple conversations with recruiters who didn’t understand why a hiring manager did not want a specific candidate. We might never know all the effort a recruiter put into promoting us with a hiring manager. Some recruiters, however, should not be in their roles. Christy tells us about a time in her career when she was referred to as “The Kraken.” Christy managed a tight team of talent acquisition professionals who respected and loved her as a boss. They knew she had high expectations of her team. Christy’s team members would have to launch programs for global clients within 30-60 days sometimes, for example. “So, my team had to be kind of like special ops because we managed the globe, and it was high pressure.” – Christy Honeycutt As she progressed in her career, Christy would be given individuals who were not performing on other teams. Before managing someone out of the business, Christy always gave people a chance to redeem themselves because until she met the person and they worked for her, she was only hearing one side of the story. Christy recounts being asked to join an RPO to clean it up. She met with each recruiter to understand the key metrics and performance indicators. Christy tells us that for any job opening (or job requisition) a recruiter was carrying at this time, they should be submitting 3-5 candidates for each job, and a manager would expect this within 2 weeks of the job opening. There was a specific recruiter who only submitted 2 candidates per week across 15 job openings, and Christy recounts the performance conversation with this person. “There are some people that are in roles that they shouldn’t be that take advantage and kind of sit back….” – Christy Honeycutt As people gain seniority in talent acquisition and recruitment, sometimes you deal with people’s egos. This is the exception and not the rule. John mentions it would probably be difficult to coast based on one’s reputation in talent acquisition. Based on the metrics for success and open job requisitions, it should be obvious who is doing well and who isn’t. Christy says this goes back to leadership. Maybe these individuals never had a boss who would hold them accountable. “If we go back to managers and leaders, most of them aren’t trained, and a lot of them want to be liked.” – Christy Honeycutt Christy is the daughter of a Marine. This means the mission gets accomplished no matter what with the fewest amount of casualties. It’s her job as the leader of a team to keep them focused on the mission and accomplishing it. Removing someone from the team may be the best option to keep the rest of the team on track in accomplishing a mission. “You’re only as strong as your weakest link, so if your weakest link is not holding themselves accountable and respecting their team, then they’re putting everybody else’s jobs at risk. And unfortunately, there are bad actors in every industry, in every role, in every organization…and we’ve all seen them. They are like cancer. They really hurt retention. They hurt elevation. They are usually the ones taking credit, taking too long at lunch, whatever the case may be…we’ve all seen them…. It all comes down to behaviors.” – Christy Honeycutt Christy thinks leaders want to be liked and are afraid of having a complaint filed against them. For example, people might file a complaint because they were not doing their job and their manager held them accountable for not doing it. “It’s weird to be in the people industry for so long because it’s just behaviors. It’s just humans.” – Christy Honeycutt Before someone shows up for work, we have no idea what may be going on in their life outside work. Christy encourages us to meet one another with more grace. “Those of you out there, if you’re lucky enough to have a job and be employed, do the job. Because there’s a lot of people that don’t that will come in and do a better job than you. Honor yourself, honor your employer, and show up. But unfortunately, there’s bad actors.” – Christy Honeycutt John directs the conversation back to hiring cycles. He has heard it’s beneficial to apply for a job opening quickly and to be in the first wave of candidates but didn’t really think about the why behind it. Christy tells us this varies based on the position, the job requirements, location, salary, and other factors. In fact, recruiters often have to reset unrealistic expectations from hiring managers (i.e. what a specific role salary should be). “If you think about a client and them opening a position, they probably needed that position 30 days before it was ever approved. So, there’s already a ticking time on the recruiter whether that’s fair or not because in the manager’s mind that role opened the second they thought they needed it. Not when they requested it, not when it got approved, but when they realized in their brain, ‘I need this position filled,’ that’s when the clock starts for them. So, it’s an unfair disadvantage for a recruiter.” – Christy Honeycutt Listen to Christy’s description of a best-in-class 4-week process from job opening to making the right candidate an offer. 20:45 – Today’s Job Market and Life Outside the C-Suite If we look at this through the lens of the current job market, how much do recruiters need to sell candidates on roles when there are hundreds of applications to sort through for a single job opening? “Tech is like recruitment, like marketing. It’s always the first to go…until they realize…it went, and we need it. So, it’s a boomerang effect with those industries…always has been, always will be.” – Christy Honeycutt Christy tells the story of being at the HR Tech conference with a young lady who was recently laid off from a tech company. This person walked from booth to booth and began networking with people in search of new roles and was able to leverage Christy to get some introductions. She had 5 interviews over the course of the 3-day event. “In the job market today, with recruiters not able to tell if it’s an AI resume or not, with them being overloaded with a vast amount of resumes…the best thing that anybody can do is make sure that your personal brand is on point. Make sure that whatever it is that you’re doing…you’re sharing, you’re engaging your community, and that you’re seen doing it.” – Christy Honeycutt Christy was part of the same tech startup mentioned above and also lost her job. But she had been working on her personal brand before that happened. Christy was speaking at events, sharing with her community, doing podcasts, and doing many go-to-market things on behalf of her employer. Christy’s heart goes out to others in her field who have been out of work for multiple years. Within 3 days of losing her role, Christy was offered 3 different C-suite positions. She turned them all down. “I’ve had that moment where I’ve realized that where I want to go and where I am are 2 different places…. If I put my focus on something, my energy is going to flow in that direction, and I need to make sure that’s the direction I want to go…. Do I want to go be c-suite and kill myself for the next 4 years? …But the reason that gave me confidence is I’m 3 days without a job. I’ve got several job offers. And I realized, they don’t care how I work with them. They just want to work with me, so why don’t I go out on my own?” – Christy Honeycutt, on the internal discussions she’s having after encountering job loss Christy understands she’s in a gifted place only because she put in the work of giving back to her community before she was in a tough spot. Her efforts include things like hosting Inside the C-Suite and doing free mentoring and coaching for others. “It’s because of all the goodwill I’ve done. My community paid it back tenfold. So set yourself apart in whatever it is that you’re doing…. Where we are today is you have to have a differentiator, or you’re going to be sitting on the shelf for 5 years.” – Christy Honeycutt Christy mentioned previously that it’s lonely when someone takes a C-suite role. How did her conversations with executives on Inside the C-Suite together with her experience in talent acquisition and recruitment impact her decision to not take a C-suite role? Christy knows that she doesn’t do anything halfway. If she were to take a C-suite role, she would be working 80 hours per week and traveling nonstop. Christy and her partner want to slow the pace down for their family, take time to travel, and do more purposeful things. She shares a story about Matthew McConaughey wanting to make the shift from romantic comedies to more serous roles to illustrate a shift of priority and focus. “Yeah, it crossed my mind. But it does not align with my long-term goal…. I realized I have a choice. You know, the universe has brought a lot of stuff to me. Is it because it’s meant for me, or is it noise?” – Christy Honeycutt Christy has shown up, given to her community in a visible way, and found her voice. But taking a C-suite role right now is not where she wants to be. Some of the job offers Christy received came from people who had been on her podcast. Christy tells more of the story of being at HR Tech and the reactions people in the industry had to her being on the market. Christy plans to continue conversations with those people about ways they can work together moving forward. “I’m really good at certain things, which you guys have broken down and helped me understand. I repeatedly get asked for those things, and those are the things I like to do. So why not go do that? Why not go be a consultant and do the things that I really like to do for people and not do the things I don’t like to do…? …I can just go do the fun stuff that they need my specialization in.” – Christy Honeycutt Christy wants to stay true to herself and honor the decision to increase bandwidth for her family. Many of the C-level executives Christy speaks to on her podcast love what they do, but they’ve had to learn to put themselves first. “I hear this more often than not. When they first start their organization, it’s business business business. Their health fails. Their family fails. So, the ones that actually made it and recovered through that little spike and actually make it out on the other side very quickly flip to ‘take care of my body (my temple), my soul, my family, then my business. It’s a battle for them.” – Christy Honeycutt At the time of this recording, Christy is thinking of starting her own firm, so she hopes she can take it slow enough to avoid these pitfalls. When we decide to slow the pace and do more of what we enjoy, can reflecting on those 3 wins from each previous job help us be confident that we can still get those wins without running at a hectic pace? Did Christy do this when thinking about what she wanted to do? Christy says she did not think about these for herself even though it would be her coaching to others in need of advice. “What I found interesting is that when you’re looking for an answer, if you actually open your eyes, it’s right there. It plays back to you. It plays back to you in conversations you have with people…. You often say what you need and what you want and where you’re at, but you don’t comprehend it. But if you hear someone you love, that you trust, repeat it back to you…it’s almost like it gives you permission to accept it.” – Christy Honeycutt Sometimes instead of giving people advice, we need to act as a mirror and reflect back what they’ve said. Christy didn’t need a C-level title. She doesn’t need to go do something to prove she can do it. She’s already done it. Christy understood she was ready for something different, even if it’s a little bit scary to consider going out on one’s own. “It’s scary to put yourself out there like that, but if you don’t, you’ll never know. I’d rather try and fail and learn than regret and not know.” – Christy Honeycutt If you want to follow up with Christy on this conversation, you can find here: On LinkedIn On her website On the podcasts she hosts – Inside the C-Suite and StrategicShift Mentioned in the Outro Do you have 3 wins from each job or at least the past several jobs you’ve held? And do you know the stories that go along with these? There are prerequisites that must be met before we can speak to our wins in an interview. It starts with documenting our accomplishments on a regular basis. Consider what the 3 wins are from your accomplishment list. Maybe you have more than 3 or need to use a different set of 3 based on a job to which you’re applying. Consider writing the story that goes with each win. It could be a resume bullet, but think of it as more detailed and something you can share in an interview. This is part of drafting a career narrative like Jason Belk suggested in Episode 284 – Draft Your Narrative: Writing and Building a Technical Portfolio with Jason Belk (2/2). We should not only write the draft but gain practice sharing the stories verbally in interviews, possibly conversations with our manager, and maybe even in conversations with industry peers at networking events (if and when appropriate). This is an iterative process! We like looking at conversations with recruiters as opportunities to practice telling our win stories. In the discussion with Christy, we heard about her experience losing a job. In Christy’s case she had been giving to her network long before this happened in a very visible way. Maybe you are doing this in a less visible way. Consider documenting that work, but make the overall intent to help others and impact people positively. It will pay off later when you need help. Christy shared an exercise in finding clarity. She knew a C-suite role would not match the pace that was aligned with what her family wanted. It wasn’t just about personal ambition. Remember to check out Christy’s podcasts, Inside the C-Suite and StrategicShift. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

Go-to-market strategy is something we often associate with a company or its products / services, but what if we could apply go-to-market to our job role? Christy Honeycutt, a talent acquisition veteran and our guest this week in episode 352, has used this mindset as a personal differentiator starting with her first job in the banking industry. We’ll follow Christy as she describes early experience as a people manager, learn why she developed a people first mentality, and recount the events that kickstarted her career in recruitment. This story helps us understand what is required to systematize the work we do and how difficult it can be for things that seem easy. Christy will also educate you on the importance of developing AI competence and the impact of recruitment process outsourcing on job candidate experience. Original Recording Date: 09-30-2025 Topics – Meet Christy Honeycutt, A Go-to-Market Perspective, Beginnings in the Banking Industry, Learning to Systematize and Duplicate Yourself, A People First Approach, Getting into Recruitment 2:10 – Meet Christy Honeycutt Christy Honeycutt has 20 years of talent acquisition experience, go-to-market experience, and some marketing experience sprinkled throughout. Christy is also the host of two different podcasts: On Inside the C-Suite, Christy interviews executive leaders to gain insight from life in these roles. StrategicShift is focused on the future of work, innovation, and AI. 3:17 – A Go-to-Market Perspective How would Christy define talent acquisition and recruitment and the differences between them? Recruitment should be thought about as more active. There is a job open with specific requirements which need to be filled based on time constraints. Talent acquisition is more strategic according to Christy. This would include understanding why a role is vacant, the succession plans, cultural initiatives, and workforce planning. Christy refers to this as “engaging passive pipelines for long-term goals.” Personnel in talent acquisition and recruitment are usually in those roles because they want to help people, but these roles may look slightly different across companies of various sizes and in different industries. How would Christy define go-to-market? We hear this term quite often but are not confident that everyone truly understands what this means. For context, Christy talks about looking at this with a lens across many different departments / internal organizations – marketing, recruitment, and even sales. “Go-to-market is understanding what is the product and who is the end user…. Am I filling a job? Then I’m going to market for that candidate that fits that job. Am I working for a tech company (which I most recently did)? Then, yes, I need to understand what is our product, who is the end user, who is the buyer…and how can I get this to market for them…to see, to use to buy, and to be delighted in? The go-to-market is really kind of a Frankenstein effect in my opinion. It’s really understanding the value and how it translates and then how you can connect the dots…. Go-to-market for me has just kind of been at my core since I was a kid.” – Christy Honeycutt For recruitment, the go-to-market is usually set based on an organization’s vision, mission, values, and culture. Christy uses the example of negotiating with her father (a former Marine) to get what she wanted when she was younger to illustrate that go-to-market can mean understanding how to sell. 7:01 – Beginnings in the Banking Industry Christy was a cheerleader in high school and got a fully paid scholarship to college, but at age 17, she was diagnosed with cancer. As a result of the diagnosis, she was not able to attend college. Christy always wanted to be a mom and did not want to ruin her chance to have children. Christy married her college sweetheart and became a stay-at-home mom of 2 children. She is now heathy, happy, and thankful she was able to have children. Christy’s father owned a nonprofit, and even while she was a stay-at-home mom, Christy was involved in marketing for nonprofits as a result. Christy also was part of the boards of her children’s schools, did volunteer work, and even taught pre-school. After moving to a new state, Christy needed to get a job to support her children. After applying at a bank, she landed a manager job. Within 6 months, the bank branch where she worked was the highest producing in the state of Texas. Christy came up with marketing initiatives to get customers to visit the bank. She gives the example of a yearly Halloween contest. At one point, the bank was robbed, and Christy learned to lead in stressful situations through this experience. She also learned that she has a photographic memory. Christy tells us her career really began in banking and then transitioned into marketing. Listen to the story about one of her clients who was a mortgage broker. Christy had 2 boys in various sports and was wearing herself out between work at the bank and home life. This mortgage broker sent an e-mail to help Christy get interviews for a role at a different bank. Christy tells the story of interviewing in the mortgage division of another bank (Prime Lending) close to Halloween. She was dressed as Lucille Ball for an event at her employer and ended up going to the interview in costume. The people who interviewed Christy loved it, and she was offered the job on the spot. 11:40 – Learning to Systematize and Duplicate Yourself “But the really interesting thing that happened is they said, ‘we want you to hire 3 of you…. What you’re doing is working, so what we’d like you to do is go have a think about how you can multiply that into other branches….’ Can you imagine sitting down and going, ‘what is it that I did today and how did I do it?’ …And, just really creating a job description, a profile, how they’re going to be successful…and then find the people and train the people? So that was my very first…experience with recruitment.” – Christy Honeycutt After removing the shock of being told to multiply herself, Christy began a process that she would repeat over and over in her career – thinking outside the box to create something special that she could automate or systematize. At that first bank, Christy managed people but had no prior training as a manager. How did she figure out how to manage people, and then how did that translate to the role in which she was asked to create job descriptions and multiply herself? We’ve heard from some guests that most first-time managers do not get training. Christy echoes this sentiment. Large banks will train you on laws and procedures, but Christy tells us she had to train herself on the people side. Mainly, she needed to learn how to manage the people, their schedules, and learn how to encourage them. Despite being the boss, Christy was still friends with the people who worked there. In being asked to multiply herself, Christy had to systematize the job she was already doing. She tells us it was a daunting task. “When you’re really good at things, what I’ve found is they seem natural to you, and they are not that hard.” – Christy Honeycutt When asked to duplicate herself, Christy downplayed her contributions a little bit. She advises all of us to step back and really think about the work we have done because we might not immediately recognize it and may downplay it in a similar way. As humans, we might at first feel like it is bragging to share the factual things we have done. Christy had to think about what she did, simplify it, and figure out how to translate that to the people she needed to hire. Christy was working for the mortgage division at a bank, and they needed to get more loans. She first sought to understand the sentiment of the bank’s customer base and if they had any needs. Step 1 was hosting a customer appreciation event. The customer appreciation event generated direct feedback on the bank’s processes and product offerings. Next, Christy sought to understand the bank’s target market, which was real estate agents. She thought about how to get real estate agents to use this specific mortgage broker. New real estate agents need help with marketing, so Christy got certified and began teaching marketing classes to real estate agents. All of the agents would eventually begin using the bank. “It’s just kind of understanding what’s in it for someone else…. I just…went step by step by step and built the framework….” – Christy Honeycutt The framework Christy mentions above outlined where the opportunities were for the bank (i.e. who might need their services), allowed for dividing up the work across divisions, and provided insight into the key performance indicators (KPIs) for measuring success. In many ways, Christy acted as a liaison between the bank, the real estate agents, and end customers. When seeking to hire people to do the work, Christy looked for empathetic people who were interested in helping others. Another avenue for the bank to increase the number of loans was working with first-time home buyers who might have poor credit. This would help real estate agents who needed home buyers. The bank started doing credit repair seminars to generate new leads. “I was bringing in buyers, delighting previous buyers, and then also going after the vendors that would help participate. Honestly, that model…has kind of been my two step my whole career.” – Christy Honeycutt Nick thinks Christy’s process is actually a three-step with the third being supplementing the above with the type of education which will both Christy and the audience she seeks to serve. Nick thinks this pattern will probably be repeated somewhere in her story as well. Christy says it actually does repeat. She recounts getting an AI-focused certification when this technology wave started catching on. “In the next 12-18 months, over 80% of all organizations globally will have adopted AI if they haven’t already. So, if you’re looking for a job, and you don’t understand the basics…AI has a lot of different names. I want you guys to think about that. That’s usually marketing.” – Christy Honeycutt Christy tells us AI agents are mostly marketing and an attempt to make things more consumable and understandable rather than some flashy new invention. Christy recounts talking to executive leaders who have mentioned having AI in one’s toolkit even as a kid is important to be relevant in the future workforce. All of us need to have more than a bare minimum exposure to ChatGPT, for example. We need to play, create, and tinker with AI tooling to develop a point of view that is uniquely ours. Christy feels AI will take jobs but that they will be lower-level things that we probably wanted automated anyway. She gives the example of a communications outage impacting airports in Dallas / Fort Worth and the decision to go get information from an AI agent on the company website rather than call the help desk. For any job you go into, expect to get questions around AI. Christy mentions a recent visit to the HR Tech conference. Every booth was promoting some kind of AI, and Christy shared with executives at the conference that buyers don’t fully understand the difference between products because “everyone is saying the same thing.” Christy reminds us there are ways to get low cost or even free education on the topic of AI so we can develop competence and a point of view. Nick shares his perspective on what he calls the “double check mark,” which is looking to educate yourself or build skills in an area that can help you both at your current employer but also make you marketable and relevant in the greater job market. Something that only helps you with your current role isn’t quite as attractive as something that can help you later as well. Ideally, you span into both categories, but it is not always possible. Christy mentions this is a very tech answer and gives the example of making a suggestion to an executive leader while advising for a tech startup. She only brought suggestions that would be attractive to / helpful to many customers (not just a single customer). When Christy did research on what was impacting customer sentiment and spoke about understanding product market fit, was that all natural at the time she did it while working at the bank? Christy says it was natural at the time. As a single mom, she needed to be scrappy. “It’s funny because as I sit back and I think…I realize everything was kind of predestined. And at the moment it just felt like I was reacting and I was doing it, but…as I do my own reflection, I’m realizing that these cycles I’ve been on have always been for a reason, guiding me to where I’m at.” – Christy Honeycutt Reflection is one way to uncover our strengths, and Christy reminds us that just because something is easy for us does not disqualify it from being a strength. John mentions that performing a skill really well is different than being able to teach other people how to do it. When something comes easily to you, it might be difficult to know how to teach someone else to do it. But it sounds like Christy had to learn how to systematize the things she did so she could train others (i.e. it was not natural). Christy says it definitely was not natural. She remembers how she felt when asked to duplicate herself. It seemed like a crazy request at the time. One thing that really helped Christy through this process was looking at job descriptions for roles similar to hers at other companies and analyzing both similarities and differences. “Everything is a learning lesson. I don’t regret any place I’ve ever worked. I don’t regret any situation I’ve ever had because it was all opportunity for me to learn how to manage through a situation (good, bad, or indifferent) and reflect on it and how I would do it differently.” – Christy Honeycutt Christy mentioned earlier that no one learns how to be a manager. She is a forthcoming author and was recently signed with Postal Publishing House, and the book will be about leadership. In the book Christy talks about how no one is trained to be a leader and how people often just kind of fall into it. She feels it is a big gap. Even as people get up to the director level and maybe even the VP level, they are still learning. “No one sits you down and says, ‘hey, these really crazy things are going to happen, and you’re going to have to respond to these humans in a particular way. And by the way, you’re human, and you might have a really bad response to what you have to respond to….’ There’s lots of things that you deal with that I don’t think anyone could prepare you to deal with. And so, you learn on the job.” – Christy Honeycutt Did the need to create job descriptions and hire people to multiply herself make Christy enjoy management more or question whether she wanted to keep doing it? Christy tells us she questioned whether she wanted to keep doing it. Her responsibilities ended up expanding well beyond the go-to-market work she was doing, and things became more complex. Christy went from being in charge of 1 person to being in charge of 4 people trying to do everything using her methodology but with their own flair. “Frankly, I got kind of bored because I created something, I duplicated myself, multiplied myself…. Ok, I’m ready for the next thing. I can do this, and I’m ready for the next thing…. I’m constantly curious, and I always need something more just to kind of keep my attention. There’s a lot of people in the industry I think are that way, especially in tech…. And those are the people that employers are looking for. They are looking for the curious people. They are looking for the open-minded individuals that want to adapt and want to learn and do more because those are the ones that have the longevity.” – Christy Honeycutt Once we master things as technical people, we often want to move onto what is next (something new to learn, a new certification to chase, etc.). 26:23 – A People First Approach Did Christy’s background in cheerleading help her in marketing? Actually, yes. Christy gives the illustration of high school cheerleading and pep squads. These are made up of people who love community and love to empower and cheer on other people. Christy reminds us that cheerleading is a sport. For those in cheer or pep squad, it’s not about wearing cute outfits. There is a commonality among the people who participate: an enjoyment of collaboration, a desire to win, and a belief that there is power in the energy they are giving. Christy likes to look at things from an energy lens. “In every industry you’ve got really good players, and you’ve got bad actors. So not all recruiters, not all talent acquisition people are really kindhearted, love what they are doing, and in it for you…. But the majority of the people in the HR and TA (talent acquisition) space generally joined that type of work because they love people, and they are fearful right now because they think AI is taking their job. And some of them it probably will, but you’re never going to get away from the EI and the EQ piece that is required in the age of AI. We need to be more human now than ever.” – Christy Honeycutt Some people in these roles may hate their job. Some may love you as a candidate but be unable to get anything through. At what point did Christy realize that for her it was more about the people? “It’s always been about the people for me. Everything I do has been about people. I’m people first just in everything I do.” – Christy Honeycutt After getting the job where she needed to duplicate herself, Christy wanted to talk to all of the company’s customers as her first task. Christy mentions the concept of go-to-market is the same regardless of the company where we work. “Your customers are your biggest resource because they will either be the loudest complainers or your biggest fans.” – Christy Honeycutt Customers with a positive sentiment toward a company (or its products and services) can offer free insight on how to serve them better. This may come in the form of suggestions for new features and capabilities or advice on overall direction, for example, and provides a perspective that a vendor cannot otherwise see. Christy has been told she is too “client advocate friendly.” When selling a product or service to a customer, if users don’t adopt it, you are only as good as the contract. Christy calls this being a one trick pony. On the other hand, we can sell a product or service and care enough to check in with customers and make pivots to make the product or service more valuable. This creates what Christy refers to as a “client for life.” “And that’s, I think, where my specialty comes from is the human side, the people side. It’s just always remembering what’s in it for somebody else. Because we all have exchanges every day. What’s in it for the other person?” – Christy Honeycutt Christy makes a hypothesis that we do this podcast to help people and because we care, and at some point in our career we probably needed what we are giving. What would you have said is the reason for the podcast based on being a listener? “People are my thing. I get the heart. I get the energy, and I think at the end of the day, we all put our shoes on the same way.” – Christy Honeycutt Christy really enjoys hosting Inside the C-Suite because it demystifies what it is like to be an executive leader. “It’s understanding how you navigate and how your priorities change…what’s now, what’s next, what’s urgent always evolves as you grow in your career.” – Christy Honeycutt 31:52 – Getting into Recruitment How did Christy end up getting into talent acquisition and recruitment? Even with her hectic travel schedule hosting events for her employer, Christy never missed a little league baseball game in which her kids were playing. At a specific game, someone asked Christy what she did for a living and if she had ever thought about working in recruitment. The person who made the suggestion helped Christy see the similarities between recruitment and marketing. “Client needs a certain thing, and you go find the certain thing. And however you find it, you find it. That’s a lot like marketing. Exactly.” – Christy Honeycutt, describing an exchange with someone who encouraged her to pursue work as a recruiter Christy went to an interview for a recruiting role and got the job on the spot. The company was bought out by Kenexa(CEO was Rudy Karsan) which was later acquired by IBM (or “big blue” as Christy calls them). Christy did recruitment process outsourcing for this company (or RPO for short) and specialized in this area for many years. She led this at IBM and later at Korn Ferry. She tells us there are so many layers to recruiting that people don’t know. Staffing agencies, for example, often get a bad reputation. These agencies are predominantly focused on high-volume hourly roles or other short-term positions. Quality and candidate experience are not always the best. These recruiters have to move quickly because a successful placement is how they get paid. “And when you do that really, really well the clients think that you’re their internal recruiter…. I think over my career, not me directly but within my teams, I’ve probably placed around 30,000 individuals.” – Christy Honeycutt, on specializing in RPO Listen to Christy talk through an example of mapping through the workforce strategy for a client that wanted to outsource global recruitment on a tight timeline. She emphasizes that when we work with a recruiter, that recruiter might not work for the company where we are interviewing. “When an RPO does a good job, not only does the candidate think that they’re an internal recruiter, but the clients think they are an internal recruiter.” – Christy Honeycutt Christy talks about making a move from being a liaison manager for a client (focused on the client’s technology sales and marketing) to managing an internal team. The client thought she was their employee. Don’t miss the part where Christy mentions she wanted to take a role as a recruiter so she could understand how to be a better manager. “While your…audience is out there looking for jobs, just be mindful that…TA, recruitment, HR…depending on the size of the organization…you may be talking to an agency. You may be talking to an RPO. You may be talking to an internal recruiter. You can ask them. They don’t have to tell you.” – Christy Honeycutt Another challenge for the job seekers out there is the amount of fraud happening. On average, every US citizen has 7 points of fraud directed at them per day. Christy mentions getting multiple text messages from companies claiming to be Randstad, Robert Half, or some other firm about jobs. It’s all fraud. Don’t fall for it! When Christy worked for Korn Ferry and another tech startup, as part of the go-to-market strategy, she created a candidate application analysis tool which informed clients about the candidate’s experience. Some clients didn’t realize, for example, that their site was down and was preventing people from even applying. This tool also informed clients about how they showed up on sites like Glassdoor and what the biggest complaints are. The lowest scores 9 out of 10 times for a company are for leadership. Keep in mind rankings on Glassdoor are from job candidates and people who have worked at a specific company, and most do not take time to write glowing reviews of an employer. “We have to give the employers the benefit of the doubt. So when you know where the sources are coming from and you’re honest with yourself on when you give feedback and how you give feedback…until we can all step up as humans and start giving 2-3 good feedbacks a day, we’re never going to balance out the negative.” – Christy Honeycutt Mentioned in the Outro Christy did a great job emphasizing that we understand what is it for the other people we work with (incentives, metrics, what success looks like for them), and that was part of executing a successful go-to-market strategy in banking and other areas. Here’s how Nick thinks a go-to-market might look for someone working internal IT: Understand the technology landscape at your company (hardware, software, cloud services and subscriptions – the overall vendor landscape) Understand the end user base you support and the capabilities you are providing to them. Think also about the value being delivered through these capabilities to both internal users and external users if applicable. Think about the capabilities you provide like products. Can your products be enhanced based on end user needs and feedback, and are we willing to take the feedback? Christy modeled the importance of understanding customer sentiment that can help us here. Will an enhancement save time, decrease cost, decrease risk, or increase revenue? These are important impact metrics to understand (and document). If you change a hardware / software vendor (i.e. a tooling change), will it disrupt your customer base, or can you still provide the same capabilities? Make sure you understand this! Is there a new capability you could provide that delivers more capability? That’s part of the go-to-market. Are there members of the end user base who need education to get more value from the services and capabilities you’re offering? Don’t forget to check out the podcasts Christy hosts –Inside the C-Suite and StrategicShift. Nick feels podcasts such as Inside the C-Suite are great sources to gain perspective on how executive leaders operate. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

Original Recording Date: 11/2/2025 Expect a Change Moving Forward – The Schedule Hi everyone – thank you for being a listener. This is a brief reminder that episodes from this point forward will be releasing every 2 weeks for the time being. Life circumstances have demanded we make this change to keep producing the show. Don’t expect any changes to our content. We remain committed to serving the technology professional and helping them accelerate career progression, increase job satisfaction, and be more effective in their existing role. Thanks for coming along with us on the journey, and it will continue. Expect to hear from us every 2 weeks from this point. See you next week for another action-packed episode! If you have ideas for a topic we should explore or a guest we need to have on the show, feel free to contact us via any of the channels below. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

What does it mean to become AI native? It’s not about using every AI tool on the market. For Milin Desai, the CEO of Sentry, it’s about becoming familiar with the tools and opting in to use the capabilities that deliver practical value. This mindset was born while Milin was the general manager of a business unit at a software company. In this role, he had to manage a profit and loss statement, learning the art of constrained resource planning and organizational adaptability. In episode 351, our final installment of the conversation, listen as Milin describes both the gravity and different intensity of the CEO’s role compared to past roles. You’ll get insight into the strategy behind enabling an entire organization to shift and become AI native, how this translates into value for customers and employees, and how the individual contributor can be a better contextual communicator when speaking to busy leaders. Stick with us until the end to understand how a set of first principles can guide our career progression if we choose to actively participate in it. Original Recording Date: 09-29-2025 Milin Desai is currently the CEO of Sentry. If you missed parts 1 and 2 of our discussion with Milin, check out Episode 349 – Expand Your Curiosity: Build, Own, and Maintain Relevance with Milin Desai (1/3) and Episode 350 – Scope and Upside: The Importance of Contextual Communication with Milin Desai (2/3). Topics – Contrasting the Role of General Manager with CEO, Embrace Practicality with New Technology, Junior Personnel and a Return to First Principles, Shifting Organizational Focus to Becoming AI Native, Contextual Communication to Leaders and Parting Thoughts 2:41 – Contrasting the Role of General Manager with CEO General managers usually own a profit and loss statement (or PNL statement). How was this different than the things Milin had previously gone through? Milin says you do have to prepare yourself for it, and his experience as part of product teams was very helpful to gain familiarity with many of the elements of the general manager role (i.e. revenue protections, investing resources in specific efforts, etc.). Things get very interesting when you are managing PNL in a constrained environment. Milin gives some insight into annual planning and the behaviors he has observed during these times. “Very rarely do people come back and say, ‘I’ve got the same org. I’m going to reshape the org, move things around, and I’m going to do these new things with the same number of people.’ I think most leaders are not very good with that philosophy.” – Milin Desai In this role Milin tells us he learned how to do planning with specific constraints in mind (i.e. stress testing as if no resources / extra people could be added), and this idea of keeping teams lean taught him about the adaptability of an organization. “I really think every organization should do that, and then, you always have the ability to go add more people…. Structurally say, ‘is this how we still want to operate?’ And we rarely do that…. I knew the numbers, the resources, and everything else. We did a lot of planning. But what I learned I needed to get better at is this constrained planning…” – Milin Desai Milin loved working as a general manager and thinking through how to optimize even if the organization didn’t get everything it wanted. “What is the hardest thing to do? To say no. What is the hardest thing for a product manager to do? Shut down a feature. What is the hardest thing for a VP of engineering to do? To shut down a product…. I’m lucky enough to have a leadership team that…thinks along those lines. We are unconstrained, but we kind of try to make sure…let’s put some artificial constraints and see what we would do different.” – Milin Desai Nick mentions this is analogous to the employee who is no longer a fit and having to say no to that person moving on with the company. What is the contrast between being a general manager of a business unit and being the CEO of an entire organization? Milin remembers some of the conversations when he was considering becoming a CEO. “Milin, are you sure you want to do this? And it was not a capability question. It was, ‘do you understand what you are signing up for?’ …It is very different. You are responsible for everything. There is no other person. There is no other excuse. There is no other system I can blame. Something goes wrong at Sentry…I am it. And I have to go to sleep every day thinking about it. I wake up every day thinking about it.” – Milin Desai, quoting a question from former boss John Martin and speaking to the contrast of being CEO compared to general manager You have to know you want to be CEO. Many people think they want to do it until they are doing it and realize how difficult it is. Milin admits being CEO has been difficult, but having a great team has been very helpful. Before taking the role, Milin spoke to his wife about it. He describes the role as “a very different intensity.” Three months into Milin being CEO of Sentry, COVID showed up. That is a challenge he never would have expected. “It’s very different to be a GM versus being a CEO. You’re using your same skills, but it’s a completely different magnitude of responsibility and impact.” – Milin Desai As a general manager of a business unit, Milin could change the trajectory of his business unit. As CEO, mistakes are much more costly. But you cannot do it in fear. In fact, for Milin, the larger impact of his role is exciting. The right partners and team around you as CEO are very important as are taking and applying lessons you previously learned. Milin continues to push himself to improve over time even after reaching the CEO level. 9:22 – Embrace Practicality with New Technology John cites technology waves like virtualization, cloud, mobile, and generative AI. With generative AI, many of us get value from it. But many people are unconvinced of the value and are even fearful it will turn into something like Skynet (a reference from the movie Terminator 2). How does Milin approach people with this mindset? Milin is practical with his approach to technology. “The unconstrained view of what AI could do…we have seen it in movies already. So, I think the unconstrained aspect of this is what we can imagine or maybe even worse…. You can almost think about that and worry and not participate and be on the other side if that happens…. Or, just practically, on a day-to-day basis, figure out what aspects you want to opt in. So, I’m more in that camp…. On the AI front, just think about how it could practically help you on a day-to-day basis versus trying to worry too much about all the aspects, some of which you absolutely don’t even control…. I think it will bring productivity in ways that we don’t even know.” – Milin Desai For example, Milin doesn’t have a voice assistant, didn’t find them useful, and did not opt in. If you’re worried about supporting a bigger cause, Milin tells us that bigger cause is going to happen irrespective of us supporting it. Instead, we should think about how to practically use AI tools and become an active voice in it. Milin tells us his wife just started using ChatGPT and loves it. He asked her the value question on whether it was worth paying for it vs. staying on the free tier after she talked about how much it helped. She agreed that it was worth the money. Milin cites the potential for productivity gains we don’t even know or understand yet. For example, imagine a robot doing laundry for you so you can do something else. Milin thinks there will be some significant value points with robotics and AI. He’s excited at the potential for optimizing daily tasks that this could bring. “Just be practical in how you’re using it and how it will bring value to your life, and the ones that you don’t find valuable, don’t do it. I don’t try every AI tool…. But the things I care about, I lean in.” – Milin Desai We don’t control the unconstrained and should not worry about it according to Milin, but we can be a positive participant in this (AI) by participating in communities that serve the greater good in this area. Milin says the idea of an AI bubble bursting will be determined over time, but transformation is happening. There are business use cases in vertical industries for AI (i.e. for medical transcribing). It’s not just people doing personal research at home, for example. The intersection of AI and robots will be an exceptional thing. We have to figure out our place in all of this, which is a harder question. “I fundamentally believe you will still need engineers. You will still need certain things. But certain functions are getting automated…. You’re going to have to figure out where is the new value being created and how…you participate in the new value system.” – Milin Desai This comes back to curiosity, asking good questions, listening, watching for where things are moving, etc. We can apply those same principles to the field of AI. Milin tells us almost every company out there is willing to let you explore and learn when it comes to AI (which means. At Sentry, people are encouraged to use the tools they want to become “AI native.” “Leverage that. Lean into it. Don’t shy away from it.” – Milin Desai, on utilizing your job role and resources to learn AI tooling and the value it can provide 15:07 – Junior Personnel and a Return to First Principles Nick wonders how junior technology personnel can develop the expertise of someone who is more senior when the senior folks developed their expertise before AI existed? Can giving a junior employee AI tooling help them gain that same level of expertise? Milin says this is about getting more “at bats.” Someone could read all about running a company or working with top leaders, but until they have done it, they cannot really understand what it is like. For senior personnel, using AI tools will remove some of the tedious tasks and be more of an accelerant. Junior personnel do need to become AI native, but in addition to this, Milin recommends spending your time thinking through failure modes and other fundamentals. “If something breaks, will I be able to debug it? What are the failure modes for a user that is accessing the system? At what point in time will we have to look at scale aspects of the system…both just scaling versus architecturally? And then you start asking those questions and putting those pieces as learning building blocks…. I think you have to think again at first level principles, system level thinking.” – Milin Desai In addition to the above questions, think about the following: Is the user’s experience intact? Does good design documentation exist? Milin says these “first principles of system thinking” develop from writing, deep thinking, thinking through things from a user’s perspective, considering failure and scaling modes, etc. “And so you build those habits, even as a young engineer…. When you get to a point, you will start asking the right questions, and AI or no AI, you’re going to be successful and valued because you’re thinking in first principles. You have to develop that, but you can develop that with AI and with the folks around you.” – Milin Desai 17:47 – Shifting Organizational Focus to Becoming AI Native With Milin’s view on AI as not pure hype, how are organizations reorganizing priorities around how products get developed, tested, and shipped? Milin tells us over 150,000 organizations use Sentry from the smallest startups to the largest organizations. The customer base scale is massive, and the feedback is constant, fast, and iterative. “We have basically told the entire company, ‘You must become AI native….’ The number one thing we did was we unconstrained everyone to say, ‘go figure out how to become AI native.’ Whether you’re at Sentry or otherwise, this is a skill you are going to need. So, participate in it.” – Milin Desai Milin says employees were encouraged to initially choose the tools necessary to become AI native, and corporate constraints would come into play a little bit later after personnel had built a skill base. The Sentry team also had a set of people building AI-specific capabilities, but the intention was not to have a single, centralized AI team. “There is a set of people who are experts at fine-tuning…the models and how everything works. But, if you want to be the company of the future, it’s not an AI team. It’s everything in terms of what you’re building has a perspective of participating in an AI native world. It cannot be that…30% of the team that is working on AI stuff, and the others are not….” – Milin Desai AI is a tailwind for Sentry according to Milin. It was a goal to take some of the things the team was already doing (i.e. products they were building) and look for ways to make those products AI native. Milin spoke to some of the work new graduates at Sentry did to build session replay summarization. This was their chance to take a project from 0 to 1. Having an AI-themed “hack week” inside the company created a new energy and air of excitement. “And so where are we right now? We basically are like, ‘what does it mean for Sentry to exploit all the opportunity it is in software?’ …It’s not constrained to a team. It’s organization wide…. Pretty much across the board, every team is going to look at what they do and say, ‘Is it a version that brings the experience forward because we now have LLMs and AI and all this new tech?’ That’s the question you have to answer.” – Milin Desai The individual teams also have to think about where the experience in their product gets enhanced with these new technologies. It might be in the front end, back end, or something invisible to the user entirely. Milin also mentions there is an internal team that owns building the core AI and infrastructure elements separate and apart from their product enhancement focus. While everyone is moving in the same direction now, this shift Milin describes came in phases. It was introduced with a little guidance and happened over a period of 3-4 months. “But you have to bring people along for the ride versus… ‘here’s what you’re going to do.’ That doesn’t work.” – Milin Desai John says at first these steps sound like ways to modernize an organization, but in this case, it’s more to keep up with current trends and new ways to provide value. Milin says it is to stay relevant. “It’s to stay relevant. That’s why I made the statement – with or without Sentry, every employee has to become AI native…. What we did was let folks opt in into kind of new areas of the product, and now everybody’s opting in.” – Milin Desai Milin says they did not need to do unnatural things to leverage AI as a tailwind. If you are in a situation where a new trend like AI has come out of nowhere to impact what you do or threaten your relevance, it might require a pause and reset. John speaks to the technology adoption lifecycle. There are bleeding edge use cases that apply to only the innovators. Next comes the use cases for innovators and early adopters. John says we can be the late majority to some of the things happening and gives the example of e-mail summaries from AI being an extremely useful of a late majority feature. We can opt into late majority features without opting into everything or opting into the worst possible outcomes of using AI. Milin gives the example of Sentry shipping a grouping feature powered by AI that resulted in big efficiency increases for customers. Most people would not know it’s powered by AI, and it was one of the first capabilities they shipped after implementing some of the internal changes Milin described earlier. Milin says our attention spans are getting shorter and shorter, and some of the capabilities AI can bring are going to help with this. 25:35 – Contextual Communication to Leaders and Parting Thoughts We spoke about the importance of contextual communication from management down to employees at lower levels and even about how important this is when using generative AI tools. Where Nick sees a lot of people struggle is when they are an individual contributor trying to be a contextual communicator upward to leaders. How can we do this well when working with busy leaders in a world where attention spans are getting shorter? Milin says we don’t really think about this. We don’t think about the potential for running into a senior leader at a company and what we would do if they asked us a question. “What tends to happen is you run into somebody who is maybe 1 or 2 levels of ownership higher than you. They ask you a question. You are deep in the weeds of solving a problem, and so you’re so lost in that problem that when you speak to that person…you may miss an opportunity to talk about why you’re solving that problem…. Always remember and always ask early on in your career…why are we doing this? How does this help? Who does it help? Just knowing that and starting to believe in that is helpful.” – Milin Desai Milin says he’s had 1-1s with people who have told him something isn’t going to work. He would prefer them to speak up and question why something is being built if it’s not going to work based on those questions above. “What is the job of somebody two levels up? They are just asking the right questions. What do you think? Is it going to solve the problem?” – Milin Desai Knowing the fundamentals as Milin outlined above (why, how / who something helps) allows you to have a conversation with a leader on the topic, and you can bring a point of view. It helps with what he calls “asynchronous communication” where you end up getting those unexpected questions about how things are going. “Just always ask this – ‘why am I doing this? Who am I doing it for? And then as a result you’ll know the value, you’ll know the persona, and how does it fit in. Those questions then contextualize everything. It doesn’t matter level 1 or level N at that point in time.” – Milin Desai Milin hopes listeners can parse out the value from this conversation. "Just come back to first principles of all the things we talked about. Be insanely curious. Be insanely active. Participate. And then everything kind of flows from there…. At the end of the day, we are only as good as the people around us. And whether you’re a manager listening, you’re an IC…remember, it’s about the humans…. Those people can only help you if you want to be helped. So, you need to take charge and ask and drive the conversation. And there will be a point where you may not be satisfied. We all are impatient. We all want to reach the summit on the very next day. Sometimes it takes time, so you have to understand what level of patience you have. But you own your path, your narrative, your direction…and you need to make sure that you get the most of an organization. I think people tend to forget that. Organizations sometimes get busy. I am not making excuses for people like me and others, but what I am trying to get at is I didn’t get here by waiting for people to give me what I believe was mine…. I actively participated in that conversation. Of course, I then had great mentors who then helped me with it. It did not come right away. I had to wait, be patient. But I’ll tell you, for the most part if you work hard, you’re an active contributor, you’re curious, you have good people you’re working for…things come along. And that formula is going to work. " – Milin Desai We cannot assume an organization is going to do wonders but should be active in the story. Milin is living proof of this. To follow up with Milin on this conversation: Follow him on X – @virtualmilin Follow Milin on LinkedIn Follow what is happening with Sentry: Sentry Blog Mentioned in the Outro There are layers of opting in throughout this discussion: Opting in to use and learn about AI tools is one aspect, and opting in to leverage the tools for the use cases that provide value is another. Milin had to opt in when he moved into the CEO role, and he has created an environment at Sentry that has enabled people within his organization to opt in for leveraging AI to provide more value to customers. Remember those 3 questions Milin mentioned: Why are we doing this? How does it help? Who does it help? Due to life circumstances, our show is moving from a weekly release to releasing every 2 weeks for the time being. We want to make it on a schedule that is sustainable and at the quality we want. When you don’t see a release next Tuesday, it’s because of this change. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

When we use a generative AI tool, providing more context can often lead to better output. What if we could apply this to our communication with other humans? Milin Desai, the CEO of Sentry, says contextualizing communication will change the way you operate. This week in episode 350, we’ll follow Milin’s story of changing companies and pursuing different levels of leadership. Listen closely to learn about the importance and impact of active listening, how practice with written communication can help us develop a clearer narrative, the skills needed in higher levels of leadership, and how we can evaluate new opportunities through the lens of scope and upside. Original Recording Date: 09-29-2025 Milin Desai is currently the CEO of Sentry. If you missed part 1 of our discussion with Milin, check out Episode 349 – Expand Your Curiosity: Build, Own, and Maintain Relevance with Milin Desai (1/3). Topics – Customer Discovery and Active Listening, Contextual Communication and Iterating on a Narrative, Scope and Upside, Necessary Skills at Different Leadership Levels, Enabling Active Participation 2:49 – Customer Discovery and Active Listening What Milin said without stating it explicitly was that we need to do a better job of asking people more questions to understand where they are coming from and what they care about. This is what Nick refers to as doing discovery, and it applies to the person working a ticket in IT just as much as the product leader or sales engineer working with a customer. “AI is best when given the best context, so contextualize every conversation. And if you contextualize every conversation, it will change how you operate.” – Milin Desai Milin gives the example of a support technician doing the work to close a ticket for someone but then taking a proactive step to let the submitter know there are other related issues you could help resolve. He classifies this as the “extra step” that some people just do without being asked. Very few people are self-aware and like to rate themselves as the best at different things. “That self-assessment is super important…. That extra juice that people are looking for is that contextualization, that personalization, that dot connecting…that is what will change you. And that comes with being curious, asking the questions, listening…active listening.” – Milin Desai Milin says active listening is difficult for him, but it’s something he has become better at over time. John says sometimes the question a person asks is not the question that person wants the answer to. It’s not up to us to just answer the question that was asked. It’s up to us to go the extra mile and ask questions to get more of the context. Milin shares an anecdote for people in customer-facing roles. Validation that a product pitch is resonating with a customer comes from active listening and questions. But there’s even more. “But you forgot to ask a simple question…in the next six months, if you had a dollar to spend, would you spend it on this? We forget to ask the most important question. If I’m going to build it, will you use it? Will you buy it?” – Milin Desai Without asking the above questions, product teams may relay that feedback from a customer was nothing but positive and not understand why product activation numbers are low. We need to figure out why a customer would use a product or feature rather than assuming they will use it when it is pitched / suggested to them. Be intentional about understanding the customer’s priority as well. “The same principles apply to development and everything else in our lives too. If you only had an hour a day, what would you do with it? Start thinking that way, and it makes things very, very simple.” – Milin Desai Nick says we could also ask about priority when pitching an internal project idea to management. Would someone approve the project in the next six months? John suggests asking how far out in someone’s priority list a project would be. What if your project idea or the product you are pitching is not on someone’s priority list? Should you just stop there? At this point with time left in a meeting you have options. Asking to tell someone what you are building is a mistake, and so is just ending the meeting. “What if you spend the next 5 minutes asking, ‘what is the most important things you’re thinking through?’ Because yes, it may not be the current thing you are doing, but again, coming back to knowing what other people in the company are doing, it could be connected to another initiative, another project, another product that the team is building. So, coming back to the same curiosity we talked about, and knowing what’s happening around you, you may find something. Or you may just learn…. But you came ahead as a high IQ individual who is saving them time, who cares about them more than they care about selling a product.” – Milin Desai It’s important that we learn to pause in this way to gain understanding. Asking someone what they feel is important or what their priorities are after they’ve said something is not a priority is an acknowledgement that what you brought them isn’t relevant. Learning more about the priorities of your audience may bring about an opportunity for a different group / team if you’re plugged into what is happening in other parts of your organization. One option is nothing comes of it, and you learn something. Nick says once we learn what someone thinks is important, we might get a much better idea than what we originally came to the meeting with. 9:00 – Contextual Communication and Iterating on a Narrative John says this goes back to empathizing with the customer and living in their shoes. Part of this job is to collect customer priorities and report it back to your organization. This information might indicate a product a company is building does not solve the right customer problems or doesn’t align with customer priority. From a career perspective, people might think they need to do all of this alone – get on the customer calls, understand what customers want, and synthesize it to relay to other teams. When Milin was a product manager, he started pulling in other team members to be on customer calls with him. This began when Milin was at Riverbed, but Milin tells us he leveraged it much more during his time at VMware. “The interpretation of that conversation can be very different…. After that call is finished, you ask for their interpretation. Did they have happy ears? Did you have happy ears? But more importantly you as a team get on the same page about the opportunity.” – Milin Desai Milin is speaking about promoting collaboration between product managers and engineering teams by ensuring the engineering team members have access to the same set of information. Getting them to hear information straight from a customer helps promote alignment better than receiving feedback only via the product manager who spoke to the customer. Being part of the live conversation is also better than only having access to the recording. Letting other members of your team that you work closely with participate along with you is extremely important according to Milin. You don’t need to do it alone. “So, I think that participation is really important, and the second most important thing in any career progression, anything from non-tech or tech, is communication…contextual communication…. Talking to a VP versus an EVP versus a CRO…everyone is different. We as humans don’t spend enough time on contextual communication in our personal or professional lives. And I would say the single biggest thing I see people make a mistake on is not invest in communication, written form communication….” – Milin Desai If communicating to an engineering team, have them feel they were in that conversation. Give them a synthesis of the problems you talked about and what happened as a result. Storytelling and communication are important to provide your perspective on what happened to others. We can write our thoughts down and then iterate on them. When the thoughts are fully formed, we can share them with a group. Spend time writing down your thoughts, and contextualize them for the audience with which you are sharing them. When we write down our thoughts in draft form, Milin says it should feel natural and not take a lot of time. The story arc can be cleaned up as a next pass / next iteration. John mentions there is a difference between a transient idea and something you take the time to articulate through writing. The latter is something you can understand and have a conversation with others about. John talks about writing as something that enables fully formed thoughts and the evolution of those thoughts. Milin had the opportunity to work for Marin Casado (founder Nicira), and Martin encouraged people to write things down because “you don’t think in PowerPoints.” Milin has developed a habit of writing over time. When he gets an idea, even if it is sitting on a train, he might write it down and save it in his e-mail drafts folder to get it out of his head. Milin will then come back to it later (a day, a week, etc.) to refine it and then share with a larger audience. Martin Casado also encouraged people to think like a story. “The art of storytelling allows you to bring a point of view to the world.” – Milin Desai Nick says this idea of writing, letting it sit for a time, and coming back to refine what you wrote sounds like a great way to prepare for scenario-based interviews. Milin shares some of the feedback he gives people who have completed an internship at Sentry. “Make sure you have a narrative around this. If you choose not to come back to Sentry for a full-time job, when somebody asks you what you did, you have a compelling narrative around what happened and what you learned…. You’re absolutely right. You need to own the narrative and drive it. But you need to find that balance between too much, too little, too boasty, or not telling enough about yourself.” – Milin Desai As we develop a narrative, the brevity and depth might change as we change roles. In Milin’s case, he moved to product management but then began to move into leadership positions. How did he see his narrative change in depth and brevity over time? Milin says it has been the hardest thing. Written form communication is hard. We should be self-aware and self-critical but not let these things affect our confidence. “I just want to make sure everybody understands when I keep saying these things, it’s not about breaking your confidence. It’s knowing who you are and then improving on it.” – Milin Desai Milin tells us he is either very verbose or very succinct, and writing / narrating a full story has taken time to improve. Milin is very good with story arcs, but it’s writing the entire story which is the hard part. “That’s been my strength. I can get you to understand the core, the why, very quickly. But then when I have to make it medium form or long form, I continue to struggle in that. That’s been work in progress.” – Milin Desai This is the contextual communication piece of things. Milin talks about his experience doing all-hands calls as a general manager or as a CEO. Giving too much information in these cases will lose the audience. Most of the time you have to find a middle ground between too much and too little information. Milin says the question-and-answer section of these all-hands calls tells you where the gaps are. He would fill in the gaps either using offline mechanisms or a smaller set of meetings to address these questions. Milin also said it took him a while to get to this point. “And it takes practice to take 3 pages and make it 1 page and make it relevant. It’s really art.” – Milin Desai Maybe AI tools can help here, practice certainly helps, and knowing your audience helps. Knowing your audience is part of contextual communication. Milin says he’s done a lot of iteration and practice to develop these skills. 17:57 – Scope and Upside Regarding Milin’s transition away from Riverbed… Milin says he really enjoyed his time at Riverbed but had hit a wall. In aggregate from a dollars and cents perspective, making the move to VMware was a step down. Six months after making the move, Riverbed stock doubled and split. “But I had zero regret, and this is super important. Why did I move? I moved because I had wanted to spread my wings more, and it looked like the organization that I loved could not make that happen. So, I had to do something about it. I waited, and then I moved on…. I had to take a step down to make that step up. I got lucky…good choice, great people, great mentors at VMware…. I had reached a point where I needed to spread my wings, and that opportunity was not showing up. So, I made the call.” – Milin Desai Everyone has their own reasons for leaving a company. Milin would first encourage us to be patient and not make abrupt decisions. We should seek to leave a company better than when we joined it. When Milin made the decision to leave Riverbed, people immediately thought it was because something was wrong. Nothing was wrong with the company. Milin needed to spread his wings. “Career trajectory does not always have to be a step up. It can be sideways or…down. You look at the opportunity…. I looked at scope, upside, and then I believed that if the scope and upside would work out, things would work out for me. And they did.” – Milin Desai Milin had the opportunity to go and focus on networking at VMware at a time when this was an emerging area of focus within the company. It was a chance to build upon his existing expertise. Milin talks a little bit about his first manager at VMware (Ushan) and how that person’s support accelerated his progression within the company. When the time came, this manager supported Milin taking on a different role within the company. “It’s crazy. I’m telling you…people make people.” – Milin Desai, on having great managers Milin would encourage listeners to optimize for scope and upside, even if you need to take a small detour. In Milin’s case, he did not know many people at VMware when he made the move from Riverbed. It was a risk he took based on the scope of the role he would be in, and it worked out. 21:20 – Necessary Skills at Different Leadership Levels John asks Milin about the difference in skills for each of the roles he has held from individual contributor to first-line manager and upward. John says getting to the next management level does not mean all the skills you had to that point are going to help you (i.e. new skills may be required). “The first thing I am going to tell you is that management is hard. You should know you want it because it’s more than you…. I want everybody kind of walking into that role to realize that it’s a lot of work, and it will never get easy.” – Milin Desai A manager has team members working for them, but there is an additional burden that requires translation of the greater organization’s expectations to your team. Milin says the skills you need as a manager are not something you can take a class to gain but rather something you learn over time. We can also learn from the great managers we’ve had. Milin knew what great managers looked like. They let him be himself, allowed him to take initiative, had high expectations, and they gave him context. Milin found it easy to manage people who were like him, but his biggest lesson was adjusting to the different ways in which people on the team operate and bring value. It was important to create a forum to enable all types of people to succeed. John says we learn how we as individuals are managed well (because it is modeled for us) but not necessarily how to best manage people who need to be managed differently (i.e. needing different types of guidance / structure / guardrails, etc.). Milin continues to struggle with this. Milin likes to be pointed in a direction by a manager, and he can do the rest. Milin would come to a manager with problems when needed, but he will figure out how to get what he wants from a manager. Milin reminds us of the time he was asked to go find a new role and how much it changed him. Learning how to manage people different than you is a skill that takes time to acquire. “There’s a point in time when it’s not about you or what you bring to a team. It’s about who you can hire….” – Milin Desai, on an aspect of rising to more senior leadership levels When Milin was moving up to senior vice president, it became more about whether he could bring in exceptional senior talent. This kind of caught him by surprise, but Milin knew he could go and figure out how to do it well even though it might not have come naturally to him. This was a new aspect of leadership after he had gained experience running a business unit and making it profitable. “If you bring in the right people, you automatically become potentially a great manager because they unburden you. They understand you really well.” – Milin Desai Milin says we should be willing to bring in people who are smarter than us, and we should be ok with that. He’s never had an issue with it, but some people do. Hiring the right people is a form of leaving an organization in a better state than you found it. Moving on from people is also something you learn as you move up. Milin calls this active management. “There’s a point in time where a person could be doing everything they are supposed to be doing. They have been with the organization, but the organization has shifted…. And this person is not able to adapt to it. It’s the company transitioning at that point. It’s not the person. And the ability for you to quickly recognize that for this phase of the journey…somebody you had loved before is not going to work out is probably one of the hardest things you will do as a people leader.” – Milin Desai When John was at Google, they talked about rearchitecting a product when the user base increases by a factor of ten. Similarly, the people organization has to be rearchitected. “There is a journey of an organization. It is a living, breathing thing, and it goes through its own phases. And through that phase, there are some people who grow through every phase and continue to be part of the organization…. There is a time when somebody who was a perfect fit no longer is a fit…. To identify that and to make that person successful in a different role in the company or something else…those were the things I had to…learn at these different levels. It’s hard.” – Milin Desai Some employees may only be part of 1 or a couple of phases of an organization’s growth / change. Milin gives the example of people later in their careers who are very self-aware. They might understand that the most enjoyment for them is found when they work in startups that have between $10 million and $100 million in annual recurring revenue, for example. Milin shares the example of bringing in someone to work with him who helped build a specific team and then others who helped scale the team and greater organization. Other senior leaders taught Milin that bringing in the right kind of senior talent would free up some of his bandwidth to be spent in other areas. Milin says he has luckily not needed to let people go because a business was not profitable. “Through that journey, the thing that has inherently worked, continues to work, is writing down my intention for the org, for the team, for the company…what we will bring to the table and keeping that written and clean 24 by 7. It doesn’t become stale…. That has been the consistent point of help besides having great people to work for.” – Milin Desai According to Milin, someone can write an 18-month strategy, but they should go and clean it up every 3 months. 29:55 – Enabling Active Participation Nick says by maintaining clarity on all of these things, it cascades to help leaders like Milin understand what the roles and job requirements within the organization should be, even if they are not formally changed. Milin says having it written down helps with everything. “It’s super hard to cascade a point of view or a vision. You have to repeat it multiple times, in multiple forums, and everything else. But if that itself is stale…it becomes really hard. So, I still to this day tell everyone, ‘give me a one-pager of where you’re taking the team for the next 3-6 months. If you don’t have that, how will you be effective?’” – Milin Desai The one-pager Milin mentioned is different than a feature or function to be built. It’s more about outlining the set of problems a team will solve in the short term (i.e. next 6 months) and then coming up with the measurements of how to do it within that specific time frame. He suggests highlighting the longer-term problems the team wants to solve as well. These things are written down and get revisited regularly by the team (maybe every 3 months) to determine if they are still relevant. Milin calls this “active participation.” “Are these still relevant? I want you all to think about it. Active participation, right? Now they get a point of view on the 3 things next six months we agree and the 4 things long term maybe we need to change or something like that. So that allows for active participation. I would say that’s another great thing I learned as my roles started getting bigger and the scope started getting bigger.” – Milin Desai Mentioned in the Outro Contextual communication has many layers to it. We can share context verbally with others but also gain it from them in the way we ask questions. We can also provide context to others through writing. Milin has done this for a long time. He will write a draft and iterate on it regularly to keep it fresh and clear. Duncan Epping uses writing to learn Episode 303 – Write to Learn and Learn to Present with Duncan Epping (1/2) Jason Belk emphasized developing his narrative through writing before talking about it Episode 284 – Draft Your Narrative: Writing and Building a Technical Portfolio with Jason Belk (2/2) Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

How curious do you think you are at work? Take a second to rate yourself. After today’s conversation with guest Milin Desai, you’re going to want to dial that curiosity up a notch. Milin is currently the CEO of Sentry, and one of the keys to his success from the very beginning was allowing the scope of his curiosity to expand over time…beyond specific projects and even beyond his job role. Perhaps without realizing it, Milin was doing the work to build and maintain professional relevance. Listen closely in episode 349 as we follow Milin from his early days as a computer science student through roles as a QA tester and software developer all the way into technical marketing. You’ll hear advice for expanding your own curiosity inside your current company, ways you can provide value to a mentor, and an empathetic approach to customer conversations that can help you build relevance and develop a strong reputation. Original Recording Date: 09-29-2025 Topics – Meet Milin Desai, A Unique Trait, Internships and Job Interviews, Curiosity and the Importance of Control, Mentorship as a Stream of Active Conversations, Beyond the Scope, Becoming Relevant in Something Different 2:40 – Meet Milin Desai Milin Desai is currently the CEO of Sentry. Sentry helps teams find where code is broken in production and helps them fix it fast, and with AI, fixing it faster is greatly accelerated. 3:15 – A Unique Trait Around 7th or 8th grade Milin recognized how much he enjoyed math and science in school. Milin had an affinity for STEM (Science, Technology, Engineering, and Mathematics). Milin cites his dad, a mechanical and electrical engineer, as a big influence. Going into 10th grade, Milin thought he would pursue mechanical engineering. Milin’s cousin Rajiv (who had worked for NASA) would come visit and began showing Milin some of the work he was doing. This is the point at which “everything changed” for Milin, and he decided to pursue computer engineering / computer science. Milin also tells us he built hundreds of websites in India during the time of dial up modems. Milin pursued an undergraduate degree at a school in Mumbai, but his family knew he wanted to come to the United States. Milin came to the United States in 1999 and attended USC (University of Southern California) to purse a master’s degree. The potential for opportunity and the vastness of the United States captivated Milin. Did Milin ever ask Rajiv what he should study, or did he naturally gravitate toward those areas? Rajiv would have conversations with Milina and show him the work he was doing. Milin started working for Rajiv while pursuing his undergraduate degree. He was building websites for companies in India. The building of the websites was interesting to Milin, but he was also doing the selling part. Milin had to make a pitch to companies explaining what a website could do for them, share the price, and collect the check if they said yes. “Not only did he influence me in kind of figuring out…this is where the opportunity is and inspire me…but he also went on to tell me that I have a unique trait where I can talk business tech selling, and I know the technology part. And I can bridge the two worlds. He was one of the early people to recommend that in the long run I may want to think about the business side or…the entrepreneurship side of things when it comes to tech, not just the programming or the systems side of things. And he in fact felt my combo made me more relevant…in that lane versus just staying a programmer.” – Milin Desai Rajiv gave Milin these cues early on in addition to inspiring him to do the work. As people who work in sales engineering today, John and Nick agree that the combination of technology and business value is very valuable. 7:49 – Internships and Job Interviews Milin began working for Veritas after he finished his master’s program as an entry-level software engineer. Pursuing an advanced degree can give you the chance to pursue internships, and Milin had a family friend working at Veritas who introduced him to the hiring manager for a quality assurance (or QA) internship. After successfully getting the internship at Veritas, Milin was doing QA for software-defined storage volume management. Milin’s work during the internship led to a full-time offer from Veritas upon his graduation. “The first break is always hard, by the way, to get. I see it even to this day with folks coming out of school. Not everyone…lands in the perfect opportunity right away, and the dots need to be connected. I’ve been fortunate enough to have people open doors and open opportunities…. But I remember being rejected a lot.” – Milin Desai Milin tells us he struggled in job interviews as a new graduate. Many of his friends from school had multiple job offers from these conversations, and compared to them, Milin had much less success getting offers outside of the one from Veritas. From a timing perspective, this was around the time of the market crash following the events of September 11, 2001. “Even timing-wise, the difference between graduating with your master’s degree a year and a half versus 2 years. That six months made all the difference. A little luck, a little timing, and a lot of support.” – Milin Desai Did the degree program Milin pursued prepare students for job interviews at all? Milin tells us that a school doesn’t really prepare you for the conversation you have in an interview. While you do learn deep systems concepts in school, for example, the interview questions are often situational. “You definitely use those concepts, but you’re never in that setup until you go through that process. And I think interviewing is a little bit of an art form. Some folks are really good at it, and some folks even study it. There is some element of that. But I think the school prepares you with fundamentals. It doesn’t necessarily prepare you for that interview per se, and you have to kind of connect the dots…. You can prepare for it. Some people are just naturally good at it, and some people like me just suck at it.” – Milin Desai Milin feels interviewing is sort of an art form. You can work to prepare yourself Did Milin think of interviews as somewhat similar to pitching a company on a website? The selling part is easy according to Milin. In this motion you are telling a story, bringing a problem statement, and delivering value. It’s less about solving some kind of algorithm but rather trying to figure out if what you have to offer will address someone’s pain point. Milin emphasizes the storytelling element of the sales process and the collaborative problem solving you’re doing with someone. It’s more of a conversation. Selling is not about getting into an extreme level of detail like a technical interview can be. Someone could easily make a mistake in a technical interview when describing a specific step in the process and get off track. People can feel a great deal of pressure when in a job interview. Milin feels job interviews are much more difficult than a business conversation. The latter is about human connection and building rapport with the other person. Milin tells us his interview style is more about building human connections than testing the limits of a person’s technical depth. John mentions the difficulty in choosing a technical interview style that is well suited for effectively evaluating multiple job candidates. Does having a portfolio of code that is applicable to the role help with this? John also brings up LeetCode style interviews if you’d like to read more about them. Milin says quickly assessing a fit can be a challenge. It can be a combination of skills and experiences with other things layered on top. Milin says the first interview might be more focused on solving some basic elements. But it’s helpful if a candidate can talk about and contextualize other work they have done (like working on an open-source project, for example). "But to get in, there has to be a common baseline, a language, a form…. " – Milin Desai, on early round interviews If interviews are challenging for you as they have been for Milin, you have to work through them over time. “In the later stages what I would tell you is what is most attractive is people who have been from what I call 0 to 1 project where they start something are through the end. The end is not shipping actually. Shipping is just an intermediate point. End is adoption and the scaling and all of those elements. And to be through that journey 1, 2, 3 times is interesting to almost every organization out there…because through that you learn a sense of people, ownership, outcomes.” – Milin Desai Early on the baseline is some kind of entry test. When looking for people with more experience, interviewers will ask about projects people have written about on their resume or elsewhere and how they solved problems within those projects. At this point, the portfolio becomes more interesting and can help you get an opportunity. We emphasize the importance of a portfolio of projects and not just a portfolio of code. 16:16 – Curiosity and the Importance of Control How did the role Milin had at Veritas shape the rest of his career? Milin says this was his first job and was an amazing experience that has filled him with fond memories of that time. Milin emphasizes the importance of help from others during the course of his career. The Veritas experience gave Milin the chance to work with great people, but he also found mentors within his area at the time (software volume management). Milin mentions a mentor named Mark who remains a dear friend to this day. “He kind of took me under his wing and explained stuff and was just there. And he didn’t need to do that…. Please, when somebody…experienced takes the time to go that extra mile you make sure you better jump on and do what’s needed. That was a friendship and mentorship I would say on a regular basis that really helped shaped my system thinking…. It was just the way we would talk about systems and concepts, and it really kind of expanded my mind…. The discussions are not always about this piece of code as much as how does this work with this part of the system…?” – Milin Desai Mark was in a leadership role at the company and understood other projects that were in the works. Milin really enjoyed learning about those things even though they were outside his area. Milin emphasizes the importance of curiosity that extends beyond what we own and even what others own. This ever-expanding curiosity was one of the most helpful things in addition to mentors early in Milin’s career. We should also be willing to raise our hands to volunteer to solve a problem or work on something extra. This quality, in conjunction with being curious and having effective mentors, was essential to Milin’s success. After completing his first year at Veritas and getting a great review, Milin’s manager told him he needed to find a different role. This was not about job performance. “I’ll tell you the positive out of it. It basically made me realize that I need to control my destiny. I need to keep working at it, not assume anything. It was the best thing that happened to me…. At that point in time, I found a different role. I found another set of great mentors. And things just took off because my mindset shifted from not just being curious and raising my hand. It changed into…I’ve got to take care of myself. No one else will. It was a healthy sense of paranoia of constantly wanting to prove myself. Again, not lack of confidence, impostor syndrome…none of that stuff. It was just about ‘am I doing everything absolutely possible that I become unshakeable?’ That was the most helpful thing that person did for me, but it changed everything.” – Milin Desai Did the manager who mentioned Milin would need to find a different role tell him he needed to search inside the company or externally? Milin had to go do the homework to assess his options for new roles. It was up to him to make it happen. “Being curious means you work beyond your project scope, you talk to other people, you get to know other teams. They get to know you. So, when something like this happens it is not like you just showed up at their door. It’s all connected in a way when you are part of something bigger than your project, your team. You take interest. You have conversations. You have lunch with people beyond your team. You do things kind of outside just general scope.” – Milin Desai, on curiosity as a network builder When a job loss type of situation happens and people know you, it is a jumpstart on internal opportunities. A mentor, for example, might vouch for you as well when trying for a new role. “At the end of the day there are humans involved in the process, and that’s where the first connection happens.” – Milin Desai 22:43 – Mentorship as a Stream of Active Conversations As Milin looks back, how would he describe ways we can be an effective mentee to a mentor? It’s not about showing up unprepared and expecting magical wisdom to come from a mentor. It’s also not about taking a wide set of problems. “It’s an active conversation. It’s a relationship. And the relationship is not transactional…. It’s a constant stream of active conversations….” – Milin Desai We should go into a meeting with our mentor prepared just like a board meeting. Take with you a set of 1-3 things the mentor could help you with. Milin suggests we figure out how the mentor operates, and figure out how to leverage this. It’s about reverse engineering what a mentor brings to see if they can bring value to you. “And it’s not like they are going to help you suddenly go from point A to point B. I think that’s another big misnomer around this. It’s just somebody as a guide point, as a reference point of…additional data.” – Milin Desai When Milin looks back at the people who have helped him, most mentors were within the same company, but there were external mentors as well. People tend to think a mentor only helps them (a unidirectional relationship). Throughout Milin’s career, he tried to find ways to help his mentors (i.e. taking something off the mentor’s plate). “It became a mutually beneficial thing where they were being successful as well in spending time with someone like me…. It’s various phases, but I always tell people there is no professional mentor. There are professional coaches. That’s different.” – Milin Desai Milin says active mentorship on scenarios or career things requires someone be in the business with you (in the same company), and it also benefits the mentor. People confuse mentors and coaches, but any given person may need both an external coach and internal support systems (like symbiotic relationships with mentors). Was it the series of active conversations with mentors that pushed Milin in the direction of product management? Milin encourages us to think back to his time focusing on storytelling and selling before graduating and put it together with his curiosity during his first year at Veritas. Milin mentions spending time with leaders who worked across different functions of the company and how interesting it was to learn about interconnected projects across the company. Now we fast forward to the time after Milin needed to find a new role. “By the way, I was an average coder, but I made up for it with a lot of testing – making sure that it worked, it worked in different scenarios, the UX, the experience…. That’s where I learned…everything is about the user, not about me writing code.” – Milin Desai Milin would send e-mails to product leaders inside the company asking if they had explored specific problem domains. He would make these messages thoughtful and include research. He would also ask questions offline after all-hands calls. Milin mentions names like Jeremy Burton and Mike Spicer as leaders who took the time to respond to his messages. The continued dialogue with product leaders helped Milin realize he wanted to try something different. “I wanted to kind of go to the product definition side because I was really enjoying it, but it was a series of all of these coming together to that culmination. That encouragement, that active encouragement from the folks I just mentioned definitely also helped….” – Milin Desai 29:52 – Beyond the Scope Did Milin have any conversations with his manager at the time about pursuing product management before he made the move? Milin feels he may have been operating like a product manager in some form by asking the right questions and being a little disruptive. He thinks people started to see this. Milin’s next role was a technical marketing engineer at Riverbed. He did have the option to become a product manager under Symantec but chose to go to Riverbed. “I made the shift first to a technical marketing engineer, and within a year they said…move over to product management…. I think people realized my aptitude, the way I was spending time, the contributions I was bringing…. I think I had to just make up my mind and start making that choice, which is what I did in 2006.” – Milin Desai John emphasizes that we do not always know how the puzzle pieces of experience will fit together later. Without exposure to different things, there is no way to put these together when it’s needed. Milin says many people want to join startups because it will allow them to do many different things in an organization with fewer people. While this is true, not everyone takes advantage of everything a startup can offer in this regard. While it is likely harder in a large organization to do this (do many different things to gain different experience), it is not impossible according to Milin. In fact, he’s changed roles within large organizations to do different things over the course of his career. “There is so much you can learn by just inherently listening for the signals, being curious about it, having lunch with different folks.” – Milin Desai Milin tells us that having lunch with different people or participating in extracurricular activities with your team can be a great time for networking. It’s something that takes you outside the scope of your role, and when you do it, you do not know where it might take you. Milin used to play soccer during lunch, for example, which gave him the chance to network with people in the bay area. Milin says we do not need to be extroverts and should do what is most comfortable for us. "If you’re a curious person and you want to learn a little bit about marketing, you can just ask. And most organizations have good people. They will respond, which is what I was telling you about when I was talking to…all these people who were like 7 levels above me in the larger organization…. They chose to take the time to respond, which created encouragement…. " – Milin Desai John says these are practical tips in going from 0 to 1 in one’s own career management. 33:40 – Becoming Relevant in Something Different What led Milin to apply for the technical marketing engineer role? It started by being ready to do something different. “I don’t even remember how I applied for it, but all I can tell you is when I spoke to the team and the people I was like, ‘wow. This is going to be so much fun.’” – Milin Desai The role as a technical marketing engineer was really about telling people how to use a Riverbed product focused on WAN optimization. We might call it developer experience or developer advocacy today. In the job interview, there were no questions about coding because this was a technical marketing job. But they gave Milin a homework assignment as part of the interview to share how he would test something. According to the hiring manager at the time, (Phil), Milin went above and beyond for this assignment. In addition to explaining how he would do the testing, Milin built a PowerPoint representing the story he would use to educate people on this scenario complete with preconditions, advantages, etc. It was the extra push on this exercise that got Milin the job. At the time, Milin didn’t understand what it meant to work for a pre-IPO company (which Riverbed was at the time). “But I didn’t even think about all this stuff. I just literally loved the people and the scope of the role, and I felt like this would be exciting. And I took it…. There will be a point in time in your career where you can choose the people you work for and choose the people you work with, and there is nothing more important than those two things in my opinion when thinking of what you want to do next. Where do you want to spend your time? And most people don’t optimize for that. They optimize for everything else…. Day to day, you’re going to spend more time with these people. As soon as I got to know this group I am like, ‘man, I want to be with this group.’ …It was the people. Just like everywhere else…it starts with people.” – Milin Desai John mentions part of technical marketing roles as well as developer relations roles is being what he likes to call “nerd famous.” You have to be a little bit of a draw for attendees. Does this align with Milin’s experience in technical marketing? Milin says yes and no. He feels the people who succeed in these roles are there because they have depth. “That, I think, should not be lost. There have been a lot of people who have come and gone if you notice in that…what people call devrel or whatever…. The ones who have survived and thrived and continue to be respected are the ones with depth.” – Milin Desai Whether it’s writing a product design document or an engineering design document, Milin tells us it is a story very much like a movie script with a beginning, middle, and end. Great storytellers who can simplify things will do well in a technical marketing or similar role. Another thing to consider is whether you are bringing value. If someone comes to talk to you about cooking and you love eating but not cooking, the conversation is kind of pointless. “When you are not famous, the way you become relevant is you bring relevance to the other person in terms of what they care about and then to be able to help solve their problem.” – Milin Desai Milin says when it comes to people in customer facing roles (product managers and many others), it is easy to get into “the diarrhea of our mindset.” People get into the mindset that they are building a feature and need to tell the customer everything about it. And sometimes customers will just let you tell them. “If you pause a little bit, understand what the other side wants, do the storytelling from that standpoint…highly, highly transformational.” – Milin Desai Milin also tells us that keeping our word helps build our professional brand. Are we doing what we say we will do? Getting someone an answer because you said you would, even if the answer is no, build rapport and relationship. The personality aspect is needed to get the best opportunities according to Milin. Milin gives the example of posting some information on bulletin boards about using Riverbed and NetApp together. People got to know him through the content he had shared and the value it brought them. Listen to the specifics of what happened when people would meet him in person. “I feel like if you do it right, you do it for your audience, you know your audience…day in the life of…be in their shoes. I think that’s super important in that TME role, in the product manager role versus the internal, inside view of…we are building something. Nobody cares about your algorithm if it doesn’t work. So, tell me how I am going to use it. If it breaks, tell me when it’s broken…all of that fun stuff. Live in the life, live in the shoes of your customer. Understand what they want, empathize with that, and from there, magic will happen.” – Milin Desai Mentioned in the Outro There is a slow build of through Milin’s experience of developing that relevance. Examples would be: Discussions with early mentors to understand systems and how projects within the company were connected It takes curiosity to understand these things, and we need to have that same kind of curiosity when we help our co-workers or external customers with technical problems. The questions Milin would ask and suggestions he would make to senior product leaders Taking the time to put together thoughtful questions and suggestions made Milin relevant to those leaders, and they took the time to respond to his messages. That kind of thing does not happen unless you are bringing something relevant. Creating the content at Riverbed Milin was relevant to others because of the content he created. We can build relevance through content we create as part of our portfolio of work / public proof of work. Much of Milin’s relevance came after he listened well or listened actively to be thoughtful in his responses. This is what we should be doing in any role that has customers (externally facing or internal customers). If you’re in IT, your customers are the people whose problems you are trying to solve or those for whom you are trying to provide a technical solution. Optimizing who we work for and who we work with is another way to remain relevant. If we like who we work for and with we will want to provide value to them and therefore remain relevant as a member of that team. We talked about mentorship in Milin’s career and the bidirectional value flow between mentor and mentee, emphasizing that the mentee should try to bring value to a mentor. For more discussions about mentoring, check out episodes under the mentoring tag on our website. We would also point you to 2 specific episodes that represent a masterclass in mentoring: Episode 288 – Guardrails for Growth: A Mentor’s Experience with Dale McKay (1/2) Episode 289 – Enhance Your Personal Brand: Feedback as a Catalyst for Change with Dale McKay (2/2) Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

As managers inherit larger teams inside flatter organizations, we might immediately point out the challenges. But what about opportunities? Despite the trend, those who seek to lead (in a management capacity or otherwise) have the chance to intentionally build a better culture. We pulled in former guests Shailvi Wakhlu, Neil Thompson, and Abby Clobridge in a roundtable format to get actionable strategies. In episode 348, we present actionable strategies for managers and individual contributors to thrive in this new environment. Listen closely to understand the importance of improving one’s communication skills, the unique opportunity and impact of the player coach / team lead, the critical elements of a manager’s role, and advice for job seekers in a tough market. Original Recording Date: 09-27-2025 Topics – Framing Part 2 of Our Discussion, Opportunity for the Player Coach, Modeling the Benefits of Improved Communication Skills, Management Support of Strong Communicators, Individual Contributors and Communication, Succeeding as a Manager of a Large Team, The Culture of Large Teams, Advice for Job Seekers in a Tough Market, In Closing 1:01 – Framing Part 2 of Our Discussion Last week in Episode 347 – Organizational Flattening: Understanding the Trend, Career Challenges, and Opportunities (1/2), we introduced a slightly different format that we’re continuing this week based on an industry trend. The trend of organizational flattening in our industry has been top of mind for us. We’re seeing the continued layoffs in tech often times result in fewer management layers and an increase in the number of people reporting to a single manager. This topic is too big and has too many angles for a single conversation. We wanted to bring together multiple expert perspectives on this issue in a single episode. We’ve reached out to a handful of former guests and sent them specific questions on this topic. Those guests were kind enough to record their answers and send them back to us. Consider this a Nerd Journey roundtable or collection of hot takes from trusted voices. Our goal is to amplify their advice and provide a diverse set of strategies for navigating this landscape. In the first episode (last week), we explored the trend of flatter organizations and the consequences for your career path and team culture. This week in part 2 we will focus on actionable insights for thriving in this environment. Here’s the full set of episode links we will share throughout the conversation if you would like to hear more from one of the former guests who participated: Shailvi Wakhlu Episode 210 – A Collection of Ambiguous Experiments with Shailvi Wakhlu (1/2) Episode 211 – Structure the Levels of Contribution with Shailvi Wakhlu (2/2) Self-Advocacy: Your Guide to Getting What You Deserve at Work by Shailvi Wakhlu A special 15% off link for Nerd Journey listeners to Shailvi’s self-advocacy course can be found here. Neil Thompson Episode 193 – Communication for Specialists with Neil Thompson (1/2) Episode 194 – Question Askers and Problem Solvers with Neil Thompson (2/2) Teach the Geek YouTube Channel Abby Clobridge Episode 292 – Library Science: Information Architecture and the Synthesis of Details with Abby Clobridge (1/2) Episode 293 – Enterprise Knowledge Management: A Consultative Approach to Solving the Right Problems with Abby Clobridge (2/2) 1:42 – Opportunity for the Player Coach We’ll start by discussing the opportunity of being a player coach (another way we often reference the team lead or tech lead role). Shailvi Wakhlu is a leadership speaker and data consultant with experience building and leading large organizations, including structuring of job levels for career paths. We spoke to her in episodes 210 and 211 She’s also the author of Self-Advocacy: Your Guide to Getting What You Deserve at Work. Our question for Shailvi: As organizations flatten and there are less manager roles, does this create an opportunity for people to become a technical lead or team lead to help the manager scale? We would love to hear any perspective you have on how the team lead / tech lead (i.e. player coach type role) changes as a result of the org changes. Even without the trend of flattening or decreasing the number of managers, there has consistently been an opportunity for people to demonstrate the mindset of group leadership. Someone could be a project lead, a team lead, or a technical lead. The technical lead focuses more on technical standards to which a team needs to adhere. “I think anything that you do that helps your manager manage the team, scale the team, grow the output, or just have better focus…has always been a good way to get your foot in the door for those type of roles in the future.” – Shailvi Wakhlu Shailvi remembers working at companies where several people wanted to someday get into a management role. Even in times of heavy hiring, there is no way to accommodate everyone who wants to eventually do this. People stepping into those lead roles would have a leg up on other candidates for future management roles. “If I see somebody is doing a fantastic job of managing a project, I know that there is a subset of manager responsibilities that they’re able to handle. If I see them doing team events…if I see them stepping up on technical leadership, defining standards…all of these things kind of point to that same larger skillset. And I always encourage that even if there is no formal capacity in which you can do this, even if you create your own opportunity and showcase that…this is a space where I see our team could improve…even without the manager title I think you have plenty of options to contribute at that stage…and definitely in this type of a market where there are less manager roles.” – Shailvi Wakhlu Shailvi believes the job market will bounce back, and when it does, there will not be enough people who have been managers and have done things like performance management, skill assessment, and hiring. People who can showcase they have some of this experience and the right mindset have a good start toward landing a management role. Before Shailvi was a manager, she was the hiring lead on her team of 2 people. Shailvi defined the standards (measurements, rubrics, etc.) for the interview process. She tells us doing this made it far easier to transition into a full-time manager role. 5:25 – Modeling the Benefits of Improved Communication Skills We wanted a perspective on communication in this current climate and reached out to a former guest with expertise in this area. Neil Thompson is the founder of Teach the Geek, an organization that helps technical professionals in STEM (science, technology, engineering, and mathematics) improve their public speaking and presentation skills. He’s also the host of the Teach the Geek Podcast. We originally spoke to Neil in episodes 193 and 194. Here’s what we asked Neil: How do you think team leads or technical leads (sort of that player coach role) play into the development of strong communicators? Where do they help people where managers cannot? Players (or individual contributors on a team) don’t see themselves as managers and would not be modeling themselves after managers. A player coach is way closer to each member of the team’s current role than a manager. Player coaches who are adept at communicating well can model these skills for other members of technical staff and educate them on the benefits (and potential opportunities) of improving their communication skills. Neil points out it could very well be a player coach was moved into that role because of their communication skills. Technical staff members are far more likely to want to invest in improving their communication skills once they see and understand the benefits of doing so (thanks to the modeling of player coaches). 7:09 – Management Support of Strong Communicators Another question we had for Neil: "What challenges will managers face trying to develop good communicators when their team is huge, and what can they do to be more effective when this happens? With a large team, one challenge will be getting buy-in from all team members on the idea of improving their speaking skills. Assuming this is the case within your organization…Neil encourages leaders to let their direct reports know that improving speaking skills increases visibility within the organization, and opportunities tend to come to those with greater visibility. Technical people will not want to be passed over for opportunities based on something they can control, especially if they recognize the reasons others have been given new opportunities was due to improved communication skills. And they would certainly be motivated to improve communication with decision makers who can give them opportunity. As part of his work at Teach the Geek, Neil encourages companies to develop speaker training programs for developing technical staff members. One challenge to this approach is getting technical staff to agree on the priorities of this kind of training program. Neil suggests sending out a survey to technical staff members to make sure this is well understood. Technical staff may want to understand how to better engage an audience, get ideas for balancing technical depth and clarity, ways to minimize the use of jargon, etc. If you do take a survey of technical staff, incorporate at least the top 3 priorities as indicated by survey results into a speaker training program. 9:07 – Individual Contributors and Communication We also wanted to know from Neil: How can the individual contributor develop those strong communication skills to build rapport and communicate the value of their work to a busy leader? If technical staff members have gone through a speaker training program like was mentioned earlier, they will want to look for opportunities to practice continued development of those skills. Neil highlights the importance of organizations offering speaking practice opportunities for members of technical staff. One easy way to do this is through a lunch and learn. This forum is a great way to allow people to give presentations covering their work progress / accomplishments that both managers and even non-technical staff members can listen to and learn from. Neil points out the usefulness of this information for nontechnical staff members such as HR personnel responsible for screening job candidates. Sitting in on these presentations can, for example, improve the quality of those screening conversations and overall candidate selection rather than relying solely on job descriptions which may be outdated. 10:31 – Succeeding as a Manager of a Large Team Another question for Shailvi: What are your top suggestions for succeeding as a manager of a large team in this environment? Shailvi says in today’s environment, the definition of a larger team of direct reports has changed. “A few years back that large team definition was…more than 8. Nowadays I think it’s very common to see people who have 8, 10, 12, 15 direct reports…and nobody’s blinking an eye.” – Shailvi Wakhlu At her previous job, Shailvi had 6 direct results that trickled down to an organization of 30 people total reporting up to her. Success when you have a large number of direct reports takes a lot of intentionality. “What is your role as a manager? One is to provide clarity for your team to make sure they are aligned with business goals…to make sure they know what is going to be rewarded, what is not rewarded, things like that. The other big piece is making sure you are available to help grow the careers of everybody who has taken a chance on you and is putting the fate of their careers…in your hands. So how do you make sure you do those two pieces successfully?” – Shailvi Wakhlu Shailvi emphasizes the importance of streamlining communication and information sharing in both directions (from you to your employees and in the other direction). Make sure people know what they can expect from you. Do people know what you will communicate and when you will communicate it? For example, will you openly communicate the necessary context so that people can effectively recalibrate? Do people have the psychological safety to share their challenges and concerns with you? Are team members comfortable sharing their professional goals with you (i.e. opportunities and growth areas), and are you providing critical feedback to support pursuit of these goals? Shailvi also highlights the way a manager delegates as key to success. Having a large team means there is opportunity for people who want to move into some type of leadership role to gain experience. “It’s very important to make sure that you are public in your appreciation for people who help you in the smooth running of the team…. If it’s a non-promotable task…if it’s a housekeeping task that nobody’s ever going to get promoted because of…do not outsource that. I think you do a disservice to people’s careers if you’re asking them to do…general housekeeping and you’re basically asking them to do it above their existing job. And, you’re never going to consider that work important enough to actually think that they’re performing at a higher level. So, delegate work that is actually useful. Delegate work that is actually helping them improve their skills and their visibility in showcasing that they have leadership capabilities….” – Shailvi Wakhlu, on managers delegating responsibility which allows the right type of experience 14:48 – The Culture of Large Teams One last question for Shailvi: How can leaders create a culture that is impactful within their organization when the structure of the organization is designed to allow less time spent with each person underneath a leader? Shailvi feels this is extremely relevant in a world where managers have too many people reporting to them. There is often not enough time to get information flowing between the manager and direct reports for the benefit of the company. Some of the work Shailvi does as a consultant is with organizations who want to build strong teams optimized for performance, productivity, and profitability. “I feel that…leaders tend to anchor on the limited time they have with all the people who report up to them that they just sort of spend that in getting status updates…. It’s very one-sided.” – Shailvi Wakhlu Status updates can be shared in an e-mail or updated on a JIRA board. “The part that I encourage leaders to think about is how do you create a situation where everybody on your team understands the link between their work and business success…where there is no ambiguity about it, where they clearly understand…this is the part of my job that is going to help the company succeed? And that is how you build that excitement with people….” – Shailvi Wakhlu A sense of personal ownership usually breeds accountability. To them it won’t just be finishing a project but rather helping the company succeed with a specific goal. “Creating that culture of transparency, open communication…I think that is something that takes intentionality on the part of the managers. It takes repetition where you keep showcasing how you’re rewarding work, how you are setting expectations. You can’t have unevenness….” – Shailvi Wakhlu Leaders should use the limited time they have with employees to understand their motivations. Work to help your people with their careers, help them understand the opportunity in front of them, and consistently provide clarity. “How you show up as a leader is something that is more important than anything else that you say. Are you accountable for your own actions? Are you taking ownership of larger pieces that are under your area of ownership? When leaders can…structure what they want to spend time on, it goes a really long way.” – Shailvi Wakhlu 17:57 – Advice for Job Seekers in a Tough Market To close our discussion, we wanted some actionable advice for navigating a tough job market. We’ll hear once again from Abby Clobridge. Abby is the founder and principal consultant at FireOak Strategies and has deep expertise in the realm of knowledge management. Abby was a guest in episodes 292 and 293. Our question for Abby: In a tough job market, what do you think job seekers should be doing to stand out that maybe they aren’t right now? Treat your job search like you would a portfolio project. Show what you are doing and what you are learning by building something tangible. It could be automating something, creating a dashboard, or writing a blog describing how you would solve a problem. Abby says we can also host micro conversations made up of 3-4 peers, mentors, or formal colleagues in a roundtable format. These can be virtual or in-person. This can strengthen your network and benefit everyone involved. We can also practice visible curiosity by posting about a book we read or a tool we used. Abby calls this “learning out loud” and something that can act as a signal to future employers that we are engaged, adaptable, and someone who wants to connect people. 19:12 – In Closing We want to say a huge thank you to all of the guests who contributed to this episode! If you want to hear more from them, you can find the full conversations… Abby Clobridge was a guest in episodes 292 and 293. We spoke to Shailvi Wakhlu in episodes 210 and 211 She’s also the author of Self-Advocacy: Your Guide to Getting What You Deserve at Work. Here’s a special 15% off link for Nerd Journey listeners to Shailvi’s self-advocacy course. We spoke to Neil Thompson in episodes 193 and 194. What did you think of this format, and what other questions need to be answered on this topic? Send us an e-mail at [email protected] to chime in. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

What happens when layoffs lead to organizational flattening, fewer managers, and larger teams? It’s a trend we’re seeing in the tech industry at large right now impacting team dynamics and career paths. To understand what’s really happening and the overall impact, we pulled in former guests Abby Clobridge, Shailvi Wakhlu, and Leanne Elliott in a roundtable format. In episode 347, we explore the trend and the unique challenges it presents to consulting firms, managers, and individual contributors working with and inside flatter organizations. Listen closely for the impact to job levels, what this means for top-tier individual contributors, how companies are thinking about knowledge management, employee loneliness and wellbeing, and where some unexpected opportunities lie for those willing to step up. Original Recording Date: 09-27-2025 Topics – Framing Our Discussion and a Slightly Different Format, Defining the Trend, Impact on Career Structure and Ambiguity, The Challenge of Reaching Top Tier Positions, Internal Risk and Potential Loss of Knowledge, Strains on Execution, Impact to Team Dynamics, From Problem to Opportunity 1:01 – Framing Our Discussion and a Slightly Different Format For today and in next week’s episode, rather than introducing a guest to share their career story and lessons learned, we’re trying something a little different. Recently we sent a follow up question to a former guest whose response sparked an idea for this format. The trend of organizational flattening in our industry has been top of mind for us. We’re seeing the continued layoffs in tech often times result in fewer management layers and an increase in the number of people reporting to a single manager. This topic is too big and has too many angles for a single conversation. We wanted to bring together multiple expert perspectives on this issue in a single episode. We’ve reached out to a handful of former guests and sent them specific questions on this topic. Those guests were kind enough to record their answers and send them back to us. Consider this a Nerd Journey roundtable or collection of hot takes from trusted voices. Our goal is to amplify their advice and provide a diverse set of strategies for navigating this landscape. In the first episode (this week), we explore the trend of flatter organizations and the consequences for your career path and team culture. Next week in part 2 we will focus on actionable insights for thriving in this environment. Here’s the full set of episode links we will share throughout the conversation if you would like to hear more from one of the former guests who participated: Abby Clobridge Episode 292 – Library Science: Information Architecture and the Synthesis of Details with Abby Clobridge (1/2) Episode 293 – Enterprise Knowledge Management: A Consultative Approach to Solving the Right Problems with Abby Clobridge (2/2) Shailvi Wakhlu Episode 210 – A Collection of Ambiguous Experiments with Shailvi Wakhlu (1/2) Episode 211 – Structure the Levels of Contribution with Shailvi Wakhlu (2/2) Self-Advocacy: Your Guide to Getting What You Deserve at Work by Shailvi Wakhlu A special 15% off link for Nerd Journey listeners to Shailvi’s self-advocacy course can be found here. Leanne Elliott Episode 237 – The Psychological Transition of Layoffs with Leanne Elliott (1/2) Episode 238 – Managers as Culture Keepers with Leanne Elliott (2/2) Episode 340 – Task Cohesion: Managing a Larger Team in a Flatter Organization amidst a Climate of Uncertainty with Al and Leanne Elliott (1/2) Episode 341 – Champion Your People: Role Clarity for the IC in the Chaotic World of Work with Al and Leanne Elliott (2/2) Subscribe to the Truth, Lies and Work Podcast 2:48 – Defining the Trend Abby Clobridge is the founder and principal consultant at FireOak Strategies and has deep expertise in the realm of knowledge management. Abby was a guest in episodes 292 and 293. We wanted to get an outside perspective from someone who works with many different organizations on various projects. Our question for Abby: Within your customer base and set of prospects, do you see companies currently doing organizational flattening of management layers with an increased number of direct reports for managers? And if you have seen it, what do you think is the reason for this? We’ve heard of 20 or more people under a single people manager. Several of Abby’s clients are going through huge changes, sometimes resulting in entire teams and departments (like IT) being eliminated. In some cases, IT work is being shifted to MSPs (managed service providers), which has pros and cons. According to Abby, the economic climate and the rise of AI adoption has made this year tumultuous for everyone. Abby is seeing companies put more and more people under a single people manager. She tells us that managers with extremely large teams have no way to build real relationships. The large team often results in employees not being able to rely on their manager for much from day to day. “That kind of dynamic is a recipe for cultural toxicity really quickly too.” – Abby Clobridge 4:25 – Impact on Career Structure and Ambiguity Shailvi Wakhlu is a leadership speaker and data consultant with experience building and leading large organizations, including structuring of job levels for career paths. We spoke to her in episodes 210 and 211 She’s also the author of Self-Advocacy: Your Guide to Getting What You Deserve at Work. Our question for Shailvi: In our previous conversation we talked a lot about job levels. Do you think flatter organizations make it more difficult to clearly define those job levels, or are big companies that are cutting head count to flatten even thinking about this? What do you wish these companies would consider? “The stated reason that companies move towards flatter organizations, I think, is because they want to get rid of hierarchy. They want to say…we don’t want the lack of a higher title to restrict you from having a greater impact on the company. And I think that’s a fair goal…. However, I think in reality how it actually ends up playing out is, one, when you have a very flat organization…people don’t know what will be rewarded. And two, there is a lot of ambiguity about what everyone’s job is…. If everyone is responsible for something, typically no one is responsible for something.” – Shailvi Wakhlu It makes sense that a company would want people at all levels to feel empowered to contribute. Accountability comes through making distinctions in roles. Shailvi gives the example of senior engineers being expected to be more on top of certain things, and the same expectation would then not apply to junior engineers. People are thinking about the kind of contributions that would be rewarded within an organization as well as how to grow their career. Typically, titles are used to acknowledge the level of contributions an employee has made. Moving from one well-defined job level to another gives a person a sense of progress and something to aim for. “So, if there is not that definition of what is expected at each level, some people…may not have the tools to figure out what they should aim for…. Instead, I think the reason people started defining job levels was so that you could anchor on outcomes and impact.” – Shailvi Wakhlu Years ago, companies would anchor on years of experience and hand out titles based on that metric, but the flaw in this approach was that it did not reward impact. A specific job level shares the expectation of an employee’s impact on technical progress for the company, business results, communication skills, etc. “If you want people to anchor on that, if you want people to strive for that higher skill set, you have to actually define them. If you keep them super ambiguous, if you keep it super hidden, then…I think that’s also a reason why companies end up with things that look like favoritism.” – Shailvi Wakhlu, on job levels Without clearly defined job levels, a person doesn’t know what they need to do to showcase the kind of impact a company would like them to have. 8:41 – The Challenge of Reaching Top Tier Positions Another question for Shailvi: We’ve spoken a lot on the show about the individual contributor’s career path or what we call the technical career path and getting up to the role of principal engineer inside an organization. Would the flatter organization mean it becomes infinitely harder to rise to the level of principal engineer, that highest tier of individual contributors? Flatter organizations are not necessarily handing out titles that can help you when applying for a different job. “Even if within your own company people know you contribute at a very high level, that external signaling may not be very obvious to another employer. When you have…principal engineer, staff engineer, those type of titles…it is easier for a new company to understand just in context that you were in the highest tier of individual contributors.” – Shailvi Wakhlu Shailvi might split this into 2 pieces – rising up inside your existing organization and transitioning to a new job or different organization which may have a harder time measuring your impact. Shailvi does not think a flatter organization stops you from reaching top-tier individual contributor. It may, in fact, open up new opportunities to work on highly impactful projects. Access to these projects is usually based on past performance on projects, how you advocate for your work, etc. “If you keep showcasing that you are capable of handling more and more complexity, eventually you will get the highest value projects that have that very high C-suite level visibility…. Just the fact that it’s a flatter org should not stop you from having impact at the highest levels of what affects the business, what has the most visibility, and what is most critical to the company’s stated goals.” – Shailvi Wakhlu The problem will come when you are trying to join an organization where job levels are very clearly defined. A company may want a principal engineer, and even if you have the impact of one but don’t have the title on your resume, applicant tracking systems may disqualify you automatically. If you are relying on people reading your resume, add as many indicators as possible that the projects you worked on were at the highest level of impact. Shailvi suggests possibly stating that the principal engineer title did not exist because of the flat organization (if that was the case). Professional networking is very important to help showcase the level of your impact if you’re looking to land a principal title somewhere but don’t have that at your current company. Shailvi mentions talking with others in our industry, talking with recruiters, and talking with hiring managers. “There are many ways that you can show up as an industry leader that are outside of your company. You can talk at industry conferences. You can have a lot of content that you put out there which makes it very clear to people….” – Shailvi Wakhlu 12:43 – Internal Risk and Potential Loss of Knowledge Another question for Abby: "Is organizational flattening causing significant skill gaps at companies and creating opportunities for companies like yours or actually making it more difficult? In other words, are companies wanting to cut employee head count also cutting down the number of consulting firms they will partner with, or are they leaning into working with consulting firms more than they were previously? “Layoffs and organizational flattening and, weirdly enough, AI…that’s all creating a heightened awareness of the importance of organizational knowledge management.” – Abby Clobridge Abby says executive teams are starting to understand the importance of having organizational knowledge captured in a way that is documented well and easy to access, reuse, and build upon. It is important to allow people to shift roles without losing more organizational knowledge than necessary. “While we’ve made huge strides with AI adoption in the workplace, there still isn’t a magic vacuum that can pull knowledge out of someone’s head. When critical staff members leave, institutional memory leaves with them. Good knowledge management can’t stop that entirely, but it can soften the blow and help organizations keep moving forward.” – Abby Clobridge Flattening is a chance to re-think how knowledge flows across your organization. Fewer management layers could mean fewer bottlenecks. If done correctly, flattening can lead to greater transparency within teams and the mindset that knowledge is a shared asset. There is a balance between keeping the right level of security and making knowledge accessible, and it can look different for different organizations. For companies partnering with consulting firms, Abby says it’s a “mixed bag.” Some companies are cutting consulting budgets, while others are shifting to more fractional and outsourced roles. It depends on the company. “To be honest, it feels a lot like the summer of 2020 where organizations were suddenly trying to pivot or figure out what they were going to do and how to handle COVID.” – Abby Clobridge 14:54 – Strains on Execution We wanted to know how this climate impacts company execution. Another question for Abby: Does the current climate make it more difficult to help your customers “solve the right problems” when the team is leaner / smaller and is under a heavier workload? How have you adjusted your strategy to help customers solve the right problem as a result of these situations? For example, does a flatter organization make it more difficult for customers to commit to spending time in the diagnosis / discovery phase because executive leaders want faster results from smaller teams? Abby says she has seen it go both ways. Some teams want to get through discovery and diagnosis quickly because they are stretched too thin, but experience has revealed moving past discovery too quickly or without talking to all the right people is a mistake. Most of the time Abby and her team have been able to build an approach with clients to balance speed with getting things right. Several new projects are focused on preparing organizations for knowledge management in the age of AI. “These are really long term investments that the organization wants to get right, so even though everyone is anxious to get started, execs realize that it’s worth a few extra weeks or a few extra interviews to make sure we’re able to get a good sense of what’s going on and what the organization is really trying to accomplish so we can give the best possible advice.” – Abby Clobridge Some companies end up making big platform or system decisions far too quickly and often times without the right voices in the room. This only leads to costly mistakes. “Technology decisions aren’t made in a vacuum anymore. Very few platforms live as silos. There are almost always downstream effects. So, if you move too quickly without requirements, impact analysis, and honest conversation about tradeoffs…you end up with ripple effects that can be very costly and disruptive. It doesn’t mean decisions have to drag on for months. The key is balance – moving at a healthy pace but giving people enough time to digest, weigh impacts, and make better informed decisions.” – Abby Clobridge 16:57 – Impact to Team Dynamics We wanted a perspective on team dynamics, so we brought in Leanne Elliott. Leanne is a business psychologist and with her husband Al, hosts the Truth, Lies, and Work podcast. We spoke to Leanne in episodes 237 and 238, and she also appeared along with Al in episode 340 and 341. The questions we’re asking her are follow ups from the conversation we had with them on organizational flattening. Our question for Leanne: We have seen companies with 1 or more pods under each manager where there is some kind of pod lead / team lead within each pod who helps the manager do things like track work, give team members feedback, etc. Have you seen this structure work well in flatter organizations? Leanne has seen the pod structure work quite well, but more often than not, she has seen it go badly. This has a tendency to create an “us and them” culture, especially when people do similar work but are part of different teams. If there is not advertisement or reinforcement of the core mission bringing everyone together, this can breed workplace incivility (cliques, gossip, division, etc.) and create microcultures. With a complex structure like this, it requires more care, close monitoring, intentional management, and a willingness to make adjustments when needed. “My worry is that if it’s not handled well, it’s not done with the best of intentions…then it can mean that people feel more disconnected, there’s more infighting, and ultimately more isolated.” -Leanne Elliott The latest State of the Workplace Report from Gallup found that 1 in 5 employees have stated they feel lonely at work. This is an organizational issue and not just a personal issue. “People often think that loneliness is about maybe being shy or introverted, but it really isn’t. There’s no link between personality and how lonely somebody feels. What does matter, according to the research, is the environment. It’s a complicated thing as well to look at your organization as a supervisor, as a colleague, as a senior manager and try and identify the people that are lonely and try to fix that. People don’t act lonely at work.” – Leanne Elliott People are skilled at masking how they really feel and may seem chatty, gregarious, or outgoing. “…because that loneliness is so stigmatized that people will pretend it’s fine rather than the fear of repercussions because that psychological safety doesn’t exist if they did speak up and say something about it.” – Leanne Elliott Having leads in each pod who are closer to the group may foster an environment of psychological safety. But, this is not necessarily going to be the same behavior senior leaders who have the power to do something to change the environment will exhibit. A lead / supervisor may recognize there is a problem with how someone is feeling but be unable to do anything to really change the overall environment. If people do open up inside the pod structure, there is a chance they will remain disconnected over time, which chips away at wellbeing. “As with anything in the workplace, these types of things to…have the most positive impact require attention, require support, and require the agility to change these experimental structures when they’re not working.” – Leanne Elliott 21:13 – From Problem to Opportunity Maybe we could look at this trend as an opportunity? Another question for Leanne: In a world where manager to individual contributor ratios are changing, does this create an opportunity for individual contributors to take more of a player / coach or team leader kind of role? Leanne does think this will create an opportunity for individual contributors to take on a coach, team leader, or supervisor kind of role. People will step up into these roles when needed, and it’s usually the more conscientious members of the team who do. Some may seek this role out of ego, but the small nature of the team will make this highly visible. It’s not usually out of ego that someone takes the role, but it can happen. If this role is an official role, it can be a great way to develop people. “It’s that chance to try out people management in a more hands-on, practical way…so less theory, on the job training. You’re close to the work as well so you understand what it really takes to deliver that rather than being a removed senior manager…. And for the group as well, people do look for someone to follow.” – Leanne Elliott For groups of this size (larger than 12 or 13), it is hard to connect with everyone individually. We would often look for a shared goal, mission, or values. People look for someone to show them what that is and how to make sense of it all. The leader in larger groups gives us clarity, sets a tone, and demonstrates what is expected. This helps employees feel safe, more confident, and like they belong (all of which are great for wellbeing and lead to team cohesion). “The issue with these types of supervisor roles is typically they aren’t formal. So, someone will step up, or maybe they’ll get nudged into it by a senior manager. But there’s no support, there’s no extra pay, and there’s no real recognition. Now, that’s fine initially. That’s what we call ‘hope work,’ work where someone can see the benefit of stepping into an informal role without any kind of extra pay or recognition on the understanding and the view that this will be for a finite period of time. And then the pay and the support and the recognition will come. If it doesn’t (and it typically doesn’t in informal supervisor roles), then that can build resentment over time, and it can lead to this person disengaging and burning out…which is a danger because typically it’s the high performers that will step into these types of roles. But when it is done properly…right structure, right support…then yeah, it can be a great steppingstone for anyone who is looking to move into a management role who doesn’t have any experience or training at that point.” – Leanne Elliott We want to say a huge thank you to all of the guests who contributed to this episode! If you want to hear more from them, you can find the full conversations… Abby Clobridge was a guest in episodes 292 and 293. We spoke to Shailvi Wakhlu in episodes 210 and 211 She’s also the author of Self-Advocacy: Your Guide to Getting What You Deserve at Work. Here’s a special 15% off link for Nerd Journey listeners to Shailvi’s self-advocacy course. We spoke to Leanne Elliott in episodes 237 and 238, and she also appeared along with Al in episode 340 and 341. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

Episode 346 is dedicated to the memory of Todd Cochrane. Todd was the founder of Blubrry Podcasting, a Navy veteran and electronics technician, a geek and lover of technology at heart, a content creator, a podcasting pioneer, and a consistent friend to the greater podcast community. This week we’re airing our full interview with Todd as a single episode (previously released in episodes 250 and 251). As we begin this week, Nick and John frame what you’re about to hear with a story from Podcast Movement 2025 where Nick got to meet Todd in person. Listen closely for the shifts Todd made to his company as market conditions changed, and think about the applicability of this strategy for your career. Original Recording Date of the Interview with Todd: 10-06-2023 Topics – Meet Todd Cochrane, Naval Service and Technical Knowledge, Program Management, An Injury and a Different Role, Getting into Podcasting and Monetization, A Tech Wave and a Shift, Diversification of Focus and Expertise, Corporate and Individual Roadmaps, Leadership and Employee Engagement, Developing a Useful AI Strategy 5:49 – Meet Todd Cochrane Todd Cochrane is the founder and CEO of Blubrry Podcasting. Blubrry is a full service podcast hosting platform. At the time of this recording they are working with around 100,000 shows / podcasts at a variety of levels (some shows using Blubrry for hosting, some for analytics, some using the PowerPress plugin for WordPress). The team at Blubrry is about 17 people, and they have been in business since 2005. Nerd Journey proudly uses Blubrry statistics and the PowerPress plugin! 6:51 – Naval Service and Technical Knowledge In vocational tech school Todd took 2 years of electronics and then joined the Navy in 1983. His official title at that time was aviation electronics technician. Todd also served as a back end operator in specialized P3 aircraft used more as platforms for intelligence collection. Todd tells us he was involved in this kind of work for 25 years. During his tenure in the Navy, Todd got exposed to something called special projects. People would bring a box for a specific function in the plane (a “box de jour”), and Todd would do the mechanical and electrical designs for these to get them in the planes quickly. Todd’s true Navy background was in synthetic aperture radar and involved work with Sandia National Labs. To pair with his deep technical knowledge of electronics, Todd started to tinker with other things like bulletin boards and downloading shareware while stationed in Guam. This was back in the days of dial up modems. “I really was kind of a geek in all aspects of job and life….When the bulletin board era died, I basically became a blogger.” – Todd Cochrane, reflecting on his time in the Navy. Todd calls himself a failed blogger, feeling he was not great at it. This was around 2002. In 2004 Todd got into podcasting but continued to work another job. After retiring from the Navy in 2007, Todd spent 12 years as a tech rep (basically the same job he had been doing but as a civilian). Todd continued to work with and for Naval personnel until 2019 while running his own company on the side. “Needless to say those were some exciting years because there was not a lot of free time.” – Todd Cochrane, on working a full time job and running his own company on the side Todd has only been out of aviation for about 4 years now but has been running his business (Blubrry) the entire time along the way since it began as a side project. Todd retired from the Navy as a senior chief (an E8). He did have the opportunity to go warrant officer but was happy being a chief, “punching out” just before hitting the 26 year mark for Navy service. This was largely because they offered him a civilian job, and he took the opportunity to make the change. Todd tells us he was exposed to a great deal of high end technology during his work (much of it will remain classified for many years). Looking back, Todd says it’s pretty amazing to see the advances in technology from 1983 when he joined to when he retired and up to the time of this recording because of the technology changing so fast. 11:08 – Program Management Was designing the boxes for airplanes like being a product designer or a product maanger? Todd’s degree from Emory Riddle is in professional aeronautics with a minor in program management, and he was able to put the program management skills to good work. For systems that the Navy personnel designed, built, and owned they had input into the capabilities desired as well as features they wanted. “It was a full scheme. Some of the systems were born from an idea – built, designed, UX, UI, the whole nine yards…that I was able to have a hand touch in.” – Todd Cochrane, on working with a team to design and build systems for Naval aviation In the last 15 years of his work, Todd says someone would show up with a box that he and others would have to wire up / connect. These ranged from computers that needed installing to electronics that need to hook into multiple systems in an aircraft. From day to day, Todd didn’t really know what might come his way. This made the job quite unique. They might get a call from a well known company who wanted them to test something, for example. “So our job was really to kind of test and evaluate, and more importantly, in a real world situation, not necessarily on some range….It was fun.” – Todd Cochrane In the case of 787 or 777 commercial aircraft, they are built exactly the same (with exception of some of the electronics in the cockpit). Often times the supply chain is setup so you could walk over to the airplane next to you and “rob it” for the parts you needed. In Todd’s situation, everything was unique, and each airplane was different in some sense. It was important to have configuration control across multiple aircraft. Sometimes they would need to upgrade multiple airplanes at a time. 14:06 – An Injury and a Different Role In 2004 Todd was hurt badly in a swimming accident in Bahrain, which grounded him from flying. Todd was in Waco, Texas doing contract enforcement – making sure taxpayer money was spent wisely and monitoring aircraft builds. Todd says he saw a lot of the government / civilian interaction during this time, and it was a very interesting job to do for a few years. Todd had insight into the process of building aircraft from beginning to delivery of and testing of aircraft. The team was multi-faceted and in multiple locations (i.e. teams with some specialties in the northern US, others elsewhere, etc.). Specific systems might require their own reviews and discussions and planning. Budget and what could be done within the time frame were also factors. It was a team effort. Todd tells us there were also subject matter experts (or SMEs) for various systems. Todd has publicly shared that his background was in electronic warfare, synthetic aperture radar, etc. while on active duty for the Navy. He would have been considered a SME for these kinds of systems during his service. Todd would work with and support the team putting in systems for which he was SME as well as the sailor who was deployed and had run into issues (i.e. provide troubleshooting / fly out somewhere to resolve the issue, etc.). The role was part design and implementation as well as ongoing platform support. Nick feels like this SME role is extremely analogous to life as an IT generalist. Todd says it would have been very bad for someone to infiltrate the software they used software. As such a number of security measures were put into place to help prevent this. The IT group gave people like Todd the hardest time because they might lock something down so tight it causes something else to break. And Todd calls this “par for the course.” Todd says having this experience set him up well for success later when he pursued working for his company full-time. “For me the transition from military to civilian was pretty smooth because I had worked with civilians a lot….So I didn’t have this mindset of someone that maybe just came out of the military that had never had a lot of civilian interaction.” – Todd Cochrane, on transitioning out of the Navy and how it might be different than others leaving military service Todd had been running his company as his part-time job for a number of years until he transitioned to working there full time. While still working in the Navy, Todd had to be very careful about keeping his business and Navy work completely separate. The separation was an important part of security clearance reviews, and Todd even had to ask permission to have his own business. Todd would leave his phone in the car during his normal workday and take business calls either during lunch or after work to help keep the separation. “But when I transitioned, it really made me realize I should have probably done it about 10 years earlier.” – Todd Cochrane, reflecting on his transition to running his business full time For the last 4 years, Todd’s job as CEO of Blubrry has been coordinating with the software development teams, production, and marketing. Todd says they use Scrum at Blubrry and that he is essentially the Scrum Master in many ways despite being the owner. His project management skills have come in handy. 19:29 – Getting into Podcasting and Monetization When Todd speaks to being in Waco, TX he was in a full body clam shell after smashing his L1 vertebrae in a swimming pool accident. Todd tells us he was lucky to be alive and be able to walk after the huge spinal cord displacement from the accident. Todd worked in an unairconditioned shop after being able to walk again (still in Waco) and was exhausted at the end of most days. He would spend evenings on his laptop surfing the internet and stumbled upon Adam Curry’s Daily Source Code, one of the early podcasts. At this time (October 2004) Todd was a tech blogger who didn’t have many people reading his site, but he liked to talk. Todd picked up a cheap portable microphone at Wal-Mart and started recording a podcast. He already understood things like XML that one needed to know to get a podcast online back then and was able to execute on his own. “Really the eureka moment came when I woke up one morning and my webhost said, ‘hey, you’re out of bandwidth. We’ve shut you down.’” – Todd Cochrane, on an interesting situation after starting a podcast in the early days There was no Blubrry at this time, and the only way to fix the problem was to spend more money on shared hosting accounts. Todd’s podcast website had to be moved around every few days at that time to keep it going. October 9th, 2023 marked the anniversary of Todd’s 19th year of doing podcasting! Todd was spending a lot of money to keep the show online. When he returned to Hawaii and let his wife know what he was doing, she didn’t really know what podcasting was (almost no one did at that time). But, Todd’s wife told him he needed to be making money from this endeavor after a year or two or would have to stop. In November of the same year, Todd received an e-mail from a publishing company asking him to write the first book on podcasting. At first he was not sure if they were serious. But it turns out they were and offered him a sizable advance to do the book even though he did not consider himself good with grammar or a writer. Agreeing to write the book fixed Todd’s money issue. Todd eventually started his own tech network and then in 2005 GoDaddy called Todd wanting to sponsor his podcast. GoDaddy is still a sponsor of Todd’s show Geek News Central. At this time Todd was one of the very few who had advertising on his podcast. He wasn’t quite sure how to charge in the beginning. After a month of sponsorship GoDaddy got around 370 customers and wanted to sponsor Todd’s show for a full year. “Here’s one of those things where you have to understand your worth, and I really had no idea what my worth was.” – Todd Cochrane, on having to come up with an amount to charge GoDaddy to sponsor his show Todd says he ultimately gave a price that was far too low (an underbid as he calls it), but in the moment he suggested a bonus if GoDaddy converted a certain number of customers as a result of the show. Ultimately Todd’s contact at GoDaddy agreed to this. The lady Todd was working with to construct a deal asked if he knew anyone else looking to advertise with GoDaddy. Todd said yes and that he needed a couple of weeks to get back to her. The tech network Todd had built had 12-13 shows he could potentially represent and take a percentage of the proceeds. “And on my next podcast I said, ‘I need a lawyer, I need a MBA, I need a graphics guy, and I need programmer. And we’re having a call in 10 days. If you’re one of those, be on it……’ And in the end we formed RawVoice, which is the parent company for Blubrry, over the telephone. And we all had regular jobs, so everyone was working this at night.” – Todd Cochrane, on the beginnings of his business Todd made the ask on his show and got all the personas he needed on a call. The company was profitable from month 1, and each member of the group contributed some of their own money in the beginning to fund the startup. Todd was told he was too old at 40 to receive a round of funding from venture capitalists in silicon valley. And it would have required the entire team to move there (not feasible with everyone having a family). “But the one thing we were always smart with is we knew that we had to have money in the bank. We knew we had to be profitable. We knew we had to make payroll because…I didn’t have $25 million of VC to use. We had to build this slowly, and that’s what we did over the years. We built it slowly and never extended ourselves too far.” – Todd Cochrane 26:16 – A Tech Wave and a Shift John mentions Todd identified what we would call a technology wave, was passionate about what he was doing, and he made a bet. Todd maybe could have gone to work for someone looking to monetize in this space but made a bet. The structures Todd had put in place enabled starting a business without too much work compared to someone with a cold start. Todd says in a lot of ways the team figured things out as they went with the first product being an “abject failure.” But the team learned from this experience and made changes to their model. "We build a lot of stuff, and if something is not working, I don’t dwell on it. I don’t ride that ship into the ground. We move on. Maybe we keep the product, and maybe we don’t. " – Todd Cochrane Todd mentions many people with a product or idea believe in it so much they burn all their money and don’t make a change or shift early enough. In the early days Todd’s company was like a media agency and represented podcasters for ad deals. Most shows they represented were fairly small, and their second product in 2006 allowed them to track podcast listening statistics. As larger more popular shows came online, Todd could see the advertising budgets shrink and shift to be put into these larger shows. As a result of seeing this trend, Todd’s company did a strategic shift to become a service provider. “So as the advertising revenue was declining the service business kind of crossed in the middle, and we dodged a bullet. We would not have made it had we not shifted to a service business….Keep your eye on the ball, what’s going on in the space. At that time I had 5 competitors. Now I have 30.” – Todd Cochrane, on a strategic company shift Todd tell us his product is commoditized today and competes today on features based on feedback from customers and the market. In the technology sector, companies have to look around and understand what is happening (cannot be blind to this). “You do have to teach the old dog new tricks. You have to.” – Todd Cochrane, on the need for companies to adapt to changing market conditions The above is also true for knowledge workers, especially with the growth and emphasis on AI (artificial intelligence). If people do not stay current and get educated on these technologies, they may find themselves out of a job in a few years. When Todd originally built his show (that first podcast), he was trying to build authority. Todd wanted a press pass to CES (Consumer Electronics Show), which he eventually did get. This was before his wife’s mention of monetization. “I did it out of pure desire just to go and hag out and check that show out….Then things kind of morphed as time went on.” – Todd Cochrane, on the reason he started his podcast in the first place 30:42 – Diversification of Focus and Expertise John says we’ve heard about startups and the term “pivoting.” It may not be a pivot of the company but a diversification of where success and money will come from (which is also true for an individual). John shares that at one point his ability to crimp a CAT5 cable was a skill that brought money in. But if he had held tight to this and focused on it holistically forever, John would not have a job right now. Diversifying a skill base or what provides value to an employer or a business (i.e. your own business) is something we can do to keep ourselves from having market forces destroy us. As we age we get more expensive to employers, making it even more important to keep our skills current and requiring that we bring expertise to our next role. Early on in Todd’s Navy career a friend / mentor named Randy gave him some great advice. “You just need to attach yourself to the smartest person in the room and suck them dry, basically learn everything they know or everything they will tell you.” – Advice from Todd Cochrane’s friend Randy Todd says using this strategy has really paid off for him long term, and he does this today with his CTO at Blubrry (someone who knows the tech well and someone that Todd trusts to provide direction). “I think it’s more than surrounding yourself. I think if you are in a field that you’re trying to stay current on, you need to become the person other people want to attach to. But when you’re early in your career it’s easy to be annoyed by that older wise individual. But they have so much experience.” – Todd Cochrane Todd tells the story of asking someone with more experience at Sandia National Labs for help on a schematic. The person told Todd exactly what to do to fix the problem (which worked). But Todd didn’t leave it there. He went back to the person and asked how they knew their suggestion would fix the problem. “A 15-minute conversation I had with him literally fixed hundreds of problems that I had going forward years in advance. When you have that opportunity to get help from…a genius and they can bring the topic down to your level, man you just need to…milk that dry.” – Todd Cochrane, on picking the brain of a brilliant colleague with more experience Todd thinks that advice from Randy (who is still a friend to this day) was one of those pivotal moments / pieces of career advice. Nick feels like the above experience is an iteration of being mindful of our gaps in knowledge just like when Todd got on his show and asked people with different expertise for help. It’s learning from others but also humility. Todd says he was a high school graduate going into the Navy and didn’t get a degree until he had been in the Navy for 20 years. In a way he was getting credit for much of what he had learned via the school of hard knocks. Todd has seen people fail because they hung out with others who may have been fun people but who just were not going to advance in a company. It’s important to surround ourselves with good people. John points out that just like skills diversification when one is riding a technology wave, it’s also about having a diverse set of people around us whose experience we can call upon to fill gaps in our own expertise. We cannot be experts in everything. Having access to others with different expertise can enable the kinds of pivots we spoke about earlier (for the individual or for a business). As company owner and founder, Todd would rather collaboratively come up with a plan with his team than just give them a directive. Todd calls himself a geek and says there are times where he wants something geeky (i.e. a feature) that 90% of his customers may not ever need. It’s important to be careful and prioritize for the 90%. There are certainly times when Todd’s team are building a feature that is intended to promote adoption (i.e. building it for only a small subset of customers) like some of the podcasting 2.0 work they have done. But these occasions are pretty rare, and the team knows why they are building it. Todd says the team are very cognizant of the products and services roadmap when making decisions, and he looks at the year’s roadmap every day. Every 2 weeks there is an oversight meeting to discuss the roadmap with other company leaders. Priorities may need to change based on the marketplace conditions. “You have to be careful. Because if you’re working Scrum…if you interrupt the cycle you could really do huge damage.” – Todd Cochrane, on being flexible in your product roadmaps 38:47 – Corporate and Individual Roadmaps Nick posits that most of us do not have a roadmap for ourselves and our careers, nor do we look at it daily. Todd says the roadmap is the company roadmap but might as well be his personal roadmap. John emphasizes the company’s execution on a roadmap is analogous to a individual contributor’s view of themselves / their career as a product. Excellence in what a company is doing today is of course important. Companies often have innovation budgets to enable building products people might not know they need until they use it / can have it (i.e. the iPhone or perhaps certain podcast hosting features). Maybe as individuals, in addition to excelling at what we do today (a baseline of excellence in execution), we should have our own innovation budget allotted for building new skills and learning about the next / current technology wave. This avoids us from being locked into excellence in only what we do today just like Todd’s company was able to shift away from being only a media intermediary in the early days. Todd says his team is fully remote but does come together a couple of times per year for planning purposes (1 time in person, 1 time 6 months later remotely as a follow up to that). These meetings are a chance to look at what is going well, what isn’t, and a chance to solicit new ideas. During these discussions, teams criticize one another and give feedback. It is a very frank set of discussions that results in action items. Todd says they try to preserve people’s feelings during the discussions, but it is about honest evaluation of how things are going. The above will be quite difficult for companies with more than 20 employees. Todd says the approach works well for his company. Todd also tells us a bad apple (1 person) can make a very negative impact on the company. This person might not be staying current or is constantly fighting with others. “Sometimes it’s better to cut those folks loose. Even though you think you shouldn’t, sometimes getting rid of that just maybe 1 person can completely change how a company’s atmosphere is and the flow and the speed….So I learned this late – that sometimes it’s just better to say ‘thank you for your work it’s time to part ways.’ It’s just like pivoting. Sometimes the employee mix needs to change.” – Todd Cochrane, on making difficult decisions around people Todd says there was someone who left the company about a year ago, and the business had a complete transformation (in a good way) as a result. 43:10 – Leadership and Employee Engagement Many people moving into leadership are not prepared for the hard personnel decisions. What are other challenges Todd has noticed as CEO, being in charge of the roadmap and the people? Todd says he has been quite lucky with very little turnover, having only a couple of people leave the company over time and a couple of others get asked to leave. Overall the team has been strong (a possible sign they are doing something right). “We all get bored if we’re doing the same thing, but we’re in a business where we can build new stuff all the time and have new challenges. So I think from my perspective…if you’re not innovating, then your employees are going to get bored, and they’re going to go some place that is innovating to give them a challenge.” – Todd Cochrane Ideally Todd wants employees to feel their work is exciting, that it is making a difference, and for them to be excited to start work on it again each day. In IT sometimes work is drudgery (or “the thunking” as Todd calls it) and is not something we enjoy doing but need to do (i.e. keeping servers up to date). Nick mentions Todd recognized the need for people to be interested and engaged in their work, and Todd has iterated upon that methodology in terms of the way people engage with the company and its products. If you’re listening to this episode and intend to become a leader but have not thought through the importance of people understanding the purpose in their work, think on it. It was extremely important for Todd to share the vision with employees. “How is my role here having a larger purpose for this organization? And hopefully that gives me some personal satisfaction and sense of accomplishment.” – Nick Korte, on the importance of leaders helping employees to understand the purpose of their work Todd says he came from a field where he was able to work on multiple projects on a monthly / semi-annual basis. This kept him excited about the job. There were legacy systems to support, of course, but there were brand new systems. “I understood that that job satisfaction of having something new to work on is fresh, challenging, you have to really think…I mean hard, hard problems to solve.” – Todd Cochrane Todd gives the analogy of working with airplanes. Both power and space are constrained resources, and there is a give and take between them. Translating this to running a company, there is server space as well as mind space. They would not want to do something that will be an extreme burden from a technical support perspective, for example. AI (artificial intelligence) has Todd a little frightened, but the strategy for the company is to not be locked into a single language model (Claude, ChatGPT, Meta, etc.). “We’re using the dumbest AI we’ll ever use today. It’s exciting at the same time, but it’s hard to pick a strategy that is not going to be obsolete in 2 weeks.” – Todd Cochrane Todd says right now (at the time of this recording), the economy is tight with podcasting being fairly flat. But he and his team have been through cycles of economic downturn and know what to expect, having been profitable every year of their existence. “As long as you keep the green line above the red line I think that’s the key in almost any business industry. Otherwise you don’t survive.” – Todd Cochrane 48:36 – Developing a Useful AI Strategy John understands the desire to stay flexible and diverse in terms of different language models and asks Todd about his AI strategy and where he feels like it will help podcasters. Todd always likes to ask himself whether something the company is doing will help the customer base by saving time or making a customer product better. Todd says helpful areas for AI use will likely be content creation and post production. Many companies are doing things related to social media, and Todd doesn’t think he wants to compete in that space. The number one question Todd gets asked consistently by content creators is “how do I grow my show?” Any use of AI tools would need to help in this area. The team at Blubrry has taken several months to think through a strategy. For those who follow Todd’s shows Geek News Central and New Media Show, he is public about the things in the AI space with which he has experimented. The “thunking” is in creating documents (outlines, drafts, proposals, etc.) and will likely be done by the AI. The creative individual will still be needed, but some of the show prep (based on creative thinking) could be handled by AI, for example. “On the other side of it, you have to be the subject matter expert of your topic, your content, so that when the production piece is done by the AI you can validate….You are going to be the person that is going to review the output.” – Todd Cochrane We need to remember that the output from AI tools will not be perfect and won’t be for some time. Todd says the work of his team will be to educate creators on this fact. Todd references a book on NATOPS with all the information needed (sort of like a bible for the airplane). There is a disclaimer on the book that it is not a substitute for common sense. For example, if an AI provides poor topic suggestions, we need to not use them. Podcasters need to know that these are merely tools to help with content creation and production. Blubrry will be working on tools to help podcasters grow their show, but it will be tricky. People need to understand the models / AI tools will lie. Todd says for a show like ours where we are having a ranging discussion, AI has a hard time summarizing it. But for shows that are one point after another, AI does well there. Nerd Journey may not get as much value out of a transcript analysis as a news show covering a set number of topics. Todd shares the results of some tests lately that were lower quality than what an intern at his company should produce. Nick feels like this is just the tools and the SME (subject matter expert) changing a little. Todd says we (as the SME) need to be able to check to see if output is too flowery, if the AI added something that wasn’t discussed in a show summary, etc. He feels the tools will get better over time (pretty quickly) but just are not there yet. John mentions these tools help with the problem of starting with a blank page as well as with summarization. It’s easier to work from a draft than from nothing. Todd says podcasters have often been lazy with show notes. “You record for your audience. You write for Google.” – Todd Cochrane on podcast creation and show notes (advice for the podcaster) As language models become more widespread searches will change, and we want our content to be easily findable. The metadata we feed into Google is becoming more important. To listen to other tributes to Todd, check out Remembering Todd Cochrane – Podcast Hall of Famer and Blubrry CEO and, GNC Host and Geek News Central # 1843 For links to the individual episodes with Todd that were combined for this special episode, check out: Episode 250 – From Naval Electronics to Podcaster and Business Owner with Todd Cochrane (1/2) Episode 251 – A CEO’s Approach to Product and Career Roadmaps with Todd Cochrane (2/2) Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

Pursuing a role in leadership is one thing, but what happens when you try to return to life as an individual contributor? Our guest, Paul Nadeau, equates this experience to having “resume damage.” Join us for episode 345 as we dive into the differences between pursuing a technical career path as an individual contributor and a career path in people management from a guest who has experienced both. Paul reveals a strategy for gaining expertise by sharing examples of his willingness to find and clean up a mess. Through turbulent times in the tech industry, how can we give to our network with no agenda? Listen to Paul describe his approach to meeting new people, supporting them through layoffs, or just providing advice…all through merely having a conversation. Original Recording Date: 08-28-2025 Topics – Technical Career Paths vs. Management Career Paths, Returning to Individual Contributor, Specialty Decisions, Nurturing Your Network and a Focus on Helping Others 3:15 – Technical Career Paths vs. Management Career Paths John mentions we have spoken on the show about the technical / individual contributor path to progression as well as the management career path. There is usually a path to stay an individual contributor in medium to large size organizations (i.e. the ability to progress to senior engineer, staff engineer, principal engineer, distinguished engineer, etc.). “If you want to progress in your career and you don’t have that path, management is not the natural thing to look at…unless you actually want to stop what you are doing and become a manager…. Becoming a manager does not make you…tech lead. It makes you manager. It’s a hard piece of advice to give somebody if they’re in an organization that does not have a next title, a next promotion for that person where they stay an individual contributor…. You shouldn’t try to become a manager. You should try to move organizations. That’s hard advice to give. I’ve had to do that a couple times.” – John White Paul recalls a conversation with his manager not long after the manager had been promoted into the position. “There’s no comparison between the management going up a chain of command and the engineer going up a chain of command. It’s a completely different skillset altogether….” – Paul Nadeau Paul tells us that as leaders progress to higher levels in an organization they take on more responsibility but also begin to manage a profit and loss center (or PNL). Rather than individual expense reports you’re looking at what the team is spending and what they are spending it on. The next level up is leading an entire division and considering how to distribute funds within your budget for salary raises, bonuses, or other types of compensation. Paul tells us that many leaders love to hand out promotions, but no one likes to fire people. When evaluating a technical career, Paul likes to think about the following: Am I having fun? Am I a benefit to the company? Where will I be a bigger benefit to the company…in my current role or in a management role? If applicable, are customers happy with me in my role (tech support, professional services, etc.)? “I think one of the big reasons why people leave companies is…whenever they say there’s no room for promotion; it doesn’t have anything to do with promotion into management. A lot of times they think that’s what it is. But it has to do with promotion of their brand, their career path. What are they doing, and how are they getting there? That’s what it has to do with.” – Paul Nadeau Management is a lot like herding cats, and according to Paul, not everyone is going to have fun doing that job. Paul has fun whiteboarding and providing technical solutions for his customers. This makes him happy. We have to define what success is for ourselves and not rely on how other people define success. Some people in technology define success as the level of management they have achieved. “Quite honestly, whenever somebody comes and says, ‘are you interested in management?’ Not really…because I can make a bigger impact here where I am now and I can go to club and make a lot of money getting there as a systems engineer…. In management…when you equate it all out, is it really as much fun? I don’t know. When you walk in and you go to dinner, nobody wants to sit with you because you’re the boss. Nobody comes to your table. Why not just be the fun individual contributor that’s the natural leader guy where everybody comes over to the table and you just kind of have fun doing what you do?” – Paul Nadeau Nick says Paul’s comments seem to hint at the importance of working for the right leader if you take on a role as a first-time people manager. Paul tells us it’s more than that. Managers have a ton of resources at their disposal, but their number 1 job is to protect the company above all else. “A lot of people say…I’m here to protect the people. No, you’re here to protect the company number 1. That’s why the company promoted you. The second thing is to protect your people. If you’re protecting the company you’re naturally protecting the people. Because now you don’t have a toxic work environment. You don’t have any kind of discord. You don’t have any kind of rule breakers. All that’s taken care of because you’re protecting the company first.” – Paul Nadeau One of a manager’s greatest resources is HR (Human Resources). “They are there as an advocate to help you as a manager to work through problems and issues. That should be your best friend in the whole world.” – Paul Nadeau, on HR Many leaders miss the opportunity to leverage HR as an advocate and helpful resource. One of the first things Paul did after becoming a leader was go make friends with his HR. He also highlights how communication with HR about more than just immediate problems can help (i.e., employees who are performing well that you want to retain). If you’re giving pointers to someone who wants to go into management or continue down that path, Paul tells us it’s not just about taking a class. You need an increased level of involvement with other people. Instead, do things to get involved in different user groups. Take on different roles that you can have fun doing. An increased overall level of involvement fosters strong relationships with different people. This is how to begin and continue building a professional network. As layoffs happen in the industry and people reign to move to different companies, the relationships can be retained. “These are still people. Humans first, right? That’s what it all boils down to…it’s still people dealing with people at the end of the day.” – Paul Nadeau 11:37 – Returning to Individual Contributor At some point after working in leadership, Paul chose to return to being an individual contributor. What went into that decision? “Actually, it’s harder to go backwards than it is to go forward. It’s harder to go from a management role into an individual contributor role.” – Paul Nadeau From the time Paul was promoted to director of worldwide services to his return to individual contributor was a span of about 8 years. Paul remembers a specific trip to Asia to spend time with a director under him and to attend to different organizational changes. It was 2 AM, and he received an unexpected phone call from a friend. Someone wanted Paul fired and wanted to take his job. Paul reminds us that at this time things were running smoothly. The services organization was making money ($48 million in the black). Employee morale was in great standing, and attrition was low. When he took over the services organization at this company after a massive restructuring years earlier, it was $18 million in the red, and the company was considering removing it completely. “The politics side of it…I’ve never done well with. I’ve never really done well with that. It is inherent. It is something that happens…. Human beings…we just naturally get political about things…. We have opinions…sometimes a little jaded opinions on somethings…or a little strong opinions…. And when the politics started to come out, I was like, ‘you know what? I’m not even cut out for this.’ And the worse it got, the less tolerance I had for it….” – Paul Nadeau Paul told his boss he wanted to move back to individual contributor again. Paul was ok with just being an individual contributor inside an organization he had built. He missed being in front of customers. “It is fun. It is rewarding to help people with their career and help them develop leadership skills that they didn’t know that they had, to see things in people that they don’t even know that they had and kind of help them evolve. However, there’s also the other side of it, which is, I can’t take this being up 17 hours a day, getting 3 or 4 hours of sleep a night, and being on airplanes all the time. It’s just taking a toll…. Everything considered, I want to go back to an individual contributor role.” – Paul Nadeau After talking through it together, Paul’s boss at the time was supportive of the move back to individual contributor. Paul also spoke to a really good friend who had progressed from individual contributor to being a peer of his in management about making the change back to being an individual contributor. At first that friend thought it wasn’t a good idea. It would remove some elements of compensation that were present at the leadership level. But, when the friend could see Paul was determined, he mentioned to Paul that there was an opening for a systems engineer. Paul made the move and took the role. After moving into the individual contributor role, Paul said one thing he did not expect was to have to still sit at a dinner table by himself. “It was so isolating. It was absolutely unbelievable. So, whenever they say it’s lonely at the top, it is. But it’s also lonely when you get back into the ranks…moving back in from management back into an individual contributor role. If I were to move into a different company where I didn’t know anybody or maybe just knew one or two people, it might have been a little easier. But moving up the ranks and back down the ranks was quite telling…. It was kind of surprising.” – Paul Nadeau Remember, Paul had gone from member of a team to leading an entire division. What we’re talking about now is going the opposite direction. Paul says he worked at his first two employers after being in the Navy for many years (over 17 years at the first company and about 8 at the second). It was all about loyalty. But, does a company reciprocate the loyalty, or would it be better to move to a different company? Even when trying to move to a new company after experience in that director role, Paul tells us the “resume damage” followed him. Hiring managers were initially hesitant to hire Paul as an individual contributor. They thought Paul might tell them how to run their team or be targeting another director role. After Paul had landed an individual contributor role, his manager or other leaders who knew about his management experience might ask him if he had ever experienced a specific situation. Listen to some of the specific situations Paul experienced when he was a leader. Would you know how to handle them? “These are all things that they don’t teach you…. There’s no book that says…go to page 15 and this is what happens when this happens…. There’s a lot of these things that you just have to kind of learn under fire. Again, that HR advisor is the person you have to go to…. Moving into those roles a lot of times is really difficult. It will follow you. Then it becomes kind of a distant memory….” – Paul Nadeau, on situations one experiences as a manager Paul says the transition would be equally difficult to go back from individual contributor to manager if enough time had passed since the last management experience. It’s not that someone would forget how to perform the role, but there is a perception shaped by amount of time not in the role one must combat. The decision points for Paul when it comes to manager / individual contributor come down to passion and what he wants to do in life. Many people we’ve spoken to who when back to individual contributor roles missed being close to the technology. Paul tells us people in leadership (like leading a worldwide services organization) don’t have time for building a home lab. You start to feel like you’re getting behind. Paul mentions it can be difficult to have your resume stand out when applying for a role as a manager or director because every organization has them. If you’re an individual contributor in sales engineering, for example, the industry is a lot smaller than you think. Many people know each other. Paul shares the example of getting laid off last year and receiving multiple calls from his network very quickly after it happened. In this industry, our reputation precedes us. And this is also the case for leaders. “If somebody were to call me and say, ‘hey, we want you in this management role….’ Sure, no problem. What’s the organization? Tell me about it. ‘It’s a well-oiled machine….’ Forget it. I don’t want it…. Anybody can just take a well-oiled machine…and maintain it.” – Paul Nadeau Paul would rather lead an organization that is in disarray and needs fixing than a well-oiled machine. You are much more likely to get more leeway for fixing big problems from your boss than when things are working well. Rather than being given a strategy on which to execute from upper management, Paul would rather build the team and develop the plan to do it. We should also remember interviews are for the job candidate to ask questions to interview the company (not just the other way around. This is especially important when applying for a management role. “During an interview process, that’s as good as it’s going to get. Everybody has their best face on at that point. So, if it’s not working at that point, forget it. Just walk….” – Paul Nadeau Ask upper-level leaders in interviews what they expect out of a leader. Paul says sometimes people cannot answer this question because they aren’t sure or haven’t really thought it through. This is the person who would be your boss. If they can’t tell you how you will be measured, that is a red flag! “Are they really looking for a partner? Are they looking for somebody that’s going to help them…get through some of these issues and problems and build an organization that’s going to be world class and is going to be top performing? Or do they just want a placeholder? Do they just want somebody there because I have a req and that’s it?” – Paul Nadeau Watch out for meaningless cliches from leaders that don’t really tell you as an individual contributor what you need to be doing. 23:44 – Specialty Decisions Paul remained in the networking and telecommunications space after returning to individual contributor. Why did Paul choose to take on different specialties over time within these areas? People listening may be afraid to specialize. All of the specializations Paul ended up focusing on came from someone telling him that he couldn’t do it or figure it out. Take ATM (Asynchronous Transfer Mode), for example. It’s a technology used to connect the world together. People thought Paul could never figure it out. But he did anyway. Gigabit ethernet came out right after the ATM wave. There was also telephony (Voice over IP / VOIP and other traditional telecommunications), and one of the companies where Paul worked helped customers in this area. Paul found himself needing to learn about 66 Blocks. “Every part of it, believe it or not, there was an overlap in it. But it boiled down to somebody said you can’t do that. And being the last of 6 kids, I got so tired of hearing that when I was growing up…. And that was a lot of the career, quite honestly, the hard headedness I guess of it and the challenge of it.” – Paul Nadeau Paul learned about Checkpoint firewalls, and when Fortinet entered the scene, he started to learn that technology as well. Looking back on the experience, Paul says the opportunities just dovetailed into one another. “You’re sitting in a room, and they said, ‘hey, we need somebody to do this.’ And everybody looks around…. Yeah, I’ll do it. It’s new. I don’t know anything about it. It’s interesting. Let’s go. What could possibly go wrong? That’s my favorite saying in the world. What could possibly go wrong? …So let’s just go jump in. That’s been my entire career quite honestly…. Sometimes it doesn’t work out so well. Sometimes it works out great. It just kind of depends. Risk taking…as long as it’s a calculated risk, it’s fine. As long as you think it through, you’ll be totally fine with it.” – Paul Nadeau Was learning something he didn’t know anything about the same as walking into an organization that is a complete mess and cleaning it up? Yes! Paul says it’s the same thing. Paul gives the example of leaving a telecommunications company to go and focus on NSX. He knew nothing about NSX at the time, but it had all the elements of his background (networking, security, etc.). Paul didn’t know virtualization, so he decided to build a lab to help himself learn what was missing at the level he needed to learn it (not at an expert level but at a level of competence for his role). It was very similar when Paul moved to his role at Palo Alto Networks. They have an enormous portfolio of products, and Paul had to put in the time to learn the products at the deep level he needed to (i.e. getting his hands on it). “If you’re looking to get into management or you’re looking to get promoted in management and you’re not looking for a mess or somebody that’s almost in tears when they interview you…then you’re not applying for the right job. You’ve gotta get out of your comfort zone. You really do. And I’m not saying go do crazy stuff, but you have to keep yourself uncomfortable in order to keep learning, to keep progressing.” – Paul Nadeau 29:15 – Nurturing Your Network and a Focus on Helping Others Paul does a really good job of nurturing his extended professional network. How does he do it exactly? Paul is a people person, referring to himself as not really introverted but not really extroverted. He likes to have face-to-face conversations with others over a meal, for coffee, etc. COVID was difficult for Paul. Paul isn’t afraid to reach out to people he has not yet met. He will introduce himself to people at industry events, share what he does, and just have a conversation. “There’s a lot of things you can glean…if you ask somebody about themselves and just sit back and listen, man, you’ll learn so much out of it.” – Paul Nadeau Paul tells us we can learn so much about new ways of thinking, progression paths in tech, etc. through conversations with others (much like we’ve showcased on the podcast). It’s ok to reach out to people we haven’t talked to in several years and ask to catch up. Paul sees this as an opportunity to pick up where you previously left off. We tend to fall out of touch with others because of various life events. It just happens. Paul is a true believer in helping others. He gives the example of the tech downturn / season of layoffs we’re seeing right now. It’s an opportunity to have a different kind of conversation with people impacted. “If there’s a layoff, I call. And a lot of times that person…day 2 is like, ‘man, I haven’t talked to anybody in the last day. It’s like all of a sudden, I had the plague. Nobody wants to call me.’ It’s not contagious. The person got hit in a layoff. What can I do to legitimately help you? And I will go to my network…but first I need to find out from you – what do you want to do? Do you want to change career paths? Do you want to stay on a career path? …This is an opportunity for you to kind of branch out a little bit and look at it. And you can have really kind of good conversations with people that you wouldn’t have if they were still employed…. It’s a different conversation.” – Paul Nadeau Once you understand what someone wants to do after being impacted by a layoff, you can then introduce them to someone in your network. Many times, that person will introduce them to someone else because they know about an opening, which creates further momentum. We should not be afraid of making an introduction for someone. Paul tells us he does not like asking for help. “But, at the end of the day, people like to help. That’s what they want to do…. You’re giving them a gift by saying, ‘hey, can you help me?’” – Paul Nadeau If you ask someone to make an introduction for you, it empowers them to take action. If people are not willing to make an introduction for you, it may be a sign of a bigger problem you have. Nick says we’re highlighting the importance of telling people the kind of help we need and what we want to do next. Paul tells a story from early in his career when a teammate of his was laid off. He did all kinds of things to try and help the person find their next opportunity, but what the person wanted was to take some time off before looking for a next role. Paul didn’t understand that when he first dove in to help and advises us to be helpful without being assertive. Paul remembers getting calls after being laid off from people asking what he wanted to do. Some of them were from managers who had no openings at the time but wanted to have a conversation. “It’s rewarding on both levels…. I know now what I can do to help them, and I know what part of my network I can introduce them to based on what they want to do next….” – Paul Nadeau A next step for some people after a layoff may be starting their own business, for example. Paul knows people who became franchise owners after getting laid off from a tech job. Paul mentioned making strong connections with co-workers as well as special interest groups. Which of these special interest groups has Paul frequented over the course of his career, and what would he encourage people earlier in their career to do? There are many different groups that meet based on commonalities like technology, veterans or something else. You might hear about these groups on Facebook or LinkedIn, for example. “If I look at a LinkedIn feed and somebody says, ‘hey we’re having a technology meeting…’ and you have somebody from 5 different companies…I know the companies because they’re in tech. I don’t know any of these people. I’m going. I’m definitely going. Because one, it puts me outside my comfort zone. Second of all, you have some of the most riveting conversations with people you don’t even know, but they’re in the same industry. And now all of a sudden you know them.” – Paul Nadeau Paul says these types of conversations could result in… Someone reaching out to you months later asking for help after a layoff – this enables the conversation about what they want to do and creates an opportunity to help Someone letting you know they will be in your area – this creates an opportunity to get together Listen to Paul tell the story of a dinner conversation that allowed him to help someone on a personal level based on previous experience. “So, it’s not just about tech. It’s just about jobs. A lot of people look at it in the wrong respect, or they look at it like, ‘I need to do it because I need to get something out of it.’ And a lot of times you’re doing it because there’s a lot you can give. There’s a lot of insight you can…give out to help other people.” – Paul Nadeau While having a professional network with strong connections can definitely help you should you lose your job, Paul tells us that’s not the way we should approach building our network. John calls it trying to put good vibes out into the universe. Paul finds people who work in technology fascinating. It takes a special mindset to get into this industry, and there is a very cool commonality in being part of the industry. Some people we meet we may only speak to once. Others we might speak with multiple times. Paul tells the story of someone reaching out to him on LinkedIn, and it turned out the two of them were at a technology conference several years before then. “It is a small world, small industry. It’s all about just getting out there and just who can you help. And then if you ever need help, hopefully it’s there for you.” – Paul Nadeau We’re going to feel better when we’re able to help someone else, but you may never know all of the people you end up helping. Paul recently learned about the impact of a conversation with someone that really helped that person after they lost their job. But Paul didn’t go into that conversation with an agenda. He was just having a good conversation. “Good people know good people. That’s what it boils down to. So, your network, if you’re a good solid person, good engineer…chances are your network is good solid people. It kind of lays the groundwork for helping everybody out. I agree 100%. It’s all about who you can help.” – Paul Nadeau This is a parallel to what we heard Don Jones mention in Episode 137 – Something to Offer, Something to Share with Don Jones (1/2) about managers not knowing if today was a good day. This is very similar to when we help someone with a job search or career advice. We don’t know what the impact is / will be. The intention is to leave a positive trail behind us. Paul says we need to be able to have confidence in what we do, who we help, how we conduct ourselves. “Everything has been a learning experience. Everything has been interesting. Have there been bumps in the road? Yes, absolutely…a ton of bumps. But it’s like anything else. If you’re on a cross-country flight in an airplane, you’re going to hit bumps. There’s going to be turbulence. You just fly through it. And then whenever you get there, you feel a little bit better about it, right? Because you made it through the turbulence…. What kind of impact am I going to make on humanity…at the end of the day? That’s the big goal right there…. How are people going to remember you? Are they going to remember you as the helpful person who just went out of their way to help people out? …It doesn’t have anything to do with money. It doesn’t have anything to do with prestige or being in a public eye. That just has to do with…being a good, solid human being. If you live your life like that…you really don’t have much to worry about.” – Paul Nadeau Connect with Paul on LinkedIn if you would like to follow up on this episode. Any subject goes. Mentioned in the Outro As technical people we sometimes jump into solutioning too quickly. When it comes to speaking to those who have been laid off, we need to ask more questions and perform some discovery. What do they want to do next? This could be an opportunity to brainstorm with that person and point out a role they could be qualified for but didn’t realize it. What if someone doesn’t know what they want to do next? Outside of encouraging the person to give it some thought, you could suggest they read What to Do Next by Jeff Henderson, which was recommended by former guest Daniel Lemire. Paul said the job of a people leader is to protect the company first and foremost. By doing that they will protect their people. This adds another element to the advice Richard Russell shared in Episode 319 – Upward Focus: Manage, Coach, and Create Value in the Space that Fits You with Richard Russell (2/2). Richard said the job of a manager or leader is not to serve their team but to provide value to the business, the organization, and their leadership. Serving the team is the HOW of doing the job and not the what. Do you know someone else who has suffered from resume damage? Send us an e-mail to recommend new guests. We would love to feature their story on the show. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

Imagine transitioning from individual contributor at a company to managing an organization of 155 people. That’s quite the promotion. How would you approach that kind of change? Before you get too anxious about what’s coming, Paul Nadeau, our guest this week in episode 344, has two pieces of advice: stay calm, and don’t panic. Paul’s career began as a Radioman in the Navy where he focused on telecommunications, but he later pursued law enforcement. You’ll hear firsthand about the experiences that cemented this mantra of remaining calm in Paul’s mind and follow him through leadership training in the Navy. Listen in to hear how a specific mix of classroom instruction and practical experience forged a leadership philosophy that is widely applicable both in the military and in the corporate world. Whether you are an individual contributor or a people leader today, you’ll learn how to identify the traits of natural leaders and understand some of the real challenges of stepping into a management role. Original Recording Date: 08-28-2025 Topics – Meet Paul Nadeau, Birth of a Specialty, The Importance of Staying Calm, Leadership Training and Gaining Experience, Assessing Leadership Talent 2:28 – Meet Paul Nadeau Paul Nadeau is a Solutions Consultant at Palo Alto Networks. Paul’s early career began with joining the Navy, but his decision to join starts even earlier. Paul grew up in the Texas Hill Country (areas around Fredericksburg and Kerrville) and attended a private school for most of his young life. Though the academics were great at private school, Paul talked his father into letting him attend public school for his junior year of high school. At the public high school, Paul started to get into trouble. At one point his father had a very frank conversation with him. “You need to do something with your life.” – advice from Paul Nadeau’s father Paul’s father was a Marine who served in World War II and was awarded a Purple Heart for his service. He suggested Paul consider joining the military. Paul’s father wanted him to have some type of trade to fall back on after military service. While the Air Force did seem appealing, Paul ended up joining the Navy in 1988. After boot camp, Paul was sent to all kinds of schools before serving on the USS America in Norfolk, Virginia in 1989. Paul was serving when Desert Storm broke out in 1990. After serving in the Navy, Paul decided to go into law enforcement (something he had always wanted to do). Though his work in the Navy focused on telecommunications / satellite communications, Paul didn’t want to keep doing it after serving in the Navy. He chose to attend the police academy instead. Though Paul enjoyed being a police officer, the pay did not support starting a family. Paul re-enlisted in the Navy in 1995 to once again focus on telecommunications, trading some of the re-enlistment bonus money to use for school. Paul says he did Cisco training, Novell training, Unix administration, and even Windows administration training. He and co-workers were pioneering running these systems across satellite links (from ship to shore). When Paul went into the Navy, they were looking for people who had clean backgrounds. He was able to obtain a security clearance after joining. 7:07 – Birth of a Specialty How did Paul end up in telecommunications after joining the Navy? At age 17 when he first enlisted in the Navy, Paul wanted to do something in the medical field. He was told no. Paul’s second choice for occupation was to be a cop. At the time, you had to have at least 4 years of service to do this. The there was an opening for a job (or ratings as they are called) called Radioman focused on telecommunications. Though the nuclear program was an option at the time, Paul wanted nothing to do with it. “Whenever we say option, it was pretty much like, ‘this is what you’re going to do. We’re going to send you over here, and you’re going to learn this….’ That’s what got me into telecommunications as a whole and into networking. Yeah, it was a good step.” – Paul Nadeau The job placements were generally based on ASVAB scores, and it was Paul’s high scores that presented the opportunities for different fields. Maybe we should have a military recruiter on the show at some point to better understand how this process works? What drew Paul to law enforcement after getting exposure to telecommunications in the Navy? When Paul was a kid (even as young as kindergarten), his dad (a disabled veteran) would walk him to school each day. Every day he would ask Paul what he wanted to do when he grew up. Paul always said he wanted to be a cop. Paul isn’t 100% sure why he wanted to be a cop from such a young age, but there was a state trooper who lived in the same neighborhood. Paul loved his car and thought he was one of the nicest guys in the world. Six-year-old Paul wanted a career in law enforcement. John asks about access to schools in the military. The training seems relevant to a field even for the person who has not yet worked in that field. Paul says his training for Cisco and Novell, for example, was delivered by a civilian instructor who visited the Naval base. It was civilian training paid for and sponsored by the Navy. After Desert Storm while still stationed in Norfolk, Paul wanted to attend Old Dominion University. He remembers having to attend in uniform, but the cost of attending was covered by the Navy. Paul wanted to take advantage of the opportunity to get more education. There was also a Radioman “A” school Paul attended and some “Sea” schools. He learned satellite communication and cryptology, for example. The training courses for Cisco and Novell were mixed into the same curriculum as these Naval schools. The schools you were eligible to attend were based on your job. Paul tells us the Radioman rating from years ago has changed to IT (according to Naval classification / rating). He remembers studying morse code and HF (high frequency) communications (ship-to-ship, ship-to-shore, communication over satellite, etc.). Radio was considered a secure space, and the personnel focused in these areas got exposed to all of the new technologies. Paul liked being able to tinker with it. In addition to attending school, working on a ship 7 days per week is on-the-job training. Paul worked 7 days per week for 7 months during Desert Storm. 14:34 – The Importance of Staying Calm How did military training translate to intense / hostile situations in law enforcement? Paul was assigned to an AMCC (American Mobile Communications Center) unit for Desert Storm, and as a result he went through a lot of training (hand-to-hand combat, logistics training, and other things one might use when forward deployed). “The number one thing that you actually learn, believe it or not, is the key to success – stay calm. Don’t panic…. Panic is the number one thing that will get you in trouble every time…. It’s kind of been the guiding light in life…that one little bit of information.” – Paul Nadeau Paul is a private pilot and understands the importance of staying calm while he is in the cockpit of a plane. This translates to so many areas of life (interactions with kids, situations at work, etc.). Did Paul do anything specific to help himself stay calm? What would he tell people who are not good at this? Listen to Paul’s story of being a field training officer during his time in law enforcement. The instinct to stay calm sort of came naturally to him. When situations begin to escalate, take a second to think about them rationally. It won’t do us any good to let our mind run away with a situation and have it take control of us. Many people consistently fight anxiety. Paul has been fortunate enough not to struggle with it. Was what Paul describes (staying calm even in difficult situations) a result of basic training and becoming a little bit desensitized? Paul tells the story of basic training and getting exposed to tear gas. “You can panic and pass out because you will. You will stop breathing and just hit the ground. Or you can stay calm and regulate your breathing and kind of center yourself. And when you do, you can…overcome the problem or issue. That was my initial wow. This is a really good thing for life in general…. Whenever you make it out, yeah, you’re coughing. You’re hacking. Your eyes are burning…. But you were still able to actually perform. You were actually able to breathe. You were actually able to say a sentence…. They want you to have that levity to do that….” – Paul Nadeau, on staying calm in basic training Paul describes a similar type of training for firefighters. You’re in a giant room of 2-3-foot deep water, and someone dumps gasoline on the water to start a fire with it. Then it’s the firefighter’s job to put out the fire. Despite instructors demonstrating how to put out the fire, people will panic when put in the situation. Some of this may go back to the training Paul received on how to perform under pressure and stress. Maybe we can practice responding calmly to high stress situations? Paul shares the story of being a newly trained police officer. After 2 weeks of training, he was sent out on patrol by the sheriff. The first thing he had to respond to was the scene of a vehicle accident (a head on collision). Paul remembers how quiet the accident scene was. He could hear the cracking of metal and steam from car engines. “All of a sudden you hit that moment of levity. Don’t panic. You can’t panic with this. You got called here to do a job. You’re going to be the only person here that can actually do that job…. You have to kind of be that leader so to speak, that calm amongst the storm, and just do your job. And it’s difficult….” – Paul Nadeau, on being the first to the scene of an accident Even if you are calm during difficult situations like the one above, Paul tells us you have to take time to decompress afterward and work through the situation mentally. “I felt like maybe there was maybe something wrong because I wasn’t breaking down…I hadn’t lost my cool with it…. I was functioning perfectly fine. Did it affect me? Absolutely. There’s no doubt about it…. If you say that it didn’t affect you, you’re not human…. There’s still that human emotion side of it. But it wasn’t to an incapacitating level.” – Paul Nadeau John has heard a panic or anxiety response is a lot like a glass of water. If the glass is close to full, it doesn’t take much to overflow. But if you intentionally keep the water level low, it takes a lot more to cause spills. Paul has seen different people handle stressful situations differently over time. It’s not right or wrong but the way they handle it. Does Paul not have an adrenaline response? A pilot needs a healthy dose of fear when flying a plane. Paul says it’s more of a primal fear response that we’re talking about. Panic in the early days of civilization, for example, might mean you get eaten. 24:26 – Leadership Training and Gaining Experience Where does leadership play into the story? In the military, ranks of E-1 through E-3 are usually entry level. Being promoted to the rank of E-4 is normally when leadership responsibility comes into play. In the area of radio, there were 2 subdivisions. E-4 was more of a leadership role in the message center because it staffed so many more people than the tech control side. Usually there is an E-5 and an E-6 to look over operations as well. Tech control – setting up circuits Message center – where all messages came in (could result of hundreds of messages per minute) Paul says you get leadership training, but it is mixed with a lot of real-world, practical experience. In Paul’s first 4 years, he made it to E-6. In the military, things are pretty black and white without a lot of ambiguity. There are situations both in the military and in the civilian world in which leaders are expected to perform conflict resolution. Listen to the lesson a senior leader in the military taught Paul after his leadership training about the difference between productivity and activity. “We have to be productive, not just active. So, it doesn’t matter if you go have 15 conversations with customers. Did you have a meaningful interaction with them? That’s more important. The same thing when you’re in leadership…if you’re not having meaningful interactions or conversations with the people that work for you or the people that you work for, then you’re missing out. You’re really missing out…. There’s a lot of things you can talk about, but it has to be meaningful. It has to be directional. That’s what I learned…and it wasn’t actually in the training itself. It was actually from a chief warrant officer.” – Paul Nadeau The activity vs. productivity idea applies to any technology job. There’s always another ticket to work on. “Each one of those jobs…yeah, you can do a lot of activity. And you can be…the person that is just burned out at the end of the day…. If you sit back and look at it…, am I truly productive? Have I actually done something that has been great for the customer, good for the company, good for me…?” – Paul Nadeau If we try to get more productive instead of more active, it could reduce our workload. Everyone around you will value this shift. Paul tells us it has a lot to do with meaningful interactions with others. Did the leadership training and the lesson Paul learned from the chief warrant officer make him want to pursue more of a leadership role in the future? “The training itself was fantastic. What I learned was how much I didn’t know. And I learned what level I didn’t know it at.” – Paul Nadeau Paul says anyone can take a group of people and manage them (i.e. make sure the tasks get completed). That’s management. True leaders can take groups of disparate people together and lead the team. When Paul was in the military, he would ask other leaders how he could help the people under him evolve in such a score-based environment. “To me, what was exciting about it was the ability to actually be able to connect and actually be able to help people with their career…. Nothing really dealt with your personal ability, your brand. You didn’t really have a brand, and then you do whenever you get out. And all of a sudden you don’t really know what this brand is because in the military you’re a collective. In the civilian world it’s more of an individual that works in a collective environment…. Taking that and fostering it was a really interesting evolution.” – Paul Nadeau Paul’s first people management opportunity in the corporate world was at a telecommunications company where he worked as an individual contributor. Paul’s neighbor worked for a power company and wanted someone to come run their operations. He had known Paul for a few years and knew he had military experience. The neighbor made Paul an offer, and he decided to resign from his employer. But the story took an unexpected twist when Paul received a call from the CEO of the telecommunications company who would not accept his resignation without a face-to-face conversation. The CEO told Paul they were about to flatten the company’s management structure the following week and made him an offer to be director of worldwide services. Paul had a good reputation, and the military leadership training made him a great fit for the role in the CEO’s eyes. “I thought about it all the way home…. I’ve been here. I know these people. I know where the problems are and where the issues are…. One of the things that I didn’t anticipate – I was a colleague. I went from colleague to suddenly I was in charge…. And there’s a big difference whenever you do that.” – Paul Nadeau, on taking a new role within his current company Paul says taking on the leadership role had a number of trials and tribulations he never expected. But it was a lot of fun and very rewarding. Paul was an ATM Engineer and then had to lead teams of ATM engineers. ATM stands for Asynchronous Transfer Mode in the telecommunications world. “I went from managing myself to managing 155 people in 3 different geos around the world.” – Paul Nadeau Paul had to manage a $35 million profit and loss center that was in disarray, his first task was to systematically understand the problems and prioritize them appropriately. It was a large, complex organization. Paul needed front-line managers underneath him, and it was important to take time to train and mentor those managers (some of which were first-time managers). “Not only am I now managing North America along with the rest of the world…now I have to train somebody on how to be a leader. Now you kind of have extra hours built into your day…. You can’t just do your job and then go home….” – Paul Nadeau, on supporting first-time managers An engineer who once worked for Paul went on to become the COO of a company in Canada. This person thanked Paul for everything he had learned about leadership while working on that team. Paul cites military leadership principles as providing the foundation of what he needed to succeed. “Everybody thinks the military is like Full Metal Jacket…. That’s not it at all.” – Paul Nadeau In his role now at Palo Alto Networks, Paul is part of the Vets Net program. The skills of military veterans are widely applicable outside the military. Was there a specific NCO leadership training track or course that was especially useful to Paul, or was learning on the job from experienced leaders more useful? Paul says it was really a mix of both. There are advancement cycles in the military during which people go up for promotion. This involves taking tests and getting recommendation letters as well as usually going before a board of review. People either get promoted or are classified as PNA (Pass, Not Advanced), but there are only so many openings. When you get promoted up to E-5 or E-6, this is middle management in the military. Once you are promoted to either E-6 or E-7, Paul says there is a structured, required class. One part of the class is instructor-led training. The second class is for reinforcement and absorbing knowledge from other leaders. Paul tells us this is a really good combination of classroom training and hands-on experiential training. Also, advancing from E-1 to E-6 in the same area taught Paul a lot about promotion from within, and he was able to apply this to roles outside the military. 38:48 – Assessing Leadership Talent Paul spoke about hiring new leaders and knowing he would incur an overhead of mentoring a new leader, which sounds like an idea built into the training he received and experienced in the military. “One of the things that’s really amazing to me, and I see this all the time…. People think that because you’re a great engineer, you’re going to be a great engineering leader. They think because you’re a great salesperson you’re going to be a great sales leader…. It’s a completely different skill set altogether. Just because you can sell like there’s no tomorrow doesn’t mean that you’re going to be a great leader….” – Paul Nadeau Paul talks about another type of person that is an individual contributor who may be struggling but has a number of really good skills we might consider leadership skills – being structured, being helpful, wanting to help people. But even if someone has these skills, would they want to be a people leader? They might not. Paul mentions cases where he tried to persuade people to pursue leadership, and they refused because they were happy in their role. There’s another group of people who want to be in management and continue to try for and chase it (like a dog chasing a car). But once they finally get the management role, they don’t really know what to do with it. Once this leader begins to struggle, morale on their team goes down. Sometimes higher-level leaders aren’t training their front line managers or other leaders underneath them. There are multiple negative downstream impacts of this. Paul thinks being a leader should be embedded within us. Even if it isn’t, people can learn how to do it. It can be difficult to find someone who has the skill set of being both technical and being a leader, but when you see it, you know that person needs to be in leadership. If Paul recognized leadership traits in someone, what would he say to the person to encourage them to pursue leadership? Paul would start by asking whether the person had ever thought about leadership. If the person did not think they had the skill set, Paul would politely correct them and tell them why they have the skills to do it. It could be transparency, conflict resolution, not avoiding problems, etc. “The second part of it is…do you know what you’re getting into?” – Paul Nadeau, encouraging someone to become a leader People might not realize managing upward is something required when you’re a people leader. You have to pick your battles, decide what to filter, and provide feedback to your boss (which might mean voicing concerns about an idea being silly). Many times, people not in leadership don’t know they are qualified for it. “You have that person in every organization that when they leave, it’s worse than if their leader left. If that first-level manager left, a lot of times that’s less of an impact than the natural born leaders that you have that are individual contributors on the team. Because that’s who actually rallies the team. That’s who actually gets people to do things.” – Paul Nadeau, on leadership qualities in individual contributors Overall, it’s a fun conversation to have with someone according to Paul, but does the person really know what they are getting into by pursuing people management? Mentioned in the Outro Paul’s move into law enforcement after being trained in telecommunications in the Navy might on the surface look like an odd choice, but he’s modeling going to try something new for the rest of us. Paul wanted to be in law enforcement from a young age. It was his ambition. Past guests like Daniel Paluszek and Brad Christian wanted to try working for startups and decided to make job changes, for example. The decision to go and try something nets us experience we can take to our next role, whatever it may be. We’re confident Paul’s time in law enforcement helped him in his next roles back in the Navy and in civilian life. Many technology companies are looking for veterans who have transferrable skills from military service to apply in our industry. For more stories of veterans whose technology careers began in the military, check out our veteran tag and list of episodes. The comment about the impact of individual contributors leaving a team made Nick think a lot about our conversations on the role of tech lead or team lead. For discussions with guests where we focused on these roles and reasons for taking them, check out these tags on our site: Team Lead Tech Lead Paul’s move to director of worldwide services and the need to focus and prioritize for a large organization reminded us of the conversation about manager priorities from Episode 328 – A Manager’s Preoccupation: 1-1 Meetings and Focused Prioritization with Joseph Griffiths (2/2) Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

Remember all the times someone took a moment to help you in your career? This act of support is what Jason Gass calls a “lost art” in the tech industry. Jason returns this week in episode 343 to share the conclusion of his layoff story. Listen closely to understand why he’s so committed to helping other people in the industry as a result of going through this process and eventually finding closure. You’ll hear suggestions and practical examples for how to keep in touch with colleagues after a layoff, and we emphasize the importance of staying on top of the job marketplace in terms of trends and skill sets. Jason will also share how managing finances carefully can provide peace of mind when it comes to unexpected job loss. Even if you haven’t been impacted by a layoff, stay tuned for practical ways of supporting people who have, and learn why keeping a pulse on the job marketplace can boost your career at your current company. Original Recording Date: 08-07-2025 If you missed part 1 of our discussion with Jason, check out Episode 342 – Planting Seeds: Networking and Maneuvering Unexpected Job Loss with Jason Gass (1/2) Topics – The Lost Art of Supporting Others, Marketplace Analysis and Skills Gaps, Things That Brought Peace of Mind, Reaching Closure and Openness to New Opportunities, Parting Thoughts and Final Lessons Learned Jason Gass joined us as a guest host for a series of episodes reviewing the book Finish by Jon Acuff and is back this week as a guest. The book series on Finish was published in episodes 272 – 275, and you can listen back to them using the link above. 3:16 – The Lost Art of Supporting Others What other types of support does Jason wish he had been given by others that he did not receive, and how can listeners better support others in a layoff situation? Jason says when people announce being laid off on LinkedIn, for example, there are a lot of responses from people. Many times, people say something like “I’m so sorry. Let me know how I can help. I’ll keep an ear out for you.” “They mean well. They absolutely do, but then shortly afterwards, they forget. They have their own lives. They are working their own jobs. They forget that you are on the market looking.” – Jason Gass Jason tells us there were a handful of friends and colleagues who were on the lookout for opportunities on his behalf. At the same tech event where Jason met a hiring manager that we discussed in part 1, Jason reconnected with personnel from a partner he had worked with in the past. By the next week, Jason had lunch with a hiring manager from that partner. Though there were no openings at the time, Jason highlights the unique role of partners that work with multiple vendors and customers. As a result of being in this position, personnel at a partner may know about open roles across many companies. In fact, Jason got a call about a possible job opportunity that originated from a partner contact while he was on vacation. Jason tells us there is a lost art in our industry. All of us started at a junior level and worked our way up to more senior roles, but it took help from others to get there. “I can map it out and pinpoint each and every person that helped me along the way in the career…. They saw something in me. They helped me. They mentored me…just taking a moment and helping out. I try to do the same thing now… We all are in the same boat. We’re all going in the same direction. Things change. Things happen. People are going to go through this, and it’s a tough situation. My thought is that…I had help getting where I’m at, especially though this transition. I should give it back to the next person that’s going through it.” – Jason Gass Jason has been known to reach out to people about job openings in a specific area if he knows about something and feels the person is a strong candidate. Is there a way to stay in touch with colleagues who stayed without it being weird and awkward? Some people think co-workers are not friends, but Jason disagrees with this. He’s found there will be a handful of work colleagues with which we stay in contact after leaving a company, but it depends on the relationship we had with that person while we were at a company. Would certain co-workers be people you would want to hang out with outside of work? This is a good screen for those you would want to keep in touch with long-term. Jason credits a former manager who created a team atmosphere where co-workers became friends. Now and then, Jason will text colleagues who remain at his former employers to see how they are doing. Those people always want to know how Jason is doing as well. “The market will shift. People will end up at different companies. You might start collaborating with each other.” – Jason Gass Jason shares a story of reaching out to a former colleague to discuss an opportunity for them to collaborate even though they work at different companies. Someone leaving a company doesn’t end the friendships made while at that company. John says there is probably a limit to the number of people we can effectively keep in touch with, and we are also at the mercy on platforms like LinkedIn of the algorithm. “You don’t get to see every first-person contact and their job updates. You just don’t. Somebody else is making that decision for you. So, you have to curate your feed and maybe be a little bit more active, too.” – John White Jason shares a story of leaving a company to pursue a role in sales engineering. He kept in touch with a core group of colleagues and even had them over for dinner recently. “A lot of them have moved on to other companies in the area. Once again, we built that synergy up when we were there. We have an ongoing group text message, and every 6 months, we try to get together….” – Jason Gass, on keeping in touch with former colleagues Jason says we might not be able to stay in touch with 10,000 people at a company, but we can stay in touch with 5. We’re looking for quality over quantity. Jason was on a webinar recently and noticed a familiar name. It looked like the name of a good friend from a former job. After exchanging some text messages, Jason found out it was the friend he thought, and they went to lunch not long after that to catch up on how each was doing. When we lose contact with a colleague for a while, it’s not something that happens maliciously. It just happens. Factors like having a family, relocating, and working at another company have an impact. Nick reiterates the impetus is on us to make the time to do things like this. We often allow the tasks of the day or week to prevent us from it. 10:14 – Marketplace Analysis and Skills Gaps As Jason looked for a new role, what kinds of skills gaps did he notice, and did he try to fill any of those during his job search process? Jason says he did spot some gaps. We tend to get comfortable working with a specific focus in a specific space and lose sight of what is happening in the marketplace. Some of the most desired skills from employers according to Jason were AI and containers / Kubernetes. “This is a whole other discussion, but what I’ve seen is that AI is going to help companies adopt containers.” – Jason Gass When cloud became popular years ago, you saw use of the term everywhere, and we wondered if it would stick. Jason says AI is in that same category today. After going through a number of job descriptions during his search, Jason started to notice specific skill sets being repeated. He ended up making a list of those on his whiteboard to either begin pursuing immediately or once he landed a new role. “Two things happened. One, it might apply to my current role. It might help me move into the next role or product set or a promotion. Two, it helps me stay relevant in the marketplace for the future.” – Jason Gass, sharing a perspective on skill sets repeated in job applications Was Jason open to pursuing other types of roles as part of his search, or did he focus only on sales engineering since that’s what he had been doing? Jason talked to some people about becoming a sales rep and even took some interviews for this type of role. It’s something he has thought about for a while, and it could be a future career avenue. “It was something totally different. It also meant that I was going to be looking for some mentorship…. There’s going to be some aspects that I haven’t done yet.” – Jason Gass, on considering roles as a sales rep / salesperson Jason also considered roles outside of the tech industry. With Jason’s love for cooking and barbeque, he thought about doing sales in the barbeque industry. Jason did reach out to some contacts about pursuing this route, but he would have been forced to relocate to take this kind of role (which was not an option). As part of this exercise, Jason found out about some expansion projects happening in his area related to this industry and asked to get connected with the local folks. This allows time to build network connections with local representatives well before Jason would want to make a move. “Can you introduce me to the local folk, the local people, so I can start building up those relationships? So…when I’m ready to maybe transition out of tech, I’ve already made, once again, really good networking connections.” – Jason Gass 13:44 – Things That Brought Peace of Mind In addition to building strong network connections, what were some of the other things Jason did in advance of the layoff that gave him peace of mind? Jason and his wife have consistently reduced their debt as much as possible since getting married. “The hardest part, I think, when someone gets laid off is…how am I going to pay the bills?” – Jason Gass Jason and his wife had a 6-month emergency fund. For most people, the largest bill is a mortgage or rent followed by car payments and other expenses like utilities, food, etc. Jason has been working toward paying off his house. Many people are totally against paying off your house early, and Jason understands this (i.e. some other investment could yield a higher return than paying off the house early). In 2008 during the financial crisis, Jason lived in Florida, which was one of the hardest hit areas. He saw many people lose their homes. “I tell people that gives me options. It lowers my risk because if I got laid off again and my house is paid off, so what? I have a large enough emergency fund to keep the lights on, food on the table, the bills paid…. I don’t have car payments. I don’t have a massive mortgage to pay anymore. It gives me options where I can take a different role in a different industry at less salary, or I can take a risk and change into a sales rep job….” – Jason Gass, on paying off the house Jason says he and his wife also looked at expenses when they sensed layoffs might be coming. They started by looking at which expenses they could cut which would not really impact them. They cut back on streaming services. Jason was spending his time looking for a new job, studying / reading, and attending network events…not watching television. One other example was gym membership. A new gym opened close to home, and Jason and his wife switched their membership to the new gym to save a significant amount of money. Jason tells us he and his wife ate out a lot due to time constraints with both of them working, but he started cooking more often because he was home during the job search. “That worked out really well because you still need to find avenues to break away. You can’t apply for a job 8 hours a day. You literally run out of jobs. So, you still need avenues. I love to cook anyways, so we just went back to doing what I always loved. But it still saved a few bucks.” – Jason Gass Remember the vacation Jason mentioned earlier? The vacation was for Jason and his wife’s wedding anniversary, and the tickets had already been purchased and were nonrefundable. Was it irresponsible to go on vacation after being laid off? Jason struggled with this a little bit. Jason and his wife decided to go ahead and take the trip, but they switched their hotel away from Disneyland property to minimize costs. Taking that short trip allowed some decompression time, and as Jason mentioned, he received a call while on his vacation and had an interview the very next week. John highlights that there were some sunk costs in this scenario, and Jason adjusted what he could to reduce the cost. When it comes to an emergency fund, we can always wish we had more. John reminds us that having something is better than nothing. We should factor in debts that need to be paid off like our mortgage / rent, auto loans, and anything else into the calculations of monthly expenses which need to be covered by an emergency fund. If you have 6 months of money, for example, you want it to be 6 months of covering everything. Jason says when he did get laid off, he and his wife were financially prepared. While this did bring some relief, being laid off is still a “gut punch.” “Let’s face it. The interviewing process is miserable…. You could spend weeks. Some of these places I interviewed with took 6 weeks, 8 weeks….” – Jason Gass With so many people to speak with during an interview process (a recruiter, a hiring manager, possibly a panel of people, etc.), it takes more time than people might think. Jason says he applied for some jobs on LinkedIn and got a rejection message 6 months later. The peace of mind from having his finances in order allowed Jason to focus on the job search process. Jason’s wife was also still working, so that helped. He also did some consulting work to bring in extra money. 20:38 – Reaching Closure and Openness to New Opportunities How do you know when you’ve reached closure after going through a situation like a layoff? The first couple of weeks are difficult. Jason says you go through depression, disappointment, and anger. “I thought I was really prepared…. Then like I said, a few days later it kind of came crashing back on me.” – Jason Gass Jason thinks closure came when he got a job offer. But there’s more. “I was so diligent at finding my next job. I had that pipeline. I had those job interviews happening. When I knew I was interviewing constantly…I knew something would pop. I knew…I would land something. I would get an offer.” – Jason Gass Knowing he had so many activities like interviews lined up helped him forget about what happened to start this entire process. “And in the end, it was a relief. I wasn’t 100% happy where I was at, so this kind of forced me into another direction…. It pushed me to the next level. It really got me out of my comfort zone. The hardest part was all the new technology that I found that I wasn’t staying on top of.” – Jason Gass From a lessons learned standpoint, Jason tells us he still needs to focus on all the things he wrote on his whiteboard (the skill sets). Many of those skills apply to his current role, and focusing on them will keep him valuable in the marketplace. Nick refers to this as the double check mark. What’s Jason’s take on continually taking interviews when we already have a job? Jason says this is a double-edged sword. Interviewing for too many jobs is unsustainable. “This is where your networking comes into play. You’re not going to find your next job, I don’t think, by just going randomly on some company website and filling out a form. It’s who you know.” – Jason Gass As we network with others, we will hear about openings, and people may even ask us if we’re interested in a role. When someone seeks you out about an open role, even if you are happy where you are now, it’s worth having a conversation. “Maybe it’s a great opportunity that you didn’t know about, and it might move you outside your comfort zone into the next level, or…what I learned through this whole process is that you make a great connection. And maybe it’s not the right time right now, but who knows what 6, 8, 12 months down the road…something might happen. You might end up getting laid off….‘Hey, I remember us talking about that position. It wasn’t the right time. I’m now looking. Do you have anything open? Have you heard anything?’” – Jason Gass, on considering new opportunities Jason stresses the importance of knowing our worth in the job marketplace and staying on top of the skill sets in demand. Assuming you do this, you can analyze whether you are happy in your current role or if it’s time to look for opportunities elsewhere. John says we should consider the opinions of others in those relationships we’ve nurtured and be willing to have a discussion if someone thinks we would be a good fit for a job. “You should be always open for a phone call. I think it’s worth listening to someone to hear what they have to say. And if they thought enough of you and think…you would be a good fit, I think that’s very valuable. Because they obviously have a good, high opinion of you.” – Jason Gass John says one way of keeping our eye on the marketplace is looking at these job descriptions to see the skill sets in demand and the compensation range (where it’s listed) to help us make decisions. We can also look at sites like Glassdoor to get an idea of industry compensation. Jason tells us keeping an eye on the marketplace is relevant to our current role and can help in conversations with our manager. If we see specific skill sets in the marketplace and work to get them, perhaps this could result in higher pay or the opportunity to move into a different role. “Just because you know what the market is on the outside and the skill sets they are looking for doesn’t mean you can’t take it internally and have a candid conversation and see if you can better yourself within the company.” – Jason Gass 26:00 – Parting Thoughts and Final Lessons Learned What are some of the final lessons learned or things Jason wishes he had done differently that we did not discuss? One thing Jason highlighted is taking more time for the situation to land emotionally up front. John suggests giving ourselves a lot of space if we’re going through something like this for emotional reactions. Jason says this is important for when we hear others have been laid off. Be conscious of this same thing before reaching out to people who have been impacted by a layoff. It might be best to wait a few days before contacting them. Jason was glad he hit the ground running after being laid off, but he didn’t even take the weekend to pause. He spent it polishing his resume. “I just went 150% into it, and for what? I could have really taken 3, 4, 5 days and allowed it to sink in.” – Jason Gass Jason says exercise or some form of release is really important as you work through the emotions of this type of scenario to prevent taking out frustrations on others. Jason doesn’t feel like he took the time to do this in the beginning because of the fast start. Other things Jason would have done differently include: Jason realized after being laid off that he had not saved e-mail addresses and phone numbers of colleagues. He had to find this information by contacting people on LinkedIn in some cases, for example. Part of staying up to date and keeping a pulse on the marketplace is keeping valuable certifications current. That means seeking new certifications that are valuable or renewing those that continue to be valuable. John mentions technology vendors often allow their employees to take certification exams for free (something to keep in mind if you work for one). Jason keeps his own subscriptions to training platforms like A Cloud Guru (now part of Pluralsight) and KodeKloud. He recently invested in training through Coursera. “Always keep learning. Always try to better yourself. And you don’t have to go out and get 20-30 certifications a year, but you can go out and knock out 1 or 2 a year. That’s more than feasible with all of our schedules. We can take one here or there.” – Jason Gass John says this is about career resilience. “This is something that I need to do for my personal resilience. You get paid for work, but you don’t get paid for career. And you’re career planning when you do that.” – John White Jason says we can turn our learning into content we can post online. If you are studying for a certification, you can take the content and post it online to share what you learned that day. Consistently posting content keeps you in the algorithm so that you continue to pop up in people’s feeds. Someone may see content you’ve posted and think of you for a job opening. If you want to follow up on this discussion with Jason, reach out to him on LinkedIn. Mentioned in the Outro In this week’s discussion, we spoke to Jason about the types of roles he was considering. This was not something he only thought about once the layoff happened. We need to consider the types of roles we might like to do as part of overall career planning. Check out the Must Have List from our friends Liz Bronson and Kat Troyer at RealJobTalk to help think through this. Check out Episode 299 – Chronic Stress: Connecting the Dots between Layoffs and Burnout with Cait Donovan in which Cait highlights getting a handle on your expenses as a first step after being laid off to provide a sense of control. Here’s a great book recommendation from former guest Daniel Lemire – What to Do Next by Jeff Henderson Check out the Unicorns in the Breakroom 6-part series of episodes on job search and interviewing starting with Episode 11 – Job Hunting. They also have Episode 17 focused on survivor’s guilt and the impact of layoffs. Remember to check out following free resources: Our Layoff Resources Page – a list of the most impactful conversations we’ve had on the show focused on the topic of layoffs. The Career Uncertainty Action Guide with the 5 pillars of career resilience and AI prompts to help you work through overwhelm, financial planning, and a layoff scenario Do you know someone who has a layoff story that needs to be told to encourage others in the community? Send us an e-mail to make guest suggestions! Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YoutTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

“Unfortunately, your role at this company has been eliminated.” These are the words none of us want to hear, but it’s a reality many in tech are facing. What would you do if that unexpected call came tomorrow? This week’s episode is one we all need to hear. Jason Gass returns (this time as a guest) in episode 342 to share his story of navigating a layoff. You’ll hear about Jason’s initial reaction to the news and what he did next to take action. Listen closely to hear how Jason treated the job opportunities he was targeting like a sales pipeline to remain focused, where he looked for emotional support, the tools that helped sharpen his resume, and how nurturing and leaning on his professional network made all the difference along the way. Original Recording Date: 08-07-2025 Topics – Jason Gass Returns, When a Phone Call Changes Everything, Sources of Support and Maintaining Connections, Emotional Balance and Job Opportunities as a Sales Pipeline, Helpful Tools in the Job Search Process, The Network Effect 2:20 – Jason Gass Returns Jason Gass joined us as a guest host for a series of episodes reviewing the book Finish by Jon Acuff and is back this week as a guest. The book series on Finish was published in episodes 272 – 275, and you can listen back to them using the link above. The book series idea came from Jason, and so did the idea for the discussion today. We wanted to take this opportunity to tell Jason’s story through the lens of layoffs across the technology industry. Many of our friends and colleagues in the industry have been met with unexpected job loss over the last couple of years. Jason says it’s been a journey going through this same process, and he’s here to share what worked and what didn’t work. 3:32 – When a Phone Call Changes Everything What type of role was Jason in before the layoff happened, and what did he like most about it? For about the last 5 years, Jason has worked in a sales engineering / technical pre-sales role for different technology vendors. As part of the role, Jason has greatly enjoyed working with both customers and partners to solve problems and improve the day-to-day lives of technology professionals. The work is dynamic, and each customer has a different problem. What was the day of the layoff like, and what was Jason’s immediate reaction? Jason was working at a company that had been previously acquired. There were changes happening, and Jason and his teammates knew they might be impacted by these changes but had no idea of when. Jason remembers getting a call to let him know his position was being eliminated. It was a very quick call and very formal. Once Jason’s phone rang that day, he knew exactly what was going to happen. “I was prepared as much as I could. It’s still a gut punch. Man, I can’t believe I didn’t make the cut. What’s wrong with me? Why was it me vs. somebody else?” – Jason Gass, on what goes through your mind in a layoff situation There was still negative self-talk despite expecting that layoffs were going to happen. Jason tells us he was laid off a couple of times during the 2008 financial crisis. “Looking back, that’s probably a good experience because I’ve gone through it once before. The one thing…I learned from that experience is these things happen, and a lot of good things happen afterwards. But it’s hard to have that lens when it first happens…. Everything emotionally hits you. All of those thoughts start going through your head….” – Jason Gass People who get laid off are worried about paying the bills, supporting their family, and how long it will take to get their next job. It’s easier to see the positives that came from a situation like this when you’re looking back on it later. Maybe someone took a different role, got to work for a different company that excited them, or even made more money. Jason says we can get complacent and lose sight of our value in the marketplace. A layoff situation can force people out of their comfort zone. John reminds us that we’re not living in the age of having a job for life. Companies can be pretty ruthless when eliminating roles, and this is a fact. Jason says back in 2008 he started thinking of himself as a line item on a spreadsheet. Though it can be hard for us to think this way, it’s business and the way the world works. “It reminded me…I’m still a player in this game, and I still have control. It’s what I do with that control.” – Jason Gass This line of thinking reminded Jason to understand his value in the marketplace and to keep his skill set current to provide options if a layoff happened or if he just wanted to make a change. Nick thinks we might not be mindful of the control we have or might not exercise it because we’re so focused on our daily work. This is partially due to craving the structure of routines. John says if we acknowledge a layoff as a possibility, it means we have to react to it before it happens (even if it doesn’t happen). But a lot of times we don’t want to have to think about it and choose the path of avoidance. If you get laid off, Jason says it’s ok to take time for yourself (a few days, maybe even a week to let the news sink in). In fact, you should. He did not do this and started making calls within 5-10 minutes of receiving the news. “It caught up with me about 4 days later. That emotional drain finally came down on me, and it mentally drained me.” – Jason Gass In giving advice to people who have been in this situation (unexpected job loss), Jason tells people it’s ok to take time to process. But after that, the job is to find a new job. This means keeping a normal, structured routine. If you get up and go to the gym every day, keep doing it. At work we would be completing a specific task / set of role-specific tasks. The tasks you need to complete after being laid off include things like revising your resume, updating your LinkedIn profile, contacting people in our network, and finding in-person meetup groups to attend. Jason emphasizes the importance of meeting people in person for professional networking and support. It’s a bit of a lost art after COVID. Listen closely to Jason’s description of one specific local meetup group supporting people looking for employment. 10:34 – Sources of Support and Maintaining Connections Sometimes when people lose a job at a specific company, they struggle with their identity. Was this a challenge for Jason? Jason has held jobs he loved, but they were not his only identity. Many people consider their work or their job the entirety of their identity. “There’s things outside the workplace that I have so much more passion for.” – Jason Gass Knowing a layoff might happen helped Jason prepare and prevent too much tying of identity to the job. But he also stayed educated on the opportunities available in the job market. Being in Dallas / Fort Worth, Jason has read about many companies moving their headquarters to this area. But with many others in the market for jobs right now, there is a lot of competition. Was there a specific process Jason went through to combat the emotional drain of the layoff event we discussed earlier? Jason says there were good days and bad days. Some days were filled with many interviews. Others were filled with rejection and news that a specific interview process would not continue. Some of the things that really helped Jason through this process were… Talking to his wife Keeping in touch with colleagues who had been laid off as well as those who remained at the company One of Jason’s colleagues created a chat group with displaced people across the country who were going through the same thing, and it was great to be connected with others who were going through the same thing. An account rep Jason worked with had been laid off a number of months prior to Jason but had gotten back on his feet. The account rep told Jason to call him any time, even if it was to vent and let out some of his emotions and frustrations. “I didn’t realize how important that was when I gave it to him until I needed that same platform.” – Jason Gass, on getting support from a co-worker he had previously supported after a layoff event John highlights the importance of having different people who can support us through these difficult situations. It’s not just family or a specific peer. It’s many others who can support us. Jason highlights the group chat as something that worked extremely well. If Jason saw a job listing that might help a member of the group, he would share it. This included roles that were not suited for him as well as roles that listed openings in multiple locations. Jason would even offer to introduce members of the group to people he met as part of the interview process where applicable. “One of the nice things is I met a lot of great people. I didn’t get chosen. I might not have been the final candidate through the process, but I made a lot of great connections through the whole process. So even if I didn’t get chosen, I still made connections where I could say, ‘hey, I know someone over here. Do you mind talking to them?’” – Jason Gass Did Jason ask people he met through interviews to stay in touch as a way to maintain connections over time? Many of the people Jason interviewed with would connect with him on LinkedIn. In cases where he was not selected for a role, people encouraged Jason to reach out to them in the future. Jason made a point of letting people know he appreciated them taking the time to interview him and would often send LinkedIn messages of thanks. Jason tells us that solution engineering / sales engineering is a big field, but there aren’t a lot of players. “I relate it to people like trading baseball cards. You start seeing the same people. They just rotate from one company to another…. It didn’t work out this time around. That’s understandable. We don’t know where we’re going to be three, four, five years down the road.” – Jason Gass John tells us hiring managers are always looking to build a bench of talent from which they can pull at a later time. Likely any candidate who made it to the final round of interviews could do the job well and is someone a hiring manager would want to keep in touch with for possible future openings. Jason tells the story of when he first got into sales engineering. He interviewed with a company and did not get the job at the time. But he stayed in contact with the hiring manager on LinkedIn. The hiring manager would see Jason posting content on LinkedIn now and then. Roughly 3 years later, the same hiring manager had an opening on his team. Jason reached out about the role, and the hiring manager both remembered Jason and said he would love to have Jason interview for the opening. 16:52 – Emotional Balance and Job Opportunities as a Sales Pipeline John brings up the necessity of emotional balance during a job search. The job search process is like sales processing or maintaining a sales pipeline. There seems to be more at stake in selecting your next career move versus making a sale. How did Jason handle the emotional regulation? Jason thought about applying for and looking for jobs just like a sales pipeline. Looking back, he calls it a marathon. Until you get an offer letter that you will accept, you keep focused on pursuing opportunities in your pipeline and generating new opportunities. This means continuing with interview processes, networking, and submitting applications. Jason was laid off at the beginning of November. He interviewed hard for 4 months and says it was even more difficult than working a normal job. “And I think the hardest part about it is that you always have to be on. You always have to be ready to take a call from a recruiter or a hiring manager…. I remember I interviewed so much in 1 week I talked so much I lost my voice…because you’re always on…. It’s hard. We’re not used to talking that long…. We’re not going out there and talking for 4, 6 hours a day like a professional speaker.” – Jason Gass At this time of year, some companies were looking to fill roles quickly. Jason recounts being out Christmas shopping and being asked if he could take a call about a job. Other times he had to take 4 calls in a row with only a short break during the entire period. Nick mentions people like Brendon Burchard work out heavily to be able to speak for 9 hours per day. Jason says he was mentally exhausted after so much interviewing, but it was good from the standpoint of having so much activity. “I knew something was going to happen. I knew offer was going to come. I just had to stay diligent.” – Jason Gass Was there a specific system Jason used to track all of the applications and interviews and follow ups he needed to do? Jason kept track of where he applied, who he spoke with, and action items. He would keep track of salary information for the roles as well. Many of the jobs had a large salary range, and it was important to see where he would be in that range. Jason shares the story of a friend who applied for nearly 1000 jobs last year. This friend had multiple resumes and was tracking which resume got the most responses and focused time on refining it even more. Many job applicants are taking a shotgun approach to applying for jobs, and it is causing some problems. A single job posting might get 500 applicants, but how are candidates filtered on the back end? A friend told Jason the number of applicants for a job on LinkedIn is really how many people clicked the link to apply. But not everyone who clicks the link fills out the application. For a position with 500 applicants, someone would remove people not in the right geographic area. That might get it down to 300. If you trim down the candidates who don’t have the right skillset, that might narrow the list to 100 people to choose from for interviews. “It’s caveats on both sides because you might be a great candidate for the role. You might read that description and say, ‘hey, I can do everything in that job. But how do I get my resume noticed if there’s so many other people?’ …There’s a lot of cloudiness in the water. So how do you make yourself stand out?” – Jason Gass 22:57 – Helpful Tools in the Job Search Process John agrees with the recommendation against playing a numbers game. He advocates qualifying the positions you’re looking for and doing a custom resume for each position. The key words and skills will be different for each job to which you apply. Job descriptions may even have variations of the same term / terms. He gives the example of MEDDIC and MEDDPICC as qualification tools for selling. The time and effort for a custom resume are significant. Jason was given advice to use AI to help with his resume. There are many tools out there. “I feel like we’re having AI wars. We have AIs writing resumes, and then we have AI analyzing the resumes before a single person even looks at it.” – Jason Gass Jason mentions LinkedIn’s Premium Career subscription as a helpful tool. There are AI tools built into it. Jason liked the fact that he could take his resume, compare it to a job description, and the tool would make suggested enhancements to the resume to fit the specific job description. Jason was able to spot patterns in the key words that would come up again and again, and using the tool helped him tailor a resume to these specific systems for job applications. “And, of course, AI is not the last step. After AI, you still need to go through and groom it. Is this accurate? Is this true? Does it sound like me? You still have to go and do the finishing touches.” – Jason Gass With the help of the tool, Jason was able to get his LinkedIn profile up to date, write some cover letters, and write some messages to contact some hiring messages through InMail. It helped make Jason’s writing better on all of these fronts. “I finally got comfortable enough just reaching out to people that I may not know.” – Jason Gass Jason made a list of the top companies he wanted to target in his job search. If he knew someone working at a specific target company, he would reach out to that person. Reaching out to people you know at companies can help you get connected with a recruiter or hiring manager and get a resume in front of them. In the case of companies where Jason didn’t have any professional connections, he would find the local sales engineering manager and reach out to that person. He calls this “planting seeds.” Jason would express interest in the company and ask these managers if they know of any openings coming available in the next few months. For context, Jason was reaching out during the 4th quarter of a lot of companies, and some tend to open new roles in their 1st quarter of the following fiscal year. John emphasizes that hiring managers like to have a bench of talent they can put into their pipeline when a job requisition opens. There is nothing wrong with contacting a hiring manager, stating that you understand there are no current openings, and asking for an informational interview. This allows the manager to get to know you a little bit and might help put you on that bench of talent for future consideration. 27:59 – The Network Effect Jason says he never turned on the Open to Work indicator on LinkedIn. “For the first few months, I just targeted my network or LinkedIn, and in the end, that’s what got me 95% of my interviews…working my network, talking to people, connecting with people through several different means and avenues.” – Jason Gass Jason got the role he has now as a result of leaning on his professional network. Jason tells us when he was first laid off, he started calling people in his network inside the company first to look for open roles. Even though his role was eliminated, Jason understood other roles within the company could still be a good fit. Jason also mentions calling a long-time friend and someone who was his sales engineer from years ago. This friend had moved on to another company over time. Once Jason relayed the story of what happened, his friend found out who the hiring manager was in Jason’s area. “He didn’t know the hiring manager. But he found who it was, made an e-mail introduction, and I found that the company was a sponsor at a local tech event coming up in 2 weeks.” – Jason Gass, on leveraging help from a friend Jason asked the hiring manager if he planned to be at the local tech event, and as it turns out, the manager would be there. After meeting the manager in person at this event, Jason was asked to share his resume with the hiring manager. Though the hiring manager shared Jason’s resume with others he knew, there were no openings at the time. But Jason’s friend reached out to him months later about something different. “Nothing came out of it then. We’re talking November time frame…. That seed that I planted in November ended up sprouting in February and then in the end landed me a position.” – Jason Gass How did Jason know who to call first when the layoff happened? Did he have a mental list in mind already? The first person Jason called was a manager of his from a previous job who had remained a mentor for many years. They had talked fairly recently, and Jason had been wondering if the role he was in really was the right one. Jason wanted to understand what else might be available and wanted to reach back out to the former manager to see if he knew of any openings. “I talked to probably a dozen people the first day. I got the call at like 9 o’clock. I was on the phone until 5 o’clock that afternoon talking to a variety of different people.” – Jason Gass Jason talked to other colleagues inside the company to see if they were safe from the layoffs or knew about internal openings in other departments. People with longevity at a company often know about job openings quickly. “I think the first good step is saying…if I don’t have to go out there in the wild, wild west and look for a whole new job…if I’m happy with the company…can I just migrate into another role? Could I cover a different territory? Instead of being pre-sales, maybe I could go to post-sales. Or could I get into consulting or something of that nature?” – Jason Gass Nick suggests if you think layoffs will happen at your company, consider making that top 5 or top 10 list of who you would call to store where it can be retrieved if you find yourself in the same situation as Jason. “I think about it, and a lot of times people reach out only when they want something. How long did they maintain the relationship? I’ve learned to try to keep some ongoing relationship with my network.” – Jason Gass People will post about work anniversaries or achieving certifications. Consider sending them a message to ask how they are doing. Suggest you catch up with them. Jason says it doesn’t have to be as frequent as once per month and could even be once per year. Jason mentions the importance of publishing content and has posted about his involvement in Toasmasters over time. He tells us this would come up in conversations when he was looking for work. “People I hadn’t seen in years. ‘Hey, I know we haven’t talked in a while, but I’ve followed you on LinkedIn and saw that you’re in Toastmasters…. I’ve always thought about doing that. Can you tell me more about it?’ That rapport that we may have had years ago just picked right up…. I find it really important to maintain some form of relationships with…my network so that when I did reach out and say, ‘hey, I’m looking for a job’ it wasn’t about what can you do for me.” – Jason Gass Jason had been maintaining relationships with people in his network independent of whether the layoff was going to happen. He reminds us that the tech space is small but ever changing. Mentioned in the Outro Any idea who you would call if this happened to you? It’s good to have a list of people in mind, and it’s good to start connecting with people in your network more often than you are now. Amidst our busy lives, we need to make time to connect with others both inside and outside our company. In Episode 317 – Own Your Job Search: Be the Captain, Find a Harbor Pilot, we talked about the concept of a harbor pilot who can help you navigate the hiring process at a company where you would like to work. Jason leveraged his professional network to do this. Plant those seeds now! Are you attending in-person meetup groups? If not, Nick suggests going to any meetup group that fits an interest you have, even if it falls outside of technology. You would be surprised at how many people you meet work in tech but look to other interests as well. Jason mentioned being part of a chat group of other people who also experienced unexpected job loss. Would you be willing to lend a helping hand to others like he has? Remember to check out following free resources: Our Layoff Resources Page – a list of the most impactful conversations we’ve had on the show focused on the topic of layoffs. The Career Uncertainty Action Guide with the 5 pillars of career resilience and AI prompts to help you work through overwhelm, financial planning, and a layoff scenario Do you know someone who has a layoff story that needs to be told to encourage others in the community? Send us an e-mail to make guest suggestions! Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YoutTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

What can you do to stand out as an individual contributor on a large team? The first step is seeking absolute clarity on your role, and it begins with an honest conversation between you and your manager. Al and Leanne Elliott are back with us this week in episode 341 to continue the discussion about life in flatter organizations with larger teams. Come learn why managers need a support network to be more effective with their team, how to gain role clarity while making your manager look good, and what it means for a leader to champion their people. Pay special attention to the list of introspective questions that can help us take control in our work environment during uncertain times. You’ll also get to hear how Truth, Lies and Work has evolved its content focus over time to serve an even wider audience and what Al and Leanne have learned as content creators. If you’ve never had a reason to watch Ted Lasso, this episode may contain a compelling reason to start. And if you’re looking for a role model for being a stand out on your team, we will introduce you to Bob during this episode. Original Recording Date: 07-12-2025 If you missed part 1 of our discussion with Al and Leanne last week, check out Episode 340 – Task Cohesion: Managing a Larger Team in a Flatter Organization amidst a Climate of Uncertainty with Al and Leanne Elliott (1/2) Topics – Go Ahead and Pull the Cord, Hiding the Wires, Gaining Role Clarity and Gracious Managers, Introspection Gives Us Control, Creating Content for the Chaotic World of Work Both Leanne Elliott and Al Elliott are back to join us for part 2 of a special discussion today. They are the hosts of Truth, Lies & Work and have each been guests on the show in the past (but never at the same time). To listen to the episodes featuring Al as a guest, check out: Episode 235 – The Best Bad Option with Al Elliott (1/2) Episode 236 – Having the Vision, Charting the Path, Removing the Blockers with Al Elliott (2/2) To listen to the episodes featuring Leanne as a guest, check out: Episode 237 – The Psychological Transition of Layoffs with Leanne Elliott (1/2) Episode 238 – Managers as Culture Keepers with Leanne Elliott (2/2) 3:05 – Go Ahead and Pull the Cord Nick says this sounds like the recent solo episode John recorded (Episode 334 – First Time Manager – Your Old Job Description Has Been Deleted) and fighting the urge to answer the question. John says that was directly from a coaching course he took as part of first-time manager training. It seems less efficient timewise when someone comes to you with a problem you could solve quickly. It’s more efficient in the long run to guide someone through learning how to solve the problem themselves even if it takes longer in the short term. Leanne says you’re building a person’s capabilities, confidence, and thinking process. This also creates a safe space for the person to ask any question. This genuine human interaction breeds trust, connection, and psychological safety. “You’re not only gaining that 30 seconds back for every problem in the future. You’re gaining enormous amounts of trust and connection, which are two vital things that you need as a manager, and generally, in organizational life we really need right now.” – Leanne Elliott Al references a recent podcast episode he and Leanne did with Andrew Palmer (the host of Boss Class) in which Andrew recounted his trip to a Toyota production facility in the UK. In the Toyota facility there was a specific cord anyone could pull to completely stop the production line. Someone may stop it to ask a question or if something doesn’t look quite right, for example. The cord is also pulled to celebrate something or to share good news. How many times do you think the cord gets pulled per day for a facility with 2000 employees? That cord gets pulled (and the production line is stopped) on average 14,000 times per day (an average of 7 pulls per employee). Al says this is a great testament to psychological safety for employees. John agrees and says it’s a testament to the organization’s culture. Al says he and Leanne asked Andrew about new employees. New employees are encouraged to pull it to get that out of the way. Leanne says good managers can give their employees the opportunity to pull the cord by asking for their feedback in different situations and giving them a voice. "You’re showing that openness and vulnerability to go, “have your say. Your voice is important here too.’ And that’s probably the first baby step…you’re literally asking them to pull the cord.” – Leanne Elliott 8:03 – Hiding the Wires In Episode 238 – Managers as Culture Keepers with Leanne Elliott (2/2) we talked about the concept of managers hiding the wires. If an organization is flatter and managers have more employees, is it more difficult for a manager to hide the wires, or is it the same? “Hide the wires” means you’re making sure as a manager that the emotional blowback or frustration from a situation doesn’t impact one of your employees. Leanne says it may not be harder or easier based on the size of a manager’s team. It’s more important that a manager has a support network with which they can share some of the emotional load or stressful situations. This could be a senior manager, a peer, a coach, a mentor, or even a therapist. “It’s finding something beyond your immediate team context and the support you need to offload that…. It’s what psychologists call emotional regulation. It’s understanding, having that self-awareness…. ‘I’m feeling angry, but expressing that anger in this context right now isn’t going to serve me or my team….’ Being mindful and having that self-awareness of how you operate emotionally in terms of your behaviors is going to have a direct impact on the mood and motivation of your team. So, if that’s not going to be positive, then hide the wires.” – Leanne Elliott, on hiding the wires as a manager Leanne says the anger or frustration mentioned above still needs to be expressed, but it can be done via a manager’s support network. John tells us it can be very difficult when you’re asked to relay something you do not agree with or have emotional friction with to prevent passing along your reaction. But doing this can cue people in a way you don’t want. Part of a manager’s job is to be an intermediary and get feedback from the people they manage, aggregate it, and send it to upper-level leaders. Don’t assume your team will have the same reaction to something that you had. Your reaction may be the result of just having a bad morning, for example. The idea may not be that bad. Try to avoid setting a cognitive bias for your team. “Either way you don’t want to put them in a position where they have to do the work to change your mind before you can explore the idea or the possibility. You want to go to neutral space to understand exactly what their thoughts are. Chances are, they’re probably going to be the same as yours. On the off chance that they’re not, then yeah, it’s worth having some patience in that moment.” – Leanne Elliott John reminds us that the person who passed an idea to a manager to relay to team members may not have been the originator of the idea either. 12:14 – Gaining Role Clarity and Gracious Managers What if someone is an individual contributor on a large team of 15-20 people? It might be difficult to stand out as a high performer or to get time and attention even just for help. What ideas and guidance would Al and Leanne offer? Al tells us it will depend on what the manager of the team is like. The manager could be overwhelmed or feel they are short on time to accomplish anything. Suppose we assume it’s a good manager who is on the lookout for high performing team members. Sales environments, for example, are very target driven. To stand out in this environment, you have to be good at sales, close decent deals, and be a decent human being. If you’re a back-end developer, the target may be number of commits or reducing the number of product bugs. It’s difficult for Al to find something universal that will make your manager appreciate or notice you. Is there something? Leanne says the example of sales is great because there is role clarity about what the job is and what the measures of success are. “There’s so much clarity in sales because as an employee you know exactly what it is that you have to do at a transactional level to deliver the outcomes of your role.” – Leanne Elliott, on role clarity in sales Leanne suggests trying to gain role clarity through an honest conversation with your manager. Many people do not have this. What if we asked our managers what their expectations are of us, the objectives we need to hit, what good looks like in our role, what the manager wants to deliver, and how to make them look great? “I think ultimately as long as you know exactly what you have to deliver and you’re doing what you can to deliver it…and where you can, above and beyond…and where you can, make your manager look good or make their life easier or the life of your colleagues easier…that’s what exceptional performance looks like to me in a non-sales role. It’s somebody who is very clear on what they need to deliver, very willing to support their colleagues in helping them deliver…for the team, and very much there as a supportive member of staff to the manager….” – Leanne Elliott This isn’t necessarily easy in practice. For you to get the role clarity we’re talking about, your manager must first have clarity about your role. But this is a great starting point according to Leanne. Should we seek role clarity from our manager on a regular basis, especially if there has been a change in team or greater organization structure, for example? Leanne says this is an opportunity to be curious, especially during times of change, and to have an open conversation with your manager. You can ask about the expectations of the team and the organization for example. This goes back to concepts surrounding the formation of teams. Leanne highlights teams forming, storming, and norming. Part of this process is getting clarity on what the team is trying to achieve and your role in delivery of the mission. If your manager isn’t providing that clarity, it’s ok to be curious and seek it out. John speaks about some administrative responsibilities of management and needing certain tasks complete by team members based on weekly deadline. There were people he consistently had to remind to complete the tasks and those that never needed to be reminded. Having a much larger team makes it even more important to be clear on required tasks and deadlines which will help the team deliver. What if we asked our manager whether letting them know something was completed before a deadline would make their job easier? “If you say you really want to stand out in a team, how many of your teammates…are going to say…‘how do I make your job easier? How do I make you look great to your boss?’ How many people would think to ask that question? So, if you are looking for that one hack…that seems to be it….” – Al Elliott Leanne would add that managers should be gracious to team members who do miss the deadlines and try to figure out why it happens (seeking to understand the barriers to task completion). Team members may be overloaded or may need to go through the process again to fully understand it. Neurodiverse colleagues can benefit from strategies like body doubling. Leanne reminds us that very few people seek to do a bad job and are doing it to be annoying. In the cases where they do, it would fall under workplace incivility. When only a handful of team members are not meeting deadlines, it could very well be there is something they do not understand. John assumes good intentions even when people miss deadlines and likes the idea of grace from the manager seat. These scenarios can be opportunities to coach and to understand what might be underlying specific behavior. Leanne recounts someone she managed being exceptional in all aspects of their role but the administrative paperwork. This person would miss deadlines, and it caused downstream problems. Listen closely to how she handled it and what happened next. “My breakthrough moment was when I said, ‘I can’t make you look good if you’re not giving me the outcomes. I know how great you are. But the people above me, they don’t know how great you are. They’re just looking at outcomes on a spreadsheet.’ And that for her was that connection….” – Leanne Elliott, on helping one of her direct reports understand the importance of administrative tasks Al mentions a French teacher from his school days who knew he was skilled in French but couldn’t grade him that way because he didn’t turn in homework. After the conversation with the teacher, Al changed his behavior and earned a good grade. In each of these examples (the manager, the teacher) made it clear they wanted someone to do well. “What a great rule of management. You want to be a great manager? Champion your people. Celebrate them. Show off their achievements, and let them know…that you are on their side and you want to show off their achievements. Because that as a manager makes me look great. If my team is smashing it, then I’m doing a great job too. We’re all on the same side. We’re all going to win together…. Imagine sitting down with your boss, and they said to you, ‘I’m on your side. I want to celebrate everything you do.’” – Leanne Elliott Al says one might be tempted to think that on a large team others have to lose in order for you to win, but we shouldn’t think that way. It does not have to be a zero-sum game. This idea of showing a team member you are on their side is a coaching moment. Delivering a message of “help me help you” with compassion and honesty can be very effective. Al mentions a recent interview with Jeff LeBlanc who did a study on kindness in leadership. In that discussion they talked a lot about the TV show Ted Lasso. Jeff LeBlanc feels Ted Lasso as a character portrays the perfect manager – a blend of kindness, thoughtfulness, humility, and an unwillingness to give up on people. Nick has never seen the show but will consider watching it now. Check it out and let us know what you think. John reference’s Ted Lasso’s commitment to a process for improving the team over the outcome of winning. 27:27 – Introspection Gives Us Control Is there a secondary theme in what we talked about of encouraging individual contributors to be entrepreneurs of their own reputation? Think about wanting to start something, wanting to solve problems, etc. Maybe we could apply this to our own reputation and ensure it’s strong? Al says in some ways an entrepreneur might not like taking instruction. “Most people want to do a good job. Most people want to be recognized for doing a good job. Is it not as simple as…well, what does a good job look like? Let me just strive to do that every single day. And then all the hacks and tricks and building your internal brand up through an organization or being entrepreneur, it doesn’t matter…. People just go, ‘Bob…he always delivers a day early, and it’s always exceptional work. And do you know what? If he’s got a problem or someone’s got a problem on a Friday afternoon, he’ll drop what he’s doing and go over and help them and then go back and finish his work. Be more Bob.’” – Al Elliott Leanne says this thought gives us control in a work environment where we feel we are lacking control. Here are some introspective questions for those feeling unsafe at work, fearful of losing their job, or who have been laid off: What type of professional do I want to be? What does meaningful work look like to me? What do I want to be remembered for? What do I want to be known for? What work makes me proud? Who am I as a person? What are my values? Examples are things like kindness, a belief in equity, etc. “It’s such a wonderful moment to actually think about what do I want work to mean to me. And in that will come an intentionality around the behaviors you enact and the way you operate in the world and your workplace…. You will craft that, whatever you want to call it – that brand, that presence, that Bob…. But I think it’s a wonderful time to do that introspection and think about exactly what it is you want to do, how you want to do it, where you want to do it…and that intentionality will trickle over time. In a world of uncertainty, what a wonderful way to feel like we’re gaining / taking some control back.” – Leanne Elliott 31:03 – Creating Content for the Chaotic World of Work As podcasters, Al and Leanne have to be very intentional about the content they create and put out into the world. The theme of a podcast can change and be refined over time. What have Al and Leanne learned from this process, and what have they learned about what culture is and is not as a result? When Al and Leanne started Truth, Lies, and Work it was about helping business owners and leaders and sharing best practices for environments that did not have the type of support internally from HR professionals or business psychologists. This intention is still at the core of the show. The changes to the show since its inception have been in line with the chaos the world of work has been through over time. They added a second episode per week called This Week in Work to help address issues no one else was addressing. There have been poor practices from business leaders such as attacking specific groups of people or in handling mass layoffs that have a much deeper impact on human experience and organizational effectiveness. “So, it’s calling out bad practice like that that is being promoted in mainstream news that this is a great thing an organization is doing. It’s not, and this is why.” – Leanne Elliott, on This Week in Work This Week in Work is mainly 3 segments: Looking at the new stories of the week – including a recent story about a company called BrewDog and steps taken to try and fix its toxic culture Highlighting hot takes or good thoughts from lesser-known industry names (i.e., occupational psychology students, new entrepreneurs, those who want to support a cause, etc.) Workplace surgery – questions from listeners sent in via e-mail and social media (many of which are now coming from employees instead of business owners) “We’re doing episodes per week, and every single week we try and make it just 1% better. And some weeks we make it 1% worse…. The core thing we want people to get is that culture isn’t about having the perfect workplace. It’s about just trying to be a decent human being whether you are a manager, whether you are a business owner, whether you’re HR, whether you’re just on the ground pulling the cord. Just be a decent human being and try your very best, and over time, it will get better….” – Al Elliott Leanne says they have also let ideas shared by guests inform the content for the show. One recent example is The truth about mental health at work, with Dr Sarah Hughes, CEO at Mind. As a result of the above discussion, Leanne and Al were encouraged to discuss how to support mental illness in the workplace on the show. Check out The truth about working with schizophrenia, with Kody Green, The Schizophrenic Hippie and Do you work with a psychopath? With Dr Abigail Marsh to cite some specific examples. “It’s moments like that as well. It’s picking up what we learn from people who are infinitely smarter than we are and figuring out ways and how we as podcasters can expand that conversation for our learning and for our audience as well.” – Leanne Elliott Remember to check out Truth, Lies and Work… On the Truth, Lies and Work website In your favorite podcast app (subscribe here) Find This Week in Work also on YouTube On LinkedIn On Instagram Mentioned in the Outro According to Brendon Burchard, the author of High Performance Habits, one of the six habits of high performers is to seek clarity. Maybe you feel like you should have already gained role clarity and are worried about asking. You don’t have to wait for an organizational change or a change of managers to ask the question if you really don’t have the clarity you need. We take a job based on a certain job description at the time of hire, and that has likely changed over time. We may just need our manager to refine the definition of success for us. Maybe there is a skill you have learned that could fill a gap on the current team. Without talking to your manager, you might miss an opportunity to stand out. The introspective questions Leanne shared were also to help us gain clarity about what we want from our work and what we value. Much like the thesis or focus of a podcast, the answers to these questions can be different over time as we grow and learn. The answers to these questions may indicate you really want to do something different or need to seek fulfillment outside of your job for the time being. We can keep asking ourselves these questions and pay attention to whether the answers change. If you want more resources for dealing with uncertainty, remember to visit these pages: Our Layoff Resources Page with the most impactful discussions on the topic of layoffs with experts like Leanne Elliott and technologists not so different from you. Our Career Uncertainty Action Guide with the 5 pillars of career resilience and AI prompts to help you work through overwhelm, financial planning, and a layoff scenario Remember to subscribe to Truth, Lies and Work Listen all the way to the end for some fun! Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YoutTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

How can managers be effective when they are expected to manage larger teams? To strengthen relationships with team members and support team cohesion, start with task cohesion. Al and Leanne Elliott, former guests and the hosts of Truth, Lies and Work join us to explain how uncertainties in the world have impacted business owners, entrepreneurs, and people managers. In episode 340, we explore the reasons behind industry trends of layoffs, flatter organizations, and larger teams. If you’re a manager in need of help or someone seeking to lead a team, Al and Leanne Elliott have practical tips to manage well in a challenging environment. Original Recording Date: 07-12-2025 Topics – Welcome Back Al and Leanne Elliott, Uncertainty’s Impact on Current Trends, Keeping the Entrepreneurial Spirit, Organizational Flattening, Challenges to Effective Management of Larger Teams, Management and Coaching 2:35 – Welcome Back Al and Leanne Elliott Both Leanne Elliott and Al Elliott are back to join us for a special discussion today. They are the hosts of Truth, Lies & Work and have each been guests on the show in the past (but never at the same time). To listen to the episodes featuring Al as a guest, check out: Episode 235 – The Best Bad Option with Al Elliott (1/2) Episode 236 – Having the Vision, Charting the Path, Removing the Blockers with Al Elliott (2/2) To listen to the episodes featuring Leanne as a guest, check out: Episode 237 – The Psychological Transition of Layoffs with Leanne Elliott (1/2) Episode 238 – Managers as Culture Keepers with Leanne Elliott (2/2) 3:13 – Uncertainty’s Impact on Current Trends Our discussion with Al and Leanne is to revisit themes of job uncertainty and economic uncertainty and to look at some trends we’re seeing. A few years ago, the job market was booming. Right now, we’re advising people in times of uncertainty. We knew Al and Leanne would have a unique perspective on this topic. We tend to have a US-centric view of things and may not have a global picture of economic uncertainty and job uncertainties. What perspective can Al and Leanne share in this regard? Leanne says in the UK uncertainty is a great way to categorize the situation. Some companies are doing layoffs, but many are taking a pause. This pause could mean lack of growth, lack investment, or a slowing of revenue. People are definitely fearful. Business owners in the UK are pursuing what’s called a lifestyle business – a business which provides a blend of the specific lifestyle and purpose that owners want. “Rapid hypergrowth is no longer the number 1 priority.” – Leanne Elliott Al says in the UK, upwards of 90% of people are employed by small businesses. Many people believe the labor government in the UK is not really doing the things necessary to stabilize commerce. “There are big businesses who are frightened as in ‘I might lose my job when a new CEO comes in,’ but the smaller businesses with say 50, 60 employees are frightened going, ‘if I don’t get this right, I’m going to lose everything and everyone’s going to lose their jobs.’” – Al Elliott Is the lifestyle business Leanne mentioned focused more on the business owner, or does it also include the lifestyle of company employees? Business owners Leanne has talked to or heard of through colleagues are mindful of their employees, deciding not to take unnecessary risks like pursuing growth during times of uncertainty. Business owners are focusing on quality, efficiency, and automation right now. In the UK specifically, there have been a number of employment laws made under the labor government which sound great but bring risk for businesses in their execution. Leanne shares some examples like rights to flexible working on day 1 and National Living Wage. While the laws mentioned above do help employees, business owners hesitate when they are unclear on how to embed those laws in their business operations (i.e., lack of guidance, etc.). They might choose to employ more contractors instead of hiring new employees under these laws, for example. Leanne thinks business owner decisions at present are being driven by uncertainty, ambiguity, and fear. 7:41 – Keeping the Entrepreneurial Spirit Does the fear Leanne mentioned crush the entrepreneurial spirit? Entrepreneurs may be leading some of these small businesses that they’ve founded. This calls back to Al’s story in the episodes shared above. “I think true entrepreneurs…they live for challenges. And when things are going well, that’s when they normally mess it up.” – Al Elliott Al thinks entrepreneurs react well to challenges in the first 3-4 years of starting a business but may struggle to be effective beyond that. He feels the current climate is just another challenge to the entrepreneur. Al highlights the UK’s IR35 and its rules for hiring contractors. As a result of legislation like this, entrepreneurs and business owners might find it simpler and less risky to hire contractors over full-time employees. There was a trend of focusing on hiring full-time employees in the last 10 years, but that may be halted or turned in the other direction because of the current climate and additional governmental rules placed on hiring full-time employees. Al highlights for us that in certain European countries, firing a full-time employee requires a business to pay the employee 6 months of salary. In Al’s opinion, entrepreneurs are more optimistic people by nature, but the decision about how quickly to scale a business by hiring more people requires careful consideration due to the current climate we’ve discussed. “I think it’s remembering that…globally and in the UK as well, it has been relentless for business owners since 2016…. There’s been so much disruption and so much change that I honestly think entrepreneurs, business leaders are exhausted. They’re burning out…. An entrepreneur wants to keep fighting. They want to keep going, but it’s how they invest their energy…. So, during this period where the business may be fairly stable, they’re finding other ways to fill that entrepreneurial need and that meaningful work they are currently lacking in a business that isn’t in a growth stage, which is hard for an entrepreneur.” – Leanne Elliott Leanne mentions change of government in the UK, the pandemic, and other changes in the context of the impact to business leaders and entrepreneurs. Business owners in the UK who have chosen the lifestyle business approach are spending more time on side hustles and diversifying what they are doing with their business. This is more about the individual business owner / entrepreneur than the organization as a whole. John asks Leanne and Al if the laws apply only to businesses of certain sizes? In the US, for example, certain laws might only apply once a business reaches a certain number of employees. Leanne’s understanding is the size of the business does not matter, so the laws would apply as soon as the first employee is hired. It is a drastic shift and a high risk for small businesses, and they are choosing not to focus on growth right now. John thinks in the US there is additional risk in growing a business past a certain size. Some owners may want to take lessons learned and start multiple businesses below that threshold to diversify instead of running just a single company. Differences in laws across countries and even states might create microclimates of opportunity for businesses (i.e. venue shopping). Al says there are conditions that allow businesses to employ and fire people easily without having to pay a large severance upon separation from the company (i.e. contract employment). This can make entrepreneurs feel more at ease about recruiting people because it lowers risk. Leanne thinks it is a fine balance. In the UK there used to be probationary periods for employees that would provide full benefits and rights at the end of that period, but now employees have the same rights on day 1 as employees with a long tenure at the company. There’s been this weird shift of power and rights between employers and employees over time (before, during, and after the pandemic). Leanne highlights a conversation with psychologist Rose Soffel from Truth, Lies and Work about the trust crisis. “We’ve had so much push and pull and power swings over the last year years… I think with the changes in laws, geopolitics…there’s so much conflict in every sense of the word… in society and in our workplaces. People are just lacking trust – trust in their businesses, lacking trust in their leaders, lacking trust in their colleagues. We’re seeing massive increases in what we call workplace incivility at the minute, which isn’t bullying or harassment. It’s a level down from that but equally problematic…. It’s infighting. It’s gossiping. It’s withholding information from a colleague. That’s on the rise because there’s this issue with trust. So, I think having these laws come in are great on paper…. While it’s great on paper and comes from the right place…how does this same law apply to a business that has 10 employees…expected to meet and work to the same expectations and laws and legalities as a business with ten thousand employees? …The idea is in the right place. The execution…they haven’t quite got right.” – Leanne Elliott 16:16 – Organizational Flattening The trust crisis and scale and workplace incivility at scale falls in line with the layoffs we continue to see in the tech industry (and in others). Why are so many organizations choosing to flatten their management layers and increase the manager to individual contributor ratios? This is a byproduct of a lot of these layoffs. Leanne mentioned these things are cyclical, and we’re swinging back toward having less hierarchy as a trend. This is perceived as more startup-like and better for innovation and collaboration by some. In the last 18 months, the lack of sufficient training for people managers has been highly publicized. Many people take on manager roles because it seems like the “next step” in their career. Leanne read a statistic recently that only just over 40% of managers ever had formal training. “More than half of our managers aren’t equipped with the skills they need to lead our people…. The managers have the single biggest impact on employee performance, motivation, engagement, outcomes, productivity.” – Leanne Elliott Organizations looking to make cuts might decide to fire managers that are inefficient instead of training them because they are also seen as expensive resources. “For me, if you have great managers, they are the people that drive the success of your business…. The last time we talked we said that managers are culture keepers…and they really are. I think it’s naïve to think that removing a manager is going to solve all these problems. It’s not.” – Leanne Elliott We need managers to help bridge the distance between the lowest levels of a company and senior leadership. Leanne says people also think the flattening is intended to make organizations more agile. Al says it’s difficult to attribute revenue directly to a manager. It’s much easier to attribute it to a resource on a production line or an individual contributor. “It’s difficult when you’re looking at a spreadsheet to see the impact of what a manager does…. If you live in spreadsheets and you’re making the decisions based on numbers, it’s a no brainer…. What they don’t understand is that the IC produces ten thousand, a hundred thousand dollars a week in revenue because they’ve got an amazing manager.” – Al Elliott Nick mentions if you’re one of the managers without training and you stay / are not impacted by a layoff, you may get more people to manage as well. John is hearing of managers getting teams of 15 and even 20 people at times. As a people manager, John would schedule regular 1-1 meetings with each of the employees on his team. But then there are all the other upstream / lateral meetings a manager has to attend in addition to these. “I’m sure these managers aren’t given more time to manage with a bigger team. They still have to do everything else they need to do in terms of their administration or their job in general. They just now have more people to manage, so we’re not freeing up time…. We’re setting up our managers yet again for failure.” – Leanne Elliott Leanne mentions a fundamental misunderstanding of relationships in the workplace and teams in the workplace, citing the work of Daniel Priestley about the 13th hire being a kind of tipping point for small businesses. This blog post cites an example from a startup. We can easily apply that to the size of a team underneath one manager. Nick mentioned failure as a manager of a large team might make it even more difficult to get back to a manager role someday. Leanne tells us impostor syndrome comes from an inability to internalize our achievements. Humans are much better at internalizing our failures. Going through the experience as a manager and the potential failure is what we call a workplace trauma (with a lowercase “t”). It can be devastating to one’s career and self-efficacy. “It’s psychological harm we are causing potentially to these managers by not giving them the tools and the resources and the support that they need. It’s highly irresponsible from organizations to take this approach.” – Leanne Elliott 22:46 – Challenges to Effective Management of Larger Teams Even in a challenging environment, is there a way that managers who care about doing a good job and have the willingness can be effective? Leanne would say to focus on the relationships with the people on your team, but that’s going to be a challenge with such a large team whether you are a new or experienced manager. “My advice to any manager in that situation is to focus on task cohesion, which is much more transactional and much easier to get right…. What’s the workflow? Who’s doing what? Who does what in what order? How does that contribute to the overall outcomes we’re trying to deliver? …If we can build in the systems and the processes that mean that task cohesion is really strong, then that means that over time we’re going to build team cohesion as a byproduct of that….” – Leanne Elliott When you work with a colleague who makes your job easier, it’s natural to want to have a conversation with them and get to know them. This kind of thing breeds workplace civility – mutual respect and appreciation (which came about due to task cohesion). Once task cohesion is in place, a manager can nurture the team cohesion. Part of the work is building the team charter for what good looks like and the acceptable / unacceptable behaviors. But there is a step beyond this that Leanne calls a “check-in” with team members that can help you spot the issues and things that are bugging people on the team. “It can be a 5-minute phone call on a Tuesday afternoon saying, ‘how are you doing? Anything making your job harder today? What can I do to make your job easier as a manager? What’s really bugging you?” – Leanne Elliott, on the manager’s check-in The check-in can be a more time effective way of troubleshooting the fires to put out as a manager. Some managers may do formal 1-1 meetings, and that is great. Leanne encourages taking the approach of genuine care and seeking to make your team members’ jobs easier. Al mentions the Pareto Principle and thinks maybe it’s more about pointing yourself at where the problems really are within the team using the targeted check-in approach rather than feeling the pressure to do a 1-hour 1-1 meeting with every team member once per week and everything else you need to do. Leanne says the check-ins should be a phone call. Sending an instant message or e-mail adds one more task to a team member’s plate that they will worry about it. “Pick up the phone. I know it might not always feel the most comfortable thing to do, but honestly once you get into the habit of it and once your employees get into the habit of…more vocal check-ins, it’s much more time efficient and less emotional load potentially.” – Leanne Elliott John highlights that a connection task may not make a quality connection, and he likes Leanne’s suggestion to strive for quality. He also mentions every member of a team does not need the same amount of time from you as a manager. That equal spread may not serve everyone effectively. Leanne says consider placing some intention toward reaching out to team members who are a bit more challenging. If you don’t want to reach out to specific members of your team, it signals that a conversation needs to happen. If you’ve worked somewhere that has had multiple rounds of layoffs, an unexpected call from your boss creates some anxiety. A manager getting right to the point when they make a call can help ease this trauma people may have. Al mentions if we get PSTD or an anxiety spike when our manager calls, it may be a sign our manager isn’t talking to us enough. A great manager checks in regularly as part of their role. Leanne was laid off (or made redundant) in 2015, and it was incredibly difficult to go through. She had a great relationship with her manager leading up to the layoff event. Managers should strive to create relationships where a call to be laid off is the last thing on people’s mind, but our current climate plays a role in affecting people. Leanne recently saw a LinkedIn post from a manager who remained at a tech company after layoffs happened. He was describing the support he was offering to the people who were leaving the organization (i.e., pointing them toward open roles, etc.) as well as to those who remained. This manager had to navigate survivor’s guilt just like other employes who remained at the company. “I think it’s managers like that that you’re never going to be afraid to get a phone call from. Because even if it is the worst, they’ve done everything they can to protect you in the lead up to that moment.” – Leanne Elliott Al mentions in the case of Leanne’s phone call when she was laid off, her boss got right to the point. Because the relationship was there, Leanne knew despite her devastation that her manager would help her figure out how to move forward. Leanne was told she had to lay off her entire team and would then be laid off as well. Nick thinks there are 2 sides to the coin. We want to have a great relationship with our manager so that we don’t immediately think the worst when we get a call, but each person has their own level of trauma / PTSD they bring to the situation that they also have to fight. John thinks this might be a cultural shift. Thirty years ago, telephones were the way people communicated, and getting a phone call was not a traumatic thing. Even today, when John’s family members call him instead of sending a text, he gets a spike in adrenaline and thinks something might be wrong. Maybe if managers are trying to establish a rhythm of calling people to check in, they can send a quick message ahead of time to let the person know the purpose of the call. Once the pattern of check-in calls is established as normal process, each call is less of a triggering event. Leanne agrees and emphasizes the need for absolute clarity. “Everything’s good. Nothing is wrong. I’m just going to give you a call at this time to check in.” – Leanne Elliott, an example of being very clear about a phone call to a direct report Leanne says she heard about a manager who told their employees they would be receiving a call regularly from the manager just to check in (i.e. every Tuesday at 2 PM, etc.). A manager can also let the first 5-10 minutes of a team call be informal conversations. It shows that this is part of the team culture and way of working. “Why shouldn’t you be the manager who just does things differently?” – Al Elliott Being the manager who does things differently is ok. You will develop a reputation within the company for operating that way and doing check-ins. It only takes a few phone calls to put people at ease about the process. Leanne says the calls have to be made with some intention. It’s not just asking people if everything is alright. Consider using more coaching type questions. “It’s almost digging in a little bit more and finding a specific thing to talk about which every good manager does anyway in terms of giving any type of feedback. It’ll be very specific and rooted context. It’s the same for these causal phone calls. If you’ve got something rooted in context, it’s going to help that conversation flow. It’s going to start to breed that…psychological safety that so people will actually feel they are able authentically open up…. It needs to be, ‘I’m going to phone you. We’re going to have a conversation because I’m generally interested in how you’re doing, what’s going on in your work world, and if appropriate, beyond that.” – Leanne Elliott 36:03 – Management and Coaching As a result of the above, Nick thinks managers should be good at interviewing people beyond job interviews to begin and continue good conversations. Is this a skill a job candidate should highlight if they want to be a people manager? Some people have fallen into communicating that they are a manager and therefore very important because they got a promotion at work. It’s partially what they have seen others do. “They just think that’s what being a manager is because they’ve seen the loud mouths who have been managers before and are really important people who run around with papers in their hand. And they don’t know that being a manager is almost the opposite. It’s being quiet, not loud.” – Al Elliott Leanne thinks it’s probably less interviewing and more about asking coaching questions. It’s about asking questions that are generally inquisitive or help someone though a thought process / something that is troubling them. If you want to be a manager, look at skills embedded in coaching like listening skills. A listening skills course or a coaching course could be highly beneficial to anyone. Coaching courses can be transformative in terms of emotional intelligence, self-awareness, engaging and interacting with other people without agenda or judgement. “That’s what I’d say is to highlight those skills – your curiosity, your ability to coach, your ability to listen. I would snap up anyone, even if they had no experience at all. I would snap up anyone with those skills into a management role.” – Leanne Elliott, on the skills of a manager Mentioned in the Outro If you’re a manager listening to this who is not getting trained, you can find that training outside your company in the form of books, podcasts, seminars, and formal training courses. In fact, Leanne recommends courses on coaching or active listening. Remember also that it’s ok to be a manager who does things differently to make an impact. If you want more resources for dealing with uncertainty, remember to visit these pages: Our Layoff Resources Page with the most impactful discussions on the topic of layoffs with experts like Leanne Elliott and technologists not so different from you. Our Career Uncertainty Action Guide with the 5 pillars of career resilience and AI prompts to help you work through overwhelm, financial planning, and a layoff scenario Remember to subscribe to Truth, Lies and Work Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YoutTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

Imagine getting 45 minutes to describe and defend the quantifiable impact of your body of work as an individual contributor accumulated over multiple years. It’s your job to convince a panel that you have what it takes to help solve the company’s biggest problems. Could you do it? Our guest Daniel Paluszek has done it successfully at 2 different technology companies to become a Global Field Principal. Much of his success in these roles is attributed to a “culmination of exposure” over the course of his career and the support of both family and managers. This week in episode 339, we begin with the story of Daniel’s move to a hypergrowth startup and learn what it was like to run his own business as the company grew and changed. When an unexpected opportunity to join VMware arose, Daniel transferred his learnings to focus on business growth for service provider partners. We also talk about the reasons Daniel pursued the role of Global Field Principal, the responsibilities of that role, and why he continues to find it interesting. After listening to this episode, we might all think differently about the importance of building a body of work. Have you been building yours? It’s not too late to begin or keep going. Original Recording Date: 06-11-2025 Daniel Paluszek is a Principal Partner Technology Strategist at ServiceNow. If you missed parts 1 or 2 of our discussion with Daniel, check out Episode 337 – Finding Drive: The Parallels of Mentoring and Technology Partnerships with Daniel Paluszek (1/3) and Episode 338 – Steady Build: Broadening Exposure and the Priceless Perspective of People Management with Daniel Paluszek (2/3) Topics – Leaping into Hypergrowth, A Culmination of Exposure, Pursuit of Principal and the Responsibility of Execution 3:06 – Leaping into Hypergrowth What did the next job transition over to SimpliVity look like? It seemed like this was a conscious move toward an up-and-coming startup and a new technology wave at the same time. Daniel says it was a conscious choice to move to Simplivity. While Cisco was somewhere that felt like home, Daniel was given the opportunity to join Simplivity when it was a startup. The industry was moving from 3-tier architectures with virtualization to hyperconvergence (a convergence of storage, compute, and networking in a single form factor that scaled out linearly). It was an exciting time for the industry as a whole, especially for virtualization. Daniel knew some of the people who had joined Simplivity. “I’ve never done a startup before, a hypergrowth company…. There were about 100-150 people when I joined. In that first year, I think we tripled the company in size…. It was something that was just an incredible experience.” – Daniel Paluszek Daniel was a pre-sales Solution Architect at SimpliVity working with both customers and partners in the southeast United States (Floride and Alabama). At Simplivity Daniel learned the skill of building your own business. He and his sales rep (also a great mentor to him) worked as one logical unit partnered together to build business. They were aligned on the priorities and focus areas. “Sometimes you have to take that leap of faith and try something that’s completely unknown. I was leaving a tried-and-true company…Cisco Systems is an incredible company…going to a startup that I had no idea where this was going to go…. Why wouldn’t I do this? There’s nothing but upside to try this and get the experience of a startup. And so, that’s what I did.” – Daniel Paluszek Daniel calls his time at Simplivity some of the most impactful years of his career. It felt like Daniel was able to fit the same amount of learning from Cisco (5 years) into 2 years at Simplivity. Daniel had to learn many functions we might think of as being outside the role of pre-sales like marketing (running campaigns, planning customer events, etc.). There wasn’t a lot of field awareness of what hyperconvergence was, so part of the job was taking time to educate customers and partners. “So, every day was about how do we not only simplify the messaging but focus on the business problems, the challenges, and how we’re directly solving those for all industries and customers. And we had to wear all these different hats.” – Daniel Paluszek “If there was any nugget of wisdom…everybody should do an up and coming fast growth company and just understand all the different roles needed and working together on building something…building a company.” – Daniel Paluszek Daniel worked on a small team and built incredible, lasting relationships with others along the path of building something extraordinary and special. He really enjoyed the period of time before SimpliVity was acquired by HPE – a great time with great people and great technology. While a role we take may change over time as a company changes, hypergrowth startups can change quickly. For example, a role may not look the same in 3-6 months. What are some of the other ways Daniel’s role changed as the startup grew that he did not expect? Daniel says you had to learn adaptability very quickly. When the company is in hypergrowth mode, you do what it takes to get things accomplished even if it seems outside of your specific role (support, product management, etc.). This requires people who will collaborate well to execute on the overall goal. As a company grows, its internal organizations grow too, and you begin to have dedicated people to perform specific roles / job functions. “The one thing that wasn’t evident to me coming from a large manufacturer / vendor was you had to do everything under the sun, and you had to wear 27 different hats. I was willing to do that…. In the early stages, my sales rep and I were doing all of that, and as the company grew, we had pre-defined people. We had a marketing person, and we had a sales development representative….” – Daniel Paluszek, describing life inside a hypergrowth startup Running your own business in this case meant hosting marketing events. That involved getting funding, coordinating with a restaurant / venue to build a menu, track event registrations, coordinating speakers for the event, and tracking follow up conversations with event attendees based on interest in the topic and products. “Sometimes you’ve just gotta do things that you may not like that are just part of getting the job done right and getting it done successfully in the interest of your company and your end customer. And sometimes you just have to get it done. I think there’s a delicate balance. In large organizations, we have clearly defined roles and responsibilities. Sometimes you’ve just gotta break that glass and figure it out after the fact, but if you’re doing in the best interest of your customers and your organization, I’ve never seen anything negative come out of that because you’re serving and bringing value to your stake holders at the end of the day.” – Daniel Paluszek From what Nick sees, Daniel has a pattern of trying new things to gain experience and learn when he feels it is something that will make him better, even if he’s not sure how it will make him better at the time. Then that post-processing Daniel has inside him will kick in so he can use the experience later. 12:17 – A Culmination of Exposure Did Daniel decide to move on from startup life because he was tired of it, or was it because of a new opportunity? Daniel’s career had been shaped by VMware from a young age to this point in time, and he was given the opportunity to work there. But this was not something he planned. When HPE (HP Enterprise) announced their intent to acquire SimpliVity, Daniel had intended to stay and see what happened. A friend from Cisco mentioned to Daniel that the VMware partner group was looking for technical pre-sales engineers, and this friend thought Daniel would be a good fit. “Two weeks later I accepted an offer from VMware in the partner group…. I went with my gut, and I said, ‘I’m going to take this offer…and see where it goes.’” – Daniel Paluszek, after being open to an unexpected opportunity Daniel was leaving right around the time the HPE acquisition of SimpliVity was closing. Choosing to take the role at VMware was a very difficult decision. The hiring manager at VMware encouraged Daniel to do what was best for him and his family. To this point, Daniel had accumulated a wide range of experience: Working with VMware technology as a customer His professional services background The focus at Cisco on the datacenter and building cloud architectures Being a part of SimpliVity and focusing on hyperconvergence “I just had this culmination of exposure and depth of experience that I was able to utilize in a role core to what I had built in the past.” – Daniel Paluszek Daniel tells us he worked for VMware for about 5-6 years focusing on service provider partners and eventually became a field principal architect. Daniel and his team members supported global cloud providers that were providing infrastructure or platform as service to their customers based on VMware architectures. Daniel worked to make these cloud providers successful with architectures that supported either a shared multi-tenant cloud or dedicated private cloud environment. During this time Daniel found an appetite for blogging. The VMware technical community was very active in this area, and it was interesting to Daniel. Once Daniel began writing blogs, he realized it could be used as a medium to answer some of the questions multiple cloud providers were asking. Through blogging, Daniel could break down new complex topics into digestible material. Daniel was writing for his own personal blog and also for the VMware corporate blog and accumulated 100-150 blog articles across both sites by the time he left VMware. Daniel eventually took down his blog site because the content was so outdated. Daniel also recorded lightboard video presentations to explain different concepts cloud providers were seeking out during that time. “It was another medium where I could articulate a message and really help the community on growing the VMware solutions.” – Daniel Paluszek, on decreasing the friction to growth of VMware solutions through field awareness and education Daniel worked in a business unit that had technical marketing and product management personnel. Daniel’s creating the content helped the overall business unit make a greater impact, and it created a collaborative, cross-functional team. “If you can collaborate and work together effectively on a clear and single mission, you can accomplish anything. And I thought we did an incredible job supporting our cloud providers and partners.” – Daniel Paluszek 18:25 – Pursuit of Principal and the Responsibility of Execution John mentioned the field principal title has come up a couple of different times in previous guest interviews. What does this title really mean, and what led up to Daniel’s decision to pursue that title? Daniel cites being part of the CTO Ambassador program during his time at VMware. Specific engineers and architects who were part of this program throughout the company would work closely with the Office of the CTO. This group was a collaborative forum for a couple of things: Working on special projects and initiatives Providing feedback to product leaders and the research and development teams around industry trends, value to customers, and much more At VMware, field principal was one job level above the senior staff level. The field principal title was a designation of global contribution and impact to others both inside and outside the company beyond the normal customers or partners you served. The path to principal for Daniel was through his value differentiated work at a partner and then supporting partners for many years. He was passionate about supporting partners in a way that had not previously been done and wanted to go through the field principal program. The principal program had an intake process to submit your accomplishments along with letters of recommendations. This was reviewed by a board who determined if you met the requirements to do a panel defense. The process is analogous to a VCDX (VMware Certified Design Expert) which was part test and a panel defense. The field principal defense was about showcasing quantitative and qualitative metrics of your impact, but it was also about how you presented a body of work containing what you have contributed and what you will continue to contribute in the future. “You had 45 minutes to present in front of a live panel…and it was a hard stop. And if you didn’t complete it, they could not grade you completely, or you would have missed the mark…. Your presentation and everything that you show in your body of work had to be represented in an executive format…. How do you represent everything in less than 45 minutes? …It’s a lot harder than you anticipate.” – Daniel Paluszek For Daniel, this was also a test of his presentation skills. Some thought Daniel might not achieve principal because of a short tenure at the company, but that only drove him to succeed. Are the skills needed for the panel defense similar to those that one would need to speak to an audience of executives and hold their attention? Though Daniel never got a VCDX, he speaks to the importance for a solution architect to understand the functional and nonfunctional requirements, assumptions, risks, and constraints. The field principal methodology followed the same patterns and system methods as the VCDX. Daniel says he left the experience with a greater awareness of the formal methodology he had learned through real-world experience. What would Daniel tell someone they should consider before pursuing a principal role? “Are you ready to have that responsibility, and are you willing to lead the biggest problems and challenges in the organization, internally and externally? …People are going to seek you out to solve these problems that others could not.” – Daniel Paluszek, on the role of a principal Danial was not a principal when he joined ServiceNow and had to go through their process to achieve principal. It was somewhat similar to what he experienced at VMware. If you sign up for the responsibility of being a principal, you have to go execute. Daniel says a principal is setting the tone and narrative for the rest of the organization. It’s about setting an example for others while you execute. Though the principal is focused on solving the company’s biggest problems, you may be working on this in addition to your daily responsibilities. Are you willing to put in the extra time required to do it? “You have to have the passion and the desire to solve these big problems…beyond your day job to really make that impact on a global scale.” – Daniel Paluszek How do you decide where to focus your time when juggling extra responsibilities and your day-to-day responsibilities? Daniel says it often means you are working nights and weekends. If you have a customer-facing responsibility, your customers should come first. Daniel made sure this was his mindset across both companies where he’s been a principal. “You have to serve your customers and your organization first, and the other priorities come second. It was all about, for me, time management and time efficiency and managing hour by hour.” – Daniel Paluszek It’s also important to have a discussion with your family about this being something you want to do. Keep up constant communication on this front. Daniel cites support from his family as a very important part of the equation that has made him successful. Listen to the schedule Daniel normally works and the intentional focus on having blocks of time for his family. One could approach this as a short-term deficit for a longer-term benefit. On the professional side, you need the support of management and leadership to be successful in your normal responsibilities and the additional responsibilities of being a principal. Daniel considers himself fortunate on both fronts to have support personal and professional. Nick highlights the fact that leadership has to sign off on / approve members of their team being promoted to principal and spending a set amount of time on projects above and beyond their normal work. What keeps the role of a principal exciting now that Daniel has done it at multiple companies? Daniel gets excited about working on the problems others have not yet been able to solve. “Many times, I don’t have a clear path to execution. I’ve gotta go figure that out, and…I gotta build a cross-functional team. And I have to look at different perspectives and what we’re trying to solve. But building that methodology and working with like-minded individuals that are scrappy, have grit, that desire to build something great just drives me. I like people that are willing to…roll up their sleeves and get stuff done in the interest of our customers and partners. And I think that’s what motivates me on a daily basis. There’s problems anywhere you look or challenges. Let’s go solve them. Let’s go conquer them.” – Daniel Paluszek Daniel considers every experience a blessing. Every experience is something you can build on to make yourself a better professional. Mentioned in the Outro Did you catch the field awareness theme? Daniel had to educate potential customers and partners on SImpliVity’s solutions when he worked for them during the hypergrowth phase. This field awareness took on its next iteration when Daniel moved to VMware. All of the blogs and lightboard videos were creating field awareness for the community of cloud provider partners he served at the time and helped the business unit he worked for scale. There’s an element of field awareness when we speak about the principal title. Other people have some understanding / awareness of the fact that these people get pulled in to solve some of the largest problems a company has or its customers and partners have. It’s worth distinguishing the way in which principal is applied to different roles across different customers. Daniel as well as many others fall into the category of field facing resources (i.e., Global Field Principal). They serve a specific set of customers or partners (entities outside of the company at which they work) as part of their role. It could be someone who is an individual contributor in technical pre-sales, professional services, or even technical support. For guests like Ken Collins or Max Kanat-Alexander, they were principal engineers, and their focus was software engineering and was likely more of an internal facing role. They still help the organization solve problems but might not be field facing. Check out their episodes for reference: Episode 241 – A Self-Taught Programmer’s Banyan Tree of Knowledge with Ken Collins (1/2) Episode 242 – Modalities of the Staff and Principal Engineer with Ken Collins (2/2) Episode 285 – Contribute Back: Embracing the Open Source Spirit with Max Kanat-Alexander (1/3) Episode 286 – Succession Planning: Delegation Skills and Technical Ownership with Max Kanat-Alexander (2/3) Episode 287 – Scope Creep: Evaluating Impact in Career Decisions as a Principal Engineer with Max Kanat-Alexander (3/3) For some episodes that provide another perspective on the hypergrowth startup, check out these with guest Andrew Miller. We also talk to him about the principal title, and in his case it is field facing like Daniel. Episode 166 – Management and the Hypergrowth Startup with Andrew Miller (2/3) Episode 167 – Pause and Step Outside with Andrew Miller (3/3) If you’re someone who has recently discovered our show or this episode, Nick would love to chat with you 1-1 (how you found us, what you were looking for, and what it made it interesting). We want to ensure our show is discoverable and findable by technology professionals who are looking to learn from the stories we’ve shared on the show. Send Nick a DM on LinkedIn or e-mail us at the address below to schedule a chat! Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YoutTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

Could a greater understanding of what people managers do make you a better individual contributor? And would it also cause you to treat your manager differently? For Daniel Paluszek, our guest this week in episode 338, it definitely did. And though this was a short stint in Daniel’s career, he refers to that experience as priceless. This week in part 2 of the story you’ll hear about Daniel’s experience working in professional services both in pre-sales and post-sales and how he built expertise to help increasingly larger customers over time. Daniel will reflect on the lessons learned from his time as a people leader, and pay special attention to the moment when Daniel turns the microphone on John during our discussion! We also explore the reasons why Daniel eventually chose to move back to the individual contributor side of the house. How do you think your mindset would be different when making a move like this? Listen to the full story from Daniel’s perspective. Original Recording Date: 06-11-2025 Daniel Paluszek is a Principal Partner Technology Strategist at ServiceNow. If you missed part 1 of our discussion with Daniel, check out Episode 337 – Finding Drive: The Parallels of Mentoring and Technology Partnerships with Daniel Paluszek (1/3) Topics – The Nuances of Professional Services, Getting to Know Service Providers, Becoming a Practice Manager, Difficult Conversations, Returning to Individual Contributor 2:46 – The Nuances of Professional Services It seems like Daniel would have been able to bring some of the government work he had done into conversations to help build credibility and relationships. Doing federal defense contracting is certainly different but provides a level of expertise that cascades to any government organization. When Daniel joined the partner, most of the conversations were about getting into virtualization, and the projects focused on consolidating infrastructure. Daniel had direct exposure and expertise in designing and orchestrating these kinds of projects from start to finish (design, build, migration, providing a day 2 runbook). Daniel had the technical expertise he needed but did not at first have the sales and consultative skills he needed. Daniel had help from mentors (his sales rep, his leadership chain, other colleagues on the professional services team) to improve in this area. Daniel would later join Cisco Systems doing professional services. This was around the time they launched the UCS computing platform. He had worked in in professional services for DynTek for a couple of years previous to making the move. Working in professional services granted opportunities to work with many customers across multiple industries. Daniel calls gaining this experience getting “at bats.” Working within a large professional services organization can also be challenging. Usually, the person who creates the scope of work for a services engagement is not the same person who will execute the statement of work. Something could have been scoped incorrectly or improper expectations set, for example. Daniel tells us part of the role was about overcoming these types of challenges and mitigating risks. “You had to work through these situations and challenges on an ongoing basis…. Not only make your customer happy (do what’s right) but also make your organization healthy from a profit and loss perspective because…companies and PS organizations, their largest cost factor is people….” – Daniel Paluszek, on life working in professional services Daniel tells us that a professional services organization has to balance executing well for customers with remaining profitable. Before Daniel joined Cisco, was he 100% pre-sales or doing a mix of pre-sales and post-sales? Daniel says it was a mix of both and refers to it as a hybrid role. He was brought in at DynTek as a professional services engineer but began getting exposed to the pre-sales side of things. In fact, Daniel wanted to learn more about pre-sales. Over time, Daniel began scoping professional services engagements and presenting to customers followed by later delivering the work (i.e., "wearing both hats). Nick stresses the importance of determining whether roles are post-sales, pre-sales, or both to ensure you fully understand. Ask these questions in interviews so everything is clear! Maybe doing both can help one decide which area is more interesting. “I also think that doing both and then doing professional services delivery for many years also shaped me into the individual I am today because I had to live and go through delivery of projects…. When I scoped it…I knew that this is something to watch out for from a field-level direct exposure perspective. So, I knew the nuances to my area of expertise, my domain, and I was able to scope it in a way that ensured success and mitigated that risk just because I had that direct experience.” – Daniel Paluszek Processes like the one described above will not scale for large organizations. Sometimes a large organization will give people the chance to move from delivery to pre-sales to round out their experience. Daniel was fortunate to have the chance to do both and gain exposure to different areas. John mentioned there is usually another level of separation and complexity in these scenarios. He highlights 3 distinct roles – someone selling a solution that includes professional services, someone who scopes the professional services, and someone who executes the professional services. John has seen this divided even further and mentions sometimes there is a special professional services workshop that helps provide the inputs to the person writing the statement of work. “Again, if we’re talking about roles and educating people about roles, the number of different types of roles that are out there just continues to amaze me. Going to school, I have no idea how you would know any of these roles existed.” – John White Daniel says for multi-pillar transformations within large enterprises, it can require subject matter experts (SMEs), architects, and engagement managers to make a professional services project successful. When Daniel began working in consulting / professional services, he started working with smaller companies. It was the move to working for Cisco that helped him gain experience working with large enterprises and service providers. Daniel speaks to the complexities of delivering engagements for these organizations. He might have to design an engagement that required dozens or hundreds of people over a multi-year period. Starting off small helped Daniel focus on understanding the fundamentals, and he was able to build upon that through varying experiences with larger customers across different industries over time. 11:20 – Getting to Know Service Providers What is a service provider? Let’s define that term. We’re talking about a company that provides a service like a cable provider, for example. They might be considered a traditional service provider. Cable providers offer telecommunications services to end users / consumers. But a cable provider can deliver services to a business too. If we’re talking about the business-to-business market, a service provider (could also be called a managed service provider) is providing a discrete service injected into a customer’s business. That service is a function of a customer’s overall organization. Daniel gives some examples Business Process Outsourcing (or BPO). This could include processing accounts payable or accounts receivable transactions. An MSP (Managed Service Provider) providing service desk operations for an end customer A service provider can help a customer scale their business. Daniel gives the example of a retail customer. Retail companies exist to sell products and goods. This is their core business – driving incremental sales of products. Anything else required to operate that business, according to Daniel, is context. In the retail example, management of back-end IT systems, management of the service desk, or management of finances and supply chain would be considered context. In some cases, companies like this will partner with a service provider (or GSI / Global Systems Integrator) to assist in these areas. “It ultimately comes down to…what is your core business, and what’s your context? And…is this something we want to staff and skill in-house, or do we want to partner with somebody that’s going to provide this as a service to us?” – Daniel Paluszek Nick mentions there is usually someone in-house tasked with working closely with service providers to ensure business operations run smoothly. Daniel says there is always an interface on the customer side, and in very large companies, it’s usually a small team which will manage the line of business in question and work closely with the partner / service provider executing much of this function. The team on the customer side would work closely with business leaders to ensure everything aligns with the business strategy. Nick liked Daniel’s description of his progression of experience from small customers up to large companies like service providers. There is an increased need for availability and resiliency as we get into talking about service providers who may have systems accessed by end customers and not just internal employees of the service provider. During Daniel’s tenure at Cisco, service providers spanned telecommunications, media, and technology partners. Daniel worked with many telecommunications providers and says it was incredible to learn about all the systems required to deliver a cell phone, for example, and the network functions that were part of it. When Daniel was working with telecommunications providers, Network Function Virtualization or NFV was the next emerging technology which extended the benefits of virtualization to help service providers in the telecommunications space provide better services to their customers. 16:12 – Becoming a Practice Manager Did Daniel go fully into pre-sales at Cisco even though he was focused on professional services? Daniel started off as a delivery engineer in the datacenter and cloud group but soon became a practice manager. During this first experience as a people leader, Daniel managed about 14 people. “It was an interesting and incredible experience…. When you get into people leadership, that’s a totally different approach and perspective.” – Daniel Paluszek Daniel had to focus on the people he managed as a first priority. That was a mindset shift. It was about supporting his people’s success by ensuring they had the necessary tools to execute. Another element of the role for Daniel was communicating things like status and current challenges to his own leadership. Daniel was a practice manager (i.e., people leader) for a little while before moving to pre-sales inside the datacenter and cloud group. What was it like to go full-time into a more focused pre-sales role and make the transition from people manager back to individual contributor? “You have to have the right mindset to manage and lead individuals from all different backgrounds and experiences and also realize that everybody operates differently. And I think, at that time, I don’t know if I was fully ready for that position…. But it was something that gave me a different perspective, which was priceless, on managing people and also providing a view into people leadership that I never had before. We will all work for managers, and sometimes we take for granted. It gave me a unique exposure into what our managers deal with and how a corporate hierarchy works within a large organization….” – Daniel Paluszek, on people leadership Daniel was asked to take the practice manager role while still young in his career. He did well and kept in touch with the people he managed. Daniel feels he may be self-critical of his time leading people, but he learned a great deal from it. Daniel really aspired to work in pre-sales as a solution architect and would eventually make the move away from people management to this type of work. John thinks many people do not realize that the move to people management requires a pretty drastic career change, even if you manage a team on which you once worked. “Your job is no longer doing the work. It’s managing the people.” – John White When people aspire to be a manager or higher-level leader of some kind, they are often looking at it only through the lens of the individual contributor and not truly understanding the role of manager is quite different. “Management and people leadership is a diametric difference, especially for technology professionals. When you get into management, you almost have to let go of the technology reins because that’s not your job anymore. And I think personally at that time, I wasn’t ready to let go of that. I think that was part of my challenge internally that I struggled with…. For you to become a successful people leader, you have to let go of the technology and having that skill because that’s not your job anymore…. I was presented that opportunity, and I took it, did the best to my abilities…and I said it’s ok to say, ‘this isn’t for me right now.’ It’s not saying the door is closed. I just don’t feel like I was ready personally for that role at that time.” – Daniel Paluszek Daniel’s mindset is quite different now than it was then, having learned much since then. After being in the management seat, John feels like he understands better now how to be a great individual contributor. Did Daniel’s stint as a manager make him a better individual contributor since he understood what managers were measuring? Daniel says yes and that he was naïve in the past regarding what his managers experienced. He is extremely grateful for the opportunity to experience the role of manager. “Putting yourself in that role, you realize very quickly, it’s sink or swim…. I took away from that experience having a level of empathy for every manager I’ve ever worked with since then. You just take it for granted because you’ve never seen it before…. It just gives you a totally different mindset. I just don’t think individual contributors understand that and realize that until they’re in those shoes…. There are things that you’re just not aware of, and until you experience it firsthand, you’re not going to see it.” – Daniel Paluszek John says often times our managers are on vacation or are on leave, and there is a chance for members of the team to fill in during these times. Even for those who have no aspirations to be a manager and just want to be the best individual contributor possible, filling in for your manager temporarily can make every employee better. Daniel says becoming a team lead can also help your manager, especially when it comes to developing others on the team. He initially thought his path to career progression was to become a manager and keep moving up. “I realized you don’t have to be a manager to help others. It doesn’t matter if they’re on your team or not. Mentoring and guidance crosses any logical boundary. It doesn’t matter where you live, what company you work with. Helping others…with their journey and their success…you can do that…. You don’t have to be a manager or a people leader for that. You can just be a good professional that helps others.” – Daniel Paluszek Daniel reminds us how much he enjoys helping / mentoring others on their personal and professional development journeys. In management, you’re supposed to do this along with all the administrative functions. Providing your objective perspective can be a great help to others. We don’t have to manage people to help people. John mentions managers might need help with the administrative overhead of the role. It’s hard to send updates on status to your management if members of the team haven’t made updates to specific systems on time, for example. 26:15 – Difficult Conversations When he was a manager, Daniel had to handle situations where people were not meeting their core job responsibilities. It was a learning experience and required having some very tough conversations with individuals on the team. Daniel asks John for his words of wisdom when handling these difficult conversations. John says a good way to prepare for this is by working on cross functional teams where you don’t have managerial or role power over someone but need to hold them accountable for completing specific work to help the overall team. Before becoming a manager, John was an account sales engineer. He would work with partner sales engineers, specialist overlays, technical account managers, and others on a specific campaign / set of activities. It fell to John as the core account sales engineer to be the project manager of these activities. “I think that it’s really good practice to have those kinds of conversations before you become a manager. I don’t think that it’s good to have that be part of your core job without ever having done it before.” – John White In the cross functional team example, we might be dependent on someone else doing something in order to complete our own work. You don’t have real power over the person who needs to be held accountable other than the power of persuasion. It’s about cultivating that influence. Once you are in a people management role, it’s important to establish clarity of job expectations. Job descriptions being written does NOT mean people have internalized them. Often times these descriptions are very broad and not well maintained. The manager can reiterate the deadlines for completing essential tasks for a person’s role and the expectations for quality. It will eventually need to be put in writing. It is essential to build relationships with the people on your team so they know the context in which things are coming to them. Do people have the tools to accomplish the tasks which are expected of them? If they don’t, just like in the case of lacking clarity, you will not be able to hold them accountable effectively. John suggests thinking about this from cause to effect. John references The Talent Code and its mention of John Wooden’s coaching method to focus on the difference between what good looks like and what a person was doing. Daniel remembers some challenging situations as a manager and needing to have some very uncomfortable conversations. He calls it a raw learning experience. We as individual contributors do not always understand what our managers go through on a daily basis. Daniel advises us to treat our managers well. John recommends the book Crucial Conversations to learn how to have the difficult conversations. It isn’t just managers that have difficult conversations. All of us do! The ability to have difficult conversations is a skill. John says we don’t want to be novices at this skill when it’s an important time to have a conversation. 32:46 – Returning to Individual Contributor How much of Daniel’s management experience was he asked to discuss in interviews for the individual contributor role in pre-sales? Is it a strike against you when you try to move back to the individual contributor’s path? The team Daniel managed did professional services delivery. They sat in the same organization as the pre-sales personnel focused on selling professional services, and Daniel had expertise in delivery and pre-sales. Daniel thinks there was probably a question about why he wanted to move to pre-sales but doesn’t feel like his management experience was looked upon in a negative light. “I wanted to get closer to the customer and closer to the solutions and technology, and that was my passion at that time…. If you’re a manager for many years going back to IC, I can see just like any other skill it does degrade over time. But, you know, in the industry I’ve seen people move from management to IC, IC back to management. I think if you have the right qualities, the ability to take on those responsibilities, and ensure you have the right frame of mind, especially when you transition from IC to manager…. I think it rounds out an individual and a professional, from my perspective.” – Daniel Paluszek Looking back, if asked to do it again, Daniel would still have taken the role in people leadership. He gained a level of understanding that one can only get by performing the responsibilities of a manager. It made Daniel a better leader. The cross functional leader (an individual contributor) has to create a collaborative team and ensure accountability while still needing to have those difficult conversations to hold people accountable. “Every career journey ebbs and flows, so I think everybody has a varied path on how they experience these things.” – Daniel Paluszek Nick thinks Daniel’s experience as a people leader was transferrable. He gained a measure of empathy that was transferred to co-workers and customers. In pre-sales, we often work with people at different levels within an organization. Daniel has a perspective from his experience as a people leader that helps him better relate to the leaders he works with consistently (in his customers or elsewhere inside the same company). Mentioned in the Outro There was a theme of scaling one’s experience in that discussion…a slow build. Daniel didn’t start out understanding how to work with service providers. It took those “at bats” he described. These were opportunities to work with different customers in organizations of different sizes. Each of them had slightly different challenges and unique needs for specific technology solutions. There were nuances to scoping professional services engagements across many different customer environments. One way to build expertise even if we want to do the same job is to scale our experience by working across different industries and environments or even supporting different business units inside our own company. What if we took John’s advice and volunteered to fill in for our manager sometime even if we never want to be a manager one day? We can approach this with the intent to learn and understand, and it can make us better individual contributors. It’s a chance to communicate with skip-level leaders and learn how to better communicate with them. It’s a chance to gain empathy for those in leadership. Debrief with your manager on how the experience goes if you decide to do it. The full context of those situations might help you learn a lot about your company and management chain. Daniel learned a lot about empathy as a people manager. One of Nick’s favorite episodes discussing empathy is Episode 278 – Uncovering Empathy: The Greatest Skill of an Inclusive Leader with Marni Coffey (1/3). How can you be more empathetic? Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YoutTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

How does one company form an effective technology partnership with another company? Our guest this week might tell you it’s not so different than a successful mentoring relationship. It requires alignment on the outcomes both parties want to achieve. Daniel Paluszek is a Principal Partner Technology Strategist at ServiceNow, and in episode 337 he helps us set some context on technology partnerships and go-to-market strategies before we discuss his personal journey to working in technology. We’ll follow Daniel through early experience working at a university help desk, learn about how he grew in scope and responsibility working for a defense contractor, understand why he later chose to move into a consulting role, and wrap the entire discussion with advice on mentoring and the importance of effective communication. Original Recording Date: 06-11-2025 Topics – Meet Daniel Paluszek, What Makes a Technology Partner Best of Breed, Tech Origin Story, Mentorship and Lessons in Developing Others, Communication through Presentations, A Step Toward Consulting 2:12 – Meet Daniel Paluszek Daniel Paluszek is a Principal Partner Technology Strategist at ServiceNow. He is part of a solution consulting team supporting ServiceNow’s global strategic partners. Daniel and his peers work to optimize the way in which ServiceNow and its global partners go to market together to solve customer business problems and build solutions that drive business transformation. On a daily basis, Daniel looks at the following: Where is the industry moving? What technology is ServiceNow developing that can apply to industry challenges? What are the customer pain points, and how can a joint strategy be developed to solve these? Daniel consistently thinks about how to solve problems, and it may not be something technical that solves a problem. ServiceNow has evolved from an IT ticketing platform to a work platform, and many of the things Daniel works on span beyond IT. 4:21 – What Makes a Technology Partner Best of Breed What does it mean to be a partner to a technology company like ServiceNow? Many listeners may not understand this. Daniel believes a partner can look at a customer from an agnostic point of view to help solve specific business or technical challenges. Partners usually work with and have a joint strategy with several equipment manufacturers (OEMs) or ISVs (independent software vendors). These can be leveraged to provide a best of breed solution that meets a customer’s requirements. Regardless of a partner’s experience, they should focus on solving the customer’s unique problem(s), and this means ignoring / removing the technology landscape to make sure they understand what problem needs to be solved. Once the problem(s) are well understood, a plan and solution can be jointly developed. Solution partners can aid companies like ServiceNow in answering customer requirements. John likes this explanation of the partner ecosystem and expected Daniel to use the word reseller, but he did not mention it. “Resell for me is a motion, a sales motion. It is not the end all or be all. There’s some great resell partners, but in my mind, in my vision, the strongest partners are the ones that encompass the entire lifecycle…. The partners that are achieving and acquiring the new business look at it from a holistic approach…not just selling a product.” – Daniel Paluszek Executive leaders like Bill McDermott talk about empowering businesses to increase revenue and productivity while reducing operational expense, and Daniel tells us this effort has to focus on the core problems. A partner may also have professionals Nick mentions being a partner may also mean the partner can do professional services for a specific technology stack tied to a hardware or software vendor. John thinks even consulting services are in service of the greater outcomes a partner is trying to drive for an end customer. The goal would not be to sell services or specific pieces / parts but to “partner” with the customer and vendors to present a best of breed solution. Daniel agrees and says it is about the outcomes we’re trying to produce with the solution. The best partners can understand what needs to be achieved, set expectations, and develop a plan of execution to get there. John says we ask people what they do because one of the goals of the podcast is to expose listeners working in technology today (perhaps in IT Operations) to different types of roles in our industry across customers, tech vendors, partners, or even system integrators. In Daniel’s case, we’re talking about a role at a large technology vendor focused on a large partner and the go-to-market partnership. Can we define go-to-market? Daniel says go-to-market is an execution path based on a channel. Daniel’s role working with partners is how the partner positions their offerings and solutions to end customers. As part of the ServiceNow team, he would work with the partner to position the overall solution to an end customer. Many technology vendors have 2 major routes to market, but some may only have 1 of these. Selling products / services directly to an end customer (called selling “direct”) Selling products / services through a partner The DNA or type of solution we’re talking about and the industry to which the solution will be sold (i.e., retail, government, etc.) will dictate what the route to market (or go-to-market) is for a company. Over the course of his career, Daniel has worked with large enterprises as well as state and local governments. The direct route to market usually means the company has field selling teams that work with end customers. This can coincide with partners who work hand in hand with these field teams. John says there are likely different go-to-market plans within a technology vendor for different types of partners but that these plans will need to be customized to a specific partner based on factors like industry expertise, the way they build relationships with customers, etc. Daniel says when it comes to global systems integrators as an example, there are normally dedicated teams to serve an industry who know the industry well (its nuances, the common themes and solutions, etc.). Daniel gives an example of the retail industry and some of the nuances around point of sale, visibility, onboarding employees and making them productive despite attrition, etc. Partners with industry expertise can share how they have solved problems within that industry and how they address the common themes and challenges within that industry. Nick says there is probably a specific way in which company leaders at technology vendors would identify only those partners it makes sense for them to work with based on specific solutions or industry expertise. Partners have to be qualified and identified before a joint go-to-market can be developed. Companies like ServiceNow have online tools to help end customers find partners with specific experience (i.e. capabilities, outcomes delivered, certifications, industries of focus, regional presence or focus). Check out the ServiceNow Partner Finder as an example. Daniel looks for partner success stories in which a partner accelerated or de-risked an outcome. Due diligence is required when building a solution for our customer (i.e. the right solution for the right people at the right time), and part of this is ensuring the right partner with the right expertise is involved. 15:59 – Tech Origin Story Daniel says he grew up in technology. His father was a programmer at Bell Labs and worked at also Sun Microsystems. Daniel remembers his first exposure to Linux being on a computer running Solaris. “I was just fascinated and enamored by technology. I started off as just a kid tinkering.” – Daniel Paluszek Daniel wanted a computer because he loved video games and obsessed over getting optimal performance. He tinkered with overclocking, for example, with a group of friends. Daniel’s first job was in high school, and he was doing computer repairs. Even though he might not know how to solve a problem, Daniel was determined to go figure it out, trying to eliminate variables along the path to a solution. After determining that he wanted to work in the technology field, Daniel signed up for the computer science program and the University of Central Florida (UCF) but would find that programming did not interest him as much as solving hardware and software issues. Daniel switched to studying Information Technology (IT) after a year in the computer science program and started working in the IT help desk for the university. While working at the help desk at UCF, Daniel remembers posting his resume for an internship program which was open to all computer science and IT students. He tells the story of getting a call about a defense contractor (Ensco) that needed an intern. They wanted someone who was interested in systems engineering and systems administration, but Daniel would have to start in the help desk. Daniel initially said he was not interested because of the focus on help desk. The person he spoke to said since this was a defense contractor, they could get him on some projects working with the US government, and that piqued his interest. After interviewing, Daniel received an offer that he accepted. This began as an internship that morphed into a part-time job while he finished his IT degree. Daniel remembers working on a defense contract for the Air Force after 1-2 years, and it was focused on Solaris administration. The experience from Daniel’s childhood on Solaris paid off here. Daniel also began working with VMware technology during this time (early 2000s) for server virtualization. The Solaris administration Daniel did was in a SCIF environment. Daniel feels like saying yes to this opportunity accelerated his exposure to a different type of technology environment and different landscape that helped him progress to where he is now. “That was really my big…initial opportunity into systems engineering, administration, and really understanding a different purview…especially in federal government contracting.” – Daniel Paluszek Did Daniel understand the differences in systems administration and systems engineering when he first received the call about the role at the defense contractor? Daniel says no. He saw administration as day 2 operational patch management applied to a specific technology platform and was doing a little bit of this in the help desk role. Daniel gained experience designing new datacenters while working for the defense contractor. One of his first projects in this role at age 19 involved designing smart power infrastructure for a datacenter. “It was anxiety inducing. I’ll just say that, and I had to learn a lot. It was also my first foray into dealing with vendors….” – Daniel Paluszek Daniel had to test technology from different vendors (hardware and software) as part of this project, and he had to learn about different NEMA plugs used in datacenters. This experience helped Daniel in future roles because he understood how power and cooling worked and knew how to design a 42-unit rack. “It wasn’t something I learned at school. That was trial by fire by experience. You were dropped into this situation. You either had to sink or swim, and you had to figure it out…. But it was my first foray into designing a solution…. And I didn’t have awareness at the time of what the methodology was. I just had to figure out how to build this and get some guidance from mentors along the way.” – Daniel Paluszek Daniel says he had supportive managers he could use to vet ideas and suggested solutions. In designing a solution, Daniel had to think about things from the conceptual, logical, and physical views of the solution. If someone listening really likes the idea of being a systems designer, how much systems administration experience do they need, if any? It’s difficult for Daniel to say someone needs to choose a specific path to be successful. An administrator of a system is exposed to how the system performs and how it behaves (i.e. real-world experience using the system). This kind of experience and exposure helps one understand some of the constraints and challenges of system design. “So as a designer if I don’t have the experience of how to manage this from a day 2 perspective, I think you missed part of the equation. I’m not saying a good designer has to have that experience, but I think it adds up to this formula that makes certain individuals unique because they have had that real-world experience. Not the conceptual view of it…they lived it. They breathed it. When something broke and it’s all hands on deck, they know how to actually…figure that out….” – Daniel Paluszek Daniel reminds us that as humans we usually learn well from the times things break. So, when something does go wrong, Daniel suggests we look at those times through the lens of what we can learn and how it will make us better technologists and professionals as a result. 25:23 – Mentorship and Lessons in Developing Others Did Daniel learn any lessons in all this about teaching people or overseeing their development? As someone who had the chance to broaden his horizons at a young age, Daniel is a firm believer in mentoring. “I think guiding others on their career journey and development is key for our industry because it gives everybody an opportunity to say, ‘how do I get exposed to what’s next?’ …I had somebody for some reason randomly pick me out of thin air when I worked at a help desk to provide me an opportunity, and I’m a firm believer in passing it forward….” – Daniel Paluszek Daniel considers mentoring the next generation pf people and professionals in this industry as something that is at the heart of his personal and professional development. How does Daniel spot people who might need some mentoring? He looks for people who have a desire to learn and challenge themselves. Daniel shares a story about a product manager who called him seeking to understand the perspective of a field-facing sales engineer. This person wanted to become a better product manager by understanding more about how Daniel and others in his role worked with customers on a day-to-day basis. He and Daniel developed a long-standing deep relationship as a result. People who want to challenge themselves to be better are often seeking guidance. Daniel mentions the importance of guardrails from a mentor in these situations. After Daniel recognizes the drive and high-performance potential in someone, he likes to take time to get to know the person and understand what they really want / what they are trying to pursue. Daniel tells us he challenges himself daily to articulate solutions better every time he talks about them, and it’s about constantly seeking to become a better professional. What guidance does Daniel have for the person who is asking for mentorship (i.e. the mentee)? Daniel encourages us to communicate the context. Be sure to communicate what you want to achieve as well as your short-term and longer-term goals / aspirations. For those in pre-sales, are you looking to provide differentiated value in a specific industry, for example? Do you want to become a subject matter expert? Are you looking to gain exposure to giving presentations? The secret, according to Daniel, is practice! When he worked for the defense contractor, Daniel had to present his physical power infrastructure solution to a large group of people (around 100 people). He tells us it was awful despite weeks of practice. “But I realized very quickly it just comes down to…you have to put in the time, the effort, the discipline to put yourself in a better position. I also had this naïve view that…certifications and certain qualifications were this end all be all…. That’s part of the equation. It’s about how you communicate, how you work through a dialogue, and that comes with experience. That’s priceless. You can’t purchase that. Yeah, you can have classes that teach you to become more of an eloquent speaker and articulate a message…but the proof is in the pudding when you’re in front of the customer, in front of the panel, in front of the event. I always process. What did I do really well here, and what can I improve on? Or what do I need to work on next time? So, I always have this post-processing operation for me that says, ‘these are things I need to improve on’ even to this day.” – Daniel Paluszek When mentoring others, Daniel wants to know what the person is trying to achieve and the outcome the person wants. He also asks why people came to him specifically and what he can help with. 32:01 – Communication through Presentations John says people often think having expertise will allow them to eloquently communicate expertise, but there’s a difference between gaining mastery of a skill and teaching someone about that skill. It seemed like Daniel realized the act of presenting was something very different. “What I realized very quickly is I really enjoyed speaking to others about a technology and also framing it in the reference that they could understand. One of the things I learned very quickly is you need to know your audience. Who are you speaking to? Who are these individuals? …You could be a subject matter expert in this technology. You have to have the context of who you’re speaking to, who you’re trying to articulate a message to.” – Daniel Paluszek Presenting a solution to an executive compared to someone who is more technical at a lower level in an organization is quite different. You need a different approach and must frame things in a way that the audience understands based on the context of the solution or situation at hand. Think about why people in the audience are there. What do they want to understand or take away from what you present? Daniel stresses the importance of meeting the audience where they are / meeting them in the middle and putting things in their terms. He learned how to apply the right context within his presentations so it would be impactful to the audience. Daniel knew after his first speaking experience that he had a lot of room to improve. But he also found it both interesting and enjoyable. Doing presentations gave Daniel a lot of energy, especially seeing people understand complex solutions or take something away from the discussion they can apply to improve their own work. “Even today, it’s about providing a level of understanding the audience can just take away. What are the key points that I am trying to drive towards that solve your issues and your business problems?” – Daniel Paluszek Did Daniel get some pointed feedback after that first presentation that led him to the post-processing exercise, or did that come only through more experience? Daniel remembers people saying he did a good job but feels they were just trying to be nice. He walked away from that experience knowing he needed to do better but at the same time really enjoyed the challenge and the impact. This presentation happened before Daniel got into consulting and started working for partners. “But I saw a spark. This was something that I really enjoyed…presenting and articulating a message. I just didn’t know at that time where that was going to lead me….” – Daniel Paluszek Around the time of that first presentation, Daniel was focused on learning everything he could and soaking in new experiences. He wanted a broad view of the industry and the market as a whole from which to learn. When new opportunities came up, Daniel would be the first to volunteer. Things he had never done were opportunities to go and learn something new and then compound past knowledge. “The words of wisdom I could give to anybody starting off their IT career or in this industry is be the first one to raise your hand. You may not know how the heck to do it, but if you have the drive and desire, you’ll figure it out. I figured it out, and I don’t feel like I’m the smartest person…. But I feel like I have that innate drive and desire to figure it out. And I set my mind to it, and I don’t stop.” – Daniel Paluszek 37:13 – A Step Toward Consulting Is the drive what led Daniel into consulting? Did someone else recognize it, or did he push into that on his own? After the defense contractor, Daniel worked for a service provider (a cable provider) for a short time. Daniel did get to go and engineer solutions that he would then get to deploy. But then he would have to maintain those solutions. The day 2 maintenance and operations became repetitive and kind of boring for Daniel. “But I just felt like it was this same cycle over and over again….” – Daniel Paluszek, on building systems and then needing to maintain them Despite this, Daniel did get exposure to new technologies during this time. The company was focused on virtualization and consolidation of workloads using VMware technologies. He felt virtualization as a technology trend was really going to take off and could see this capability was driving good outcomes inside his employer like simplifying the architecture, but Daniel says he didn’t realize the economic impact of using virtualization technology at that time. Daniel had an interesting opportunity to work at a small partner in Tallahassee, Florida called DynTek Services. The role was a systems engineer for the consulting / professional services arm of the company. “At the cable provider, I started seeing these partners come in and out and really help us with our technology…. It just seemed so fun to me…. They can come in to a customer and present a solution, work with us on deploying it, ensuring that it’s working for us”, and it really changes our paradigm. So I said, ‘I’d love to do something like that.’ Needless to say, I got this opportunity…and that started my consulting career. No prior experience…I was just an engineer at the time. I didn’t have any pre-sales experience, but I worked with a sales rep who was an incredible mentor to me." – Daniel Paluszek Daniel says the sales rep was kind enough to “show him the ropes” once he joined DynTek. Their focus together was on state and local government. This sales rep was kind, true to his customers, and developed long-standing relationships with people when it came to solving problems. The sales rep had built strong relationships, and when the customer needed to solve a new problem, they would seek his advice. “He treated companies and organizations in state and local departments with respect, with honesty, in an ethical way, and always made their lives better and their organizations better. So, it was a great learning experience for me. Wow, this is incredible. I can learn and really experience the people side of it and how to have the interpersonal skills and work with dynamic situations…but also bring in technology. And it was almost like a switch turned on in my brain that said, ‘this is incredible. This is what I want to do.’ Because I felt every week it was something new. It was something dynamic. It was a new opportunity or a new customer problem came up, and we had to go solve it…. We had to orchestrate and build a solution that was compelling enough for them to say, ‘yeah, we’re going to buy off on this, and you’re going to help us go deploy this.’ …This is exactly what I was looking for that I didn’t have before.” – Daniel Paluszek, on working with a great sales rep Mentioned in the Outro Did you hear the parallels between mentorship and technology partnership? If you’re seeking a mentor, you want someone with expertise in the area where you need help just like a technology company or end customer would seek a partner with the right level of expertise. It has to be good for both parties. It’s good for the mentee because they get to develop in a specific area, and it’s good for the mentor because their experience is valued and applied in the right place. Daniel talked about spotting individuals who had high performance potential and a specific amount of drive. This is also analogous to finding the right partner. Mentorship is something we should all be doing to develop others and to make our industry better. If you are seeking a mentor, be prepared to communicate why you specifically picked someone to mentor you in an area. When Daniel mentioned guardrails as key to mentorship, we immediately thought of the discussions with Dale McKay on this topic: Episode 288 – Guardrails for Growth: A Mentor’s Experience with Dale McKay (1/2) Episode 289 – Enhance Your Personal Brand: Feedback as a Catalyst for Change with Dale McKay (2/2) We heard about the importance of effective communication to different audiences in our industry in this episode as well. Many different guests have stressed a similar emphasis on communication. Former guest Neil Thompson of Teach the Geek wrote some good articles on importance of developing strong communicators: How Tech Leaders Can Develop Strong Communicators Why Technical Leaders Need Strong Communicators Neil joined us in Episode 193 – Communication for Specialists with Neil Thompson (1/2) and Episode 194 – Question Askers and Problem Solvers with Neil Thompson (2/2) if you want to go back and listen. If you want to get better at doing presentations check out our Presentations Tag with links to episodes that discuss this topic. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YoutTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. 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Looking back on one’s career, it might be easy to connect the dots between job roles you held in the past, but what can we really do to influence where the dots are placed in the future? Srikanth Bollavaram took an approach that pulled opportunities in his direction. What if you could do the same? This week in episode 336, we continue the discussion with Srikanth and focus on his consistent openness to taking different roles across various areas, many of which came to him at the suggestion of leaders who knew his reputation, skills, and capabilities. In the cases where a new role pushed Srikanth out of his comfort zone, personal growth and more opportunities always followed. It suited his desire to keep learning. Srikanth found over time that leadership isn’t a specific title or role. It’s a responsibility you have that could be an aspect of many roles. Srikanth also stresses the importance of defining your non-negotiables like self-care and family as a leader to help manage time constraints. Original Recording Date: 03-30-2025 Srikanth Bollavaram is a product development leader with experience spanning the financial, railroad, and consumer packaged goods industries. If you missed part 1 of our discussion with Srikanth, check out Episode 335. Topics – Gaining Experience along the Path Less Traveled, Connecting the Dots Backwards, Leadership as a Responsibility, Time Constraints and Non-negotiables Before we begin, did you do the homework we assigned last week? If not, we highly recommend you go back and listen to this episode before listening to part 2 of Srikanth’s story – Episode 325 – Overwhelmed by Ambiguity: DevOps, Innovation, and the Search for Clarity with Daniel Lemire (3/4). 3:18 – Gaining Experience along the Path Less Traveled Was it normal for people who were brought in for roles like the one Srikanth had to have or be very interested in both business and technology operations and the marrying of the two? We would probably classify this type of role as operational technology today. When Srikanth first started working for the railroad, he began working on the digitization of the customer interactions. He did not go directly to the operational side. “First, you have to gain some credibility in whatever you do. It doesn’t matter what that work is.” – Srikanth Bollavaram In those days, customers might call, fax, or e-mail the railroad. Srikanth’s role was to digitize all customer interactions end-to-end. This included building, tracking, tracing, payments, and more. After working on the digitization for a couple of years, Srikanth started noticing several other interesting projects. The work on control systems he mentioned earlier was the result of the opportunities given to him over time. “A lot of times it’s not me seeking. This is actually a very repeated pattern in my career. People identified me as a potential candidate…and then pulled me into those roles, whether it’s an architect role or even a principal engineer role…. The leaders in the company identified me as a potential candidate and just started giving me those opportunities.” – Srikanth Bollavaram The control systems were part of a project for the railroad’s dispatch center, which orchestrated all switches, signals, and communication to locomotives. At the time Srikanth was selected for this project, it was not going very well, and it was not considered a good move to take on the role. Srikanth tells us he likes to choose the “path less traveled” to see what happens. “If it is interesting enough and challenging enough, you just go and try it, give your best, and see what happens. That always, at least to me…worked out well. I gained an experience which I wouldn’t have if I thought what would have been best for me rather than looking at my superiors…. They’re telling me, ‘hey, maybe you should do this.’ I probably would have chosen something in my comfort zone as an extension to my comfort zone. All these things actually pushed me completely out of my comfort zone…. Especially if you have been asked to do it, and if your seniors trust you enough so that you could do it, just do it. You may not like it initially, but that would add a very valuable experience for you.” – Srikanth Bollavaram, on considering opportunities 6:37 – Connecting the Dots Backwards Did Srikanth’s move into the railroad industry also involve shifting from individual contributor to leader? Srikanth began as an individual contributor when he was working for the railroad but transitioned quickly into a technical lead role and then into more of an architect role. These were moves up into leadership type roles. “Instead of seeking for a next level job, you try to do a next level job…in your current position, and then that automatically opens up positions for you. And I think pull is always better than a push in my opinion. Creating those opportunities and making you as an ideal candidate is how I operated…. It all depends on…where you are in your career and what that involves…. How many changes can you adapt at the same time…not only in career but also family wise…? …That’s why when somebody asks it’s always based on the context at which you are taking that decision.” – Srikanth Bollavaram Srikanth tells us the shifting of roles may involve a relocation or moving to a new company. For those who have children, consider their age and where they are in school to determine how changes you make will impact family stability. According to Srikanth, we should seek to make ourselves candidates for multiple things and not just one thing through building credibility and gaining critical experience in different areas of a company. Srikanth once received advice to think of himself like a stock. If you are traded out in the open market, you should always be more valuable in that trade than to the current company. In this way you’re providing more value where you are operating because it’s like they get the stock at a discounted rate. Instead of focusing too much on a level you want to achieve, improve your skills and capabilities so that you give more value to where you are currently operating. John mentions patterns we’ve seen related to the idea of growth vs. comfort. When we are comfortable, we are operating fully within our capabilities, but growth means learning and pushing beyond what is comfortable. It helps to have people pushing us to grow. Srikanth also mentioned being pulled into specific roles, which speaks to having a strong brand within the organization as someone who can adapt, problem solve, and troubleshoot effectively. It means people recognize you as having the skills and abilities to perform a role when opportunities arise. Additionally, it can be difficult to move to a new company based solely on having a strong internal reputation at your existing company. With the above items in mind, let’s talk about Srikanth’s move into leadership and out of the railroad industry. Srikanth says if you are comfortable in your job, you are likely not growing. If you have good leaders and mentors as Srikanth mentions he did, they will be able to spot some of your gaps / blind spots and suggest ways to fill those gaps. Srikanth tells us that moving out of the railroad industry was also a family decision. The family lived in a small town and wanted to move to a warmer climate. Srikanth’s kids were in elementary school, and he had extended family in the Dallas area. Srikanth viewed changing companies as something that was better to do earlier in his career rather than later. Initially, Srikanth thought he would still be working for the railroad if his family relocated, but that was not the case. Srikanth saw a leadership opportunity at a different company that needed someone to build digital platforms, and he had experience from the railroad industry which would easily transfer. “I had a very good knowledge in terms of how to build those platforms, so I took that as an opportunity to come and start a new career in the CPG (consumer packaged goods) industry. But what you said is totally true. You just have to start from zero again in terms of your credibility and your relationships. It’s going to be a struggle, not only because you’re trying to build that within the company but you’re adapting to a new environment, new city…. It was a bit stressful to be honest at least in the initial years….” – Srikanth Bollavaram Srikanth was excited about building a new team culture. He was energized by the opportunity to build internal products and solutions. The team needed to think about how to build and make the platforms like a product. Srikanth says they were buidling the capabilities in the cloud, and it was very exciting. “In terms of leadership, first you have to establish yourself as a credible leader. You have to bring along your team. I think that’s something from time to time you have to go through. You have to go through this phase of reinventing yourself….And you can always say this looking back.” – Srikanth Bollavaram Srikanth reiterates that the change was more for family reasons than for a different position or to move up. John says being able to tell a story looking back does not mean we know at the inflection point we know what the story is going to be. There is a range of possibilities in any decision. Srikanth says if you’re very clear and focused about exactly where you want to go, that is a good thing, but he likes to remain more open. “I am going to trust the process and see where it leads me, and what I learned in the process is establishing the relationships, building credibility. And while you’re working, not only think for your success but how do you make sure you’re always thinking of people who are working, how they are going to be successful? If you…go with that attitude – more of a team culture, your peers and colleagues…how do I make them successful, not just me? …You go through these projects or programs or roles…. It’s beautiful afterwards. The relationships you establish are long lasting if you go with that process, and that to me is more valuable than any roles or positions you held….” – Srikanth Bollavaram Though we can connect the dots backward, Srikanth encourages us to think about the following when looking forward to increase the likelihood of good things happening because people will remember you. Are you developing future leaders? Are you making others successful and not just you? Are you learning and getting out of your comfort zone? 17:53 – Leadership as a Responsibility Is what Srikanth shared above what it means to truly progress as a leader once you become one, or are there other aspects we’ve overlooked? “See, when you are a leader, the most important thing is you have to deliver the results. That is non-negotiable. But then comes how you do it…. I think you could achieve the results in various ways.” – Srikanth Bollavaram If a leader can deliver the results through empowering people, being open, understanding yourself, and create a positive team culture…that leader can look back and be proud of the results. This part is personal to the leader. Srikanth mentions reading the book True North: Discover Your Authentic Leadership which talks about leaders operating and delivering results based on their values (values being personal to each leader). As a leader Srikanth adopts the things which are important to him without compromising the results. “As you go up in the organization, it’s very hard to execute, deliver the results in the right way. But that’s where the real leadership test comes. Leadership is…to me a responsibility. It’s not a title. It’s more of a responsibility…towards the people you’re working with and toward the mission at hand….” – Srikanth Bollavaram Each leader has a mission to deliver results which is usually based on the purview of their team and the internal organization in which it operates. When a leader is open to opportunities and is given a new mission to lead a different team, how do you make the transition while maintaining relationships with the former team and building up those with the new team? First, it is about not only your success but also the success of the people working with you (on your team and beyond). “Whenever I take up a role, what I see is…you’re there for a reason, to solve a problem. If you do it effectively, within a year or two, that position shouldn’t be there technically…. If you develop appropriate leaders…identify the leaders who are taking more responsibility and you grow them, any of them should be able to take it and run with it.” – Srikanth Bollavaram Srikanth says when you’re given a leadership position, if you streamline it, you create an opportunity for future leaders who can take that role later on. You can also leave that position in a better state than when you started in it for the benefit of your successor. “If you do that well, you don’t really spoil any relationships because you’re growing the people. You’re solving the problem…making it…. If you create a system effective enough, it probably can run itself.” – Srikanth Bollavaram Srikanth takes the above approach in every leadership role he takes – leaving things better than when he initially started in the role and in a state such that someone else on the team can run the team. Maybe this approach is similar to parents training their children to become adults and to need their parents less over time? Srikanth reminds us that the aspiration of a leader is to leave the place in a better state than in which you found it. You can do this successfully by developing the next generation of leaders and ensuring the mission is not compromised. John mentions the theory of constraints and reminds us that we don’t want to engineer a system where the leader is the constraint. We don’t often think about leaders being a constraint. It’s usually something on the operations side that we think of being a constraint. But if a leader is the constraint, it is likely a leadership issue. “But if the leader is there catalyzing a change that perpetuates itself beyond the leader’s presence, that’s a successful change.” – John White Nick says a move to a new position is identifying and exploiting the next constraint. Srikanth said his team did this very successfully when building digital platforms that were resilient and self-healing. They did things that at first didn’t even seem possible by eliminating one constraint at a time. 25:06 – Time Constraints and Non-negotiables Nick mentions one big constraint for leaders is time. How can existing leaders and prospective leaders manage their time to focus on the most important things? “I think about this in…multiple layers. First is take care of yourself…. Have a good fitness regimen…. Because if you can’t take care of yourself, you can’t take care of either your family or the team…. It gets really important to maintain your health, not only health in terms of physical fitness but also mental fitness…. What helps me is learn some kind of meditation…where you kind of take all the noise out and reset your mind from time to time. I think those are very important.” – Srikanth Bollavaram Right behind taking care of yourself is taking care of your family and fulfilling your responsibilities to the family. A job, for example, can be replaced. You and the role you play in your family cannot. Srikanth tells us when it comes to work, it is a process of continuous learning. Each day, he is trying to learn how to manage time better through developing new leaders, new processes, and new systems. All of these together allow for an operating mode that helps manage and reduce the number of exceptions to this operating mode over time. “I think you have to continuously learn too because a lot of stress comes when you’re only seeing problems day to day. You may be solving the problems, but you have to have something else to enrich your mind other than the work and activities outside. I think it’s all about balance. It will go off balance many times, but it’s how quickly you come back to it is the key.” – Srikanth Bollavaram Srikanth says we put some guardrails in place like planning fitness time and vacation time and working everything else around them. These breaks are needed and allow for rest and rejuvenation so we can come back and operate effectively. “Work-life balance…I think it’s so intertwined now. It’s very difficult to say what that is…. You just have to within your context create that and what works best for you…. I would say your self-care and family…are non-negotiables.” – Srikanth Bollavaram If you want to follow up with Srikanth on this conversation, you can contact him on LinkedIn. Mentioned in the Outro We heard about it last week and this week. Srikanth was open to new opportunities throughout his career to gain different kinds of experience across different areas. Family was a big factor in job decisions for Srikanth, and along these lines he cautions us to be careful not to change too many things at once. How many changes could you handle at once? We might not know until we try it. The episode we assigned for homework, Episode 325 – Overwhelmed by Ambiguity: DevOps, Innovation, and the Search for Clarity with Daniel Lemire (3/4), was an example of someone taking on more change than they could handle at once. It was, however, a learning experience for Daniel. Many times Srikanth needed to make a job decision because a leader suggested he take a new role. Those leaders understood Srikanth’s capabilities and skills because he had built credibility through delivering results. We did not talk about it in the interview, but Srikanth must have been communicating his accomplishments to his leaders in 1-1 meetings. Srikanth encouraged building our skills and capabilities over seeking a specific job role or title. It’s skills and capabilities that help us meet job requirements. Have you taken time to think about the skills and capabilities you need to build for what’s next? What areas do you need to sharpen, and what are some new areas in which you need to build some skills? You might need a mentor or someone else to give you advice on these topics. Srikanth spoke about stepping into people leadership. His path, like that of many other guests traversed through technical lead. He was also an architect and even a principal engineer. It was not an immediate jump from individual contributor to people leader, but at each step, there was an element of leadership in these roles. Part of the mindset shift in being a people leader was to focus on the success of others – building future leaders, improve processes, and build helpful systems. Did you notice he’s still building systems even as a people leader? Here’s a episode on the decision point between individual contributor and people manager that pairs very nicely with this episode – Episode 244 – An Array of Decision Points with Tim Crawford (2/2) . Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YoutTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

How honest should we be in job interview situations when it comes to what we don’t know? Srikanth Bollavaram, our guest in episode 335, would encourage transparency in these situations, but we should also find a way to communicate what our capabilities are and our potential to meet the challenges of a role. Srikanth is a product development leader with experience spanning the financial, railroad, and consumer packaged goods industries. His story showcases stepping beyond building systems to become a well-rounded leader capable of driving real business impact. Listen closely to the story of an unexpected job assignment in Switzerland that jumpstarted Srikanth’s embrace of industry expertise. Pay special attention during this interview to learn from Srikanth’s experience: Supplementing technical skills with business acumen and continued education Embracing the mindset that every challenge is an opportunity, even if it doesn’t seem that way at first Explaining complex concepts through the lens of practicality to stand out as a job candidate Original Recording Date: 03-30-2025 Topics – Meet Srikanth Bollavaram, Practical Approaches to Mechanical Engineering and Computer Science, Relocation and Experience as a Consultant, Execution and Delivery, Continued Education and a Step Beyond Building Systems, End-to-End Solutions in the Railroad Industry 2:13 – Meet Srikanth Bollavaram Srikanth Bollavaram leads a product development organization for a global consumer packaged goods (or CPG) company. His organization is currently focused on building a product for a major business transformation. Srikanth is originally from India but had the opportunity to relocate a couple of different times beginning early in his career. Srikanth relocated first to Switzerland to work in the financial industry and then later to the US. Today Srikanth and his family reside in Dallas, Texas. 2:54 – Practical Approaches to Mechanical Engineering and Computer Science Growing up in India, Srikanth wanted to be an engineer. He was curious about how to build things and how things worked. But at that time there was a general expectation to become either a doctor or an engineer. After being unable to dissect a frog in middle school, Srikanth realized his path was engineering. When you want to be an engineer in India, you have to pass a test similar to the SAT. Based on overall rank, students in the top 1% get to choose their major. Most pursuing higher education would go to either a government school or a private college. Srikanth had only a couple of minutes with a counselor to choose between pursuing mechanical engineering at a top state school or attending a private college to focus on computer science. At the time, Srikanth chose mechanical engineering because he had always wanted to go to the school where this program was offered. While he did like mechanical engineering, Srikanth wanted to be a computer science engineer as well. Many of his courses for mechanical engineering were computer courses, and he focused on the practical uses of computer science for mechanical engineering tasks. John mentions listeners might not know that the test and ranking Srikanth mentioned in India is nation-wide. Universities might differ on the requirements for entry based on your ranking. Srikanth mentioned there was a state-level test in addition to the nationwide test, and based on your ranking you get a choice of major. But you don’t know which major you will get into until you go to counseling. When Srikanth graduated there were not many national or state-wide engineering colleges. Now there is a quite a bit of choice for students in India. Was engineering as a discipline of study as interesting as Srikanth thought it would be? Before he began studying engineering, Srikanth says most of his education leading up to high school was heavily theory based. Srikanth tells us this did change but not to the extent he would have liked. Srikanth tells us engineering designs were basically hand drawn 2-dimensional models. He was studying computer languages and wondered if he could draw a design in real-time on a computer screen, which provided an opportunity to experiment and observe. Srikanth says he was more comfortable with the hands-on aspects of learning than the theoretical parts. There were lab exercises, but they weren’t representative of real-world scenarios. Srikanth was also studying thermodynamics. While they did have labs, if he wanted to see how energy transfer worked (i.e. heat energy converting to electrical energy), Srikanth could go to a power plant to see the entire process. The practical aspect was more interesting. “In engineering what I tried to do is focus less on academics but more on the practical applications of those academics, and that turned out…in my favor…. When I was graduating, all the consulting companies were coming and interviewing, and they were more looking for that broader application or mindset, and it was easier for me to get selected even though my academics were not the top in the class. But I had a broad variety of experience both in computers and engineering, and I could explain things in an easy way.” – Srikanth Bollavaram Consulting firms partnered with many of the universities and would interview graduating students for jobs. Srikanth mentions a computer-based consultancy that was willing to consider candidates from various majors (including mechanical engineering, for example). The consulting firms might ask candidates to take a competency test or conduct interviews to determine how candidates solve problems. Nick says the desire to understand how things work and the practical application of it sets someone up nicely to be able to communicate how things work in a simple way. Srikanth remembers a specific question from his interview about internal combustion engines. The internal combustion engine had been built based on Western designs, but Srikanth explained an example of how Indian engineers had built a stabilizer for fuel efficiency when vehicles traverse rough terrain. Srikanth’s approach to answering the question from a practical standpoint instead of solely a theoretical one really impressed the interviewer. John mentions being able to ground complex concepts in reality and explain them in a way people can understand is something solution engineers constantly have to do, but as a skill this is useful in any discipline or field. Srikanth stresses the importance of taking the time to understand a problem and its practical applications before narrowing to solution. John says this feels like it falls into a pattern we’ve seen in the past. If you think you understand a concept, can you write down an explanation of it in your own words that you will be able to read and understand at a later time? If you cannot explain a concept to yourself, you might not understand it as well as you thought. Srikanth remembers working for a leader who shared a similar lesson related to design. Put the design on paper, and try to explain it to yourself. This process would help someone think through all of a design’s implications and remember more about it in future days and even months afterward. Was this process of explaining things to cement learning something Srikanth found himself doing when he made the move into consulting after graduating from school, or was it later in his career? Srikanth thinks it was later in his career when he moved to technical leader and architect after some coaching from his leaders. Earlier in his career, Srikanth was a programmer driven to learn new concepts through testing and asking questions. 13:59 – Relocation and Experience as a Consultant Srikanth tells us that his relocation to Switzerland was somewhat unexpected. At the time, he was a programmer, and he really wanted to go to the US. Srikanth had heard about a project in Switzerland that would last a few months and was eventually told he had to go. When Srikanth was chosen for the assignment in Switzerland, he did not know what type of work he would be doing. Srikanth learned he would be acting as a liaison between the customer who had hired his employer (a consulting firm) for the project and the IT team. “A lot of times people are observing you, what you do…. Your skill set or what you are is determined by what people are observing. And they somehow thought that I was a better fit for this.” – Srikanth Bollavaram Srikanth remembers his boss on the customer side asking him a lot of business questions the first time they met. In that moment, Srikanth was honest about what he knew and what he did not know but also spoke to the things he could potentially do. “Talking about relocation…it’s all about context…. A lot of it is built on how you take it. I could have been sent back on the next flight because I was not fit for the job, but I talked to him and explained what I know and what I could do potentially based on if somebody could give a training. So, they sent me back on a business side training for like 3 days to get up to speed quickly. Initially I was supposed to be there 4 months, but they liked my work. So, they extended me for like 2 years…. I was a consultant. You just have to go and look at the job you have been assigned, not necessarily just ‘this is what I am going to do.’ What is the problem at…hand? …Do it well, and if you don’t know, build that trust you don’t know but you will learn and still do it. It was a great experience from that regard. It could have ended up otherwise. But it’s what opportunities come to you, and then how…you take it and run with it…makes the difference.” – Srikanth Bollavaram, on being a consultant John reiterates the lesson here in being honest about what our capabilities are and are not. It’s not just about what you don’t feel qualified to do. Speak to what you can do and how you would get up to speed to do what a hiring manager / employer would need you to do. Srikanth tells us it is about building trust and then following it through, even if extra effort is required in the beginning to serve the needs of the problem at hand. Even though Srikanth did not know what the job was initially, he was curious enough to learn and focus on solving the problem. Nick thinks the manager in question really had 2 choices after understanding Srikanth’s current competencies. There is a lesson here for those in the manager’s seat to consider giving people the chance to learn something if they have the potential rather than dismissing a candidate because they don’t fit exactly what was needed. Srikanth feels he has had leaders in the past who provided him with a chance to adjust and still execute. Even when we are competent, we still might struggle when initially pursuing something new (i.e. a new assignment / job, a new project, etc.). As a people leader now, Srikanth tries to keep these things in mind when considering the holistic candidate based on the lessons he has learned and the opportunities previously granted to him. 19:20 – Execution and Delivery What kind of pressure did Srikanth feel (if any) knowing he wasn’t fully qualified for what he had been asked to do? Though he did take the training, was there something more? The first days of training helped Srikanth understand how the business ran and what they were asking him to do. This helped him feel more confident. Srikanth also built relationships with others during the training to contact in the future for guidance if needed. After about a week, Srikanth was much more confident. He also describes making an intentional mindset shift. “I knew the programming. I knew all this. But this is something I cannot learn anywhere…. This is once in a lifetime opportunity. If I put in enough efforts, I could learn quite a bit in this area. So, I got more energized by that…. There was some…impostor syndrome, but I believe early in your career you are kind of ignorant to some extent. The excitement to learn and the opportunity overshadowed me, at least initially…. There is so much to learn, so let’s go and learn and do it.” – Srikanth Bollavaram The company’s business was related to the Swiss stock exchange, clearing, and settlement on a domestic and international level. Are some of these things we’re discussing inherent in the consultant role? Usually this is someone from outside an organization who is brought in to give some feedback or to solve a problem. Srikanth tells us there was a specific problem to solve. The company who had hired him was working with a specific 3rd party company to build a solution. There were some gaps between what the business wanted and what was being provided, and they needed someone in the middle to help. There were not really product-focused roles at this time. Even business analyst as a term was pretty new. They needed a mix of technical and business knowledge to ensure the appropriate requirements were gathered to design and deliver a solution for what was needed. The company who hired Srikanth’s company wanted an external entity to provide the technical skills they were lacking and to execute the project representing them. John says we might think about this today as being an external product manager who works with an external contractor that is developing a product. “In a lot of ways, I was holding my own company people accountable to deliver that sitting on the other side, which was a bit awkward at that point…. But I think that was a very valuable experience because at the end that drives trust and accountability in a way that was not existing before.” – Srikanth Bollavaram John says a company might do this to not ruin a relationship with another company. It would allow someone else to act as the “bad guy.” Srikanth says whether you’re a consultant or in any other role, it is about building trust, keeping your promises, and then executing and delivering. 24:51 – Continued Education and a Step Beyond Building Systems Nick sees elements of leadership in Srikanth’s role. He was in an interesting spot between the business and the extremely technical side, which provided multiple options for a next career step. How did Srikanth decide what to do next once the job in Switzerland came to an end, and how did the previous experience influence his decision? “That did kind of teach me you just have to be multi-faceted. You need to…gain a well-rounded experience. Work on the business side. Try to understand the business. Do various roles…. Take whatever the role is thrown at you. Don’t ask whether it is specifically this or that. Try multiple areas, and then you can choose which direction you want. And that also enables you to be a well-rounded person.” – Srikanth Bollavaram Srikanth wanted to come to the United States, and he would end up working for a credit rating agency, which he describes as a completely different challenge. At the time, this was not an extremely intentional choice, but Srikanth would later embrace an intentionality in his career, changing areas every 2 or 3 years to gain more experience. John highlights the collision of / tension between 2 ideas here. First, there is confidence – determining what an employer needs and figuring out how to deliver it regardless of your current skill set. The second is the lesson Srikanth learned about intentionality as a contributor to career growth. Srikanth mentioned upon coming to the United States, he also wanted to continue his education in addition to working full-time. He would enroll in a master’s program in MIS (management information systems – which we refer to as a computer science related field). Even after completing the master’s program, Srikanth would take courses in leadership, program management, and other areas to add another layer to his skill set which he says was very much needed. John highlights the MIS degree program as one of the few that could have at that time pointed Srikanth toward what we call IT (information technology) today. Srikanth tells us the MIS degree was a combination of business, information technology, economics, and finance. Srikanth knew programming and how to build systems, but these additional courses provided a more complete picture. “…I believe 5 years into my career at that point, and I knew the programming. I know how to build the systems. At that point, I felt that it was more appropriate to not only build the systems but also understand the other aspects to be more complete.” – Srikanth Bollavaram 29:24 – End-to-End Solutions in the Railroad Industry Nick mentions that the studies compliment Srikanth’s desire to build things and understand how they work. One of the best ways to figure out how something works is to build it. When Srikanth joined the railroad, he discovered there are few industry specific products for the railroad. In fact, most of the technology solutions needed to be engineered and built in-house. They needed employees with both software and hardware expertise. Some of the hardware components on a locomotive were very specific, for example. Srikanth says working for the railroad really satisfied his desire to build things. “I was very surprised to see how technically advanced the railroad information technology or engineering were. That’s where I would say I cut my teeth…. And the leaders there were just fantastic, even coaching and…growing us in the way that we could solve those bigger problems.” – Srikanth Bollavaram During his time working for the railroad industry, Srikanth had the chance to be part of large programs which made a big impact both on the overall railroad industry and the greater US economy. John highlights that this is an industry specialized enough to be somewhat unfazed by advances in commodity technology. It requires the operations teams to have an end-to-end system where they own all the parts or what John calls “owning things end-to-end.” Commodity items purchased off the shelf might need to be tuned to the specific use case (i.e. ruggedized hardware, for example). This was at a time before internet of things was really a thing. Srikanth tells us it was about building end-to-end solutions and thinking about how to productize them to sell for other railroads to use. He gained some design experience during this time as well. “Everything is an opportunity. When there is not a solution, you build it, but you can also productize and market it.” – Srikanth Bollavaram Srikanth describes the introduction of a safety mandate for autonomous control of trains and needing to build something that could adapt to future technological advances. While autonomous control would stop a train if a human could not, it also introduces other considerations which must be addressed. Srikanth was fascinated by the process of building real-time control systems. He stresses the importance of having deep engineering talent to support the end-to-end solution from a software and hardware standpoint. These control systems are also safety critical. “You need to make sure it not only performs the function…you asked to do but in all cases,…the safety of the system is not compromised. So, you have to think of all those boundary conditions as well.” – Srikanth Bollavaram Nick feels like this is a great blending of the computer science and engineering background Srikanth had. Did Srikanth seek out the railroad industry specifically, or did the opportunity come to him? Srikanth says he did not seek it out, but it was a logical decision. He had moved from Switzerland to California and would then move to the midwestern United States for the railroad job mainly for family reasons. Srikanth says his wife was studying at the University of Nebraska at the time. “It happened to be the best decision…in terms of…combining all of those experiences and really growing myself. It was a very good environment to nurture the talent, experiment, do things, even sometimes fail…but recover and really enjoy the engineering work.” – Srikanth Bollavaram, on relocating to the Midwest for a railroad job Mentioned in the Outro Srikanth understood the technology but spotted opportunities to learn about the use and impact of technology within the scope of a certain industry’s business operations. The industry exposure and experience was the opportunity for learning in his mind. These decisions took Srikanth’s knowledge beyond just building systems. It was a great exercise in truly understanding all the requirements a system must meet (including architectural considerations, design implications, etc.) based on the business need. If you are looking for other stories of guests who embraced industry expertise to progress in their career, check out these conversations with Amy Arnold about her experience in the public sector: Episode 281 – Packets Don’t Lie: Quality of Service for Technical Exploration in Network Engineering with Amy Arnold (1/2) Episode 282 – All the Networking Things: Project Management, Pre-Sales, and Broadening a Technical Specialty with Amy Arnold (2/2) Building end-to-end solutions required supporting every piece of the solution. This was truly product management and treating the solution like a product. While the railroad productized the solutions to sell to other railroads, not every company may productize things to sell outside the company. They may productize to use internally for different business units with different use cases. The product mindset can still be an effective approach. Remember, if you are looking to progress into product management, you do not need to limit your search to only technology vendors. Product management roles can exist in many different places. Your homework before we release part 2 of Srikanth’s story is to listen to this episode featuring Daniel Lemire’s story of taking on too much change in his career at once: Episode 325 – Overwhelmed by Ambiguity: DevOps, Innovation, and the Search for Clarity with Daniel Lemire (3/4) Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YoutTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

Imagine developing a set of skills that enables you to get a management job, only to find you have to throw away the entire toolkit that made you successful. This is the jarring reality for many new managers, a career change that is less of a step up and more of a step over into a completely different profession. This week in episode 334, John White flies solo to share a candid teardown of his first two and a half years as a first-time manager. He unpacks the great “unspoken skill swap” required to transition from a top individual contributor to an effective leader. Drawing from his own journey and advice from past guests, John offers a realistic preview of a manager’s daily reality, covering the jarring shifts in responsibility from doing the work to setting the context, from having the answers to finding the resources, and from individual achievement to enabling the success of others. Original Recording Date: 06-29-2025 Topics – The IC-to-Manager Skill Swap, From “Do-er” to “Enabler”, Navigating Organizational Dynamics, Proactive Preparation for Management 1:01 – Your Job Description Has Been Deleted Imagine the skills that you had to develop in order to stand out as an individual contributor. Imagine that the managerial job that you get as a result uses almost none of those skills in your day to day Join John on a reflective journey on the realities of becoming a first-time manager. 3:25 – The Teardown – Learning the New Job Description Teardown 1 – From “Doing the Work” to “Setting the Context” The first jarring skill swap is moving from being the best individual doer to someone who communicates strategy and ensures operational smoothness for the team. John recounts his initial instinct as a new manager to immediately re-engineer his team’s reporting process. He recognized this as the wrong move, an attempt to act as the head practitioner rather than the manager. He advises new managers to adopt an “Imitation before Variation before Innovation” framework. Your first job is not to innovate but to create clarity and stability. You must first crawl by understanding why things are done the current way, then walk by making small tweaks, and only run with a major overhaul once you have a deep understanding of the context and have built trust. 7:20 Teardown 2 – From “Finding the Answer” to “Finding the Resources” As a manager, your value no longer comes from having all the technical answers yourself, but from ensuring your team has the tools and connections they need. John shares his experience of becoming a manager at a new company for a product he had never been a sales engineer for. He knew he would never be the top technical expert on the team. His instinct was to dive deep into the technology and certifications, but he realized his true job was to unblock his team. The key shift in mindset is asking “Who knows the answer?” instead of “What’s the answer?” A new manager must learn to tap into the team’s collective knowledge, relying on tenured members and peers to draw organizational maps that reveal where to go for help and how to solve problems. 11:02 Teardown 3 – From “Individual Contributor” to “Organizational Politician” A skill that is often celebrated in an individual contributor—fearlessly asking challenging questions to find the best idea—can be detrimental for a manager. The new job requires managing up and sideways to protect the team and secure resources, which involves navigating a complex political ecosystem. John learned this lesson the hard way, realizing that asking pointed questions in a leadership meeting could be seen as confrontational or critical rather than constructive. The new skill is understanding influence, timing, and venue. You must learn to have tough conversations privately, build consensus before a big meeting, and strategically navigate the chain of command to get your questions answered effectively without undercutting others. 15:04 Teardown 4 – From “Did I Have a Good Day?” to “How Can I Help?” The metric for a “good day” changes entirely. As an IC, satisfaction comes from completing tasks and making tangible progress. * As a manager, you can end a day full of back-to-back meetings feeling like you accomplished nothing. The new job is to measure your success through the output and growth of others. John emphasizes that your most powerful tool is the one-on-one meeting, and the most important question you can ask is, “How can I help?” “A good day is when you leave your team members more clear, capable, and confident than you found them.” Your job shifts from being a do-er to an un-blocker, and your long-term success is the sum of your team’s successes. 17:01 Teardown 5 – From “Interviewer” to “Owning the Hiring Process” Transitioning to management often means moving from occasionally helping with interviews to owning the entire, complex hiring process. This responsibility extends from crafting the job description to ensuring the new hire is successfully onboarded. A manager must coordinate with recruiters, budget approvers, and a cross-functional interview panel, all while ensuring consistency and fairness for every candidate. This involves evaluating not just skills, but also understanding a candidate’s weaknesses and gaps, what training would be required, and how they compare to the team’s needs, turning it into a highly complex project management challenge. 20:00 – Synthesis – How to Build Your New Toolkit So, how do you develop these new managerial skills, perhaps even before you have the title? John provides actionable advice for aspiring managers. Start by observing your current manager like an anthropologist—decode the “why” behind their actions. * Become an interviewer by taking other managers out for coffee to ask about the unseen parts of their job, such as handling performance conversations or advocating for budget. Finally, find low-stakes opportunities to practice influence without authority by volunteering to lead small cross-functional projects or mentoring junior employees. Call to action: perform a “micro experiment” in your next team meeting by holding back an answer and instead guiding the team to their own solution with questions. This feeling of guiding, not doing, is the core sensation of being a manager. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YoutTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

This week in episode 333 John flies solo in a discussion of using AI to help generate high-quality career documentation. Original Recording Date: 06-23-2025 Topics – Refresh LinkedIn, Rewrite Your Resume, Outline a Blog Post, with AI as a Career Co-Pilot 01:03 – Introduction This episode provides tactical advice for technology professionals on how to level up their career documents, such as resumes and LinkedIn profiles, by using Generative AI as a “thought partner.” The goal is to improve career resilience in times of economic uncertainty. 2:03 The core philosophy presented is that when using AI, you must be the “thought leader,” and the AI should serve as your “thought partner.” This model, first encountered by the host in Geoff Woods’ book The AI Driven Leader, ensures you retain control over your career narrative and authentic voice. 2:35 – Act 1: The Philosophy 3:00 The roles in this partnership are clearly defined. As the thought leader, your job is to set strategy, own the message, provide the raw material (your experiences), and make final decisions. The AI’s job, as the thought partner, is to help brainstorm, suggest angles, challenge assumptions, structure thoughts, and rephrase sentences. 4:26 A key warning is that recruiters and hiring managers are becoming adept at spotting low-effort, inauthentic “AI slop.” An imperfect but authentic resume or performance review is considered far more valuable than a generic, AI-generated one. You can’t blame the AI for mistakes; you are ultimately responsible. 4:50 – Act 2: The Playbook To get consistent, high-quality results from AI, John introduces a five-step method detailed in his blog post, Wielding the AI Chainsaw, a Starter Technique Toolkit. This process is designed to move from a simple request to a collaborative and structured session. Step 1: Persona Prompting: Tell the AI who it should act as (e.g., a career coach, a skeptical engineer). Step 2: Knowledge Generation: Have the AI pull foundational facts or frameworks relevant to your task before you begin. Step 3: Task Specificity & Interactive Context Building: Give the AI a specific goal and instruct it to ask you clarifying questions to get the context it needs. Step 4: Scaffolding: Provide the AI with a precise structure for its output. Step 5: Reflection: Ask the AI to critique its own work based on your goals. 7:07 Workflow 1: LinkedIn Profile The discussion details how to apply the five-step process to improve your LinkedIn “About” section. Starting with your own messy first draft, you guide the AI by assigning it the persona of a senior technical recruiter (Step 1), asking it for the critical elements of a great profile (Step 2), having it ask you questions about your draft (Step 3), requesting specific outputs like opening hooks and keywords (Step 4), and having it review its suggestions for tone and authenticity (Step 5). 11:44 Workflow 2: Resume or Self-Assessment This workflow demonstrates using the five steps to refine accomplishment descriptions. * The process involves assigning the AI a career coach persona (Step 1) and using the STAR (Situation, Task, Action, Result) method as the foundational framework (Step 2). You provide a project description and a relevant job description, then have the AI ask questions to align your project with the STAR method (Step 3). The AI is then tasked with restructuring your description into powerful bullet points (Step 4) and finally, reviewing those points for quantifiable impact and conciseness (Step 5). This framing is valuable for both resumes and internal performance reviews, but it must be based on your actual experience, never fabrication. 15:02 Workflow 3: Blog Post Outline The final example combines skill development with the practice of “learning in public.” To brainstorm a blog post (e.g., “Why Network Engineers Need to Learn Python”), you assign the AI a dual persona of a content strategist and a skeptical senior engineer (Step 1). The AI then generates potential objections a skeptic would have (Step 2), helps you brainstorm persuasive arguments by asking questions (Step 3), creates a structured outline for the post (Step 4), and reviews that outline for its persuasiveness and suggests a compelling title (Step 5). 17:07 – Act 3: Homework Listeners are given homework to practice the full methodology. The task is to take one bullet point from their resume, find a relevant job description, and walk through the five-step process with an AI to rewrite it using the STAR method. This exercise is designed to build a repeatable skill for wielding AI with intention. 19:34 Conclusion The episode concludes by emphasizing that AI is a powerful tool, but its effectiveness depends entirely on the thought leader wielding it—you. The ultimate goal is not to become an AI expert, but to be a proficient user of the tool to cultivate a more resilient and well-documented career. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YoutTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

This week in episode 332 we’re joined by guest Erin O’Quinn. In this part 3 of our discussion with Erin we’ll discuss her career journey through leadership, advocacy, and supporting women in tech. Original Recording Date: 05-14-2025 Erin O’Quinn is a senior manager of customer advocacy at a sizable tech company. If you missed part one and two of our discussion with Erin detailing her early career, check out Episode 330 and Episode 331. Topics – Career Progression and Leadership Evolution, The Power of Customer Advocacy, Navigating Workplace Challenges as a Woman in Tech 4:05 – The Transition to Senior Manager and Director The transition to senior manager and then director involved a shift in perspective from being an individual contributor to an enabler for the team. Erin O’Quinn explains that a higher title can help get a “foot in the door” for important conversations. 04:40 A key lesson in moving to a director role was realizing the job is not about personal delivery, but about empowering the team to deliver. Erin’s success became synonymous with her team’s success. This involved trusting the team and intentionally not being the expert on everything to allow team members to own their areas of expertise. “I made a point of not knowing everything on purpose when I hit the director level, because I didn’t want to be the expert on everything. I wanted somebody else to go, ‘Oh, Erin, we’re going to you for this.’ [I’d reply], ‘Actually, you wanna go to my team member who is doing this, and that’s their area of expertise. They know this account better than I do,’ and letting them take the ownership. Not everybody above me had always done that. And giving that opportunity for [the team member] to say like, ‘My boss thinks I own this,’ it gives them a space to step up and into where they feel like they have more control of their own trajectory.” — Erin O’Quinn 05:50 When promotions or title changes aren’t possible, a manager can provide growth by giving team members ownership and opportunities to expand their skills. This includes building career paths and being okay with team members leaving for roles that make them happier, ensuring the manager isn’t a gatekeeper to their career progression. 07:04 To learn how to have effective career conversations, Erin spoke with other managers, took their advice with a grain of salt, and analyzed different approaches. She adopted a practice of listening without judgment and evaluating new ideas, even uncomfortable ones, to determine if they were better for her team. 08:04 Having a mentor who was recently in the same role was invaluable. This mentor provided a 360-degree view, sharing perspectives from leadership and helping to avoid potential mistakes. 09:18 A manager’s role includes identifying and clearing “landmines” for their team to make them more successful. Erin emphasizes making this responsibility explicit to the team, which encourages them to be open about challenges and fosters a learning environment where they were more willing to discuss challenges. This meant that Erin heard about all the challenges, not that it was her role to solve them all. Sometimes it was a challenge the individual needed to handle, but at least Erin heard about more challenges and could sometimes help. 11:47 Erin distinguishes between project and program management. Project Manager: Like an event manager, they see a specific task from “birth to death” with a clear finality (e.g., building one car). Program Manager: They create and maintain a continuous system or cycle (e.g., building and running the factory that manufactures cars). The focus is on iteration and improvement of the system itself. 12:42 While Erin considers herself more of a project person who enjoys seeing a definitive end to a task, she stays engaged with program management by focusing on how to enhance the “project experience” for new people encountering the program. This reframing keeps the work interesting. John notes that sales engineering has some parallels, where a specific sales campaign might be akin to a project, but the overall process of how sales campaigns are handled over time is akin to a program. 17:16 Customer Advocacy The discussion turns to customer advocacy, which is a program designed to understand and share customer stories. It’s not about taking credit for a customer’s work but about highlighting how they solved a universal business challenge using a specific technology. 17:59 Customer advocacy provides mutual benefits. For the customer: It validates their project, helps secure internal budget and mindshare, and can serve as a recruitment tool by showcasing the cool technologies they use. For the individual: It elevates their personal brand, positioning them as an expert and giving them a platform to build confidence and public speaking skills. 22:28 When a customer is hesitant to share their story, the first step is to simply let them talk about their work in a low-pressure environment. By asking sincere questions and helping them see the broader impact of their work (e.g., “you’re taking this pain out of their lives”), they often realize their story is important and worth sharing. 24:28 Women in Tech For women in tech facing hostile or unsupportive environments, it’s important to first have a direct conversation with a manager about the perceived challenges. Taking on side projects can also provide visibility outside of a difficult team dynamic. 26:06 A challenge for women in tech can sometimes come from other women who have had to fight to be seen and adopt a competitive, “Highlander” (“there can be only one”) mentality. A frank conversation can help, but the first step is to ask to understand the situation. 28:27 It’s crucial to avoid a zero-sum game mentality. Lifting up a colleague, especially a junior one through mentorship, can be multiplicative for the whole team rather than a loss for one individual. 29:07 A subtle challenge for women in tech is being pigeonholed into “office admin” or emotional labor roles, like party planning, simply because they are women. Erin advises saying “no” to these assumed tasks. 31:03 Micro-aggressions, like being called “dear” in a professional setting, are real and their impact stacks up. While they may not be intentional, they can be infantilizing and add to the emotional baggage of being in a minority position. Allies can help by being aware and addressing these moments. There’s even more emotional labor involved with handling these situations. 34:49 Working mothers often carry an additional, invisible workload. They are frequently the default parent for school issues and bear the mental load for things like teacher appreciation week, which can lead to exhaustion. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YoutTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

Looking to improve the performance of your team? Improve the way they communicate, and you just might surprise yourself. When we take the time to understand how people like to be communicated with and how they like to communicate with others, it changes everything. In episode 331, Erin O’Quinn is back with us to share what it takes to create a safe space for collecting ideas from members of a team so that all voices are heard and the right people get the credit for great work. You’ll hear all this through the backdrop of Erin’s experience as a team lead and people manager, and you won’t want to miss the story of how Erin shifted her personal brand to improve her own job performance in the process. Original Recording Date: 05-14-2025 Erin O’Quinn is a senior manager of customer advocacy at a sizable tech company. If you missed part one of our discussion with Erin detailing her early career, check out Episode 330. Topics – Elements of Leadership and Experience as a Team Lead, Giving Others a Voice and a Space for More Contribution, The Tactics Behind the Strategy of People Management, Promotion and Personal Brand 2:49 – Elements of Leadership and Experience as a Team Lead To this point we’ve talked about a lot of projects with which Erin was successful, and people started to give her more. In all of these cases there were elements of leadership in getting the project accomplished by working with others. Let’s explore how Erin moved into the team lead role. The team lead guides a specific group of people toward a goal and is usually not the people manager of any member of the team. A team lead could be leading a team of people who report to many different managers, for example. Erin began leading programs in her twenties, but at first, some of her colleagues with more experience were apprehensive about Erin’s placement in that position. Erin remembers having great managers who would sense a conflict coming and have a conversation with people before Erin did as a form of blocking and tackling and supporting her in these situations. “With the team lead piece it’s figuring out how to get a successful delivery of something. You may not always run each of these people’s schedules or timelines, so it’s being that program or project manager. And you have to deliver a successful result. Usually for me, with these marketing pieces, it was to an event or to a point…. It was going to have a final point and stop. There was a put up or shut up moment that will happen for every single thing that I touched, and you will know if you succeeded or your failed because it happened or it didn’t. And if it didn’t, then we have another problem, and that’s another conversation you’ll have with your actual manager.” – Erin O’Quinn Erin says the team lead role is about learning how other people work, and one of her biggest challenges was figuring out how to best communicate with people. She gives a few examples: People take criticism and feedback differently. Some people are very shy in a group setting and don’t feel comfortable speaking up, while others are loud and consistently speak up in a group setting. Erin gives the example of navigating how to take feedback from the person talking the most in a meeting as well as feedback from someone who sent an e-mail or had a 1-1 conversation with you after the meeting because they were not comfortable speaking up in the meeting. “Being able to hear the different levels of voices as a manager of a program or a project or a team became one of the challenges that I got really excited about because I knew so many people…they were geniuses when you would put them on a stage or get them speaking to people, but they would get in these…quagmires when they were talking to their managers because they didn’t know how to speak to that one individual.” – Erin O’Quinn Erin saw this kind of thing happening and didn’t want to be in this situation. She also did not want to be the future manager who didn’t let a top performer shine due to not knowing how to make them look better / get seen in the best possible way. Erin would e-mail the team to communicate decisions in a way that showed the rest of the team how she was going to take in team member feedback. She gives the example of sending a message and adding in an important context point one member of the team brought up to her directly. “It became a learned process to how to work together…. A lot of times the loudest person in the room is the one that gets heard the most, and that’s the way that you always go. But…they realized that sometimes there was a benefit to the other quieter voices actually having a say or letting them own a piece of something in a different way and letting their creativity shine in a new way that maybe would have been squashed down in a bigger group so that everybody had something that they had ownership of. There was more pride. That allowed the team to do more things better because they were willing to do it that way. And it was a lot of fun.” – Erin O’Quinn, on being a team lead 7:41 – Giving Others a Voice and a Space for More Contribution Did experience as a team lead get Erin comfortable to start looking for a people manager position? “I think I was always looking for a people management position, but being a woman in tech…there’s a tendency that if you’re not already qualified to do the job you’re taking on you don’t apply for the job that you’re taking on, that you really want.” – Erin O’Quinn Erin mentions there is statistical data supporting the stark difference in the likelihood of applying for a job between women and men. Women feel they need to have significantly more of the required skills for a specific job before they are comfortable applying. It’s been harder for women to get into upper-level management because they are more tentative and don’t push because they think they shouldn’t unless they are perfect for the job. “I think there’s a little bit more bravado that comes from a lot of guys where they’re like, ‘I want that so I’m going to go for it’ versus women who say, ‘I’m qualified for it so I will go for it.’ One is a lot harder to do than the other.” – Erin O’Quinn Erin was on a team that was half men and half women with each person having their own communication style. Erin noticed women on the team would be collaborative with each other and work together well. If put into a larger group with men, they would often not speak up the same way they would if part of a group of all women. “So, figuring out how to be the voice willing to come over the top and say, ‘such and such has an idea or such and such has this approach…let’s look at all of them together’ became my superpower…. And it didn’t have to be me. If anyone else put a new idea on the table let’s at least look at it because even if it wasn’t the perfect idea, it’s going to spur on ideas from others that maybe leads to that perfect idea or a better idea than just the one that was shouted out the loudest. That’s where I started to learn the team management skills….” – Erin O’Quinn Erin first had to learn how to lead a group of people, and the people manager skills came only after getting to that position. Were people initially uncomfortable with their ideas being shared with the entire team if shared with Erin 1-1? Thinking back to the first time this happened, Erin shared an idea without asking first because the person was not comfortable speaking up in larger groups. After doing this Erin went back and spoke to that person 1-1. Everything turned out ok in this case. After later becoming a team manager, Erin would have these conversations with people beforehand to ensure it was ok to share their ideas / feedback with the larger team. As part of these discussions, she would help team members understand the value of their idea to the larger group and both the timeliness and urgency of sharing the feedback. In early management roles, Erin liked to make deicisions, go fast, and consider the right factors and team member input before a decision couldn’t be reversed. John says in an ideation phase, having more ideas is better than having less. But judging the ideas is a separate phase entirely. Erin says it should be but may not always happen that way. “If you go into a room with a lot of people and there’s different levels of role within that room…if I’m not at the bottom, I try not to talk first. There’s a power with having a title or having an experience or what have you where if you say, ‘this is my idea,’ some people who are junior might go, ‘oh, that’s THE idea’ not ‘this is an idea.’” – Erin O’Quinn Even if a person with a high title says something just to get the conversation going, junior team members may think their opinion will not matter. Erin stresses the importance of letting more junior people share ideas first. The team can then iterate on those, and junior team members will not be afraid to participate. It puts everyone on equal footing. Erin tells us there have been a number of times where she asked a question about something a senior leader said in a meeting because she felt like it was a safe enough environment in which to do it. She made sure to ask questions before a decision was made so as not to question the direction set forth by the leader. “If we’re still trying to figure it out or trying to sus out what the goal is, throw everything up then, and don’t be afraid…. If I was doing this with one of my teams I would always start…asking other individual contributors first…. Where should this go? What is your idea? What problem do you see with this? Give them a space to critique somebody else, or give them a space to critique somebody who is more senior to them, even if they have the same title, because a lot of times…some people put a lot of value and weight to somebody else who has years, age years, on them…. The world is changing all the time, and somebody who is looking at it with fresh eyes may have a better approach. And there’s nothing wrong with listening. Even if you disagree with them, hear it out first, and then decide…is what they said worth it? I think a good manager and a good team lead or a project lead can provide a lot of space for more contribution so you don’t get stuck in a ‘this is how we do things.’ I think that is one of the challenges of being at a bigger company. Because you’re working with a matrixed organization and a big machine, you gotta do all these steps and all these processes, but sometimes if you don’t stop and look at the machine, you can’t figure out how to change it. And you will be left behind by these small, nimble organizations.” – Erin O’Quinn Erin has seen very experienced colleagues think they are right because of the extent of their experience, but they might not be. Try listening to fresh ideas and being open to new perspectives. Ask the newest member of the team how they are looking at or seeing something. This can open up questions and topics of discussion that can lead to better results. Erin reminds us there is no harm in asking for this kind of feedback early on. Nick loves the idea of providing a safe space in which people can give feedback and share ideas. Did sending out people’s ideas to the team make them more likely to speak up in future discussions? Erin likes to give credit for concepts. While we do have to be careful about adding ideas after an open discussion concludes to not look like we’re pushing a personal agenda, Erin wanted to let her teams know that people who may have been quiet in the room were indeed participating. Their participation was in a different way than others, and that is ok. It may feel like a time suck, but Erin tells us it is well worth it to take the time to go through a process to understand how people like to be communicated with and how they like to communicate to others. “Understanding that process really can make a huge difference in how a team functions. I’ve been on very dysfunctional teams. I’ve been on very, very streamlined teams…. One of the teams that I was on…it was a great team. Everybody loved each other. Working as individuals with each other, everybody got along, but there were some communication challenges. And we went through this process and learned that certain people, even if they were quiet people, they communicated in a different way than you expected them to….” – Erin O’Quinn The communications exercise Erin mentioned above cleared up a lot of misunderstandings with one particular team and made a massive difference in the way people worked with one another. Erin shares an example of how understanding communication styles helped junior team members gain confidence, dispel fear, and collaborate more effectively with other teammates faster than they would have without that understanding. “If you build the team, you know the players on your team. You kind of know what you’re bringing into a group. If…you’re inheriting a team, setting a level playing field for how people talk to each other is very helpful so that everybody understands the communication process.” – Erin O’Quinn 19:04 – The Tactics Behind the Strategy of People Management When Erin got the manager role, did she feel she was fully qualified before she applied? Erin says she had no doubt at that point and that she probably should have tried it earlier. Erin is in customer advocacy / customer references, and it’s a pretty flat organization. “It’s hard to move up when everything’s pretty flat. Your responsibility changes. Maybe you mentor more or you guide more or you’re seen as an expert by more people. But you’re rarely moved to a different layer of management because it’s usually a fairly flat organization.” – Erin O’Quinn Did Erin seek out the manager role, or did someone encourage her to do it? Erin thinks she had been speaking to her manager about it. She was given a promotion but not necessarily to manage people. When asked what other kinds of things she wanted to do, Erin said she wanted to have a team. “I want to have a team, and it’s not because I need more people, necessarily, to do everything that I’m doing. But, I think that I’ve picked up rapport and skills that I could help others navigate these things in a more meaningful way…. I can help somebody else. That’s why I wanted to be a people manager.” – Erin O’Quinn Erin cites having excellent managers in the past who were great mentors that walked her through processes even when they were very busy. She was able to observe how those managers did blocking and tackling, learn from their strategic thinking, and understand how decisions were made. She was able to understand “the tactics behind the strategy” to make it easier to move into people management later. “Not everybody is cut out to be a people manager. I think there’s a lot more people who could be amazing…thought leaders or individual contributors, and there’s no harm in that. And a lot of tech companies have realized some of the people who are genius level individuals are not designed to have a team of 50 report to them because that takes them away from what they are amazing at…. For me, I realized that there’s only so many things that one human being can do at a time, and I think I’ve picked up the skills and the abilities to actually be able to help others even if what they’re doing is not my expertise. I don’t have to train them in my image. I just have to be able to give them the space and the tools so that they can do what they’re going to be good at.” – Erin O’Quinn Erin has also seen examples of very bad managerial conversations. She mentions one instance of a manager reprimanding an employee who was never told until the reprimand that there was a problem. “In a space where people don’t want to be the bearer of bad news, sometimes it’s ok to be the bearer of bad news. You have to actually just say it.” – Erin O’Quinn, on giving difficult feedback Erin shares the story of having a discussion with someone about specific challenges. The person thought everything was fine and working well, but that was very different than how things were being perceived by others. Erin had to give the person some very candid feedback on how what they were doing was being perceived, making sure not to label it as right or wrong. This person needed to communicate their successes and the gaps more effectively to their management. Erin took the time to coach this person in better ways to communicate via the quote shared below and helped develop a plan for improvement. In the end, this person thanked Erin for the feedback and help because they did not know. “You can’t do that. Until they know that you are the expert, they won’t necessarily believe that saying ‘we’re good’ means anything. So, you gotta prove first that you get it, you understand the metrics the way that they need to see the metrics, and show them repeatedly that you’re delivering these results. And then, after that, if they see the pattern, then you can say ‘we’re good’ and they know that that means that you got all of these metrics down and we’re set…. But until you can articulate it and speak it in the same language, that’s not how it’s being seen.” – Erin O’Quinn, feedback to someone on how to better communicate with leaders Erin likes to address things early on to avoid “kick in the pants” moments like the one shared earlier. If you see something, you should say something. Erin might send someone an e-mail with feedback after a meeting, for example. She encourages team members to take credit for the work they are doing. It is better for a team member to talk about the great work they are doing in front of others so they get the credit. If Erin mentions it, she might get the credit instead of the team member (which she does not want). Erin has even encouraged peers of hers to promote themselves in front of others so that the team overall looks stronger. “The rest of the people are why I’m a leader – because they’re doing all these amazing things, and these are all the amazing things that they’re doing. Give yourself credit. Don’t just say, ‘this happened.’ Say, ‘I helped this happen’ or ‘this happened because I did this work.’ And show the work…. Being able to help people toot their own horn is one of my favorite parts of being a manager.” – Erin O’Quinn Erin tells us there’s a misconception about customer advocacy. People think stories being out there make them magically appear. It takes work to identify the story and give someone the space to tell the story that can then be packaged into something amazing. It’s the extra pieces brought to the story that make it work, and people deserve credit for shaping that final product. Nick likes the way Erin didn’t label anything as good or bad when giving difficult feedback to someone and focused only on how someone’s actions were being perceived. We need to give people a context to work in. If we tell someone something is wrong, they need to understand what is wrong and what is right. We have to set a context and tell a person what people are seeing and the mismatch between what others see and what they are trying to do. Erin likes to help the person build a plan to get the person closer to where they intended to go. “There’s a lot of people who are great at promoting other things, but they’re not great at promoting themselves. For a long time, I was in that boat….” – Erin O’Quinn At first Erin felt like promoting herself and her work was bragging. She wanted to be humble and stay behind the scenes when it came to event marketing. Erin says we cannot move forward if we don’t talk a little bit about what we’re doing. 27:25 – Promotion and Personal Brand John feels like we’ve been talking about personal brands in the last few minutes. What’s Erin’s take on personal branding? Erin says a brand is the feeling we get when we perceive something. When we see company logos of brands, there’s an instant emotional reaction of some kind that happens. “A personal brand is, ‘what does this person mean to you in the context of work?’ Straightforward. Everybody’s got one whether you want one or not.” – Erin O’Quinn Erin says she re-built her personal brand during COVID but didn’t realize she was doing it at the time. She had a number of personal challenges during the lockdowns in addition to just COVID. “Being a mom with a kid at home going through personal stuff during COVID, and everything was on display because everybody’s working from home. It takes a lot of effort to have your business persona and your home persona, and I realized that I was putting up a lot of effort to separate them…. I stopped trying to separate that and just be more present, more me…. I realized that what people said was professional was just being in a box, and I kind of threw the box out.” – Erin O’Quinn Erin had been told earlier in her career what being professional or being approachable looked like. There were some other preconceived notions as well. “I kind of scrapped it and said, ‘I think I’m good at my job because the people that I work with appreciate my candor. They appreciate my sense of humor or my approachability. Just do that and be that all the time. Why try to be something else if it’s working?’” – Erin O’Quinn Erin realized she did not need to separate those parts as much and could bring her personality into all parts of her job. It was ok to do it. After making this change, Erin felt more comfortable, and because she was more comfortable, she was more approachable and able to do her job better. Being more present as a person allowed Erin to have better conversations with co-workers. She was more candid and open. Erin was able to approach customer conversations very differently than before as well. “It makes it easier to have the conversation, easier to do the next step, if they are talking to a person as opposed to a role. Once I figured that out and let it go, my job got so much easier, and I got better at it too.” – Erin O’Quinn Erin has been able to maintain this brand and attitude ever since making the change. Multiple times she has been able to approach something differently or ask in a different way to encourage someone to share their story with the customer advocacy team. It helps eliminate doubt. “Any time I can do that to help somebody get their story out in the world, I’m in to help that.” – Erin O’Quinn John refers to this as injecting human and personal relationships into a business process to remove friction. Organizations are ultimately made up of people. “I think if people realize that they’re working with a person and that person has thoughts, feelings, and emotions you are more beholden to act. If given the opportunity, I’d rather have the conversation in person. I’d rather have it on Zoom than on the phone because I can see your reaction or you can see my reaction, and you know that I’m being genuine. You can’t fake real. You can try. You can be the best actor in the world. You can know how to cry on command or whatever, but there’s a falsehood to it. And I’d rather just be genuine, make an ask or connect with somebody, and it’ll work better. It’s helped me maintain more meaningful work relationships over the years…my whole career, quite honestly.” – Erin O’Quinn Mentioned in the Outro While not mentioned in the episode, Erin has used empathy as a skill in effective team management. This pairs very nicely with Marni Coffey’s use of empathy to build inclusive teams in Episode 278 – Uncovering Empathy: The Greatest Skill of an Inclusive Leader with Marni Coffey (1/3). Erin’s focus on improved communication even as a team lead was also a focus on developing the people around her. If you listen to Marni Coffey’s story of becoming a team lead in Episode 279 – Change Management: The Hardest Leap and Developing People with Marni Coffey (2/3), this theme of developing others is reiterated. We’ve heard multiple guests reiterate the need to develop others to be successful as a team lead. Even if you’re not a team lead or a manager, you can figure out how to best communicate with your co-workers by just asking them. Brad Pinkston told us way back in Episode 84 – Management Interviews and Transitions with Brad Pinkston that one of the first questions he asks a new boss is how they like to be communicated with. We can also blend our personality into our communication with people to strengthen connection. There were a number of motivations for becoming a people manager in that episode: Helping other people avoid mistakes Make sure people receive credit for the work they are doing and that they can communicate their work to management in an understandable way. Some of Erin’s work as a manager is getting employees to advocate for themselves to tell the story of the work they did to achieve an outcome. Hopefully you’re communicating the work you are doing in 1-1s with your manager, but don’t forget that documenting your accomplishments is a pre-requisite to these conversations! Erin paid attention to things her managers did well (i.e. how to have difficult conversations) and what some did not do well. Check out Episode 244 – An Array of Decision Points with Tim Crawford (2/2) as a compliment to this episode with some extra considerations on the decision between individual contributor and manager. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YoutTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

Being a utility player in the sports world is one thing, but what does a utility player look like in the tech industry? Erin O’Quinn, our guest this week in episode 330, says it takes a willingness to learn, approaching what you learn as something that can help you later, and a willingness to advocate for yourself. Erin is currently a senior manager of customer advocacy at a sizable tech company. After studying communications in college, Erin’s first roles were in marketing communications, where she became well versed in the logistics of events like trade shows and developed a distinctive advantage by saying yes to new tasks / projects (even a little IT support for her employer). Throughout this first part of the story, Erin learned what she wanted most from a company’s culture, what it takes to develop a corporate brand, and how to communicate effectively with executives. As you listen to this episode, think about this – what is something you could say yes to today that could help you grow in the future? Original Recording Date: 05-14-2025 Topics – Communications and the Work of Marketing, Experience with the Cultural Elements of Tech Companies, A Return to the Tech Industry, The Strategic Side of Marketing, Communication with Executives 2:15 – Communications and the Work of Marketing Erin O’Quinn is a senior manager of customer advocacy at a sizable tech company. She has conversations with account teams and end customers to truly understand how customers use specific products, the benefits they have received from those products over time, and how success has impacted careers, teams, and the overall business. Erin tells us it’s a fun job. From where Erin began, it’s been a long, winding road to get to where she is now. Upon starting college, Erin planned to be a psychologist and counsel people in a 1-1 staetting. The school she attended (University of California San Diego) had a psychology program more focused on behavioral psychology and less on how people interact. As a result, Erin decided to pivot to studying communications. This ended up being a natural shift. The communications program focused on mass communications and communications as a social and cultural force. Human information processing concepts brought in some psychology as well. Erin refers to herself as a media junkie who wanted to understand how it influences people Some of Erin’s first roles were in MarCom positions, but not all were with technology companies. MarCom is marketing communications, but with marketing in general, the same terms can mean different things at different companies. “If you ever look at job descriptions and you see a title, you can’t just go by the name of a job. You actually have to look at what the job description is to figure out if what you think it says is what it is. But marketing communications at that point meant more of the mass communications…creating publications….” – Erin O’Quinn, on MarCom positions In college Erin became the editor of a newsletter. She learned how to do layouts and graphic design in addition to doing some writing. Her first job was with the San Jose Real Estate Board, made up of local chapters to help members become realtors. Erin would send out the newsletter, but the company also realized Erin knew how to fix computers. When people had questions and IT was not around, people would ask Erin. She became the IT department and the marketing department. The company was switching from Novell to Microsoft. They wanted Erin to help with this transition, and when she asked for formal training to fill knowledge and experience gaps, it was denied. She was worried a poor outcome could be career limiting and began looking for other jobs. The transition to Microsoft, however, did go smoothly. “But I did switch from there into tech because I realized I enjoyed the idea of being a little more hands on with technology, but I like the marketing side. So, I went to a tech company….” – Erin O’Quinn The company Erin worked for developed a back end for search engines like HotBot and Yahoo. Erin accepted a job as an executive assistant at this company but told her boss she would only take it with the understanding that she did not want to be an executive assistant in a year. “I told my boss at the time, ‘I will take this job if you promise me that I won’t be your assistant in a year. ‘I knew that I wasn’t somebody who wanted to be an administrative assistant. I wanted in at the company because it sounded fun and the people were interesting. And I loved not being the smartest person in the room. I was guaranteed to do that at this company. I knew I would be learning all the time.” – Erin O’Quinn Around 6 weeks into the job, Erin was asked to help support the company at a trade show. She expressed a willingness to learn and said yes to her first trade show. The next time she was asked to support the company at a trade show, Erin had to run the entire event in New York City to fill in for a colleague. She learned about unions, working with vendors, and how to set up the booth at the trade show. Since it was a small team, Erin needed to know how to demo the company’s products, who to ask if there were in-depth questions she could not answer, and how to talk to anyone who came by the booth whether it was a CIO or any other member of a technical team. Erin loved the events side. It allowed her to work with many different people at the company. She liked the challenge of either figuring things out or failing. Were there other reasons Erin didn’t want to be an executive assistant long-term? Being an executive assistant (or EA) was more about taking care of an individual and less about doing the work of marketing. Erin was more interested in the marketing work than being a support character. Erin had worked in her own department before and was changing jobs to become someone’s assistant. After developing skills and experience in her previous marketing role, she wanted to keep growing. Many assistants stay in those roles for a long time, and Erin didn’t want to stay in it long because the shift to something else is more difficult if you are an assistant for a long time. Erin wanted to set the agenda and intention with her boss up front, and it made things easier to shift out of the assistant role later. “I wasn’t asking for crazy money. I wasn’t asking for a lot of things, but if I was willing to fight for myself that way up front, he knew that I was going to be somebody interesting to work with. And I think that actually helped me get the job…. I love being a generalist whenever possible. It’s more fun.” – Erin O’Quinn Erin was focused on ambition and optionality. Had Erin been interested in writing up to the point of doing the newsletter to make her a well-rounded communicator going into marketing? When in college, Erin assumed communications entailed either being in front of a camera or writing, thinking she needed to build skills in both areas. Erin tells the story of working with her roommate to resurrect a specific newsletter for the university. Erin used her experience in layouts, and the roommate did the editorial part. Even after Erin and her roommate left the university, the newsletter continued to build momentum thanks to their initial commitment to get it going again. Erin also did an internship at a phone book company. The phone books were published in English, Tagalog, Chinese, and Vietnamese to serve a large Asian community in San Diego. Erin would take translated ads and do layouts as well as reach out to local politicians to get endorsement letters. “I started advocacy in college, whether I knew it or not. I just followed the transcript and did it. It kind of got me set up, I guess, to do it later in life.” – Erin O’Quinn 12:28 – Experience with the Cultural Elements of Tech Companies What did the moves look like once Erin moved on from the executive assistant role? Erin grew up in the San Francisco Bay area and has been surrounded by tech since birth. Some of her family members worked for HP for their entire career. Erin’s mother works in the biotech / pharmaceutical industry, and her dad worked as a punch card programmer before he went on to a career in sales. Tech was booming at this time. There were lots of job opportunities, and it seemed like a good industry to enter. The web was still pretty new. Erin had learned HTML in college and filled in once when a webmaster (or website administrator) left. Erin worked on promotional items and ran events. Because she was good at it, Erin was asked to run all the trade shows for the company, and it became her primary job. This involved things like handling logistics, working with product management and product marketing teams, and sometimes working with development teams. Erin had to ensure the technical specifications for what would be demonstrated in the booth were properly captured and that the booth was set up properly. Understanding servers and networking was very helpful because Erin helped set up the booth and especially in cases where they had technical issues at the booth. Erin needed to know other things like how to have people behave, how they should dress, the colors to use, and how to handle marketing for the events. Erin says she eventually became the promo queen at this company. “I was always having fun and always getting to learn. I never felt like I was being stuck in a role. If I wanted to know something different, I asked the question. That first tech company I worked at was very happy to get me involved. They had a very open culture.” – Erin O’Quinn Erin describes some of the cultural elements at this first tech company where she worked (during the .com era) – super soaker fights, barbecue competitions, etc. “…Different levels of creativity. I loved seeing that it wasn’t just the people who were supposed to be creative. By outside standards everybody assumes that in marketing you’re supposed to be the creative ones because you’re coming up with the visual and the brand and the words. But I loved how creative the development teams were and how creative the IT teams even could be at times…. I gained respect not just for people’s technical knowledge or how they could wordsmith but seeing every person at this organization as wholistic people who have multiple skills. I think that also prepared me for being able to move into different organizations after that in a more meaningful way….It was a blast.” – Erin O’Quinn The unique nature of Erin’s role allowed her to meet every person at the company that went from 65 people to 1300 people at one point. Erin worked with events, internal events, and internal communications. She would assist with content creation for company meetings and handle the meeting logistics. What did Erin take away from this experience in terms of the company culture she wanted for future jobs? Erin calls out the way people interacted and supported each other as something she really liked. There is a difference between doing an activity because we have to and doing it because we want to spend time with the people involved in the activity. “To work with people that made me happy to be in the office with every day was something that I decided I needed in a career, and that’s something that stuck with me….” – Erin O’Quinn Based on the cultural exposure she’d had to that point, Erin was able to look at a new company and contemplate what about it she wanted to be a part of. Erin took a brief break from working in the tech industry after a time of layoffs at her company and worked as a merchandising coordinator at Technology Credit Union. The company had a dual focus – expanding their membership and to whom they were allowed to market. Erin realized quickly into the merchandising coordinator that the work came in spurts. Promotions happened once per quarter and took about 4 weeks to handle effective. Things were quiet the rest of the time, and Erin didn’t like this. As Erin began looking for other things to occupy her time, she found a couple of different teams inside the company with no support from marketing. The first was the business development team who would reach out to businesses (tech companies) and promote membership. “And what I rapidly realized was that the people who were doing that were very good at business development at a credit union, but they didn’t know how tech people thought. They didn’t know their audience.” – Erin O’Quinn Erin felt her experience running tech events could help the business development team communicate more effectively with their audience. She created some marketing packages with branded designs and supported their events. The business development team needed to rethink items they might use for free giveaways because of the tech audience, for example. There was a mortgage team Erin worked with to build out their first set of marketing materials to be seen as consistent with the organization. Erin continued to expand her reach in addition to supporting the promotions each quarter. Helping those other groups as well made the job much more interesting to her. Did the additional work Erin did increase her value to the overall organization? She believes it did. The job market was tough during this time, but for credit unions it is about growing and maintaining the membership. Erin was primarily concerned about 2 things – being useful and picking up skills. Previously when she worked at the tech company, Erin was learning on a daily basis. “How can I make sure that I keep that trajectory? Because otherwise, I will get bored, and I don’t do well in boredom…. So, I wanted to find ways to keep myself entertained, and I did. But it drew me back to tech.” – Erin O’Quinn Did Erin communicate the additional work she was doing to her leadership in 1-1 meetings, for example? Erin’s manager knew what she was doing as did the vice president (VP) above her manager. Sometimes the VP would assign her exploratory projects or ideas to test directly. She would get random tasks. They didn’t always lead somewhere, but each one was an opportunity to learn something, making it interesting for Erin. John says Erin was a utility player in this role. She agrees and says this is a pattern for her over time. Erin tells a story from her previous role at Inktomi that involved buying as many matchbox Ferraris she could purchase in San Francisco as a joke for the CEO of the company. “I always ended up with these very bizarre tasks because I would just be up for whatever was needed.” – Erin O’Quinn Breaks between event seasons gave her the room to be creative in the work she took on. 23:55 – A Return to the Tech Industry When Erin transitioned back to working for a tech company after working at the credit union, she returned to a MarCom role and at first wondered what the pace would be like. She worked for a startup-like public company called Opsware. Erin’s first project after getting the job was focused on the company’s new executive briefing center. She tells the story of needing to have a chairman make some final decisions and then slammed into him by accident in one of the office hallways upon their first meeting. Despite the collision, she did get the answers needed, and her managers were impressed. Part of Erin’s work was doing case studies and trying to establish a corporate brand. The company was also building their sales teams around this time. Erin would work with different groups to make usable tools to serve those teams. As the company became more event focused, Erin jumped back into trade shows again, and since this was her comfort zone, anything else they did would be easy. “I was able to bring some of my expertise in the job, but I was also spending a good portion of the time learning about the technology…. I went from a caching and search engine company into a true enterprise software company. I didn’t know what that meant. I didn’t know how the sales teams would operate. I didn’t understand what was needed, but I learned fast because everybody was willing to talk to me and tell me. Being in a company where they want you to learn and they force you to learn, I was all in for drinking from that fire hose.” – Erin O’Quinn When Erin asked people to show her how to demo products so she could fill in for anyone working the booth as needed, they were a little surprised. Erin was insistent on learning the products, only wanting people to help her understand the pitch for a basic understanding, which opened the door to pass a conversation on to someone else if more depth was needed. As the product portfolio expanded, Erin continued to learn the remainder of the products. Erin refers to her time at Opsware as fast, furious, and fun. She later would go on to work for VMware but realized she was at the first VMworld event representing Opsware. At that conference she ran into a number of former colleagues from Inktomi. “That is when I realized I guess how strong of a world technology really was and that who you know sometimes comes in handy.” – Erin O’Quinn Erin also tells us she stores many different pieces of information in her memory that she will find a use for some time later. How you packed a suitcase might help give you a creative idea for shipping something to an event, for example. Candy is expensive to get through customs when going to Europe, for example. Certain things we learn which we will never forget come in handy in other parts of our job. 28:29 – The Strategic Side of Marketing In addition to tactical items, did Erin get involved in some of the strategic sides of marketing like cultivating the voice of the brand? Erin says she worked on a lot of the presentations for the company. She cannot take credit for the voice of the company but was able to work with a marketing agency her company worked with. They had to figure out how to make something look simple and complicated at the same time or prove the complexity was there without showing it to make the message more accessible to people. Erin worked on creating the visual identity of the company and not specifically the brand or logo. Part of that work was translating what they wanted (which might be complex words) to someone who was very graphically inclined in a way that was understandable. “How do these pieces of information get carried through so that it can be explained either very simply, or prove that complexity to show that we’re handling the complexity in a simple way? That process definitely has helped me along the way…. It was learning new skills more around translation and connecting than it was about how to build a strategy for that company until we were acquired, and then I got a chance to do a little bit more hands on with some of the strategic planning.” – Erin O’Quinn, on developing a visual identity for the company Opsware was acquired by HP and became part of HP Software. Once this happened, Erin was one of the only people from Opsware who was not placed in product marketing. They left Erin in corporate marketing, but she did not really fit into a specific bucket because she is a generalist. The event team thought Erin worked for them for a long time, but they later realized she was not part of their org chart. Erin still supported some of their events. Erin was able to work with the brand team, the search engine optimization team, and some others. “Every skill you pick up at some point in your career is going to help you some place else whether you know it or not. That would be one of the biggest things I could stress in that journey for me.” – Erin O’Quinn In working with the brand team, Erin also worked with executive communications for different types of events (a user conference, a sales event, etc.). She was more focused on logistics but got to be in the room to hear conversations about how to convey strategy. “So, I didn’t shape it. I never would take credit for any of those parts, but being there and being in that room where it happens, you learn a lot as to how that works…. You can see the process and then extrapolate that into something else that you can actually build yourself later.” – Erin O’Quinn 32:52 – Communication with Executives Did Erin apply the thing she was learning from being a part of the executive communications in her own communication with executives? This is very difficult for the individual contributor. Erin says her first 3 jobs working in small organizations really prepared her for this. She knew the CEO at each of those companies on a first name basis. This experience built a fearlessness when communicating with executives. Erin tells the story of a developer who came to her at one of these companies and said he wanted to start a cricket team. When Erin encouraged him to go speak to the CFO (whom she knew on a first name basis), he was terrified. Erin offered to introduce this person to the CFO to make it easier. “By knowing them and them knowing me and becoming more comfortable just remembering that they’re people before they are anything else made it much more comfortable for me to do that. So, I do feel privileged that I had that opportunity, but it stuck with me.” – Erin O’Quinn When we speak to executives as experts in what we do, we need to remember executives are experts in what they do (running something much bigger). Understand what an executive’s position is and what matters to them about what you’re going to ask. You might need to give them more context to understand the full details of what you’re asking or understand that you’re asking the wrong person. If you need an executive’s buy in on something, Erin suggests getting to know the person’s executive assistant. “They are much more approachable as a rule, and they are the gate keepers to a lot of executives. So never, ever, in any company treat an executive assistant poorly because they are the most helpful people on the planet. Or they can be very difficult if you treat them badly.” – Erin O’Quinn, on treating executive assistants well. Executive assistants will let you know what your level of access is to an executive. Never take it personally if an executive assistant provides feedback on a better way to approach something. Take it as information they are giving you to help you. When someone tries to help us by explaining their expertise, we should listen and not take it as a critique. “A lot of people can take critique very personally, and the only way to grow, I think, is to be given guidance. If everything that you do is perfect the first time, you don’t get an opportunity to learn because you don’t understand how to fix something. It just means you’re lucky in some situations…or you’re not stretching. If you’re not willing to step out of your comfort zone every once in a while, you’re not going to get that chance to grow…. If somebody offers you an opportunity, unless you know you can’t really put the time into it, say yes. Say yes as often as your schedule will allow because it’s some form of a skill that will help you…. Don’t necessarily go too far backwards, but if something is new, sideways or up…say yes because you never know what skill or what contact or what benefit you’re going to get out of that.” – Erin O’Quinn John says we’ve boiled down this pattern to “if you’re always comfortable, you are never growing.” If Erin gets too comfortable, she gets bored. Boredom is her brain’s way of saying she isn’t doing enough and to try something else. How do we know what we should say no to? We should not take on more than we can physically do or our time will allow us to do successfully. If we need to sacrifice quality in our base work for something, it is not something we should do. For things you really want to do but really don’t have the time, Erin would recommend addressing it with your manager. Communicate the value of what you want to do, and ask if there’s a way to make better use of your time to do it. Be willing to advocate for yourself with your management in this way. This shows initiative and indicates career growth. It might let your manager know that you’d like to do more or take on more responsibility, and it gives them an opportunity to provide some of that rather than you seeking it elsewhere. “Don’t be afraid to have the conversation with your manager. If they say no, then you know where they stand, and that’s not a bad thing either because sometimes they are also doing things to protect you. They may know something big is coming, and they don’t want you to take on something you can’t handle because more is coming in short order.” – Erin O’Quinn Mentioned in the Outro We can advocate for ourselves or the work we do and its impact / value. When Erin reached out to local politicians for endorsements, it was about the work and its impact. The story was similar when Erin started helping other teams inside the credit union who did not have support from marketing. She knew her work would be valuable to help them. When advocating for the work we do, be sure to communicate the work you do and the impact you’re making in 1-1 meetings with your manager. Erin did this, and we think it’s part of the reason she was given more and more responsibilities. Erin advocated for herself and her career in when taking the role as an executive assistant through the transparent conversation she had with her manager at the time. Erin also advocated for herself when it came to having others show her how to demo products in the booth at a trade show. We also see an element of how industry expertise can apply to another company not focused on the same industry. Erin used her knowledge of working at a technology company to help co-workers at the credit union understand technology professionals as an audience to improve the message. Maybe you have a deep expertise in regulatory compliance or working through audits. Maybe you’ve worked for a service provider or hosting company and can take some of what you have learned to another company to improve their operations. Maybe you worked at a technology vendor or value added reseller and can help improve vendor relationships for the company. Amy Arnold used her expertise from working in the public sector to be effective in future roles such as pre-sales. Check out these episodes for more of the story. Episode 281 – Packets Don’t Lie: Quality of Service for Technical Exploration in Network Engineering with Amy Arnold (1/2) Episode 282 – All the Networking Things: Project Management, Pre-Sales, and Broadening a Technical Specialty with Amy Arnold (2/2) Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YoutTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.

How should we be managing our careers during times of uncertainty? News of layoffs and economic uncertainty induces paralyzing fear and anxiety in many of us. What can we really control in the midst of it all, if anything? This week in episode 329, we’ll talk through a 5-pillar framework with actionable steps you can take now to be more proactive in your career even when it’s a difficult job market. Whether you’re employed and feeling uncertain or recently unemployed, we’ll share prescriptive advice and helpful AI prompts for forward progress so you can work through the challenges and not get frozen in worry. Be sure to check out our free Career Uncertainty Action Guide to access the AI prompts discussed in today’s show. Original Recording Date: 05-15-2025 Topics – Facing Uncertainty with an Actionable Plan, Pillar 1: Building Financial Resilience, Pillar 2: Maximizing Current Job Performance and Visibility, Pillar 3: Execute Strategic Skill Development, Pillar 4: Effective Networking and Relationship Building, Pillar 5: Managing Your Mindset and Control Your Narrative, AI Prompts and the Call to Action 1:30 – Facing Uncertainty with an Actionable Plan Though not feeling 100% when this was recorded, John and Nick wanted to get this episode on an important topic out in order to help our listeners. Maybe you’re coming into this episode with a lot of anxiety. We continue to see news about tech industry layoffs and economic uncertainty. It feels pretty heavy. We spoke about fear, uncertainty, and how to take control in Episode 70 – Taking Control During Uncertain Times. Maybe you feel secure but are hearing whispers about layoffs at your company and are beginning to worry. Maybe you’ve been impacted by a layoff. We see you. We hear you. Maybe you’re trying to recession-proof your skills, feel stuck at your current employer, or have become highly specialized and don’t know what to do. Wherever you happen to be, those feelings are real. The biggest challenge we each have is the risk to job security and financial stability. Though it may seem wrong, forces outside of our control do affect our careers. Today our intent is not to sit and dwell on problems like a difficult job market. We’re focusing on a practical plan to help you regain a sense of control with actionable steps you can take to proactively navigate this period. Our purpose is to provide career advice we wish we’d had earlier in our careers. We want to help listeners accelerate career progression, increase job satisfaction, and be more effective in your existing role. When things feel unstable and when we see layoffs at our company or in our industry, it’s ok to take more of a defensive approach. It’s rational to feel anxious when finances and job security are threatened by layoffs or economic uncertainty. It’s ok to feel that way. We’re here to help channel that energy into proactive career management. We’ve broken this down into 5 pillars / 5 areas where you can take action starting right now. Building financial resilience Maximizing your current job performance and visibility Executing strategic skill development Engaging in effective networking and relationship building Managing your mindset and controlling your narrative 5:01 – Pillar 1: Building Financial Resilience A buffer against the risk of layoffs and income instability is having a savings account with 3-6 months’ living expenses. Do you know the real numbers for your household expenses? If you don’t, take time this week to determine what they are. What is that bare bones minimum set of expenses? How long could the savings you have right now actually last based on your expenses? In Episode 299 – Chronic Stress: Connecting the Dots between Layoffs and Burnout with Cait Donovan Cait Donovan mentioned You Need a Budget or YNAB as one option to help track your expenses. There are certainly other tools to help with this. Maybe you could decide right now which subscriptions you would cancel or what you would stop spending on if your source of income was suddenly cut (i.e. job loss). We covered some of these items in Episode 57 – Preparing for Unexpected Opportunities Part 5 – Personal Finance. Having a liquid savings account that you can easily access and eliminating high interest debt will bring greater peace of mind if something happens to your job. John is thankful for the jobs and roles he’s had over time enabled him to build an emergency fund. He shares how much peace of mind it brought after being laid off from Google in 2023. Catch the full story on that in Episode 220 – John Got Fired. “It let me basically wake up, read the termination e-mail, and go back to sleep. I didn’t even wake up my wife to let her know. This is not great news, but we are in a financial position to survive. And it’s not a problem.” – John White, on the peace of mind that comes from having an emergency fund Nick mentions he’s had success with building up savings by making it automatic. Maybe you could make an automatic draft from each paycheck to consistently save more starting right now. John mentions he has a separate savings account for his emergency fund that money goes into every time he gets paid. It’s a great psychological barrier to spending any of it. Having an emergency fund in an account that is separate from everything else is step 1. Once you have started this and are contributing to it, then you can begin shopping for a high yield savings account which could earn you something on an annual basis. It’s important to know and understand the benefits you’re getting from your employer. Do you know, for example, what the company policy is on severance packages in the event that they have layoffs? Is that in an employee handbook somewhere? Consider the cost of things like COBRA in your state (continued health insurance after job loss for a period of time). Expect an increase from what you were paying through your employer. In the case of a mass layoff, there may be a 60-day WARN period in your state. Do some research on this. John mentions if it’s a small layoff, the company may not be required to do this. Make sure you understand the vesting schedule for any applicable retirement accounts tied to your employer or RSUs (restricted stock units) that are part of your compensation package. We’ve created a guide that we will reference again a little bit later in the discussion. In the guide is an AI prompt focused on finances that you can use with ChatGPT, Claude, or your favorite generative AI tool. This prompt will interview you to help work through assessing the current state of your finances (which is often a high stakes emotional process). It considers things like understanding savings, retirement funds, current cost of living, and what you could cut out in an emergency. The prompt also has some examples of how the conversation might go. We hope you find it helpful! The link to our uncertainty guide and a link to the above prompt can be found here: nerd-journey.com/uncertaintyguide. 10:50 – Pillar 2: Maximizing Current Job Performance and Visibility Our best defense against being let go or laid off is demonstrating that we are providing value to the organization. Visibility builds internal leverage and credibility in both uncertain times and in more prosperous times. Ideally, we want our personal brand and reputation to stand on its own and make people hesitate to cut us because of our importance to the organization. Action points for this pillar… We talked about some of this in Episode 70 – Taking Control During Uncertain Times, and it’s worth your time to go back and listen. Track your accomplishments, and focus on the quantifiable results you have delivered or the impact you’ve made. Quantify whenever possible! Think about reduced process time, value delivered to a project, etc. Leverage feedback from others to quantify your impact. Think about how you can be valuable and adaptable. What is the unique combination of skills you use to bring value to the organization? Proactively make your impact known by: Giving your manager updates Sharing wins in team meetings when appropriate (not in a boastful way) and offering to help others Documenting your contributions Documenting our accomplishments / contributions is the required input to be able to tell the story of what you are doing. Remember that writing is thinking as we discussed with guest Josh Duffney back in Episode 156 – Better Notes, Better You with Josh Duffney (1/2) and helps us formulate the way to say things. We should be sharing our accomplishments with our manager in 1-1 discussions. That would not be the entire conversation, but if you can share something that worked really well, share it. Keep a copy of your accomplishments saved somewhere in your personal files so you have access should you be separated from your company. Documented accomplishments should translate to bullet points on your private resume or LinkedIn describing the quantified results. John suggests we consider practicing the 30-60 second value statement out loud so we can easily explain it if someone asks. It’s important to understand whether you are or are not delivering value to the organization. One way to get feedback on this is sharing with your boss. If your boss says something wasn’t valuable, at least you will know. An episode that pairs nicely with this advice is Episode 284 – Draft Your Narrative: Writing and Building a Technical Portfolio with Jason Belk (2/2). It’s important to acknowledge that we can follow all the advice given in this episode very well, be valuable to an organization, and still be impacted by a layoff. The advice we’re sharing is critically important because if you are terminated, the work you have done turns into something that builds your resume with quantifiable value statements that you can demonstrate and speak to effectively. From there you can customize your resume for an application based on what they are looking for in the job description. It’s worth putting in the effort now. 15:31 – Pillar 3: Execute Strategic Skill Development We want to give ourselves industry longevity in our careers and increase the optionality, regardless of whether we stay at a company or go elsewhere. Think about the key skills you have today. What will be resilient and valuable in the market? Maybe it’s knowledge of public cloud technologies, a scripting language or automation framework, cybersecurity concepts and principles, or foundational awareness of AI (artificial intelligence) and machine learning. Don’t overlook the fundamentals! As you think through the skills you want to build or sharpen, consider the following: What will help you be better at your job right now and prepare you for a future opportunity? Is the skill area you’re looking at focused on a technology your company already uses and plans to use long term? Do you need to go deeper in this area or learn more about it to make what you’re doing more valuable? Does this focus area provide growth for you? Joseph Griffiths told us in Episode 327 – A Passion for Growth: Storytelling and Interpersonal Skills with Joseph Griffiths (1/2) that growth can take different forms throughout our careers. Growth for you may mean technical skills, but it could also be communication skills. Will the skills you are building be valuable to other companies? Investigate job descriptions to get feedback on the skill(s) to intend to sharpen or build before taking action. Look at job descriptions for roles similar to yours, closely related to yours, or something you aspire to do. Each job description will have required skills that you might not have today. Nick says you’re looking for a double check mark. How can you execute on either building a new skill or sharpening an existing one? Employer training budgets – do you have funds from your employer to use for this purpose? If paying for training yourself, consider cost-effective options like Pluralsight, Udemy, Coursera, or many others. Consider free options like YouTube as well. What if you blocked 2-3 hours of your week for learning? Maybe it’s during work hours, but maybe it’s on your own time. Be consistent, and treat it like an important meeting you cannot miss to build skills over time. John mentioned a resource called Google Cloud Skills Boost that is somewhat neutral in its technology approach which helps you learn transferrable skills even outside Google Cloud technologies. Many companies have public facing training / lab resources which are free to low cost. What if you only have limited time for strategic skill building? How does one decide what to learn? If you had a list of 3-4 things that give you the double check mark as we discussed, you should think about which one is most valuable to both what you do today and what would be next (i.e. longevity in the market). Nick suggests weighing value to your current employer at 60%. It’s important to be good at what you do to continue doing it for the time being. John says this also depends on how uncertain you feel about your position. If your company is having consistent layoffs and things in your role feel very uncertain, for example, you may want to prioritize the skills that are more valuable in the job market. It’s important to tailor the selections to your situation. Also consider your learning style. Do you prefer to start with going as deep as you can in a new area or with a high-level conceptual overview? Think about technology waves and trends. What is interesting to you? What is real vs. just hype? Consider investigating areas that might be the next technology wave. These suggestions are great to keep in mind as we proceed to the next pillar. 21:46 – Pillar 4: Effective Networking and Relationship Building Invest in this now because your network is your safety net, information source, and opportunity, engine. It becomes even more important when things are uncertain. John references an epidemic of AI-generated resumes and AI screening tools that’s causing a bit of a grid lock. Employee referrals are even more important now. Remember the people who refer you for a job role are going to get asked about your strengths and if you are a fit for a specific role. Even an indirect referral such as someone telling you a company is hiring for a specific type of role is helpful. You can investigate this role, see who you might know at the company, and determine if you might be a fit. We don’t want to start building a network when we begin to feel uncertain, but if that’s you, now is a great time to begin. We want to do it consistently and continuously over time if possible. We want to nurture network connections but adapt to what is happening right now. John recommends leading with empathy and checking in on people in your network. Ask how they are doing right now. Offer to help or share relevant information before you ask for anything. Don’t forget to do networking inside your company. Understand the challenges of others outside your team. Who are those leaders within the greater company that you might be interested in working for? Many times, in an economic-based layoff, people will be given time to find other roles within the organization upon being terminated. For networking external to your company, LinkedIn is extremely valuable. Consider participating in online / in-person communities related to your job or the technology you use. Stay engaged with these communities! Actions you can take… Identify 3 people in your network that you haven’t spoken to recently. Reach out this month just to connect with them and see how they are doing. Nick suggests combining this with pillar 3 and asking people what they are learning about and why they are learning about it. This is not asking for a job referral but rather a curiosity and opportunity for feedback on what you want to learn / the skills you plan to develop. John went to LinkedIn and downloaded his connections to a CSV file. He chose a few different people at random to contact based on the strength of connection to that person. This exercise only costs you time. Each person you contact will have a different perspective on the job market, the technology community at large, and the skills that are needed to thrive within it. It provides a diversity of thought that we can learn from. John would highly encourage a similar process for you. Start with people you can think of inside your network, and don’t forget to choose some people randomly. For more tips on professional networking, check out this recent episode for advice – Episode 307 – Sales Skills: Professional Networking and Continued Practice with Ramzi Marjaba (1/2). 27:27 – Pillar 5: Managing Your Mindset and Control Your Narrative The actions we’ve discussed may seem difficult to take. Fear can cause paralysis and lead to poor decisions. It’s ok to feel fear, but we want to shift our focus to the controllable things we discussed in pillars 1-4. Combat paralysis and inaction by taking action. Consider breaking larger tasks into smaller tasks. If you need to update your resume, it might seem like a mountainous task. What’s the smallest possible step? Maybe it’s updating a job title. Could you schedule 15 minutes to do that today? Even small progress is still progress that we can celebrate. It’s about small, incremental gains over time. See also our discussions on Finish by Jon Acuff with guest host Jason Gass, specifically the one about using data to celebrate progress: Episode 272 – Book Discussion: Finish, Part 1 – The Day after Perfect and Cut Your Goal in Half Episode 273 – Book Discussion: Finish, Part 2 – Deliberate Time Investments and Avoiding Distractions Episode 274 – Book Discussion: Finish, Part 3 – Get Rid of Your Secret Rules and Use Data to Celebrate Your Imperfect Progress Episode 275 – Book Discussion: Finish, Part 4 – The Day before Done and Perfectionism’s Final Roadblocks Try reframing your perspective. Could this time of uncertainty push you to learn something new you had deprioritized? What if this leads to a role that is a better fit for you? If nervous or anxious energy keeps you up at night, what if you worked on learning something fun for an hour to make yourself tired? Reading a book is a great way to learn and to wind down in the evening. John recently took some time to reboot his blog site – vjourneyman.com and made a blog post describing the way he setup the new site. When John started, he wasn’t even sure his WordPress site was still running. But he broke the task down into smaller pieces, eventually changing to a static site instead of just a WordPress site. John says it was a fun small project he did on his own time that got him energized to write more content. The energy carried through to his day job, and he’s been energized to write more content moving forward as a result. John mentions an article he’s working on about effective use of AI prompts. Stay tuned for that once it is published! Nick says when he takes a break to work on podcast stuff he can feel a difference in energy. John and Nick remind listeners that they are not immune to times of uncertainty. John’s blog project is an example of something he did to energize and empower himself. John is also modeling a pattern we’ve seen – developing proof of work / learning in public. We talked about learning something new in pillar 3. If you’re learning something new, could you write about it and publish what you learned or put your scripts on GitHub? Think about what you can generate that is public facing so people can understand what you’re learning and how you think. This is one way to own your story. John’s blog project illustrates adaptability, resilience, and proactivity. He built a new blog site and is planning to write content on topics he’s not previously written about. When the task list gets long, it’s hard to decide what you should do next. Sometimes we just need to pick something we can finish instead of spending energy picking which thing. If something is easily classifiable as in the top 5 things we need to do, it’s fine to go ahead and do it. If someone needs to reclassify your tasks and let you know something is an emergency, you will probably hear from them. 34:17 – AI Prompts and the Call to Action John created an AI prompt to help with our mindset. This is another outcome from John’s tinkering with generative AI. He prefers Google Gemini, but the tool doesn’t matter so much for you. The mindset prompt can be found in the uncertainty guide. Copy and paste it into your generative AI tool of choice. The prompt will instruct the AI to be a helper and motivator for you and help unfreeze you. It will interact with and brainstorm with you on the most important actions to take a positive step forward and could even create a prioritized checklist for you. The page on our site containing the prompt will have an example output for reference. Your interaction will be unique to you based on the answers you provide. Remember this does not have to be perfect and that something is better than nothing. If you do use the prompt, we’d love your feedback! Reach out to John or Nick on LinkedIn or e-mail us – [email protected]. Your action challenge is to visit nerd-journey.com/uncertaintyguide to download the free career uncertainty action guide which includes the advice from today’s episode with checklists and AI prompts to help you. The resources inside the uncertainty guide are divided into two categories – employed but feeling uncertain or recently unemployed. This is about helping people. If you can help us, help people, we’d really appreciate that. Remember we also have a Layoff Resources Page that you can utilize. We believe you can do things to influence your career path even during difficult times. You cannot control everything, but you CAN control what you do. So, what will you do? Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YoutTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.

Your manager has a preoccupation, but do you know what it is? The answer reveals a clue about their focus and the culture this manager will foster. Join us in episode 328 as Joseph Griffiths shares advice for making 1-1s with your manager and skip-level manager more productive, guidance for the aspiring managers listening, and observations from managing both technical and sales teams. We look at all this through the lens of a manager’s focused prioritization, the difficult part of being consistent, and the reasons we should all use boundaries and limits to improve the quality of our work. Original Recording Date: 04-17-2025 Joseph Griffiths is a tech industry veteran with experience across technical sales, enterprise architecture, and systems administration. If you missed part 1 of our discussion with Joseph, check out Episode 327 – A Passion for Growth: Storytelling and Interpersonal Skills with Joseph Griffiths (1/2). Topics – Optimizing 1-1 Meetings with Your Manager, Priorities as a Manager, Observations from Managing Different Personas, Manager Preoccupations and Culture Indicators, Advice for Future Managers 2:55 – Optimizing 1-1 Meetings with Your Manager What would Joseph tell the individual contributor who isn’t used to 1-1 meetings with their manager or doesn’t know how to leverage them effectively? “Everyone appreciates a human perspective…. If I as a manager come to the table and say, ‘here’s my agenda for the 1-1 that I expect you to do every week,’ it’s going to be real hard to come to me and be honest about the things you’re struggling with. It’s really, really hard to talk to someone who’s only business. As a manager it’s a lot easier if I just keep it business because then if issues happen or stuff it’s less emotional entanglement. But I think it’s the wrong way to do it. My job is to serve the people. My goal for 1-1 was to first breed trust and comfort.” – Joseph Griffiths The secondary goal of Joseph’s 1-1s was to allow the individual to share items that require his help, encouraging honesty about the challenges. Sometimes, a manager does need to use the 1-1 to deliver specific information that is best shared 1-1 (i.e. compensation changes, policy changes, etc.). Joseph usually had 1 thing he wanted to cover with the individual per 1-1. The rest of the meeting was for the individual to control the agenda. Joseph would recommend we take 5 minutes before a 1-1 with our manager to think about the overarching challenge we’re having rather than what is top of mind. “It’s very easy to walk into there and come out of a bad meeting the hour before and go, ‘I just had a horrible meeting and this is why.’ But is that really the problem, or should we be talking about something that is bigger or wider or more challenging? I think spending 5 minutes preparing with a OneNote sheet or a Notepad or whatever and just writing down…these are the 3 things that I want to talk about…and I need either some guidance for them or I need you to knock down a wall. That’s another one. Ask your manager to knock down a wall.” – Joseph Griffiths, on 1-1s with your manager Every manager is different, so you will need to feel things out with your manager when it comes to knocking down walls. Joseph says we can also bring ideas to the 1-1 for things that might improve the health of the business. If our manager agrees with our ideas, they can support the ideas and give us greater visibility within the organization. Joseph mentions when we have an idea, it is unique and special. But it’s also something we are likely to spend extra energy and effort doing. Joseph consistently sought to support innovative ideas from his team members and promote them up to his leaders. This kind of thing makes both the manager and more importantly the individual contributor look good. People often bring only their problems to their manager, but don’t forget to bring ideas too. Nick says we could all use more practice thinking about those higher-level problems. Even front-line managers need to do this when communicating with their own managers (i.e. think a level higher). Joseph tells a story about a friend of his who is a CEO. This person goes to lunch with his team each Friday. Afterward, he gets a pencil and a pad of paper, turns off his cell phone, and goes to a nearby park to think about his business for a few hours. Anything that comes to him gets written on the pad of paper. On Monday morning, the CEO begins executing on the things he thought of while at the park. This exercise allows him to be more proactive. “I think we could all benefit from turning off the notifiers, turning off the noise, and spending an hour just thinking about where we are and actually making some plans. That proactivity is missing…. The notifiers in the world that we live in are very dopamine driven by trying to get you to react…. We get so busy that we’re reacting to everything that we don’t take time to think, and then we don’t prioritize the most important activities….” – Joseph Griffiths, on a CEO friend’s proactivity It’s easy to be overly busy. Someone once told Joseph, “Busy is the new stupid.” While he did not understand it at the time, he certainly does now. Take 5-10 minutes before 1-1s to think about what you want to say. These 1-1s are opportunities to expand your influence. Take advantage! What about 1-1s with a skip level leader? Joseph encourages us to get a human connection with them just like you would with a customer. This could be the sports team they like or something else. A human connection opens the door to more conversations in the future. “You don’t want to stand around and complain…not a good move. You want to have a conversation that leaves that person thinking, ‘this is a really smart person. This is a person who is doing really good work.’ So, the best thing you can bring to that are stories of things that are going well with your customers in sales or going well with your job function. Those stories are going to be something that they take away from that and share with other people. You’re going to be giving them value…human connection and value are the 2 things you want to provide in that skip-level.” – Joseph Griffiths Second-line managers have direct reports who are managers. They have heard about all the problems and know what is going on because they talk about them daily. Joseph says the skip-level 1-1 is not an opportunity to illustrate problems. 9:42 – Priorities as a Manager How do you optimize your tasks as a manager and focus on the right things? This is something from Nick’s perspective, Joseph did very well as a manager. “It is really easy to get engaged in lots of things and doing lots of things ok. It’s much harder to be engaged in a few things and do them spectacularly. In any company we work for we will have millions of opportunities to do things. We need to choose to do the things that are, number 1, aligned with the role that we have…what we’re getting paid to do…and secondarily the things that have the highest overall payoff for the effort.” – Joseph Griffiths As a technical sales manager, Joseph had a key performance metric – the quota. It’s the only measurement that matters in sales. Joseph also had a team, and he had customers (the company’s customers). He often had to ask how what he was doing helped him hit the quota. There is a natural quarterly cadence in sales. There are a number of activities which happen automatically as a part of this cadence. “It can get very easy to just follow the cadence like you’re riding up and down a hill. And cadence is actually good. What you need to do is understand what you have to insert into the cadence to achieve the results of your KPI.” – Joseph Griffiths If Joseph knew his team would need 60 days to perform a necessary task in the sales cycle, he would plan for them to start those activities 180 days in advance, so everything is complete before it’s time for deal management. Sales can be somewhat unpredictable, so you then focus on what’s most important. “For me, my first job as a manager is the people that report to me. They are the most important thing.” – Joseph Griffiths Joseph shares the story of a former manager named Josh. Anytime Joseph would call Josh, he would pick up the phone and tell Joseph “I have as much time as you need.” It wasn’t that Josh wasn’t busy. He just made time for the most important things. We should prioritize things by importance and let other things slide by. Joseph could vacuum his floor every day, but he doesn’t. He puts up with dirt for a couple of days and then vacuums. That is prioritization. Prioritize by importance within your job function. This principle does not change regardless of your job level (individual contributor, manager, vice president, owner of the company, etc.). Delegate to others if it is their job, and let them fail if needed. Do we lose sight of what the priorities are because of having too many tasks? Joseph says it’s negative aversion. We don’t like to say no and are afraid we will be perceived negatively if we do. We can lose sight of priorities at times, but it’s challenging to say no to things. Joseph once had a manager named Adam who told him, “You need to learn the great art of no, however…. You need to learn that because everything to you is, ‘yes and I’ll do it myself.’” Joseph doesn’t suggest we directly say no. We can be helpful without taking on things as a personal challenge. People don’t want to be seen as the one who says no or that they can’t do something. People also don’t want to be seen as someone who is overloaded. Both are triggers to people telling themselves they are unreliable. “As a society, Americans are people pleasers.” – Joseph Griffiths 15:12 – Observations from Managing Different Personas At technology vendors, there is normally a team of salespeople managed by a sales leader and a team of sales engineers managed by a technical leader. At times in his career, Joseph as the technical leader has needed to help manage both teams. What were some of the nuances of managing the technical side and the sales side that Joseph learned? Joseph has needed to do this 4 times as a manager, and in every case, his business partners had incredible sales teams. “The people I was working with were really good, really mature, and knew what they were doing. For the most part, I don’t know that they needed that much management.” – Joseph Griffiths, on filling in to manage a team of salespeople Joseph says salespeople are often more willing to express emotion, frustration, and challenge. Contrast this with technical people Joseph worked with who would bottle it up and go take it out some other way. “It was not unusual for one of the salespeople to call me up and yell at me. I never had that experience with my technical sales team…. They would yell at me and just need to vent the emotion. And after they’d get that venting of emotion out, then we could have a conversation about what the problem is and how we can fix it.” – Joseph Griffiths Joseph observed that when salespeople came to him, they had already tried a number of avenues to solve a problem with no luck, and they expected immediate action. His technical team, by contrast, would usually give more advance notice of a problem. What salespeople needed was for Joseph to understand the problem, assure them he would help figure out a solution, and then get them to a solution. Joseph also noticed salespeople were experts at using manipulation and emotion to get what they need. They approached conversations as a negotiation, which was not something Joseph’s technical team did. It took him a little time to get used to this approach. “That’s just my limited experience observations. I loved working with sellers. I have so much respect for them because they do some of the hardest jobs. They find 999 noes before they find a yes, yet they get up every morning and go find that yes. And they get up every morning and keep pushing…. I couldn’t be more proud of the people I’ve worked with and how hard that is to do every day because I can’t do it every day, but they did it. They are amazing, amazing people. Probably the most resilient people we’ll meet on this earth are salespeople. I don’t know anybody else who can get beat up that much on a regular basis from both directions, both their management and their customers, and still keep getting up every morning. But they do it.” – Joseph Griffiths How does this differ from the technical team Joseph managed? The technical team didn’t normally bring problems in an emotional state. It was more about communicating the logical problem and sharing a potential solution. “Technical people want to learn skills. Salespeople want to be inspired…. It’s interesting to see the difference in development models. What I really need to do is just inspire people that it’s possible and give them the tools to go inspire their customers. That’s what salespeople need. Technical people…they need to feel confident about the solution. They need to feel confident about the capabilities that we’re offering and how we’re doing it.” – Joseph Griffiths A salesperson practices their craft most of the time by doing their job. A technical person might practice their craft by tinkering in a lab environment, reading a book, or something else. Suppose you provide a great sales pitch to a salesperson. They can repeat it and sell it. A technical person will, after hearing a great sales pitch, want to know how the solution works. 20:09 – Manager Preoccupations and Culture Indicators How has Joseph built a positive team culture during his time as a manager, including when he first started and during times of uncertainty (i.e. a pandemic)? Joseph mentions a researcher who created a culture indicator and made the claim that “culture is set by the first-level manager and their preoccupation.” There are 3 preoccupations for front-line managers. They reflect how easily information flows within an organization. Power – gaining more of it Rules – following the rules Mission of the company – achieving it Startups, for example, are mission-based organizations. Communication is wide open from the CEO down, and employees have many different responsibilities. The US military is a good example of a rules-based organization. There are rules for how much water to drink, what time you eat and sleep, and other things that make up a day’s schedule, etc. Operating on rules brings consistency of operation at a wide scale. “Every captain of every boat in the sea knows exactly what they’re supposed to do and where their orders are supposed to come from. It’s a very good structure for executing the same everywhere.” – Joseph Griffiths The one we see most often in corporate America is the manager pre-occupied with power / progressing up to the next level of leader. “They (companies) have all these things that they do to try to promote their culture. None of that matters if your boss is pre-occupied with getting their next job because that culture does not exist for you under that structure. Yes, the rest of the company had that. You don’t. The interesting challenge is yes, CEOs can set culture, but I wish more companies would spend more time ensuring that they have healthy culture at the first-line manager level because that’s where it really matters. And the problem is the mission, the culture of the company, rarely becomes the mission of the individual managers, especially in larger corporations…. I believed that when I was a first-line manager, that was the best place to establish culture, and that culture existed in my team and couldn’t go wider than that.” – Joseph Griffiths Managers pre-occupied with power don’t usually want to expand their team culture wider. It is their own desire to advance. Power-based culture is based on controlling the information (a selfish scenario). Motivations for being pre-occupied with power could be due to fear, because it’s the only way the person has ever known, or that it’s the best way to gain the next job. “Individual motivation is individual. It’s about preoccupation. If you have a manager that’s only pre-occupied with making themselves look good, it’s pretty obvious to you pretty quickly. And you’re just going to hope they go away eventually.” – Joseph Griffiths Was it easy for Joseph during his time as a manager to observe these preoccupations in his peers who were also managers? Joseph says we can observe it in others this way, but he was fortunate to be surrounded by peers focused mostly on the mission of the company and creating great cultures for their teams. “A lot of that is because our manager at the time, at that first round of hiring, was incredible at building that culture. So that was the preoccupation of that manager, and it became obvious in the people that she was hiring. This is where it does matter is the preoccupation…as a first-line manager, my boss’s preoccupation also affects my experience. Same thing just one level higher…every level creates its culture. Are we a collaborative culture that we’re working together to try to win together, or are we in competition against each other for who can do best?” – Joseph Griffiths Joseph defines culture as a preoccupation with something. “What are you pre-occupied with every day? That’s your real culture. We have lots of things that we profess to be culture, but when you sit down and you don’t have anything else you have to do, what do you do? You’ll figure out what your culture is pretty quick.” – Joseph Griffiths The question about preoccupation is an interesting one we can ask ourselves. Joseph says a lot of time is spent worrying about company culture, especially in hiring practices. Some companies have a top-level preoccupation with making money and nothing else, while others may have a top-level preoccupation with selling products and trying to do the right thing for the world in which we live. “It’s very hard to be a great manager in a terrible top-level culture…. Experiencing in our local area is one thing. What do we have above us that’s creating an overarching pressure on that? It’s very hard if you’re in a highly rules-based organization…trying to build a culture of mission-based focus can be challenging.” – Joseph Griffiths Joseph recommends 2 books by Mike Abrashoff describing how he revolutionized the Navy (one of the worst performing ships in the Navy) through changing the culture to a mission-based culture while still following the rules: It’s Our Ship: The No-Nonsense Guide to Leadership It’s Your Ship Joseph shares a story from one of the Mike Abrashoff books. On Sundays there would be a meal for the entire crew on the deck of the ship. The officers would cut in front of the lower ranking service people in the food line. Captain Abrashoff went to the front of the line and started handing out plates and was the last person to get his food that first Sunday on the ship. This was Abrashoff’s initial step toward changing the culture from the top level, changing a rules-based organization into a mission-based organization. 28:57 – Advice for Future Managers If someone is passionate about changing the culture of a team / organization, should they become a manager? “How about the inverse? If you’re considering being a manager, you should think about what kind of manager you want to be. And you should probably base it on…an investigation of the managers you’ve most liked working for and the ones you have not liked working for and figure out what those differences are…. For me, it’s do more of the positive. Don’t do any of the negative.” – Joseph Griffiths Joseph remembers a discussion he had with one of his first managers at VMware. Here’s what Joseph wanted to know. What did all the good managers you’ve ever had have in common? It was a specific set of behaviors. What did all the bad managers you’ve ever had have in common? This was also a specific set of behaviors. Joseph’s daughter works at Taco Bell and is currently getting insights already into what she does and does not like in managers. The assistant managers at the store are also very young and inexperienced. “Think about the times when you’ve done the most work, when you’ve grown the most. You probably connect that, generally, with a really good manager…. Sometimes it’s just a situation where you’ve been forced to grow by discomfort, which also happens. But I prefer to grow by comfort, feeling trusted. Should you think that you want to change the culture and that’s why you should become a manager, teams have their own culture with them as well. Some teams have a culture of cutthroat let’s win no matter what individually. Some of them want to help each other out…. It’s going to take time to change one culture to the other, and you can’t get too frustrated by that. Mike Abrashoff didn’t fix the boat in 1 week. It took him 9 months.” – Joseph Griffiths Should people be thinking about the time and effort required to become a manager before taking on the role? Should we assume it will automatically be more than being an individual contributor? Joseph learned his manager Josh had many things to do but chose to give attention only to the most important things. Joseph shares a story from his time at IBM working as a consultant for a large, multi-tenant service provider. His wife came to an office lunch event, and it turns out people had a huge misconception about how much work Joseph was forced to bring home as a result of the role he had. Joseph’s wife told his co-workers he didn’t bring work home outside of handling critical outage situations. “We, especially since COVID, have consistently allowed our lives to blend.” – Joseph Griffiths Joseph would work past 5 PM as a manager only for customer events (part of working in sales) and for total meltdown problems. There were very few total meltdown problems over the course of 3 years. Most days he was finished by 5 PM. Joseph would block 4-5 PM each day for administrative catch-up work, only accepting meetings during that time if they were critical. “I think that we get way more done when we give ourselves limits, when we have balance…. I’m a firm believer that we’ve got to create boundaries so that we allow for the things to happen that need to happen in our lives. And when those boundaries become blurred, we produce far less. We are less sharp. We’re less available. We’re less there. We do not get more done by more hours. We get less done.” – Joseph Griffiths In our previous discussions with Joseph about VCDX, he shared that 1 extra hour in his day helped him accomplish that goal over a 9-month period. Much like Josh, Joseph had to spend his time on the things that were priority. Since he worked in sales, customers came first over anything else, and that priority was the same for members of Joseph’s team. Nick says people seeking leadership / management roles need to learn to set the limits and boundaries as Joseph said, but they should also be modeling this for their team. Nick shares a story about how Joseph modeled this idea of boundaries and limits for him. You can hear more of this story in Episode 179, but there was a specific year during which Nick had to work during a holiday. Joseph told Nick there was no need for him to work on a company holiday, and if something was an emergency, he should call Joseph and let him take care of it. “I do think that we will wake up after the 40 years of working and ask ourselves a question of who we’ve become, and I hope we like the answer. My answer is not going to be I’ve become a great sales leader. My answer is going to be the person, the character that I’ve developed. And part of that is learning to balance the priorities…. The challenging thing that we look at in our lives is balancing those things, and it does help when we are the same person at work as we are at home…. I think that there are times where we’re tempted to do things that are outside of our values and character in our employment in order to get ahead, and I think those are very dangerous things. Be true to yourself. I’m a big fan of character…. I encourage people to spend time thinking about the person they want to be at the end of those 40 years because you don’t want to be a 65-year-old retiree who doesn’t like yourself. It’s not a good place.” – Joseph Griffiths Joseph recommends everyone strongly consider their motivations before becoming a manager. Being a manager is one of the most thankless jobs someone will have. It’s easy to measure the impact of individual contributor actions / behaviors like a presentation, a project, etc. As a leader, it is much harder to measure these things. “I measured my success as a leader in how hard it was to leave that job. If it was hard for me, that means I did it right. If it was easy for me to leave the job, I didn’t do it right. Think about that before you get into management because we need great managers who are dedicated to lifting other people up. We don’t need more managers that are dedicated to their careers.” – Joseph Griffiths Joseph would love to see more managers who lift others up and celebrate the differences people on the team bring. He appreciates how different the members of his team were and appreciates getting to learn from those differences. Mentioned in the Outro Are you having regular 1-1s with your manager? If you are, how regular are these meetings? Are they in-person or remote? Consider approaching these meetings mindfully, and put some thought into what you want to discuss during that time beforehand like Joseph recommended…especially if you are part of a large team and have limited time with your manager. Could you write down 3 things you’d like to talk about with your manager in advance of your next 1-1? Spend time thinking, even if it’s 15 to 20 minutes. This is also a time to bring ideas. Maybe you have an idea for how to do something differently or a project you’d like to work on. This time with your manager can help you determine the value of your idea to the team or the organization, and even if it is not, at least you know. It may just mean you haven’t clearly articulated the value of what you are proposing. Consider taking notes during these meetings. This discussion with Joseph aligns with what we heard from Leanne Elliot in Episode 238 – Managers as Culture Keepers with Leanne Elliott (2/2) about managers being culture keepers. Are you considering people management? Think about the actions and behaviors of both the good and bad managers you’ve had. Then ask several people you know the same question to get a nice list of what each type of manager looks like. For some examples of the actions and behaviors of good managers, check out these episodes: Episode 115 – High Flyers, Solid Players, and A Good Manager with Jeff Eberhard (1/2) Episode 138 – Apprentice, Amplifier, and People Developer with Don Jones (2/2) E-mail us the actions and behaviors of the best managers you’ve had, and we will read them on the air in a future episode! Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YoutTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.

How well do your personal and professional life align to your passion areas? For returning guest Joseph Griffiths, seeking mentorship helped uncover his core passions (service, honesty, faith, and growth) and fueled the decision to pursue people management. This week in Episode 327, Joseph details his transition from solutions architect to business solution strategist and why he sought mentorship along the way. You’ll hear about the impact of storytelling in executive conversations and job interviews as well as the concept of a value hypothesis. Joseph shares a perspective on management interviews, leading seasoned teams, and the critical nature of interpersonal skills for career advancement. Original Recording Date: 04-17-2025 Topics – Joseph Griffiths Returns, Storytelling and Conversations with Executives, Discovering Passion Areas, Management Interviews and Interpersonal Challenges, A Passion for Growth over Technology, Leading a Familiar Team and Progressing as a Manager 2:15 – Joseph Griffiths Returns Joseph Griffiths has worked in technical sales in some form for the last 10 years. Before that, he worked for a multi-tenant service provider and the state of Ohio as a systems administrator and enterprise architect. Joseph last joined us as a guest in Episode 18a and Episode 18b. At that time, we spoke to Joseph about his experience as a solutions architect. We wanted to learn more about what made Joseph want to pursue people leadership within technical sales. Full disclosure – Joseph was Nick’s manager up until about 4-5 months before this recording took place. But Joseph and Nick knew each other for many years before Joseph became Nick’s manager. Nick invited him to speak at Spiceworks user group events, for example. 3:55 – Storytelling and Conversations with Executives Going back to when Joseph was a solutions architect, his role was focused on understanding the pain and gain from a business perspective for customers. He would often run workshops to understand the current state (pains that exist) and build the future state (the gains a customer could get). As the company changed over time, Joseph’s role changed to business solution strategist. While the role was similar, it had a greater focus on speaking to C-level executives. Joseph recalls meeting some wonderful people on this team who taught him how to talk to executives and how to do value management. What was the biggest lesson Joseph had to learn in order to communicate effectively with executives? “You have about 30 seconds, and you better be talking about money. That’s the short version of it.” – Joseph Griffiths A good friend of Joseph’s is an assistant CFO at a large corporation, and Joseph decided to pick his brain on how and why certain IT purchases get approved, and others do not. “And he said, ‘it’s really simple – story and a spreadsheet…. You had better tell me a story that makes sense to my accounting brain, and you better have a spreadsheet that shows me how we’re going to make money, save money, or reduce risk with the spreadsheet…. Those two things put together…if the numbers make sense on the spreadsheet…I’m going to approve it. You come to me with a story about how you’re going to install some new widget, go find the money in your budget. You come to me with a spreadsheet, but the story doesn’t make sense, go find it in your budget. You want money outside of your budget? They better make sense in the form of dollars.’ And so, for me, the biggest thing to learn was I had 30 seconds with a customer to establish why they should keep listening to me, and it’s always dollars.” – Joseph Griffiths, on learning to speak with executives The executives Joseph would speak with likely would need to sell their ideas to a CFO or CEO to get new purchases approved. The business case has to be about making money (improving revenue or margin, for example) or saving money. Joseph had to learn to talk in dollars and understand how the money was being used. This is good advice even if you don’t work in technical sales. Anyone trying to get a purchase approved within their company needs to understand how to speak the language of the decision makers and make an effective business case. Listen to the example Joseph shares related to putting gourmet coffee machines in gas stations and why someone thought this was a good idea. “At the end of the day, businesses speak dollars. It doesn’t matter if you cannot convert what you sell into some sort of dollar metric. You’re going to have a hard time getting approval outside of budget times…. If you really want to accelerate a sales cycle of whatever you’re selling…you need to start to talk about to dollars and the impact to the business of the dollars.” – Joseph Griffiths Was there discomfort in needing to talk about money? Joseph says it was uncomfortable for him initially and for the team he managed. The challenge in these situations is we do not have all of the information. Joseph tells us about the idea of a value hypothesis and sharing this with a customer. “You have a hypothesis of what you think the value is, and it’s going to be wrong. That’s something that…I had to learn early on and sit in front of a customer with the wrong value hypothesis…. I had to be brave enough to put that number in front of them knowing that it’s wrong and having them correct me.” – Joseph Griffiths This exercise was difficult for Joseph. He wanted what he was sharing to be correct. But in sharing the detailed value hypothesis with a customer, Joseph was able to learn the real numbers. It creates a conversation and collaboration with the customer to adjust and correct the hypothesis. Outside of talking about dollars, Joseph has really embraced storytelling in his discussions. What made him put such an emphasis on this skill? Joseph tells us he’s in the middle of writing a book at the moment. One of the chapters is focused on storytelling. “Storytelling is elemental to humans as a race. One of the amazing things about storytelling is it allows you to learn something and be surprised, which are both dopamine hits. That’s really critical in our world where everything is centered around dopamine hits.” – Joseph Griffiths If someone tells us we are doing something wrong, we could be defensive, submissive, or react in any number of ways. It’s not going to motivate us to change. But, if we were told an engaging story about someone who went through something similar and have a realization while hearing the story, it would motivate us to change. “The real power of stories is you see yourself as the protagonist, and when you see yourself as the protagonist of my story, and I’m leading the journey along, you can come to some very interesting aha moments that are very powerful and motivating for you…. Instantly you want to take that story and tell other people so they can have that same aha moment because every time we have an aha moment we feel smart. We feel like we’ve discovered something amazing.” – Joseph Griffiths Most religions in the world and their teachings are based around storytelling. Joseph also tells us that stories have applications at different times in our lives. Stories allow us to use our intelligence to come to some incredible conclusions. Analogies (a close sibling to storytelling) are also commonly used by technical sales professionals to explain difficult concepts. They are useful to help with understanding but miss the aha moment that comes from using stories. Joseph would highly recommend using stories in any kind of selling (even if selling a project or idea inside your own company). After learning to tell stories with dollars, what kind of feedback did Joseph get on his approach from executives he spoke with? Joseph remembers one instance during his time as a business solution strategist involving the CIO of a company who was near the end of his career. This CIO became very interested in coaching people. After Joseph did a presentation with a value hypothesis at the front of it, the CIO looked at him and said, “That’s impossible.” This was a challenge, and Joseph had to make a decision on what he would do next. When Joseph pressed forward a little bit, the CIO stopped him and provided the same response. When Joseph asked why what he proposed was not possible, the CIO provided some of the most useful financial information about the company anyone on the team had learned to that point. It led to a number of sales. “We have to be able to stop and say, ‘why?’ His why was totally different than I thought it was.” – Joseph Griffiths After this specific incident, the CIO in question told Joseph he should have stopped the first time and asked why. This CIO continued to provide feedback to Joseph after future conversations. “That’s one of the biggest dangers…. We’re afraid of those yellow lights or the red lights that come, and we try to speed through them. Never a good idea…just let them talk.” – Joseph Griffiths, on discussions with executives and being challenged Joseph says some of his stories have not landed with people, but the only way to get better at storytelling is to practice. Joseph mentions a friend and co-worker of both his and Nick’s joined Toastmasters and improved his storytelling ability. It’s a great place to get some practice. 13:10 – Discovering Passion Areas Joseph’s role as solution architect and business solution strategist was more of a technical overlay. What titled him toward management? The answer lies within the things Joseph is passionate about – growth and change, for example. The business solutions strategist forced a lot of growth for Joseph. Joseph enjoys being of service to others. In his role as an overlay, he was able to serve account teams inside the company and customers. “I’ve always really found that I am happiest when I’m helping other people.” – Joseph Griffiths This same desire to be of service has driven a number of Joseph’s colleagues past just being technical workers to working in sales, customer success, or some other similar role. When COVID hit, the role Joseph was in as a business solution strategist was becoming less and less utilized (less opportunities, less in-person meetings, etc.). During this time, Joseph found himself struggling to feel happy. He was employed by a company that was doing well and even getting feedback that he was doing well in his role. But Joseph did not feel like he was really being of service to other people. As Joseph started to explore other career opportunities, he joined a mentoring program. This program allowed mentees (like Joseph) to connect with leaders in different business units for mentoring. “I’d had lots of mentoring from my business unit people, but it was somebody totally outside of that. His name is Zac. And the first thing Zach had me do was do this survey that helped me understand myself. One of the things I learned from that was…that I’m passionate about growth and service, honesty and faith. Those are my four things that I’m passionate about.” – Joseph Griffiths Zac had taken the survey earlier in his career and encouraged Joseph to take the survey and fill out a rubric to see how well he was fulfilling his passion areas at home and at work. “And I saw a lot of gaps there. And so, he and I started exploring other career opportunities that would scratch those gaps that were being missed. I had always had some interest in being in management, but I wanted to do it for the right reason. I wanted to know why I was doing it, not just because it was a logical next step in my career…. As a manager a lot of your job is promoting growth in others, serving them, and helping them look good…not looking good yourself. I always struggled when I was on stage receiving an award. It felt weird. I didn’t like it. I much prefer to see someone else on my team on stage getting an award. That means I did my job right.” – Joseph Griffiths Zac created formalized mentoring when he worked with Joseph and would ask a lot of open-ended questions so Joseph could talk through different things. Joseph did seek mentorship from others who provided specific, prescriptive guidance. He tells us the combination of both approaches is exactly what was needed. Working with mentors helped Joseph understand he needed to try people management. “You owe it to yourself to try it once in your career and see if it’s something you like doing or not.” – Joseph Griffiths, quoting a friend’s advice Nick has heard that in many ways, being a people manager is analogous to being a parent. We cannot fully understand what it is like until we do it. Joseph says as a parent there is a need for authoritative control and direct teaching. Joseph tells us the teams he managed were comprised of people who were highly capable. His job was to provide guidance to team members and promote growth in areas that were blind spots. “I was blessed with a very mature team and a team of people who were very good at their jobs and had been doing it for quite some time. Because of that, my management was very different than a bunch of college graduates…. I guess a lot of that depends on your situation, but I didn’t use a lot of authoritative power with my team. It was not necessary or helpful. I spent a lot more time telling them that I trusted them and just trying to remove roadblocks for them.” – Joseph Griffiths 18:11 – Management Interviews and Interpersonal Challenges What was the interview for a management role like for Joseph compared to when he interviewed for an individual contributor role? Joseph had worked with some of the people who would be interviewing him when he was a business solution strategist, and they were kind enough to provide some guidance. When interviewing for a people manager role, there’s a pretty strong expectation that you will bring a visual or a set of slides to the interview. It should cover areas like your management style, what you want to do in your 30-60-90-day plan, and an overview of who you are. “They want to see that you came prepared to tell them who you are, why you want the job, and what your plan is once you get it.” – Joseph Griffiths, on management interview expectations After getting specific guidance from a co-worker, Joseph created a presentation to use in the manager role job interviews. Joseph would recommend answering questions with stories or examples rather than a simple yes or no. Stories land much better with the interviewer regardless of the job you’re seeking. Being a manager does not mean you need to be a robot. You can have emotions about things. In one round of interviews for a people manager role, Joseph remembers being asked what he was most scared of. At this moment, Joseph shared a story about a conversation he’d had the previous day with a co-worker. The co-worker was a woman who was getting harassed at work and needed advice. Joseph listened carefully, provided some suggestions (i.e. that the woman share the situation with her manager for support and help, etc.), and offered to take another call if the person needed to speak further. What scared Joseph the most was having a future employee call him in that same situation. It was an emotional moment during the interview. “Those are the kind of things you have to think about. What are you going to run into, and do you want to deal with that? The one thing about being a manager is your job moves from dealing with customers to dealing with interpersonal problems. Ninety-five percent of your work, the stuff you have to deal with is interpersonal…and that stuff’s hard.” – Joseph Griffiths Was Joseph trying to help people with interpersonal problems regularly even before he was a manager? Yes – Joseph found himself doing this regularly as an extension of his desire to be of service to others. He has helped others in this way for most of his career. Joseph tells us most any book about advancing your career will have a chapter or section about interpersonal issues. He remembers reading a book about an executive coach that the board of directors would hire at a company to help work through an interpersonal issue (i.e. a CFO or COO who is a problem). “The problem is always they have a blind side in understanding how their behavior impacts those around them negatively. So, the higher you get in your career in a company, the more it becomes about interpersonal capabilities and your ability to influence others and less about what you can do. And that’s the reality of the world. We get paid for our ability to deal with interpersonal challenges not our ability to be the smartest person on the earth.” – Joseph Griffiths 23:07 – A Passion for Growth over Technology Joseph is someone we know who has achieved multiple VCDX certifications in the past. Was there any point at which Joseph was afraid of losing technical chops during the transition to focus on the interpersonal issues that come with being a people manager? Joseph reminds us that technology continues to change. Around 4 years ago many people were focused on blockchain. Right now, and probably in the near future people are focused on AI. We’re not certain exactly what it will be like in 5 years. “The reality is that technology changes very fast, and you can’t keep up. No one can. What you can do is have a foundation of understanding how technology works and educate yourself as you’re going along.” – Joseph Griffiths Joseph says he was the most technical when he was working to configure servers, network, and storage every day. That was 10 years ago. Though Joseph’s technical chops have been going down since that time, his salary has been going up. While there is nothing wrong with being someone who is extremely technical, Joseph believes interpersonal skills will be more valuable from a compensation perspective in the long run. “At the end of the day, I’ve never been concerned about becoming less technical as long as I’m growing. Because remember, one of my passions is growth…and it doesn’t have to be in technology. It can be interpersonal.” – Joseph Griffiths In the last few months since leaving a management position, Joseph has spent time learning AI and programming. He’s enjoying doing this, and more importantly, it’s growth for him right now. Joseph feels if you’ve shown aptitude in learning technical skills, you can do it again in the future. Nick reiterates that growth can translate into a lot of different things that aren’t necessarily technical things. We may not always understand this when we work in technology. When Joseph was early in his career as a systems administrator, he did not understand this. Joseph tells the story of a time during his role as a lead systems administrator when his manager left the company. The open manager job was posted, and both Joseph and one of his peers applied for it. Both went through the interview process with their director. After going through the interview process, Joseph’s director stated he was not getting the manager job and gave some very pointed feedback – “you’re not ready for it yet.” Joseph was gracious at that moment but was devastated to hear this. “My initial response was the same response we all get – defensive. He doesn’t know what he’s talking about. I can tell you… 14,15 years later, he was absolutely right because I was focused on being the best technologist. Leading people is a totally different skill set, and I hadn’t shown any of those skills or developed any of those skills. And I was interested in doing things authoritatively…. That’s not a good way to lead people. It’s not a good way to run an organization. And he made the right choice…. He had the courage to give me some very real feedback that I didn’t understand until years later. And I’m thankful to JJ for that. We’re friends to this day…. When I became a manager, I was ready for it. I wasn’t then, and it would have been disaster…. A lot of people get into management because they think it’s the next step in their career because they’re the best technical person they can be. There’s nothing wrong with being the best technical person you can be and staying there.” – Joseph Griffiths Make sure you understand yourself and why you want to pursue people management. Otherwise, Joseph would advise not pursuing it. We need good managers in companies and want to avoid having poor managers. If someone wants to stay technical / stay individual contributor and there isn’t a role at your company, it might mean changing companies. There’s nothing wrong with being extremely technical and continuing with that pattern throughout your career. “My passion is growth, not technology. You might be passionate about technology, and if you’re passionate about technology then there are plenty of places to go and…great careers in being the greatest technologist you can be. The only guidance I would give you is find a specialization, specialize in it, and prove that you’re the best in that specialization. Don’t be a generalist.” – Joseph Griffiths The growth would come through developing the specialty based on Joseph’s guidance. He tells us that being a generalist can sometimes block your progression path. If you want to be the best administrator of a specific type of storage array, for example, go do it. You would likely end up working for the vendor who makes the storage array if you have that depth of expertise. Nick suggests maybe we should choose our specialty strategically for longevity. Joseph mentioned his brother-in-law’s 23-year career in the Army as an officer. After getting out of the military he struggled to find a civilian career. Once Joseph asked his brother-in-law about the work he did, they found he managed 10,000 people at an Army base. But he wasn’t wording it that way on his resume. “You get specialized, and you don’t translate it to other things. You’d be surprised. The people who were doing blockchain 4 years ago…they’ve got a lot of the basis of understanding AI today…. I just suggest that we’re all going to pivot throughout our career. I’m in the middle of a potential career pivot trying to figure out what I want to do next, and maybe it’s management. Maybe it’s not. As I do that pivot right now, all the things that I learned before are benefits.” – Joseph Griffiths 30:35 – Leading a Familiar Team and Progressing as a Manager What approach should someone take when they are peers with certain people and then become the manager? This is a pretty common question and something Joseph was asked during interviews for the people manager role he occupied. If no one else on the team was interviewing for the people manager role in addition to you, Joseph recommends doing some things to build trust: Meeting with the team to acknowledge team members are good at what they do Admit you have a lot to learn Seek feedback and guidance from team members on what is / is not working, where people need help, what individual team member challenges have been “Ultimately managing people is a game of trust. If they trust you, they will want to do what you ask them to do. If they don’t trust you, they will question every motive and struggle to get those things done. It will be drudgery.” – Joseph Griffiths If someone else on the team was also interviewing for the manager role but lost because you got it… Have an honest conversation with this member of the team, and offer them the chance to get feedback from the interviewers on skills gaps. Give this member of your team the opportunity to develop into that manager role by being the second. Let them fill in while you’re out of the office, for example, to provide some experience and help deciding if people management is really what they want. If this person becomes very unhappy as a result of not getting the manager role and discussions don’t become more positive, it may mean the person needs to move on to some other role. Find out what the person wants to do, and help them get there. Earlier in Joseph’s career when he didn’t get the manager role, it was time to move to a different job. It was (at the time) Joseph’s way of finding something that would give him the opportunities he wanted. “The other thing that I learned from Zac…my mentor in management…sometimes what you want to get done and where you want to go is totally right. But you’re not going to do it in your current organization because sometimes no one sees a prophet in their own land, so sometimes you’ve got to go to a different organization to get what you want. Don’t be afraid to jump and try something totally different because managing people is managing people. If you think that you need to be really good at the job that you’re managing, you’ve missed the boat. The people that you’re managing are really good at the job. That’s why they’re there, and they can help you understand what’s necessary to be successful in the job. I don’t need to be the smartest engineer to manage solutions engineers.” – Joseph Griffiths What are some of the challenges to progressing in your career once you become a people manager? “I consider progression growth of myself, not career ladder. So, what are the things stopping me from growing?” – Joseph Griffiths One thing inhibiting growth could be running into the same situation over and over again and not having opportunities to grow and change. Joseph will often tell his manager not to let him get bored in his role, which can happen every few years. Without enough change, he will get bored and not grow. If we’re talking about progressing to second-line manager (or manager of people managers)… Joseph would recommend determining if this role is aligned with your passions before pursuing it. If it is aligned with your passions, Joseph emphasizes the importance of understanding the greater organization. To a large degree, this is about people and politics. “Some organizations are focused on execution – getting things done. Some organizations are focused on marketing – looking good, looking like you’re getting things done. You need to understand which kind of organization you’re in and do the appropriate type of activity to the appropriate people. But ultimately, the next step of your career…is going to be managing a large group of people. You’re going to get that because you’re able to manage a large peer network of people and manage up to them. You need more people saying ‘yes, that’s the right person for the job.’ And that only happens because they know you…. The day of being handed a job or being tapped on the shoulder…it’s not the culture of corporations is America anymore. You’ve got to put yourself out there and say, ‘I’m looking for that job’ and convince a wide net of people that you should get that job. And that’s something that especially technology people struggle with.” – Joseph Griffiths Mentioned in the Outro If you could interview a former boss on your podcast, what would you ask? Joseph is more passionate about growth than technology, but he emphasizes that growth can mean different things for each of us at different times in our career. Growth might mean learning a new skill, sharpening an existing skill, expanding the scope of the problems you need to solve, working in a specific job role, or working at a specific type of company. Joseph’s suggestion of finding our passions and aligning them to a specific role pairs nicely with Tim Crawford’s advice on the decision between pursuing management and staying an individual contributor from Episode 244 – An Array of Decision Points with Tim Crawford (2/2). If you’re looking for more on how other guests have used storytelling in their careers, check out these episodes: Episode 122 – Write, Interview, Tell Your Own Story with Brianna Blacet (2/2) Episode 301 – Always a Winger: People Person and Unapologetic Marketer with Amy Lewis (1/2) In Joseph’s story we also see a theme of needing to seek an outside source to learn more about ourselves. In this case it was working with a mentor. It’s amazing how questions from other people can provide clarity. You can also listen to our recent episodes with Daniel Lemire on how he sought clarity from different sources: Episode 325 – Overwhelmed by Ambiguity: DevOps, Innovation, and the Search for Clarity with Daniel Lemire (3/4) Episode 326 – AI Mistakes: Focused Resilience and a Specialization Bet with Daniel Lemire (4/4) Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YoutTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.

If you had something to share, what would you say, and how would you say it? Daniel Lemire asked himself the same question in the process of creating AI Mistakes. As it turns out, AI Mistakes isn’t just a platform for learning in public. It’s something Daniel must be doing. Want to know why? After completing the vision board and gaining more perspective on the layoff event that would change his direction, Daniel knew where to begin. But it took time to translate what he had written on the post-it note about his needs in a role to a role at a specific company. Through intentional mindset shifts, feedback from others, and additional help from a mentor, Daniel chose to make a bet on generative AI. Join us for episode 326 and the exciting conclusion of Daniel’s story. We’ll discuss how the specialized pre-sales role at ServiceNow really is a culmination of Daniel’s experience to this point and how he’s filling some of the sales and marketing gaps from back when he was an independent consultant. Original Recording Date: 03-20-2025 Daniel Lemire is an AI Consultant working for ServiceNow. He’s also the creator of AI Mistakes. If you missed parts 1-3 of our discussion with Daniel, check out Episode 323, Episode 324, and Episode 325. Topics – The Next Right Thing and the Genesis of AI Mistakes, Gaining AI Expertise, Mindset Shifts and Greater Clarity, A Role in Pre-Sales, Transition to Working for a Technology Vendor 3:14 – The Next Right Thing and the Genesis of AI Mistakes John wants to hear more about the genesis of AI Mistakes. The timeline starts when Daniel found out that he was in the group of people being laid off. “So, here I am…I think I’ve got things figured out. I’ve done really well. I think I’m going to get a really great appraisal for having taken care of business and done a good job, but actually, I got nothing…. Even now I still don’t know what anybody actually thought of my performance that year that I figured things out.” – Daniel Lemire, on not getting a performance review Though Daniel’s role had been eliminated, he and others were asked to stay on at the company until sometime during the following year (required to get a severance). Daniel recounts having to comfort his team about his departure. They had not learned to regulate themselves as Daniel had. “You’re going to be fine. You know what you’re doing. We’re putting you into a position to be successful going forward. You don’t need me to be successful. You just need to know that you can do this, and you’re good at what you do…. It just means that my next thing isn’t here, and that’s ok. I would not have been capable of having that conversation even a year prior because I hadn’t done the work that I needed to do to understand.” – Daniel Lemire, on comforting his team when delivering the news of his role being eliminated Daniel says this moment was a big confidence builder, and he feels he handled it very well with his team. Many of Daniel’s colleagues who were also part of the layoff did not handle it well. They were very angry. He reminds us these kinds of events are very difficult to go through. Having a severance package certainly helped provide Daniel time. Daniel mentioned his brother went through this kind of situation and did not receive a severance. Years early, Daniel had planned to stay as long as the company would let him, believing if the company decided to end his employment that it would likely result in some type of severance. He and a number of colleagues decided to focus on doing a good job and to deal with job loss if and when it came rather than living in fear about it. Daniel cites this mindset shift as an important point in his maturity to prepare for when the layoff eventually impacted him. “When I got the announcement that that road was going to end, that was like a golden ticket for me.” – Daniel Lemire Daniel ended his consulting business in 2009 after signing an agreement to work at PepsiCo. He was going “all in.” Once he knew his employment would be ending, Daniel continued to do great work until the very last day nearly 6 months later (something he’s very proud of). This was the catalyst for starting AI Mistakes. Daniel filed the paperwork and started developing a plan. He had learned a lot over the years since his last stint as an independent consultant and wanted to be ready for a potential return to it. “Sales and marketing is a thing that matters, and you’re going to have to do it. And I’m ready for this.” – Daniel Lemire Daniel assessed his preparedness for the uncomfortable parts of consulting if he was to return to it after the layoff. It was at least an option. “But the name AI Mistakes came out of the recognition that that is how we learn the best. Even at a very technical level…you have to learn doing it the wrong way to understand what the right way looks like…. That’s why you don’t become an architect the minute you step out of college. You haven’t had enough opportunity to make big enough mistakes…. Everybody’s made a big mistake. If you talk to anybody in operations, I guarantee you they have a sev 1 story.” Daniel Lemire Daniel highlights some of his biggest growth moments being when he really broke something. During these times other people had to pitch in to help fix the problems. We want to foster work environments so people can make mistakes that are not career ending or that they cannot recover from. 9:20 – Gaining AI Expertise Was AI a focus for Daniel when he worked on the innovation team? Daniel says there were several projects the greater innovation team worked on which were AI heavy. The exposure to AI for Daniel began by observing other members of the team and learning about it in the background. Someone was building models to improve manufacturing, and Daniel was able to see the progress and the outcome of that work, which sparked an interest in AI. “The difficulty for me was I couldn’t do any of that work. I just knew that that was the right thing to be doing…. Sometimes my role in innovation more often exactly opposite of what I had been doing previously in my career. Every job I’d had at PepsiCo was being the subject matter expert. I was the big brain. The moment I stepped into innovation, all of that basically went away. The only thing I was really good at that I brought to the team was helping with architecture and mapping out how the systems should interconnect and how we should prosecute the program of dealing with all of the things. I was no longer the expert that knew how to do the specific thing. I was working with the team to make that happen.” – Daniel Lemire A colleague on the innovation team told Daniel about GPT-3 and how it was actually beginning to work. After this conversation, Daniel got an OpenAI account, but despite thinking it was interesting, he didn’t really know what to do with it. At least initially, Daniel couldn’t find the value in this tool. “That is the number one thing I took away from my time in innovation…. What is the value, and how do you succinctly articulate that? …It can be the best technology. You can have the smartest people. But, if they are not willing to put their money to it, it doesn’t matter.” – Daniel Lemire Especially when communicating with executives, being unable to clearly articulate the value of something means it will not get funded. When ChatGPT happened, Daniel recognized it was going somewhere and began spending his time using it. While he initially did not know what to do with GPT-3, Daniel had used Stable Diffusion to generate images for some of the presentations he built during his time on the innovation team. Daniel had originally bought a couple of desktop computers with NVIDIA graphics cards to mine Ethereum as part of his innovation work. He mentions researching cryptocurrency and blockchain (and specifically NFTs). The best way Daniel knew to learn about these technologies was to build a lab at home. Once there was no way to mine Ethereum any longer, Daniels’ lab environment was left idle. He decided to use it for Stable Diffusion and began to learn how the models worked. “So, I quickly became very familiar with those AI things, and then everything just kind of fell into place…. I’ve learned enough in an enterprise environment that I can actually consult and help people understand what the next thing is that they need to do…. A colleague at work said to me, ‘you know a lot, and you’re not sharing enough.’” – Daniel Lemire The feedback from his colleague is what prompted Daniel to start a YouTube channel for AI Mistakes. See also the YouTube Feed on the AI Mistakes Website. “If I really do have something that’s useful to share, who am I going to share it with, and how am I going to do that?” – Daniel Lemire For many years Daniel would watch YouTube videos in the evenings to keep up with technology trends. Since this helped him learn things, he could provide content for other people to learn in that format. Daniel was also used to writing newsletters for innovation, and he began his own AI Mistakes newsletter. You can view the newsletter and subscribe to it here. He also had the previous consulting experience to lean on. When Daniel was thinking through what would come next for him, he felt AI Mistakes could be that paycheck. He decided to treat it seriously and focus on it. “I went from one day going into the office at PepsiCo to the next day sitting here working the same amount of time building all of the things around AI Mistakes…. I get excited about something, and I get after it. And that’s what I did…. But, having done that vision board, I also knew that…I’ve gotta focus on all of the things. I can’t just be narrow on one thing. I’ve got to think about the bigger picture.” – Daniel Lemire Daniel reiterates that he did take a trip with his wife at one point to celebrate their anniversary. 15:11 – Mindset Shifts and Greater Clarity Daniel feels the work for AI Mistakes (preparation, getting better at speaking, building more expertise, etc.) and the repetition put him in the position to be successful in his interviews at ServiceNow. He knew what to say and how to say it in these discussions, which was backed by proof of work and expertise (his content). Having the public proof of work helped tremendously. Daniel has been able to monetize his YouTube channel as well (something he is very proud of). “It was the iteration and the feedback that I got from doing that that helped me get better and put me in a good position for the next thing, and the mindset things that I tackled in the process gave me the confidence I needed to go into that room and have that conversation on the interview…why I was the right guy for that next thing.” – Daniel Lemire Daniel also mentioned some mindset shifts during all of this such as needing to be working on something even if he could not immediately show the payback on that effort. Daniel needed to have confidence that he was doing the right work focused in the right area and that if he kept doing it good things would happen. When the severance check ended, Daniel did not yet have the next thing figured out. That was a very stressful time. Not long after this, Daniel once again gave up and relied on his faith just as he did after learning a career as a pilot in the Air Force was out of the question. The act of giving up and the steps afterward shaped what happened next. Shortly after giving up, Daniel applied for the role at ServiceNow. John mentions the post-it note did not mention anything about making a living as an AI influencer and coach. “I was looking for insights in many different places.” – Daniel Lemire At the DFW Prayer Breakfast, someone introduced Daniel to a CIO who would end up mentoring him. After a brief phone conversation about mentorship, the CIO sent Daniel a list of questions he needed to answer before they could continue. The questions were to help Daniel determine what he wanted. “To be fair, my needs were pretty ambiguous as it came to a role, and the questions that he was asking me were very much more focused on ‘what kind of role do you want from a career perspective…what job do you want?’ I couldn’t answer it. I didn’t have that answer.” – Daniel Lemire Daniel tells us the job role didn’t matter compared to what the job would do to fulfill Daniel’s needs as a contributor to an organization. He had applied to jobs as an architect, a product manager, an engineer, a leader, and even some focused on DevOps. None of the interviews for these types of roles worked out. After answering the questions the CIO / mentor proposed, Daniel clearly understood he was willing to make a bet on AI. It was a trend / area he believed to be bigger than cloud and mobile combined. A new role needed to be something with generative AI within the scope of things which were familiar to Daniel. The questionnaire from his mentor also helped Daniel sort out the type of company where he wanted to work. Initially, Daniel did not think enterprise was where he needed to be, but it turns out after further reflection, Daniel’s skillset would provide more value to a large enterprise. If Daniel had insisted on his future being an independent consultant, it might have been driven by ego. “AI Mistakes is one of the things I must be doing. There is a very clear calling for me to do that. The calling for me in doing that though isn’t that’s where I need to be earning what helps me take care of my family. That doesn’t mean there’s not a future for that to be the case, but that’s not the reason for the existence.” – Daniel Lemire 20:38 – A Role in Pre-Sales In the last couple of years, Daniel has recognized his lack of deep sales and marketing experience. He is consistently learning new things in his role within the go-to-market organization inside ServiceNow. Daniel says he’s not putting a limit on the number of years he plans to stay in the role. “It’s creating value. I love having the conversations. I feel like I’m really actually helping people… It is fulfilling the post-it note in ways that I could not have imagined…. I think the reason I needed that job was that I wasn’t going to get all of those things from just doing AI Mistakes. Or perhaps I couldn’t get to those things in the time that I needed that to be the case.” – Daniel Lemire, on his role with ServiceNow Daniel confirms his current role is a pre-sales role and that back when he knew things were going to change for him at PepsiCo, pre-sales wasn’t even on the consideration list for what might be next. Daniel loves his current role working in pre-sales and mentions it contains so much of what he needed. John thinks another role which could have fulfilled the post-it note for Daniel is technical marketing. “The thing that I didn’t understand about sales from the very beginning was that it’s not about getting somebody to give you their money. That’s what we all think about when we think about sales, right? It’s transactional.” – Daniel Lemire Daniel has read a lot about sales in the last 24-36 months, recognizing that even if AI Mistakes could make money, he would eventually need to make a sale. “And that’s probably a big part of why I was able to get a role in pre-sales because I didn’t walk into that just being a technician. I walked into that with many volumes of sales learnings in my back pocket. And having done inside sales doing innovation at a corporation meant that I had many conversations trying to convince somebody to give me their money to go and do the innovation thing.” – Daniel Lemire Nick says Daniel’s role as an architect even contained a sales element, especially when encouraging colleagues to adapt cloud and DevOps. The role at ServiceNow was a good fit for Daniel because of the time investment he made. “There’s no reason to buy the technology unless it solves a problem, and you have to get to the heart of the problem. What is the why? Why does this thing matter?” – Daniel Lemire We need to be able to answer those why questions both for us and for other people. John mentions taking a value selling course when he first got into pre-sales and the emphasis on understanding the buyer’s metrics for business success. After a decade in IT Operations, John had never once asked for his manager’s metrics for success. Daniel said he never really had to do this until he was on the innovation team. As an architect, he usually had to convince technical people that something was the right answer, and it never really left the technical domain. Daniel recounts a professor from his graduate program saying, “we have an alignment problem. People that do technology don’t know how to explain to the businesspeople why the technology matters, and until you solve that problem, things are going to go sideways. It really is that simple.” This alignment problem is the number 1 problem both technologists and businesspeople have to solve. John says many people don’t know if they are working on something which makes their company money. It is often easier to keep your job when you work on something aligned with revenue as opposed to something viewed as a cost center. Within a cost center, there is always pressure for the cost to go down. When something is generating revenue, the discussions are more about return on investment. Daniel says it took him reading The Phoenix Project to understand these things even after obtaining his graduate degree. It took the enterprise context as well. All things considered, Daniel says he would not change a thing. 26:51 – Transition to Working for a Technology Vendor What other challenges does Daniel see based on his experience moving from being a technologist to working for a technology vendor? Daniel says he needed to separate himself from needing to have a specific level or title and be willing to put himself in a different position. Daniel is a higher-level individual contributor at ServiceNow in his pre-sales role, he has no direct reports. He works with sales executives and other solutions consultants to help customers. “I had to have the experiences in being a manager and being in charge of the technical things and being the architect and driving the programs to be able to sit down with the people that are at our customers to help them negotiate the challenges that they’re in. But that has nothing to do with a title. That was something that I didn’t understand until I got into it. The reason I was able to get the role at ServiceNow…was because I wasn’t overshooting where I could add value.” – Daniel Lemire John mentions often times an entry level pre-sales position is a mid-career position. There are more junior versions of this role to allow entry for people earlier in their career. In order to generate value in a pre-sales role, it takes many different types of experience and skills. Overall, Daniel doesn’t think he is missing any of the other challenges of stepping into the role. He gives credit to the team who interviewed and hired him and recognized he could do well in this role. In his current role, Daniel works with many different sales teams as a technical overlay / specialist. He is not dedicated to a specific set of customers but rather is a dedicated resource to internal sales teams for supporting their customers. Daniel shares a recent story of getting some very positive feedback on a customer presentation from the account team he was supporting and stresses the importance of feedback for his own improvement. “I tell the account team…‘when we’re done, I want your feedback. If it’s bad or good I need to know because I’m going to touch a lot of other customers, and if there’s something I can improve, I need to get to work now.’” – Daniel Lemire Daniel is very mindful of trying to balance being confident with preventing himself from being too confident. Nick re-iterates what Daniel told us earlier in our discussions – “in the absence of feedback, you can be open to experimentation.” John likes to label his performance in situations as performing well or performing poorly. Doing well or doing poorly does not make a person good or bad. Daniel didn’t expect this but views himself as a performer. It’s about how he can serve others in the moment. Nick says it’s the value he can deliver. If you want to follow up with Daniel on this conversation, you can: Contact Daniel on LinkedIn Learn about his work with AI Mistakes, including his YouTube Channel Mentioned in the Outro Daniel needed additional clarity from a mentor to gain the clarity necessary to translate what he had written on the post-it note to a role at a specific company. If you or someone you know has been impacted by a layoff event, check out our Layoff Resources Page for access to the most impactful discussions on the topic of layoffs with industry experts and technologists like you. Daniel’s statement of “you don’t need me to be successful” and the need to comfort his team about his departure reminds us of Marni Coffey’s story. Go listen to Episode 280 – Life after Layoff: A Leader’s Sense of Duty and A Series of Good Conversations with Marni Coffey (3/3) to hear the parallels. Daniel made a bet on generative AI. When we make a bet on a technology, we want something with longevity in the market that needs the attention of our skillsets. We want it to still be relevant by the time we have enough expertise in the area to get a new job, for example. Compare the way Daniel decided to that of Brad Christian in Episode 264 – Back to Basics: Technology Bets and Industry Relationships with Brad Christian (2/2). Both are valid sets of reasoning. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YoutTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.

What happens when there is too much change at once after making a job change? Daniel Lemire had learned the principles of DevOps and combined it with his experience as an infrastructure architect to advocate for the adoption of new technologies and processes within a large enterprise. But when Daniel changed roles to focus on innovation and became a senior manager at the same time, there were many challenges for which he was unprepared. In fact, at times it was overwhelming. In the 3rd installment of Daniel Lemire’s story in episode 325, you’ll hear Daniel’s reasons for focusing on innovation in the first place, why he continued to persevere through challenges, the stress and impact of layoff events, and the unexpected way he found clarity amidst the ambiguity. Original Recording Date: 03-20-2025 Daniel Lemire is an AI Consultant working for ServiceNow. He’s also the creator of AI Mistakes. If you missed parts 1 or 2 of our discussion with Daniel, check out Episode 323 and Episode 324 Topics – A Personal DevOps Value Story, Planting Seeds of Innovation, The Challenges of Impactful Innovation, Progressing from Overwhelm to Clarity 3:33 – A Personal DevOps Value Story Daniel needed a reset and to determine how he could contribute to the organization where he worked. That’s about the time he discovered DevOps. After a recommendation from a colleague within the security organization, Daniel read The Phoenix Project, and it has changed his career trajectory for the better. He read the book not long after its release. Reading the book also changed the way Daniel thinks so he is able to help companies create value. “…When I read it, I didn’t understand what was so great about it. I just knew there was something there that I needed…. I read it and I got really excited about it. But I didn’t really know what to do with it.” – Daniel Lemire Not long after reading The Phoenix Project, Daniel recommended the book to a colleague who worked on the security and compliance team. There was a character in the book named John who starts off being very stressed but for whom things improve greatly during the course of the story. “After he finished the book, he came back to me and he’s like, ‘let’s do something with this….’ I still didn’t know what to do with it.” – Daniel Lemire Daniel’s colleague recommended they start by meeting and having a conversation. After their initial meeting, Daniel and his colleague started meeting on a weekly basis. They started talking about The Three Ways and how these could be applied to make things better. Daniel and his colleague gave a presentation to a large portion of the IT Operations team to share thoughts on the way people do work and how to improve it. “It really helped them think through some of their organizational challenges and the things that needed to be done because that was also a difficult time across our technology organization because of the big changes that were being made. But the lightbulb didn’t really all the way come on for me until The DevOps Handbook came out and I got the concrete ‘these are the things that matter to a technology organization.’ So much of what I think about from a technology manager perspective has literally come out of that story. It is The Phoenix Project helping me related to what was going on and then the handbook giving me the tools to do the things that mattered that have enabled me to grow my technical accumen into an organizational behavior mechanism…. Ultimately if you can’t apply the lever in the right place, it doesn’t matter…. You can have the best people. You can have the best technology. But if you don’t solve the right problem, you’ve done nothing. That is a contextualization on many different levels.” – Daniel Lemire Daniel cites The Goal by Eliyahu Goldratt as another very influential book. He says it helps you understand systems at a bigger level and would recommend it to any technologist, referencing the drum buffer rope concept. We must be able to do the right things within the right context to create value. Daniel achieved continued success applying the principles of DevOps which allowed him to continue into a management role at PepsiCo. Before Daniel was a manager, he needed to work with and influence people to do technical work across the organization. These people didn’t necessarily work with him on a daily basis or have a rapport with him. Learnings from his study of DevOps came together in a meaningful and useful way in these situations. Daniel cites understanding the metrics needed to get the kind of feedback you need as an example. Reflecting back on it, Daniel was excited about what The DevOps Handbook promised. The book’s introduction was telling a value story for the application of DevOps, including examples of organizations that had used the principles of DevOps to increase performance. “You needed everything that was in the rest of the book, but what got me excited was what those things could do. Understanding that promise of improving the system got me thinking more about how to build an effective system.” – Daniel Lemire, describing the introduction of The DevOps Handbook as a value story for DevOps 9:26 – Planting Seeds of Innovation Daniel was already helping colleagues understand how to make effective technical contributions to building systems. The principles Daniel learned from The Phoenix Project, The Goal, and The DevOps Handbook allowed him to push these conversations beyond just the technical – into the business domain. “You’re never going to be successful in architecture if you’re not able to encapsulate the business domain.” – Daniel Lemire It’s important to be able to explain why we do technical things. “Architects, in my view, are really masters of making tradeoff equations. In the infrastructure space, you can install a single server to do something, and you can get that system in place very quickly. But it’s fragile because if any individual component failure comes into play, you can’t do anything. So, you have to build these failure domains that allow you to maintain the integrity of the system, but that’s more expensive…. When I think about what I learned from DevOps, it is balancing those two equations.” – Daniel Lemire Daniel distinctly remembers a chart having to do with the number of developers working on a given project. It’s the Mythical Man Month concept. He gives the example of a baby’s development. It takes 9 months. This is a known limitation of the system. Daniel says architects understand technical limitations in specific areas but also overall system limitations. The limitations are used to make the right decisions in conjunction with the requirements to meet the business need so the overall program can be successful. “The better you are at putting those pieces together, the more successful you’re going to be in solving the problems that the organization at large has.” – Daniel Lemire According to Daniel, an architect doesn’t just put technical systems together and stop there because it can limit one’s success. Daniel mentions receiving guidance from people in the DevOps community to extend his skills beyond the technical. While learning DevOps did afford Daniel the opportunity to do some interesting work as an infrastructure architect, but he eventually reached the point of needing to do something different. Daniel remembers completing a specific exercise for his personal development plan focused on the kinds of things he wanted to do in his career. Daniel wrote down his desire to be an architect and focus on innovation. Daniel was a competent infrastructure architect who understood the challenges of the role very well. He experienced successes driving new technologies like DevOps and adoption of cloud technologies and was extremely proud of those efforts. The next architectural project for Daniel was building a very critical business system in the cloud. It was interesting but not interesting enough. “I knew exactly where I was headed with that program. I thought it was interesting, but I also thought it was boring. And that’s not what I wanted to do next…. I saw the pain that was coming for me by doing this next big thing. I wasn’t excited about it, and I just couldn’t put myself in that position going forward.” – Daniel Lemire Daniel mentioned many corporations across the world have a lot of work to do when it comes to cloud technologies. We are great at adding new technologies but not so got at getting rid of the old ones. The Phoenix Project describes problems and challenges that are applicable to many companies. We can learn from other companies without having to go through the pain. 15:07 – The Challenges of Impactful Innovation “And, oddly enough, an opportunity opened up for me to get to that next level and be a senior manager and go do innovation. Man, I was so excited about that.” – Daniel Lemire Reflecting on it, Daniel was very good at introducing critical new things within the company. He points to the beginning of cloud dialogues with colleagues and how their reactions changed from initial confusion and detraction to full support within a couple of years. “I was one of the guys that said, ‘yeah, we need to go do this.’ I don’t think I was wrong, and DevOps was the same way. Some people were like, ‘I don’t know why this is your thing.’” – Daniel Lemire Daniel mentions conversation he had with a mentor who disagreed about DevOps being what the organization needed to solve certain problems. At the time, Daniel knew he would not win that battle. “The challenge I always had with him was – he’d throw me off my game. He’d ask a really intelligent question that I had no way to answer. I liked that about him because every time I got in a conversation with him, he’d point out something I hadn’t thought about…. Any time I showed up with something like, ‘hey, we need to do this’ he would throw a curve ball at me that it would take me weeks to solve or in some cases months…. He wasn’t wrong…it just turned into this wall for me. Even now, looking back on it, I know that I was fundamentally right in saying this is what we need…. You can take the right next step and not be able to explain why it’s the right next step in the moment, but it’s still the right next step.” – Daniel Lemire, on overcoming challenges when presenting new ideas Trying to answer the questions his mentor asked might keep Daniel from getting things accomplished because he was determined to fill the gaps in his knowledge. John has empathy when it comes to the constant question of changing systems. “At least I know the problems of the system that I know, and new systems bring new problems.” – John White, paraphrasing The Systems Bible John highlights the difficulty involved in knowing whether someone is bringing up an 80% objection or a 20% objection. We generally manage to the 80% because managing to the 20% can cause different issues. See also The Pareto Principle or 80/20 Rule. Daniel has emphasized this theme more often lately in his consulting role. Many of the objections people raise are part of the 20%. Looking back, he is not sure if the objections his mentor raised would fall into the 20%, but we as technologists today spend way too much time on the 20%. John says a lot of time will be spent on the 20% regardless of the efficiency of the 80%. Optimizing the 80% provides more time for the 20%. “I was just really tired of dealing with the 20% all the time, and I really wanted to be able to do a lot of things…. There’s the 80% of the problems that you can solve very, very quickly, and then there’s the 20% of the problems that you just have to spend a ton of time to get there.” The same is true with expertise, right? You can be 80% effective at a brand-new thing in a short period of time, but to get that last 20% it takes much, much iteration. Having spent a decade in infrastructure, I became far too focused on the little bitty things." – Daniel Lemire When he worked in infrastructure, some of the projects Daniel worked on were measured in years. In infrastructure, one cannot take risks. It’s important to put in a reliable system. Daniel needed something different. The opportunity to move into innovation solved this problem. It allowed for fast iteration on things. Daniel tells us he did more projects in innovation than his entire career in infrastructure because of the nature of the beast. Was getting to work on many different projects in innovation something Daniel considered to be a bigger impact? Daniel says no. “So much of the things that I worked on in innovation became shelfware. You can drive a lot of excitement about something new, and you can run an effective proof of concept and show that something is valuable or not valuable. But it doesn’t mean that somebody’s going to stand up and say, ‘I’m ready to go try this,’ especially in an enterprise environment because even ROI often times is not enough to satisfy the ‘why are we doing this?’” – Daniel Lemire Daniel would not say it’s impossible to inject innovations into an enterprise successfully, but he highlights a number of challenges from experience. When Daniel began the work in innovation, he didn’t actually know what it took to do the work of innovation at an enterprise level. It took Daniel years to make progress on cloud and DevOps within the organization. This effort requires addressing multiple dimensions – educating others, building technical accumen, governance, politics, governance, the organization in which you’re operating, and the monetary aspect of it. These are also true for innovation. “What I didn’t understand when I started the journey was that I was signing up to do those things in a much shorter period of time than I was really prepared to do. I knew what to do. I had not done enough repetition to be very effective at it. Now the good news is because I was in innovation the repetition happened a lot faster, but it didn’t make my boss happy that I wasn’t very good at it….” – Daniel Lemire What does not very good mean? Daniel says he did not understand the practice of innovation well enough. It requires doing some very specific things, and upon taking on the role, he was ignorant of those things. Daniel did a lot of reading to get up to speed on these items. Daniel refers to a conversation with Jensen Huang and a journalist about Starting NVIDIA. If Jensen had known what he was signing up for when deciding to start NVIDIA, he probably would not have done it. Daniel says this parallels his experience in innovation – not understanding or appreciating what he had signed up to do. There were some challenges to taking the role in innovation that Daniel needs to share with us. Daniel knew some members of the innovation team and felt he would have fewer interpersonal challenges. He was ready to tackle something new, excited about this opportunity, and understood it would be a difficult task. “I’m aggressively going after jumping into the deep end because consistently…if I throw myself into the deep end, I’m going to swim.” – Daniel Lemire Daniel accepted the role of senior manager of the innovation team in February 2020 right before the global pandemic really started in the US. He was not prepared for it. In some ways Daniel feels like it may have been a mistake, but in other ways he doesn’t have any regrets about taking the role. “In fact, I can remember very clearly the conversation I had with my manager in completing in completing my objectives review going into my 4th year in innovation…. My manager says to me, ‘Daniel, you’re not good at this.’” – Daniel Lemire Though it was a tremendous challenge to meet his manager’s expectations, Daniel understood his future success hinged on getting good at the different elements required to perform the role well. Daniel’s manager eventually took on a different role within the organization. It was challenging for Daniel to have his manager leave knowing he had disappointed his manager with his performance. “It was basically the next month that things started to click for me. He wasn’t wrong in that I wasn’t performing well for the things he needed me to do well at. It was almost in the next breath that things really locked in, and it all started to make sense for me…. I’m also not going to tell you that I immediately went from being not great at this thing to being the best there is….” – Daniel Lemire Daniel says things start to make sense after a certain amount of iteration and feedback just like some children need to fall down many times before learning to walk. Nick gives the example of James Dyson’s relentless drive to iterate and get to a working prototype. See also Invention: A Life by James Dyson. Maybe Daniel’s manager leaving forced him to step up and do better? Daniel isn’t sure what made the difference, but he knows it was what he needed and has been a major contributor to the work Daniel has done subsequent to the position in innovation. 27:27 – Progressing from Overwhelm to Clarity Was the point at which everything started to make sense close to the time of Daniel’s exit from PepsiCo? When Daniel had the tough career conversation with his manager about his performance, he knew he was close to turning a corner. Daniel didn’t plan to seek out a new role just yet. This scenario destroyed Daniel’s confidence. He didn’t fully realize how much of a problem this was at the time. When Daniel’s boss left and he asked about applying for the director position, Daniel said he did not want it. “Somebody had just told me I wasn’t good at doing those things. Why on earth would I sign up for more responsibility when I’m not good at the things I’m already responsible for?” – Daniel Lemire Looking back, Daniel thinks he should have signed up for the director role, feeling he was capable of doing the job. The team had no director for a period of time once Daniel’s manager left. Daniel encouraged one of his very capable peers to take on the director role and had no issues working for a different manager in lieu of removing himself from the director role candidate pool. During this period, Daniel continued to improve his skills as an innovation manager, filling some of those earlier gaps he had. “Right about the time I’m feeling pretty good about where I am and how I’m seeing things and being able to classify and organize and execute the things that I think need to be done…the earthquake happens.” – Daniel Lemire, describing a pending layoff event Daniel could clearly see what was happening over time from his learnings getting the graduate degree. He and his peers in the infrastructure space knew there was a larger organizational plan happening. The only real opportunities in the infrastructure space within the company were if you intended to become a director, senior director, or vice president. "All of us at one point several years ago kind of looked at each other and said, “are you going to hang around until the end, or are you going to jump and go somewhere else?’ I’m a really loyal guy. That’s just part of who I am. It’s really hard for me to pick up and leave because I’m invested. That was what was in play for me. I was just really invested in being a part of the organization….” – Daniel Lemire Daniel remembers getting the opportunity to move into the innovation group. He was moving into a different area and did not feel he would have an “end-of-the-road” problem like in the infrastructure space. It could potentially be the next 10 years of his career. “One of the things I also knew moving into innovation was our innovation team directly reported to the CTO, and the reality of that relationship is if you aren’t satisfying the objectives that the CTO has, you don’t have a reason for existence. So, you have to be very good at delivering on what you’re promising. The stark reality was that as a team, holistically we weren’t delivering to all of the objectives that the CTO had. So, something had to give, and in this case, it was me. I was the one that got cut from the team.” – Daniel Lemire Many were surprised that Daniel was impacted by the layoffs. Daniel doesn’t think performance ratings played into this but isn’t sure. Reflecting back on it, the role in innovation had too much ambiguity for Daniel while he was doing something very different. The time period in which all this happened also made this difficult. “It was too much at once, and it took me years to figure out how to navigate that well and to get back on the horse well.” – Daniel Lemire, thinking about his role in innovation. There are some good things that happened during this progression leading up to the layoff event that Daniel wanted to share with us. A couple of years before Daniel was laid off (and before he moved to the innovation team), one specific round of layoffs of his colleagues created an extraordinary amount of stress on Daniel, and that stress made him sick with gastrointestinal issues. Daniel’s direct boss was impacted at the time, which made it very difficult. “But I learned a lot from that situation because I had not learned how to regulate my emotions attached to what was going on. I was so invested in my reputation and my title. That was what was really important to me, and I didn’t understand that I needed to focus on everything about what I was doing, not just my career…. I needed that recalibration, and I also needed to focus on my health a little bit more.” – Daniel Lemire Joining the innovation team took away the immediate stress. Even though Daniel wasn’t performing as well as he needed to within innovation, it did not come with the same amount of stress as when he worked in infrastructure, and it was an entirely new set of challenges. Daniel was able to recalibrate what it meant to be in a future round of people leaving the organization. “I was able to contextualize what that meant and recognize that that really didn’t have anything to do with me and that sometimes these thigns happen and that I just needed to get myself in order. No matter what was going to happen, that was on me to do, and nobody else could take responsibility for that. So, in some ways it was accepting that responsibility of ‘I need to be in charge of the whole me.’” – Daniel Lemire Daniel mentions that his wife made a decision to go and get some coaching to improve herself, and it impacted him in a very positive way. Daniel was in a bad place, and his wife shared some of the learnings from that coaching with him. At one point Daniel’s wife encouraged him to make a vision board that covered all areas of his life. This was close to the time Daniel had the difficult conversation with his manager in innovation. Daniel’s wife had already made one for herself, and it was extremely helpful. “I’ve gotta tell you guys, there’s something much bigger at play because it was almost the next moment after finishing that vision board that things started to happen…. I honestly believe that if I hadn’t done the vision board that none of those things would have happened. I really think that was the trigger. It was me getting clarity on what mattered.” – Daniel Lemire As a result of making the vision board, Daniel had the overwhelming need to get a LinkedIn subscription and to share content with people. Daniel refers to the things that happened next as “a snowball of change.” “I need to be in a position that I can uniquely fill, to use all of my skills and not just be managing tasks, to apply technical experiences to make the organization better, and to build systems that help people and have my contribution valued.” – Daniel Lemire, sharing what he had written on a post-it note after completing the vision board exercise Daniel says it was completing the vision board and getting the clarity that launched him into a “next phase.” For the first time in several years, he knew what he wanted. At one point he had been merely going through the motions so he could recover from the overwhelm of too much ambiguity. While still on the innovation team, Daniel was starting to think about the type of role he wanted next. “If I had the permission to do something or anything, what would that be? One of the things that I outlined for me was doing things that were outside of my specific role because that was part of how I had been successful in my past, and I knew I needed to get back to that.” – Daniel Lemire John pointed out that nothing on Daniel’s post-it note said he needed to be working in innovation or that he needed to be a senior manager. It was much more general. When we cut it down to the core, for Daniel, it wasn’t about the title or the area he was working in. Daniel says he needed to get clarity about what was important first before his “what’s next” could begin. Nick remembers having lunch with Daniel around the time of the layoff that impacted Daniel and hearing his idea. Daniel’s idea and proposed direction seemed extremely clear based on the time at which the lunch occurred. Daniel says Nick observed the output of Daniel getting the clarity he needed. Daniel also tells us he did not appreciate the importance of getting this clarity and at some point along the way had stopped seeking clarity. "…There’s no reason that you have to abdicate your responsibility to understand what it is that you should be working on. We should all be working on something at every moment, and we should be intentional about the things that we’re working on. I let go of my initiative because of the ambiguity. I didn’t have a rudder, and I wasn’t doing the things that I needed to do to get that rudder back. And I take responsibility for that. I really do. I think I could have done a better job of navigating that situation if I had thought about what I needed to prioritize and thought about what it was that I needed to be doing. And I also needed that…because it got me asking…‘ok, that’s all done. Now what?’ I can’t go back and change any of that. It doesn’t matter. What am I going to do now? " – Daniel Lemire Daniel refers to the scene in Frozen 2 where Anna sings about “the next right thing.” “It’s reflecting on those ideas and those thoughts that was also the genesis of how I wound up falling into this AI Mistakes thing that I started.” – Daniel Lemire Mentioned in the Outro This was another story of someone impacted by a layoff event. If that’s you or someone you know, check out our Layoff Resources Page for access to the most impactful discussions on the topic of layoffs with industry experts and technologists like you. The clarity Daniel gained allowed him to reframe the layoff event, and in seeking the clarity, he figured out what he wanted and needed in a job role. It was the vision board and going through that exercise that made the difference. Nick suspects there is some parallel or possible overlap in the vision board and the Must Have List that Kat Troyer and Liz Bronson (the hosts of RealJobTalk) shared with us a while back. We usually don’t take the time to perform these types of exercises because we’re overwhelmed or have too much work to do or get distracted by other things. Maybe you need to spend time seeking clarity. When Daniel mentioned he wasn’t sure what to do with DevOps after learning about it, Nick thought this sounded like more missing context. It reminded him of the mix of concrete and abstract learning that Erik Gross spoke to us about in Episode 267 – A Theme of Learning with Erik Gross (1/3). Daniel’s ‘what now’ question reminded Nick of what Cody de Arkland shared in Episode 86 – Emotional Tech Support and Debugging with Verbose Logging with Cody de Arkland – stating lives and careers are like seasons. It’s more about when is next than what is next. Daniel also shared some book recommendations after this recording that we will mention (both available in audio form): What to Do Next: Taking Your Best Step When Life Is Uncertain by Jeff Henderson Imaginable: How to See the Future Coming and Feel Ready for Anything―Even Things That Seem Impossible Today by Jane McGonigal What did Daniel mean by starting AI Mistakes at the end of that episode? We’ll share the story next week as we conclude with part 4? Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YoutTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.

When you’re missing a specific experience in your career, how do you get it? Daniel Lemire was missing experience in a large enterprise to pair with the things he learned from pursuing a graduate degree. Join us this week in episode 324 to hear the story of what happened when Daniel got that experience that provided the missing context to apply what he learned. Throughout this discussion, you’ll notice Daniel’s continued openness to new opportunities lead him from a contractor position in a large enterprise all the way to technical lead. There’s also a parallel process of Daniel’s development of expertise and credibility alongside his observations of the enterprise organization as a whole that encourage us not to limit our focus only to the technical work we’re doing. Near the end of our discussion, Daniel shares his perspective on an organizational decision to begin outsourcing and the way it impacted his work. What would you do in that situation? Original Recording Date: 03-20-2025 Daniel Lemire is an AI Consultant working for ServiceNow. If you missed part 1 of our discussion with Daniel, check out Episode 323. Topics – Missing the Context of Experience, Unexpected Opportunities, Confidence and Feedback, Enterprise Experience Meets Educational Background, Gaining Organizational Perspective, The Cascade of Objectives, Technical Leadership and a Change in Strategy 3:03 – Missing the Context of Experience Daniel said after completing his master’s degree at UNT he did not have the context of experience to pair with his education. As part of the master’s program, Daniel got an education in marketing, management, and technology. In class, they might have a discussion about how CIOs make decisions or have a guest speaker to provide additional context from the business world. “I knew what the right questions were, but I didn’t understand why those were the right questions. And it was a real challenge for me because I couldn’t place what I was learning…. I was learning the right things. They really were the right things, but I didn’t know what to do with it. The curriculum I took in getting the master’s degree was exactly what I needed to be successful in a large enterprise. But because I had only ever done the independent consulting, I had only ever worked with very small companies, companies that had less than 100 employees…. So much of what I was learning about management discipline and program development and project management was for these really big organizations, and I didn’t have the context to understand why all of those things were necessary….” – Daniel Lemire, thinking back on his master’s degree program Daniel makes a reference to the 150-person relationship limit known as Dunbar’s Number and says this requires very different business management techniques. Upon finishing the graduate degree, Daniel had learned 3 very critical things: Daniel discovered through conversations with classmates and through completing specific projects that he had an aptitude for the subject matter. He also realized the program had been the right place for him. Daniel knew he had a lot to learn but that he was missing enterprise experience. It was something he really needed to get the full value from what he had learned pursuing the graduate degree. “The third piece of it that I didn’t understand until much later was that journey of taking turns between being overprepared for something and getting into something that you’re overwhelmed by. That’s yet another dichotomy because in some ways by getting the graduate degree I was overprepared for an enterprise environment, but from an interpersonal and from a political and…just being one of many in a corporation, I was totally unprepared for that experience because everything I had ever done up to that point was at a much smaller place.” – Daniel Lemire Daniel was the only IT person when he worked at the Conroe Medical Education Foundation, and there were only about 20 employees. Through his consulting work building websites, Daniel interacted with several companies across various industries. He mentions one of the largest had about 80 employees. 6:54 – Unexpected Opportunities Daniel shares a story of crossing paths with an acquaintance who had been the systems administrator at the Texas Women’s University (TWU) Police Department but was moving to a different job. “Sometimes you find somebody else that’s technically good and you know who they are, and you remember them. This was kind of one of those deals…. I’m doing this grad school thing while I’m kind of just paying the bills doing the consulting thing. So, I was ready to take on another opportunity.” – Daniel Lemire, on a chance meeting with an acquaintance who got him a job Daniel was asked if he’d be open to doing something different and possibly taking over at the university police department. After saying yes, Daniel spent a year working at TWU while he finished his graduate studies, which provided the opportunity to learn about a completely different type of business (a police business). Daniel spent time understanding what the police officers did and spent time building systems. One specific example of a system Daniel built (or contributed heavily to building with others) allowed students to buy a campus parking pass on the university’s website. This was his first experience working on an integrated system. In everything he did, Daniel’s intent was to solve problems. There wasn’t a guidebook or manual to build things like integrated systems. Another example of a project from his time at TWU was building a customized alert system for the university based on programmatic scripts (which acted as a stop gap until a vendor solution for this could later be put in place). “There’s no guide for this. I just know what the technology can do, and I know what my skillset is. We put the things together and built something that solved an immediate issue…. Even TWU as big as it was…I was just in the police department. That was a big place, but my place inside that big place didn’t take advantage of everything I’d learned in getting the grad degree.” – Daniel Lemire While Daniel was working at TWU and wrapping up his graduate degree, he received a call from a gaming buddy from his time as an undergraduate who suggested he consider a role at PepsiCo. The role Daniel’s friend mentioned was a contract role for loading operating systems on servers before they get shipped to specific sites. His friend’s description of the role was a little nebulous. As a result of their discussion, Daniel got connected with the recruiter for this role. He was intially worried about asking for too much money but found what he asked for was in range per the recruiter. Daniel was really excited about the possibility of a full-time role. After Daniel was passed along to the hiring manager to interview for this role, the manager asked him how he felt about working weekends during the interview. Daniel was honest and communicated working on Sundays was not something he could do. After the discussion with the hiring manager, the recruiter called Daniel to let him know it wasn’t going to work out and that this was a weekend job (not something that was previously communicated to Daniel as part of the process). “This isn’t going to work out because this actually is a weekend job. And I didn’t know that. That wasn’t disclosed in the conversations she and I had or in the job description details that were in front of me. I was just answering the questions honestly because that’s what the right thing to do was. That job didn’t work out for me….” – Daniel Lemire Daniel could not commit to the schedule for this role because it conflicted with his church activities. A few months later, the same recruiter called Daniel saying there was another open position for which he might be a fit. This role was better pay than the first one he had interviewed for and was more focused on the systems engineering work Daniel had been doing. This job ended up being a role on the same team as the friend who recommended Daniel apply at PepsiCo. Daniel’s friend removed himself from being part of the interview process to prevent conflicts of interest. Daniel built a good rapport with one of the decision makers and was hired quickly as a systems engineer. He started with PepsiCo working on Windows Server automation. Daniel was considered analyst level and not a lead engineer. Daniel says he had been doing more programming and coding than working with hardware coming into this role, and he was able to learn a great deal in this role. “That then was a huge opportunity for me because I got to get into something that was completely new. The hardware focus was something that I wasn’t used to…. I got to go deep into something I thought was going to advance my career because I didn’t know enough about hardware. I got to work on a team inside of an enterprise, and I really wanted that enterprise experience after I got the grad degree because I had all of this stuff in my head that I couldn’t really quite use yet.” – Daniel Lemire At TWU, there was no need to decide which server vendor to use. A specific vendor was the established server provider. The paycheck for this job was a great opportunity for Daniel to provide steady income for his family. They were able to buy a house and discuss starting a family. There were opportunities all over the place after starting at PepsiCo. Getting in and doing well could set someone up for a career there rather than just a job. 15:14 – Confidence and Feedback When Daniel was only doing consulting work, he was not around other people doing the same type of work outside of some mentors who provided guidance. Being in the graduate program put Daniel around other people doing similar work and helped him understand he had the ability to do well in this field. It produced a confidence that seems to have catapulted him through the interviews for roles at PepsiCo. In the last couple of years Daniel has learned how essential confidence is in getting us to what’s next. Daniel has seen a number of people be overconfident and run into numerous problems as a result. A sensitivity to these kinds of people may have affected the way he thought about confidence in the past. “Finding the way to get yourself the self-confidence so that you can convey what you know to other people enables you to explain the value that you can create for them, and that’s how we do business together.” – Daniel Lemire Nick mentions an element of feedback as well throughout Daniel’s story from teachers and friends. His friend recommending the role at PepsiCo is the next iteration of that feedback. Daniel tells us he was not seeking feedback early in his career, but he was getting it. “If you asked me about it now, I would expressly tell you that feedback is probably the most important element of being successful. It’s going to give you an early warning sign when you’re on the wrong path, and it’s going to push you in the right direction when you’re on the right path.” – Daniel Lemire Daniel remembers a book he was reading back when he and his wife were dating that encouraged only dating people you are serious about. Otherwise, it is a waste of time. Daniel says feedback is how you prevent wasting your time. In Daniel’s case, feedback he received was unsolicited early on. Nick has heard podcasters say that getting no feedback (good or bad) about your podcast is a bad sign. Daniel works from home and puts post-it notes on his monitor that only he can see. One of the notes says, “what experiments are you doing?” “In the absence of feedback, you can do experiments and see and evaluate yourself. Is this moving me in the right direction? …The reality is it creates the delta between what you’re doing and what you could be doing…. If you are changing things, generally you are going to get a response. Either somebody’s really going to like it, or they’re really going to hate it. But either way, you’re going to get some feedback.” – Daniel Lemire John says a corollary to not getting feedback is perhaps no one cares enough. Even if someone cares negatively and thinks you’re wrong, at least someone cares enough to criticize and maybe set you on the right path. “Whatever you’re doing, make a ripple.” – Daniel Lemire 20:39 – Enterprise Experience Meets Educational Background Once Daniel started working in an enterprise environment at PepsiCo, did everything he had learned in his graduate program start to click with his experience immediately, or did it take a while for that to happen? “I can tell you that basically from the moment I landed, everything started to make sense about that grad degree…immediately. I felt like I was Superman and had X-Ray vision because everywhere I looked the pieces were fitting together…. The part that I didn’t appreciate about knowing all of that was the engineer in me was also immediately frustrated because I could see where things were broken, and I wanted desperately to fix them.” – Daniel Lemire Daniel was able to understand how upper-level leaders were making deicisions thanks to what he had studied. As someone new to the organization, it was important to execute his job well and build credibility. Credibility was necessary for speaking up later in attempts to impact organizational decision making. “I’m delighted to say that was the easy part. Being good at the thing that I was responsible for was what allowed me to consistently exceed the objectives that were handed to me. And to a large degree they were handed to me…especially in the early days of making any kind of decision about how things were going to work. It was just ‘this is what we need to accomplish. Go get it done.’” – Daniel Lemire Daniel enjoyed writing code and working in the server lab to make things work. He was a contractor in the beginning and was left out of organizational politics. Daniel reminds us that contractors should stay out of organizational politics because it can lead to trouble. Daniel did well in his role as a contractor and was helpful to the people around him, earning a reputation that would get him to full-time employee status about 1.5 years later. Daniel even did well enough to negotiate a little bit on his full-time employment offer. “I could that time as a contractor as my time at PepsiCo because, really, the things that I was working on were my responsibility. I owned the thing that I was given.” – Daniel Lemire Though it no longer removed him from politics of the organization, being a full-time employee meant Daniel got to be part of the progression and accomplishments of a large enterprise. He enjoyed seeing the datacenter and how computing was handled at the scale of the organization’s needs. Daniel knew the combination of growing himself, doing the technical things that needed to be done, and leveraging his graduate degree would help him progress within the organization. The company made investments in Daniel as an employee in the form of training, for example. Was this Daniel’s way of answering the question from the person at church from long ago about what he was doing to grow himself? Yes – it’s about having a vision and intention for where you want to go in the future to avoid standing still. Daniel brings up the physics concept of entropy. Standing still means you are degrading. “You’re always in some phase of change, so if you have any control at all, make sure that your phase is going up and not down. Because if you’re not paying attention to it, entropy is playing on the system, and things are going to naturally degrade.” – Daniel Lemire 25:10 – Gaining Organizational Perspective John mentions Daniel’s first experience in an enterprise was in a very large one. For very large enterprises, it takes a lot of time and effort to move in a direction the organization is not already moving (i.e. the container ship analogy). How did Daniel see this in his experience? Daniel started in an individual contributor role. He was not responsible for a program or for people. The graduate degree gave him the context to interpret different situations within the company. “In any sufficiently large environment there are the official things, the things that everybody says because it’s what they have to say or it’s the dialogue they have to carry through. Then there are the things behind the scenes, the real actual games that you’re playing, and there’s a whole different set of rules that are associated to that. And the sooner you can understand the difference between the rules they say they’re using and the rules they’re actually using, the more likely you are to be successful. And to me, that graduate degree gave me to tools I needed to understand not just what was said but what was not said and what that meant for me. So even though I didn’t have that responsibility, I could see the things that were being done from an organizational perspective and translate that into being able to decipher what the bigger next move was.” – Daniel Lemire In Daniel’s role as an individual contributor, he knew they needed to iterate on a server build or support new equipment with hardware refreshes over time, for example. The technology strategy of the organization and business leader perception of the technology organization were things Daniel could still observe in his role. “I was able to see both the good and the bad from a position that I could learn a lot without having to carry any of the responsibility about making those decisions. And I think that was really the thing that shot me ahead from my enterprise career perspective…. I was able to gather a lot of information in a very short period of time because I was able to contextualize it with the graduate degree.” – Daniel Lemire Many of Daniel’s peers who didn’t have the same education had trouble making sense of things the company was doing (i.e. why decisions were being made certain ways), even to the point of frustration at times. Even if Daniel didn’t agree with a decision, he could contextualize it and understand it. Did Daniel try to explain some of what he knew / understood about the organization from his education to his colleagues, or did that feel too assumptive? Daniel says he’d be willing to have a 1-1 conversation with people about his observations. In the audience of an entire team or a senior leader, Daniel held his tongue. Looking back on it now, Daniel thinks he could have provided more value by sharing some of his analysis of the situations with others. “…I did have some of the right ideas, but what I didn’t have that I now fully comprehend is I didn’t know how to say things in a way that would be received well. In other words…my early days…while I was good at providing critical feedback, it was critical feedback. I didn’t know how to say things in a way that was polite or nondestructive…. I had some critical moments in my career where I had some very critical feedback, and I let it out in a way that was not constructive or useful. And that limited what I could do from a career perspective…. So, it’s kind of one of those double-edged swords. Don’t bite your tongue unnecessarily, but at the same time, be sure that you can say it in a way that is constructive and helpful.” – Daniel Lemire Daniel says the internalization of frustration has come out in his tone at times. Even now, Daniel has to be mindful of not putting himself in a situation that is overly stressful or frustrating because those conversations don’t usually go well. Daniel might have known the right thing to do but didn’t know how to convince others or use what he knew to persuade them. Daniel highlights how valuable it was to bounce ideas off his peers within the company. We can easily recognize who knows their stuff / area really well and might seek these people out for a discussion. It’s important to be really good at what we do. Daniel says it can lead us to new opportunities because people seek us out as experts. “That’s why you have to balance the doing the things that you’re not good at and exercising the things that you are good at. If you get too far into the doing things that you’re not good at, it lessens the number of opportunities that you have. So, you have to be really strategic about diving into the deep end too far. You have to continue to do the things that you’re not good at but do it in a way that leverages the things that you are so you don’t get into the red zone. That’s one of the things that I’ve learned, and we’ll touch on that a little bit later…. The very first thing I took away from that experience was find the right people and talk to them on a 1-1 basis…. Finding great people is a huge career builder.” – Daniel Lemire Talking to the right people 1-1 allows you to test out what you’re seeing and get some feedback. Also, these discussions allow you to identify who you can work well with to take advantage of it later on in your career. 33:42 – The Cascade of Objectives Does finding the right people mean building champions for your personal brand? Daniel says yes – this idea of brand building is true everywhere. “You have to be able to tell someone in a very short period of time what your value is, and that is your brand, no matter what you’re doing, no matter how large or small the organization is. You do have to think about that to some degree and have a plan for that. That’s something I lucked myself into.” – Daniel Lemire Daniel can look back and see that he was doing the right things to build a strong personal brand early in his career, but he didn’t quite understand what he was doing at the time. Nick thinks most people do not know how to succinctly articulate the value they bring to situation / job / role without some reflection, writing, etc. We can get some of this from the feedback received from others. Daniel was having conversations with other people 1-1 but was not consciously thinking of what things he was doing should be put on his resume. Daniel worked for a company which required employees to write down and track their yearly objectives (including evidence of progress made to reach those objectives). This helped him think through resume-type items. It is a benefit of working for large organizations (mandates to use specific systems to complete these types of exercises). “I can honestly say with reflection that that’s one of the best things an organization does for their employees because it forces you to do something that will make you better whether you want it to or not…. If you’re in a position today where you’re not given that system, the best thing you can do for yourself is to literally write it down. What are you going to do? And then look at it again multiple times to ask yourself ‘what am I doing about that’ and ‘how did you do so far?’ The most successful people write it down. They think about it. They talk about it, and then they write it down and then evaluate it later. And that is so essential, and I didn’t really appreciate that until just recently.” – Daniel Lemire John mentions in his most recent role he was asked to go through the OKR (objectives and key results) process. He had done this before at Google. In a leadership position it can be harder to take OKRs from an upstream leader and then re-contextualize for downstream team members. But it does provide a common understanding of how everyone will be measured. John agrees writing and tracking objectives can be a great resume builder. It helps someone articulate how they were measured and the steps they took to accomplish the objective(s). Daniel calls this process a cascade or translation of the objectives down to a manager’s direct reports. This process was one of the most difficult things for Daniel when he was a people manager (the translation process). “Whether or not you’re great at it, you have to do it because if you are not doing it, the people that you’re responsible for supporting and helping don’t get the context that they need for why it is they’re doing what they are doing…. Just improving yourself in a vacuum is actually one of the biggest roadblocks to organizational success…. That’s what a critical manager does…they make sure that the individual is able to grow and carry through the responsibilities but to do it in a way that it doesn’t jeopardize the rest of the system. So, in some ways you might say that those middle managers are the transmission that connects the engine to the wheels. You can have a great engine, but if it never gets connected to the wheels, you’re not going anywhere.” – Daniel Lemire When people get really good at building their own thing, it might not interface well with the rest of the organization. Daniel mentions he sees many people get excited about what they can do with AI. It may be empowering to an individual, but we might want to jump in to make ourselves more effective without considering the larger organizational impacts doing this will have. A senior developer might be able to build great applications with AI (perhaps even using AI for the things they might ask a junior developer to do), but not working with a junior developer means the person is not being fostered to develop into a senior developer. There’s a downstream impact here that comes up later on. “The other thing that as individual contributors and managers that we should all be thinking about is, ‘how do I optimize for today without putting myself in a difficult situation for tomorrow?’ We have to think about both the short and the long term, and we have to help the rest of the organization do that as well. That’s probably the challenge for the next decade as we get the most advanced technology that man has ever seen and try to put that together with humans.” – Daniel Lemire 41:05 – Technical Leadership and a Change in Strategy What made Daniel move toward people management in the first place? He shared some insight into this earlier, but we want the full story. The first step in the process was moving from build engineer to technical lead. Daniel tells us he was not responsible for managing direct reports in this role but focused on making a greater impact on the overall team and the work they were doing. Daniel says progressing to technical lead was a natural progression. When he looked around, Daniel once again realized he had an aptitude in this area. After observing the systems and the way work was done, it naturally led Daniel to persuade members of the team to take slightly different approaches that were more optimal. It was about influencing the direction of the work people on the team were doing and how they were thinking. Daniel shares an anecdote from his COBOL class in college. When students were getting caught up in small details, the professor commented that the class “couldn’t see the forest for the trees.” The professor reiterated to the class that they were focusing too much on the small details and not thinking about what they were trying to accomplish. The above is exactly what kept happening in Daniel’s technical conversations with others. Daniel had to encourage people to look at the larger picture, and it kept happening. “And that just sort of kept happening. It was just sort of a natural progression to where I was helping them with those individual things that they needed to accomplish but also helping to make things mesh more easily as we had to put things together because I was consistently finding myself in the situation where I had to negotiate the interface between the work that we were doing and the value that it was creating. I didn’t understand that at the time, but that’s actually what I was doing now reflecting back on it.” – Daniel Lemire Daniel might have to tell someone that reprogramming a specific function again and again was not going to deliver the results the team needed (build a server faster). Sometimes an optimization we are making will not improve the system, and value only gets generated when the system is improved. Daniel says he spent the middle decade of his career in that contextualization area we spoke about earlier. He was at PepsiCo for nearly 16 years. The first couple of years were getting technically oriented and finding ways to contribute to the team. The career progression of others gave Daniel the opportunity to move up / progress within thr company. Daniel would ask for specific work / projects, and his manager could see his talent and would in the future look for opportunities to leverage those talents. “They understood that I was capable and that if they gave it to me, it would get done well. That made things better for them, and that made things better for me.” – Daniel Lemire In being the technical lead, Daniel appreciated that he did not need to deal with HR things. In this role he was able to accomplish a number of things he is very proud of but also limited his growth from a manager perspective. “I don’t have any regrets about not moving into that manager space sooner…. I was able to observe all of that without having to be responsible for it. For me, that responsibility is a mantle that I want to put on, but when I do put it on, it is something that weighs me down. There is a cost for me in taking on that. I take it very seriously.” – Daniel Lemire Daniel stayed in the technically focused contributor role for a long time. He did not have to take on being someone’s manager and existed to support others technically and to help them grow. It was the organizational strategy inside the company that started to affect Daniel’s career trajectory. There was a lot of outsourcing happening for various reasons (optimization, globalization, etc.), and it impacted Daniel’s colleagues over time and the relationships he had built with them. The changes meant Daniel had to seek out new people to work with on various projects, and instead of working in the same office as Daniel, these people were in a different part of the world and from a different culture. “You’re building your network. Every person you have a good rapport with that goes somewhere else…that creates totally new avenues of opportunity for you.” – Daniel Lemire Daniel was frustrated that colleagues had to leave the company, but he also had work to do and decided to focus on what needed to be done (the things he could control). This was building Daniel’s frustration in ways he did not understand at the time. Daniel says he often tries to compartmentalize things and uses the analogy of a waffle to illustrate. “Don’t think about just work or just family. Sit down and think about all of the elements of your life and how they are going to fit together. Because if they don’t fit together, it will come around to bite you later.” – Daniel Lemire, on compartmentalization The organization’s decision finally impacted Daniel. The company decided to outsource all infrastructure services. This was a very challenging time for Daniel. He had to hand over systems and processes he had built to someone he had never met. It was a difficult reality but a reality he had to face. “It was to the point where my management team actually said to me at one point – ‘Daniel, you don’t do that work anymore. That’s not yours. That’s not your job. Your job is to make sure that things get done, not how they get done.’ And I had a really hard time with that…. A big part of my pride was the work that I had produced. Essentially, what that meant to me was that the work that I had done, that I had spent the better part of a decade to be effective at, really was not valued…. There was a time of struggle there for me, and that began the sort of searching mode…going back to the very early experience where I found out…that’s not where I’m going to be now. Now what? And it was because I recognized that what I was doing was no longer the path forward, I kind of had to have a reset.” – Daniel Lemire Mentioned in the Outro It sounded like gaining the enterprise was the right place for Daniel. Doing his work well was the groundwork for developing a great reputation, but Daniel was also observing the organization and looking at the way decisions were made. At first, he did not have the influence to change any decisions, but he got at least some influence at the technical lead level. This began with remaining open to new opportunities just like in his early career (i.e. recommendations based on the feedback from others). As he started to observe the enterprise of PepsiCo, he began looking for new opportunities inside the company. These types of opportunities didn’t exist at the companies where Daniel had worked previously due to their size. Does your company have you set and track objectives? If so, are you doing it well? If you don’t have this requirement, you can still document objectives and progress toward them on your own. Maybe we should document and track our experiments too. Nick thinks we should still track things even if they initially seem unrelated. They might be more relatable to your next role than you think! Other episodes that pair nicely with this episode: Episode 284 – Draft Your Narrative: Writing and Building a Technical Portfolio with Jason Belk (2/2) Jason Belk reminds us of the importance of a career narrative. We need documentation of the work we are doing to generate and practice that narrative! Episode 267 – A Theme of Learning with Erik Gross (1/3) Erik talks about a moment when his classroom learning in the Nuclear Engineering program met experience. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YoutTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.

If your career was a product, what would the current release notes say? Just as product managers launch a minimum viable product (MVP) and enhance it based on customer feedback, Daniel Lemire unknowingly began building his career this way starting in high school. This week in episode 323 you’ll hear about Daniel’s early aspirations to be a pilot in the Air Force and the phone call that forced him to change directions. It was a reliance on his faith, his aptitude for computers, and an openness to feedback from friends and teachers that prompted Daniel to study management information systems in college. Follow along as we explore the timeline over which Daniel decided to become an independent consultant, gained technical expertise and experience through building systems to deliver value, and ultimately decided to pursue an advanced degree. With each decision along the way, Daniel chose to take a step forward very much like a product release adds features and enhancements. If you thought of where you are now as a MVP, where could you go from here? Original Recording Date: 03-20-2025 Topics – Meet Daniel Lemire, An Early Deviation from the Plan, Self-Awareness and the Gift of Explanations, A Tinkering Instinct and the Cycle of Confidence, Consulting and a Return to the Familiar, The System Builder, Thoughts on Product Management, Getting an Advanced Degree 2:31 – Meet Daniel Lemire Daniel Lemire is an AI Consultant working for ServiceNow. He gets to speak with senior leaders about the use of artificial intelligence in their organization specific to the ServiceNow platform. It’s a pretty popular topic of conversation these days. Daniel enjoys driving influence and helping organizations create value, and throughout the course of his career, Daniel has learned to calibrate the use of technology against the creation of value. 3:39 – An Early Deviation from the Plan How did Daniel get into technology in the first place? Daniel’s middle school had a computer lab, and he and several others were part of a computer club. In addition to this, Daniel was fortunate to have a computer at home in the early 1990s and play games on it and discuss computers with friends. Going into high school, Daniel wanted to be a pilot. He wanted to attend the Air Force Academy and eventually become an officer. Daniel was working to do everything he could to hit that goal. Daniel tells the story of a phone call from an Air Force recruiter during his sophomore year of high school. During the course of that phone call, Daniel learned he was disqualified from serving in the Air Force because of his asthma. “So immediately I found myself in this position of…if it’s not the Air Force, what are my plans? …Am I just going to go find a school to become a pilot and continue down that path with a different means, or am I going to do something completely different? …Honestly, I kind of threw up my hands, and I said a prayer. I said, ‘God, this is what I wanted to do, and this is not how I thought this was going to go. What should I do?’ And, over the next few weeks, the computer thing became increasingly an area of focus.” – Daniel Lemire Conversations with friends and some teachers helped Daniel realize he had some talent when it came to computers. They encouraged him to spend time in that area. From then on, Daniel would find ways to do different things with a computer because it was something he enjoyed. “Any time you can take something you enjoy and turn that into value is really great.” – Daniel Lemire As a senior in high school, Daniel took a computer maintenance course and learned all about computer hardware. Taking this class provided things to Daniel that he did not know he needed. Daniel was good at using Microsoft Office software and really enjoyed programming after taking a course on it. Daniel also took a typing course from a typewriting teacher. Students took it as if they were using a typewriter. Making 3 errors meant you failed the typing exercise. Daniel says he was not great at not making mistakes back then but understands he would not type at the speed he does now without the experience of taking this course. High school courses set Daniel up nicely to choose a computer-related course of study in college – Management Information Systems (MIS) or Computer Science. When taking tours of potential colleges, Daniel would visit the computer lab on campus and make sure he visited both computer science and business information systems personnel. Since math was not Daniel’s primary interest, the business side of computing was better suited for Daniel. Daniel ended up at the University of North Texas (or UNT). Daniel says one of the biggest benefits of their program was learning both new and older technologies. When he entered UNT in 1999 it was one of only a few colleges that allowed students to work on a mainframe. 8:59 – Self-Awareness and the Gift of Explanations Nick likes the way Daniel handled the setback related to being a pilot and putting his effort into an alternate path. Most people would have had a lot more trouble. Daniel says he didn’t have enough life experience to dissuade himself from taking the next right action. Nick points out Daniel had enough information to select a course of study that fit with his strengths and his interests in the best way. Daniel says self-awareness is not something we talk about enough. “I’m very much a striver. I will do things that are very hard for myself just because I want to accomplish something really big, and there is absolutely a time for taking on those big things. But you also have to do it from the context of…what am I good at, and what can I get started with right here where I am?” – Daniel Lemire Daniel says it wasn’t just his interest in computing that drove him to it. It also had to do with other people’s observations of his interest in it. As a result of both, he was open to pursuing computing in his course of study instead of continuing to search. In high school, students were given some recommendations for future courses of study – something in thr arts, something in science / math / engineering, or some sort of specialization in a different area. Daniel says he was ok at math but really enjoyed physics because it was very conceptual. He would work on math problems and make simple mistakes. “…so being able to capitalize on the part that I was good at in getting into that computing career I think was the other piece of it – knowing that I was good at it and being convinced in the shortest time possible that that was the path for me by being open.” – Daniel Lemire Did someone encourage Daniel to look at both the computer science and management information systems options when he was visiting colleges, or did he naturally investigate both on his own? Daniel listened to the feedback he was getting from high school teachers, and he specifically mentions his typing teacher. Daniel took the typing course as a sophomore in high school, and that teacher recognized his aptitude with computers. Daniel would help her from time to time and would later become her teacher’s aide. In a number of their conversations, the typing teacher would ask about Daniel’s future career plans. Daniel says it was not a coincidence that he had this teacher in his life at the same time the Air Force said no to him. John says around this same time many people might have said they were good with computers, but they likely meant they were good at playing computer games. This is very different than using computers to solve problems and seeing them as systems because you’ve taken the time to understand the internal mechanics of the system. Daniel says having access to computer technology at home what critical in all of this. Daniel tells the story of trying to tweak configuration files on his computer to get a game to run and breaking everything. Daniel’s mother had a friend from church who was able to come over and fix the computer problem. “He could have showed up and been like, ‘Daniel, what an idiot. I can’t believe you would do something like this.’ He could have fixed it and just walked away, but he took the time to sit me down and say, ‘ok, I see what you did here. Now let me explain it to you so that you can understand it.’ It was that taking of the time that really made a difference, and I haven’t forgotten that because we get so tied up in ourselves that we forget what it is to give that kind of a gift to somebody else. That’s an invaluable opportunity, and I learned so much through that and was able to convert that into a win time and again because somebody invested those few minutes in me by explaining something I just didn’t understand.” – Daniel Lemire 16:28 – A Tinkering Instinct and the Cycle of Confidence John says listeners recognize the tinkering instinct, and the experimentation we participate in through it ends up benefitting us. Losing some of the fear of doing irreparable harm to a system allows us to learn even more. Daniel feels this played a big role in his story and has told people he is addicted to the “undo” button. “The further up in the career you get the more likely it is you’ll get yourself in trouble by making a bad decision, but if you’re able to identify those areas where you make mistakes less often or you can set things up in a way that you can make those mistakes without them being harmful…I really think that is a key to success.” – Daniel Lemire Daniel stresses the importance of opportunities for iteration. How often do we put ourselves in situations where we don’t have to get something right the first time so we can take advantage of an opportunity for growth and learning (i.e. a new skill, a new system, etc.)? “Any time you can setup a scenario where you don’t have to get it right the first time, but you can benefit from it if you do is so essential to the journey…. You can really get ahead when things are going well but avoid yourself getting into an unrecoverable situation from there on out.” – Daniel Lemire Daniel mentions the Agile methodology and cites a quote by Jeff Bezos about making decisions that are easily changeable if they start you in the wrong direction. “I don’t need to know that this is the right answer right now. I just need to know enough to make the next step. That’s where I was in the early part of that career…. That showed up again and again as I continued my education…. It really became critical when I got out of college.” – Daniel Lemire Going into college, Daniel didn’t know the world was about to have an internet bubble burst. He was very excited about working for EDS (a premier IT company many people wanted to work for) and felt he was well-prepared to do that. Daniel talks about taking an internet computing course in which students had to build a business plan for an internet-based company and then execute on it. There was a competition as part of the final exam involving a mock proposal. Daniel was on one of the 3 teams which had to deliver a presentation at the offices of Sabre. He learned 3 things from that experience: One doesn’t need to know everything to do something impactful or interesting. It’s about knowing enough to build a business plan and a prototype you can showcase for feedback. Near the beginning of Daniel’s presentation at Sabre, the computer crashed. He had printed out the speaker slides and notes and knew what points to hit to finish the rest of the presentation. The very first time Daniel needed to present in front of a group, his hands were shaking. It took many presentations in front of people to get over it. Doing the presentation at that time was a huge deal for Daniel because he was not comfortable as a presenter. Having those notes eased his anxiety. We should not underestimate the value of preparation when going into an intimidating situation because it can boost our confidence. “It’s funny how your current experiences can crystalize that looking back on those moments. And I can absolutely tell you from a career perspective, what I didn’t appreciate at the time was how much a difference that confidence made in my success…. I totally understand that now because I had to go through the entire cycle of you’re confident, you’re not confident. How do I get that back to do and tackle the next big challenge?” – Daniel Lemire 23:12 – Consulting and a Return to the Familiar John points out Daniel’s willingness to attack something he was not comfortable with. We’ve previously seen a pattern John refers to as Smart Kid Syndrome which hinders growth when people do not invest in weak areas so they can be perceived as being good / highly skilled at things (i.e. the opposite of a growth mentality). In Daniel’s case, he found the things that made him feel comfortable in uncomfortable situations and went back to them. Not long after the presentation at Sabre, Daniel obtained his degree but could not enter the workforce. There were no job openings, and it was a time of many layoffs. Daniel had no choice but to fall back on some of the things he knew to make himself successful. Daniel had proposed to his wife before that last year of college, and they were married the summer after graduation. His wife got a job as a graphic designer to provide planned family income. “I fell back on what I knew, which quite candidly, was what I learned in that ecommerce course.” – Daniel Lemire Before most people really knew what building a web presence for businesses would mean long-term, Daniel knew it was something he could do. He began a journey as an independent consultant. It was something he knew how to do and a place he could create value without a full-time job working for a specific company. “I kept looking for that opportunity to work for somebody else, but it never materialized. And I made the best of the situation I was in…. I have a marketable skill. I just have to find somebody that wants to pay me to build a website.” – Daniel Lemire, on going into consulting after college Small jobs here and there helped Daniel improve as a consultant. Daniel tells the story of moving back home for the summer before his last semester of college. At his father’s medical clinic, the systems manager suddenly quit. This was 2002, and the clinic adopted an electronic medical record system. It was critical that the systems stayed running to handle the patient load. Daniel’s father asked him to fill in until they could find someone to take the role of systems manager full-time. Daniel understood what his father’s business did at a high level, and he chose to take the opportunity, knowing he would learn something from the situation, even if he was only needed for a short time. “I wound up spending nearly the entire summer there, and while I was there, we kept finding things that I could help out with. I could build a database for tracking the number of patients they were caring for. I built a payroll management database where they could keep track of time off and holidays…. I built a whole bunch of systems, actually. It was well more than just doing the networking and the PCs. And of course, there were things that I was out of my depth at. But you make those mistakes, and you learn. And in an operational environment having the wherewithal to just fight through and not give up on the problem and stay late until you get it working was really the key to the success in doing that…. I carried that into the consulting business…. That had convinced me…that I do know enough about this and that I can do the things that need to be done. Now, I just need to find the right people to do it for.” – Daniel Lemire 28:41 – The System Builder Was Daniel finding the problems in that environment that he could solve and providing the solutions because he decided to go have conversations with people about what they were doing, or was it based on ideas he got by being put into the environment? Daniel says it was a combination of both. For example, he could see a process and the amount of labor it took to complete the process like working with patient records. Daniel cites some early daily conversations with one of the head nurses about the work she was doing. Daniel could see the head nurse was reinventing a solution for the work she needed to do each day. He knew it was a repeatable process that could be turned into a database system that would make the nurse’s job easier. “I wasn’t afraid of that because I had done enough in the college courses to know that I could do it and that it was going to be a functional system that would add value.” – Daniel Lemire, on building a database system for one of the head nurses at a medical clinic The head nurse began to tell other people in the office about what Daniel had built for her. The accountant / payroll specialist asked Daniel if he could build her a system to track nurses and their time off. Daniel says this was much more technically involved than what he did with the head nurse. The accountant knew what she wanted and knew enough about how the system should function so that Daniel could ask deeper questions to capture the requirements and how data should be tabulated and calculated. “Reflecting back on that journey, one of the things that I have a much better appreciation for in my late career is that idea of getting quick success on something that’s going to get you momentum in the right direction.” – Daniel Lemire We can often get into something that is too much of a challenge or something so valuable that we won’t do it unless someone pays a high price for it. To Nick, this sounds like perfectionism. Doing great work without thinking about how to make it perfect seems like a dichotomy on the surface. “But the truth is, no one ever does anything perfect the first time, so the art of perfection isn’t about how you get it right the first time. It’s about how you keep at it until it’s good, and I understand that now in ways that I couldn’t comprehend back then.” – Daniel Lemire 33:12 – Thoughts on Product Management John says Daniel’s colleague in payroll sounds a lot like what we might call a product manager today. Product managers guide the product vision, help establish a minimum viable product to release and then foster feature enhancements and their priority over time. The idea of a minimum viable product and adding features over time is to get feedback along the way instead of building something huge and fully featured without any feedback until its release. Daniel tells us about being a Windows guy from the beginning. When his wife had to use a Mac for graphics, he didn’t understand why someone would want a more expensive computer with less flexibility (i.e. computer games). The growth of computing has a ton of lore behind it. We can’t really think about the PC without thinking about Bill Gates and the work he did. Daniel mentions what Bill Gates did with the acquisition of DOS. Gates developed a reputation early on for developing applications (Windows, Office) that worked well enough to do a job despite not being particularly well engineered. Daniel says Microsoft was likely as successful as it has been from the willingness to put products out there to create value, even if the products were not perfect. “I want to call out to all of my friends in technology not to underestimate how important that value proposition is for everything that you do. We get so caught up in the technical that we don’t think about that. That’s why that role I think has become so essential…. We know what we want sometimes, and we’re just frustrated if we can’t get it…. You need somebody that can sit between those two positions and sort of negotiate between multiple different parties…. And that’s what they master – that balance between being the best and getting something done.” – Daniel Lemire, on the role of the product manager A product manager consistently calibrates between being technically great and getting something completed. This takes into consideration the needs of developers and the demands of a business end user. Daniel feels the product manager’s role is becoming more important and not less when it comes to nascent technologies. Nick thinks a product manager is a personification of the inner struggle with perfectionism. Daniel says sometimes the product manager acts as a tiebreaker when there is gridlock between 2 sides so action can be taken. “I think that’s the key. Whatever it is, be taking action.” – Daniel Lemire 37:47 – Getting an Advanced Degree Daniel had some success with consulting and making money. He built a content management system before WordPress was a thing and expanded it into tracking customers and contacts. Daniel is still very proud of this work. In a lot of ways Daniel is a contemporary of the ServiceNow founders, but the ServiceNow founders were way better at product market fit. “Sometimes it’s not how technically talented you are. It is finding the right people to work with that makes the big difference…. When I found a customer that would let me really geek out and build them a big system, we both won…. That’s what I wanted to do. I just wanted to build great systems. I didn’t want to be a sales guy. I didn’t want to be a marketing guy. That was not something that I was prepared for or had a desire to do, and I also recognized that I just wasn’t any good at it. Sometimes you have to cut your losses and go with the things that excite you.” – Daniel Lemire Daniel learned about moving toward interesting things during his high school experience (i.e. how he got into computers). Once Daniel got a job doing work for a client, he would get so into it that he would stop doing marketing and sales. After finishing a job is when Daniel would start thinking about his next consulting engagement. He might spend a month or more trying to figure out how to land the next customer. At this point, Daniel started talking with other people about his path forward from the current state of consulting. “I wasn’t finding great success at doing the consulting thing, and I knew I had the aptitude to really create value. I just wasn’t…in the right place.” – Daniel Lemire Daniel recalls someone older (probably from church) asking what he was doing to allow himself to grow while he was in this “middle space.” Daniel thought about the question and said he would like to get an advanced degree at some point, but he knew that would be expensive and really needed to make money to support him and his wife (who had just enough to make ends meet at the time). “If you’re thinking about an advanced degree, your life is never going to be less busy because you’re going to add all of these things that you want to do. You’re going to have kids. You’re going to have a career. You’re going to be doing things with your family and your church and your community. If you feel like you have time to take something else on…just go get that advanced degree now while you have the time.” – Daniel Lemire, on advice he was given Daniel started to look into the advanced degree and learned a program at UNT would let him double dip from undergraduate coursework and reduce the number of hours for a master’s degree significantly. Daniel was able to complete the degree slowly over about 3 years, feeling it was a much better use of his time. “It gave me a much better appreciation of how businesses worked. The challenge was I didn’t have the context of experience to put with it.” – Daniel Lemire Mentioned in the Outro There is an element of humility involved when we realize we cannot solve a problem by ourselves. Daniel said a prayer to ask for wisdom after his plan to go into the Air Force wasn’t going to happen. He was also open to receiving feedback from other people who had ideas about what he should do. Part of the humble attitude we need to have is this openness to accepting suggestions. In Daniel’s case, it made sense to act on the suggestions. It may not mean that in your case, but be open to the feedback so you can process it before making a decision. The idea of taking a step forward even if you need to reverse it later sounds like a way to fight against perfectionism. We talked about product maangers doing this. It’s persistence without perfection. Listen to complimentary advice on perfectionism from the following episodes: Kellyn Gorman spoke to us about – accepting work that is good enough and calibrating the quality of our work based on time constraints in Episode 320 – Becoming DBA Kevlar: Roadblocks, Perfectionism, and Technical Orienteering with Kellyn Gorman (1/3). We did a 4-part series to review Finish by Jon Acuff full of strategies for fighting against perfectionism: Episode 272 – Book Discussion: Finish, Part 1 – The Day after Perfect and Cut Your Goal in Half Episode 273 – Book Discussion: Finish, Part 2 – Deliberate Time Investments and Avoiding Distractions Episode 274 – Book Discussion: Finish, Part 3 – Get Rid of Your Secret Rules and Use Data to Celebrate Your Imperfect Progress Episode 275 – Book Discussion: Finish, Part 4 – The Day before Done and Perfectionism’s Final Roadblocks Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YoutTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.

Why do you think women leave careers in technology? Sometimes they are bullied, but sometimes it’s the loneliness. This week in episode 322, Kellyn Gorman shares the story of what moved her to start Women in Tech programs in the technical community, the lessons she learned from the Microsoft community, and what it was like returning to the Oracle community after an absence. You’ll hear about diversity, equity, and inclusion programs and some of the benefits and drawbacks they can create based on the experience of Kellyn and her husband. Even advocates and community warriors need support from others and time to recharge. Kellyn shares how she is able to achieve both to continue supporting the community she loves. Listen closely to learn how can you foster a more inclusive community for women in tech. Original Recording Date: 02-21-2025 Kellyn Gorman is a database professional who has worked in the technology space for 25 years better known as DBAKevlar. If you missed parts 1 and 2 of our discussion with Kellyn, check out Episode 320 and Episode 321. Topics – A Lonely Place in Tech, Returning to the Oracle Community, Encouraging the Contributions of Women in Tech, The Backlash of DEI, Being the Messenger and Getting Support 3:31 – A Lonely Place in Tech Did Kellyn’s initial struggles with public speaking and the challenges recalling her presentation topics have something to do with a lack of women attendees at the events, or was it just due to the large social setting in general? “Being a woman in tech, especially a data infra specialist like I am…I’m not on the analytics side. I’m very large database. It’s a very lonely place.” – Kellyn Gorman In 2011, someone Kellyn hired a woman she had previously worked with to come work with her again. “I didn’t realize. We communicated differently between each other, and we had a great interaction. It was so nice to have someone else there that I could go to lunch with, that I didn’t have to worry about…. It sounds sad. I don’t want that. I want to feel the same way about guys that I work with. I love the guys. But it was different…. She was pretty much bullied out of the job, and I was angry…. This is the last woman that leaves. I had looked into the history and of the 8 women I worked with in my career, at that point 5 of them had left tech. I scheduled lunches with them, sat down and talked with them, and found out they had all left for all the same reasons when you got down to it. They had all left because of the sheer loneliness, the isolation, the lack of collaboration…and sometimes bullying. And it was just really sad. And I didn’t realize that I was often bullied, that I was often isolated and everything else. And I said, ‘we’ve got to fix this.’ So, I started doing Women in Tech programs within the Oracle community.” – Kellyn Gorman Kellyn started the Women in Tech organizations for Kscope (an Oracle Developer and Technology conference) in Europe many years ago. By the time Kellyn left, the women attending RMOUG went up to 22% from the former 7% because of these programs, and there were more women getting into the Oracle ACE program. Kellyn would bring in different sponsors to promote women in tech. She would also get allies and other Oracle ACEs to personally promote specific women in the community and people of color. “I took this stuff on head on. They’d come back and go, ‘she’s not technical.’ The women I’m talking about is now the lead speaker for AI in Oracle…. Absolutely took no prisoners. Did I get shot as the messenger? A lot! Worth it…I am Kevlar. I will be bulletproof as long as I can.” – Kellyn Gorman, on moving a community forward Kellyn says the Oracle community has grown a lot. Listen to the way she describes how it once was when it came to treatment of women in tech. “Now they’re more likely to be allies…. That means they’re growing too, and that’s what we want. It always has to be based on education, not on persecution…and we focus on that. And I learned that very much from the Microsoft community. The Microsoft community is much farther ahead than the Oracle community on those situations. They police their own. When somebody gets out of hand, the guys are right there behind the women going, ‘no, you will not do this. This is not good.’ They expect that equality, that inclusivity, and I think that’s really essential that you see that growth. As long as there’s growth, as long as you’re moving forward, that is extremely important. That’s kind of where I take this.” – Kellyn Gorman 7:53 – Returning to the Oracle Community Kellyn has returned to the Oracle community after having to walk away from it for a little while. She is working to breathe some of the energy into it gained from being part of the Microsoft community but doesn’t feel she is quite there yet. “Well, I don’t know if I’m there yet…. For women in tech, we call it the death by 1000 pin pricks. It may be death by 1000 cuts, death by 1000 small bullet dings. I am the messenger that got shot a lot…. At a certain point I stepped away from the Oracle community and was like, ‘this is not healthy. You’re taking too many hits for too many people. You need to go where you’re safe and loved. I am very safe and very loved in the Microsoft community. So, I did that…and it really was helpful.” – Kellyn Gorman On the Microsoft side, Kellyn knew who paved the way for women in tech and understood the challenges involved. Kellyn shares the story of returning to Oracle Cloud World after a long absence. She had not been there since 2019. “…People coming up to me and giving me hugs and saying, ‘I couldn’t be where I am without you….’ I thought that no one remembered. I thought that no one cared.” – Kellyn Gorman, on returning to Oracle Cloud World John mentions that he loves being judged by the people he helps. Kellyn says it was lovely to know people cared about the efforts she had made during her earlier time in the Oracle community. It was an emotional moment. Shortly after the conference, Kellyn was approached about speaking at the Oracle Data and Analytics Conference and Kscope. She has been confirmed as the keynote speaker for BOTH events! Kellyn had submitted talks to both conferences, and they were moved up to keynotes. “‘We feel that you kind of got a raw deal with Oracle, and we want to fix that.’ Those kind of approaches…you didn’t even realize people noticed the hits you were taking, you know? So that definitely has been really nice. Not only am I coming back into the Oracle community, but I’m coming back in a way that I’ve got keynotes. I have articles that are being published in a number of top magazines. I am able to contribute in a way that is very powerful…. I had this conversation the other day that they were having problems with the haters, and I said, ‘don’t ever even pull yourself down into that level. Always work up. Always stay up. Don’t ever let them pull you down.’ This allows me to go back into the Oracle community and not be pulled down by anybody, to be able to do the best that I can do and focus on that…because I was anxious about coming into the Oracle community again, anxious about the challenges and those feelings….” – Kellyn Gorman Previous experiences in the Oracle community made Kellyn worry about getting into uncomfortable situations at events. A lot of events for the Oracle community may not have codes conduct or may be serving unlimited alcohol. This type of atmosphere lends itself to uncomfortable situations for women. “In the Microsoft community, there are very strict code of conducts. There are very high expectations, and there are people looking out for each other. That makes a huge difference. That takes a huge weight off of people when you’re there as a woman in tech, and I would love to see that at all communities. I don’t think people understand how important that is. We’re there to learn.” – Kellyn Gorman John mentions it is disappointing to hear about events with no code of conduct. Kellyn mentions how proud she is of the Kscope event organizers. When she expressed the importance of a code of conduct, organizers immediately implemented it as part of the conference. “We joke about it, but nobody wants the red card…that says you violated the code of conduct. DO not get a red card!” – Kellyn Gorman Nick says we’re highlighting important considerations when joining a technical community. This can be approached similar to the way Kellyn looked for new jobs – approaching people on the inside to gain perspective. Get perspectives on women in tech from people in that community, ask about codes of conduct for events, etc. Kellyn is also part of DevOps communities, which we didn’t get a chance to discuss. Kellyn tells us she is just now getting involved with the Postgres Conference. Many people she knows from the Oracle and Microsoft communities are attending. Kellyn shares the message she had printed on some stickers as a reminder to others in the community. “Assume that she is technical and capable of breathing fire. This is a saying that’s gone around the Microsoft community for a very long time. But I think we almost need little pins that say that just to keep us safe. It’s really important…. If I walk into a conference and I’m here to interact with my technical community and talk to people about tech and the only questions I receive are ‘how is your husband? Are you still living on the floating home? How are your kids?’ If I just get that over and over and over again, I wonder why I attended an event. This is with me speaking this has happened. So, I know it’s happening to other women, especially women that may be younger than me.” – Kellyn Gorman Kellyn has given the keynote at an event being only 1 of 3 women at the entire event. She later attended a Girl Develop It event that had all women and only 1 man in attendance. “It’s really interesting how the events are changed and how the interactions are and everything when you change up how inclusive or how different the attendance is for the people that are there.” – Kellyn Gorman, speaking of her experience at different community events 15:25 – Encouraging the Contributions of Women in Tech This change up in inclusivity comes from leaders and board members of the community in question. Should someone consider speaking with those people before they join a community? Even for local events, the board members for specific communities / user groups will often say they wanted more women speakers, but even those women who could have given a talk didn’t submit anything. Kellyn shares a story of approaching different women to be co-authors on an Oracle Enterprise Manager book. “I approached a couple different women that I really wanted on the book that really knew their stuff. And they were like, ‘well, let me think on it.’ And then they kept coming back, and they were like, ‘well, I want to make sure that I can do this.’ They wanted to make sure they were 110% sure they could do it; they wanted to make sure they had everything. I had guys who barely knew how to spell Enterprise Manager, and they’re like, ‘I can do it.’ It was insane…. It’s so important for women in tech and anywhere really to stop being so hard on themselves and really jump in. You’ll figure it out later. The women that do that really do as well or better than the guys around them. You gotta stop worrying so much.” – Kellyn Gorman Kellyn feels her brain is wired more like many of the guys who had the attitude expressed above – jump in and figure things out along the way. Most women are not wired this way. They want to know they can contribute, they can succeed, and that they will not let anyone down in the process. Kellyn says people don’t often encourage women not to worry so much. People often second guess women, and women are taught to second-guess themselves from very early on. Take the example of a young boy bothering a young girl and the girl being told he probably likes her and that she misunderstood. Kellyn remembers her daughter coming home describing the same situation. It wasn’t that the little boy liked her daughter. It was bullying. “To break ourselves out of that mold and just say , ‘I’m going to do this, and I’m not going to care what anybody else thinks’ is very hard…. I just learned really early on that most people are full of it and that I shouldn’t listen to them.” – Kellyn Gorman John mentions the behavior of bullying is not an acceptable output regardless of what motivations might be behind it. John likes Kellyn’s call out of differences in personalities such as the hesitance in committing to co-authoring a book due to a feeling of unworthiness. This is similar when men and women apply for jobs. “A lot of times women will look at a list of skills that are being looked for or responsibilities and say…‘I’m missing two out of the fourteen, so I’m not going to apply….’ Some men will go, ‘well, I have two out of those fourteen. I’m probably the top candidate.’” – John White Kellyn is proud of men for confidence but wants more women to have that same level of confidence. She has helped other women negotiate severance packages, job level classifications, and other things. “Women are really good, by the way, at negotiating for other women. They should always bring another woman in because…we will fight to the death for each other…. People say we’re not as good at negotiating for ourselves. We are very good at negotiating for each other, and I do think we just need to talk it through….” – Kellyn Gorman Kellyn says women are told not to be bossy or brazen, and it hurts them in the real world. “But I also think a lot of women…they don’t submit talks because they don’t think anybody wants to hear what they’ve got to say. And a lot of women have a lot to contribute.” – Kellyn Gorman 20:23 – The Backlash of DEI John talks about a book he read by Alison Fragale in which the author speaks to behaviors in the corporate world which are viewed as positive for men but negative for women. While this certainly needs to change, the book covers some ideas for mitigating this in the meantime. Kellyn and her husband have worked together 4 times in total and have a unique working relationship. At Microsoft, Kellyn and her husband worked in the same role and on the same team. They have even served on the same boards together. The two of them have even written e-mails for each other to see what would happen. “…Something that was a little shocking to him was how he could say things, but I couldn’t. There were other times where he would know I was going to do better with some people. There were other times where I would be like, ‘you need Tim. You need to send Tim in. These guys will do better with Tim.’ There was also these challenges of recognizing that DEI made me look a little better than him…. My husband can’t go to his boss and go, ‘I need an ally. I need sponsorship to get my raise.’ I would automatically be given it. There are these challenges, these hard conversations that we have to have….” – Kellyn Gorman Kellyn left companies making more money than her husband was at times because it might have looked better to give raises or equity to a woman. She reminds us it is important to push to have uncomfortable conversations about these types of situations (even if no one wants to have them). Based on what we have discussed so far, is Kellyn discounting herself in this scenario? No. "The truth was I would be negotiating for myself, and then I would have a boss come in going, “women are bad at negotiating for themselves. I need to back Kellyn up.’ I was a win-win every time.” – Kellyn Gorman Kellyn shares the story of when HR at a specific company challenged her salary. “And I hadn’t thought about this beforehand. It just popped out of my head. I said, ‘I feel that if I didn’t stick to my guns, I’d be letting down women in tech everywhere. Best response I could have ever said! Nobody asked about my salary again…. At the same time, my upcoming boss came back and said, ‘Kellyn earned that salary. She should be getting that salary, and no one should be asking her about that salary.’ He was there to be my ally.” – Kellyn Gorman, in response to HR questioning her salary and an example of her boss as an ally Kellyn shares a different scenario related to promotions when her spouse was given a new title at a higher job level but she was not. She had been doing the job for 1.5 years but was not given a promotion despite being promised it. A mentor suggested Kellyn hold her boss accountable for this, and Kellyn told her boss she earned it and needed to see the promotion within a year’s time. She got it, and her boss was an ally. Kellyn and her spouse were then back to a level playing field. Stock awards are a little bit different according to Kellyn. “It happened most of the time with nobody in the room, and it just looked cooler to give it to the girl. That’s when the inequality came out. If you didn’t have those DEI programs though, I think it would have been the opposite way…. That’s my partner down there and my equal, and he’s actually been in tech longer than me. If I had won it one year and then he won it the next, that would have been one thing. But after 5 years that they kept giving it to me… nope. I felt that was unfair.” – Kellyn Gorman, on stock grants John says in the case of stock grants even our advocates may not been in the room when awards are discussed and given. “They’re not small awards. But you recognize the pattern, and again…AuDHD…we see patterns. You saw who was being awarded what and you recognized it was a great achievement of understanding DEI, but there’s also that backlash of DEI. If you don’t have honest conversations with yourself saying, ‘did I award this because DEI looks cool? Or did I award this because I have somebody who deserved this?’ That’s extremely important to still follow through and keep yourself accountable.” – Kellyn Gorman 26:44 – Being the Messenger and Getting Support We heard earlier that Kellyn lost the fear of putting herself into scenarios no one ever wanted. Did she also lose the fear of uncomfortable conversations at some point? Was it a progression like the improvement in her public speaking? Kellyn says this is part of her personality. Her mother used to say, “Kellyn tells me things I don’t want to know.” “Even those in the Microsoft community are aware that I’m brought into difficult conversations. I am the messenger…. I was the messenger in the Oracle community that they didn’t want. In the Microsoft community I’m the one people bring in…. I am the equalizer. It’s weird.” – Kellyn Gorman John points out an element of self-awareness in Kellyn. She knows when she needs to care for herself and cannot be the advocate all the time. “Sometimes the Kevlar needs to be repaired.” – John White Having hard conversations and facing anxiety / fear is a skill. Those people who are surer of themselves and have confidence (like what Kellyn described as being willing to figure things out) are better suited to step into the line of fire and advocate for others. Kellyn says she has received tremendous community support in the role of equalizer / warrior. Kellyn also receives support from her mentees, often becoming close friends with them. Kellyn gets up early On Thursdays to mentor someone in another country, for example. “Those people are also often my roommates at different events. We’re friends as well.” – Kellyn Gorman, on support from her mentees Kellyn remembers forming “pods” with other women in the Oracle community across the country because there were so few of them. They could communicate and share with each other. “This was a bad day. I just need somebody to hear me. Those are important friendships to have. Those are important support structures to have. And I think that’s what women in tech more than anything will have. So, when I say that I need support…I have that. I have a lot of friends. I have a lot of allies. I have a lot of support people. And that gives me strength. I’m also naturally kind of a loaner too.” – Kellyn Gorman When Kellyn is overstimulated by too much noise, she can put on her Apple AirPods to block out all noise. When she needs time to recharge, most people know it. While attending events, Kellyn takes time for self-care. She might need to do that instead of attending an evening event. “I have no guilt about taking care of myself and doing what I need, and when other people need me, I make sure I have those reserves that I can be there. I don’t think there’s ever been a time where I haven’t been able to give of myself what other people need because I am very big about making sure I do the self-care that I need, that I have the reserves that I need, and do step back. I would not have signed on to go back into the Oracle community if I didn’t feel that I was capable of it and it was going to disturb my peace.” – Kellyn Gorman By thinking through situations from someone else’s perspective, Kellyn also has to help her friends set boundaries to care for themselves. “I was taught very on to think with my head, feel with my heart, say what I mean…don’t get any of them confused. Keep them compartmentalized, especially when you’re trying to make decisions…. If you’re angry at somebody there’s a reason you’re angry. Really think it through and figure out why you feel what you feel. I think that’s extremely essential. Don’t get them all meshed up together and say things that really aren’t the reason for that. You have to take some time and figure it out. I’m not one to say something that I don’t mean. It just doesn’t happen with me. I will step back and work through things. I have to. But it has served me well so far.” – Kellyn Gorman Kellyn thinks about what she wants to achieve, what the other person wants to achieve, and how they can move forward together. This strategy has worked very well over the years. Parting thoughts Kellyn says it’s been incredible to fall into a technologist role accidentally. Today, these kinds of opportunities are rare. We have people coming out of school with Data Science degrees who cannot get data analyst roles. Kellyn was doing desktop support, and someone suggested they make her a DBA. She would later work for Oracle and Microsoft. The opportunities Kellyn has received are thanks to support and allyship from others. “Even though I give myself credit for self-care and working hard and doing all these things, there’s been people behind me the entire way. I could not have done it by myself. It absolutely takes a village, and I try to give that to other people. I want other people to have the things that I have had. I think that’s essential for us to continue technology in a path that’s healthy.” – Kellyn Gorman Kellyn wants to make sure we use AI the right way. She sees entry-level technologists and wonders how they will gain the level of experience that she has. Kellyn has to address the University of Washington in support of tech careers, and sometimes she isn’t sure what her approach will be or the recommendations she will make to those looking to get into the field at this moment in time. If you want to follow up on this conversation with Kellyn, check out: Kellyn’s Blog – DBAKevlar Contact Kellyn on LinkedIn Mentioned in the Outro Special thanks to former guest David Klee for recommending we have Kellyn on the show! Nominate a woman in technology that you know needs to have her story told to be a guest on our show by sending us an e-mail – [email protected]. If you nominate someone who is a guest on the show, we will send you Nerd Journey stickers as a thank you for supporting women in technology. Listen to the following recommended episodes for more perspectives from women in tech: Caitlyn Bryan was mistaken for an assistant but was the salesperson supporting a customer Episode 111 – A Career in Technical Sales with Caitlyn Bryan Part 1/2 Kate Emshoff shares the challenges of remote job interviews for women and some tips for the career minded mothers out there. Episode 117 – Bold Moves and Blind Spots with Kate Emshoff (1/2) Episode 118 – The Career-Minded, Curious Mother with Kate Emshoff (2/2) Dr. Sirisha Kuchimanchi talks about STEM careers and how we can encourage young ladies to go into these fields. It has to start early. Episode 245 – Technical Careers and Championing Women in STEM with Dr. Sirisha Kuchimanchi (1/3) Amy Arnold speaks about mentoring other women in network engineering and mentions the Women in Cybersecurity community. Episode 281 – Packets Don’t Lie: Quality of Service for Technical Exploration in Network Engineering with Amy Arnold (1/2) Ashley Connell speaks about the gender imbalances within the Spiceworks community and some of the discomfort it caused. She also talks about supporting women returning to the workforce through her business, The Prowess Project. Episode 96 – Sponsorship, Dreams, and the Path to Entrepreneurship with Ashley Connell Episode 97 – Building Your Own Business From Idea to Operations with Ashley Connell We don’t always know the impact our efforts or the example we set will make on others just as Kellyn learned when she returned to the Oracle community. Tom Hollingsworth had a great quote about burnout happening when you think no one else cares. Check out Episode 127 – Countdown to Burnout with Tom Hollingsworth (3/3). We hope you find a technical community that can support you and all other members. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YoutTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.

How do we determine if a manager is the right fit based on our personality, values, and the way our brain works? Kellyn Gorman diligently investigates a potential manager before taking a job. As someone with autism and ADHD, having a supportive boss is critical to her success. This week in episode 321 we’ll explore how Kellyn got into both the Oracle and Microsoft communities and the reasons she is adamant about developing public proof of work (like blogs and public-facing presentations) that showcases mistakes on the path to learning. Listen closely to follow Kellyn’s transition from Oracle community group participant to leader, from public speaking novice to keynote presenter, and the differences she observed when participating in the Microsoft community. Original Recording Date: 02-21-2025 Kellyn Gorman is a database professional who has worked in the technology space for 25 years better known as DBAKevlar. If you missed part 1 of our discussion with Kellyn, check out Episode 320. Topics – Interviewing and Qualifying Managers, The Importance of Proof of Work, A Tale of Two Technical Communities 3:00 – Interviewing and Qualifying Managers Kellyn had mentioned not wanting to spend time on things which are not valuable, but she has developed a way to determine if sources of information are valuable over the course of her experience. In some cases, she is creating valuable resources that do not yet exist for the benefit of others. Kellyn has also learned how to determine if a manager will be valuable to her and fit in with the way she likes to work. How can listeners ask the right questions to determine if a manager is the right fit for the way they like to work? Kellyn says often times when we interview, getting the job is the main focus, which is understandable. If it is not the right job, it can put you in a very bad situation. With Kellyn being AuDHD, having a good boss is essential for her to be successful. Many times, when Kellyn is being interviewed, the people who are interviewing her have read her blogs, the books she has written, or have seen her speak. “They know me. It’s very normal for them to go, ‘I don’t have to give you a technical interview. I already know what you know.’ Ok, well then I get to ask questions.” – Kellyn Gorman In a job interview situation, Kellyn likes to ask questions about how a manager assigns work and the regularity of updates they need (i.e. regular check-ins vs. clear communication of the deadline and nothing more). She does not work well with micromanagers and needs autonomy and trust from her manager. “Go ahead and run the race. I don’t need to know how. That’s important to me. I am a professional. I am going to do the best job and really take care of that company and be extremely loyal. I need them to trust me to do that.” – Kellyn Gorman When Kellyn worked for Microsoft, a mentor encouraged her to take the Clifton Assessment, and it has been extremely valuable. Kellyn says one’s assessment can change over time and will re-take it now and then. The assessment tells someone what you will be like as an employee (skillset, potential, weaknesses). Kellyn likes to give the assessment results to her boss as “an employee manual.” Not all of them, however, take the time to read it. “The ones that read through that…I know I’ve got a good chance of having a good boss. If they just throw it aside…they don’t even take the time to read it…may have problems. They’re not even curious enough about me to read that assessment. And it’s not a long one. The top-level assessment is like 5 pages.” – Kellyn Gorman Kellyn’s Clifton Assessment says she is a strategic thinker, a go getter, and that she does not need a lot of management. People can tell her what they need, and she can figure it out from there. Kellyn is looking for a manager who is flexible and trusts her to go and do her job. They need to understand the deep expertise she brings to the table (Oracle expertise, for example). Kellyn wants to make sure a manager understands the challenges of being in an older technology space but operating across a broad set of communities. “I have what’s called…a Lego brain. If you want to know how your technology fits into every other technology, I can tell you. You want to build out a solution and market it to any different provider no matter if it’s Google or Microsoft? I can architect it for you…. That’s all I do for one company right now. I build them solutions. I architect them, and they take them and market them. And it’s awesome, but I needed a boss that understood that…. I need Kellyn’s Lego brain for this.” – Kellyn Gorman A good manager for Kellyn won’t try to control or stifle her talents but will enable her to leverage them to build the solutions she delivers to the company. How does Kellyn prioritize what to address about the way she likes to work during the interview process and what is ok to save for after she gets hired? Kellyn addresses a lot during the interview process, and she interviews for long periods of time. Kellyn spoke to her current manager for a period of 4 months before she was hired. It was a similar time period when she went to work for both Microsoft and Silk. Speaking with other individuals inside a company who can answer specific questions is very important to Kellyn as part of the overall process of seeking a new job. Our contacts are extremely important. Kellyn tells the story of taking a role at Oracle and making good decisions with the help received from Mary Melgaard in navigating the job offer process. When Kellyn went to Microsoft, she contacted Bruno Borges for help. When seeking a job with Silk, it was Tom O’Neal and Chris Buckle who helped Kellyn navigate the process. Upon coming to Redgate, Kellyn had help from Louise Domeisen. “I want to feel secure. I need that secure feeling that I’m making strong choices and understanding.” – Kellyn Gorman Kellyn has also negotiated other opportunities outside her job responsibilities with potential managers. That negotiation process / those types of conversations can give you insight into what someone will be like as a manager. 11:18 – The Importance of Proof of Work John highlights Kellyn’s emphasis on having proof of work that people can learn from and even discover her by as well as a strong professional network. Kellyn advises every mentee she has to blog and do public speaking. “I am out there. People already know what I know, and it’s a way for people to comprehend and to get a jump in. I have not had to go look for a job in over a decade. We’re talking a good 15 years. People have come to find me and said, ‘we want you….’ It’s really important to be out there. Be present. Just be the best that you can be and show what you can do…. People will come find you, and they will offer you jobs.” – Kellyn Gorman Kellyn’s job at Redgate as an Oracle Advocate began with an ask that she work for them as an engineer 10 hours per week. The Redgate advocacy team would later decide they wanted Kellyn to join them but initially did not realize she was already working for Redgate part time. They offered her the Oracle Advocate role without needing to interview for it. When Kellyn went to join Silk, she had reached out to Silk and 2 other companies stating her readiness to leave Microsoft and requested they create a role for her. Silk provided exactly what she asked for (a role that would put her skills to work). Kellyn also tells the story of someone asking her to take their role at Delphix. John references themes of learning in public and documenting your thought process (as a beginner or otherwise). We have discussed these with previous guests, aligning with advice from the book Show Your Work by Austin Kleon. Documenting our successes and failures makes our writing more approachable to those who are beginners or less knowledgeable in an area. John asks Kellyn to contrast how this strategy can help those who are entry level or early career in a specific area compared to those who may be more experienced or subject matter experts. Kellyn has been blogging on DBAKevlar since 2008 and regularly models documenting her mistakes for people to see. Kellyn calls out one mistake she documented related to an Oracle upgrade. Publishing our mistakes showcases our humanity to others. We make mistakes just like everyone one else. Kellyn uses the example of her son thinking she was perfect and helping him understand she makes plenty of mistakes. Kellyn used to see posts from people in the industry detailing the incredible things they were doing. As a result, she thought those people never made mistakes. Kellyn stresses the importance of showing when we mess up and how we cover from it. Kellyn’s husband was her first mentor and worked with her when she was a junior DBA (database administrator). Kellyn’s husband shared a story with her about a mistake he made related to removing a large database index. Her husband’s boss didn’t get upset but rather was focused on moving forward after the mistake. “And that was it…. It happened. Let’s take care of it. And when you hear that from somebody as prolific as my husband was in my view at that time, you start to understand it’s important to share those mistakes. It’s important to talk about your journey.” – Kellyn Gorman If you read Kellyn’s blog, she started off as a DBA learning things the hard way. While Kellyn was documenting things for herself, she also thought others might find her writings interesting if they were published in a blog. From there, Kellyn continued to grow and do more. “This is my path in tech. This is what I’m doing. If you find it interesting, go ahead and read it. If you don’t, I’m alright with that too. It’s alright. I may need this next week when I forget what I did in 10g, so we’re good.” – Kellyn Gorman, on blogging John says Kellyn is demonstrating that she does good work while documenting the outcome as well as the process. Part of Kellyn’s personality is a desire to make others better and to help the community. Kellyn says this is part of the reason she adores the Microsoft community. “I ended up blogging a lot more on the tech community for Microsoft than I did on DBA Kevlar for…recent years.” – Kellyn Gorman, on how her blogging changed after she went to Microsoft Kellyn had been blogging weekly on her own site for years but wasn’t able to keep up the same pace after joining Microsoft. After Kellyn left Microsoft, she added the content to DBA Kevlar so it would be retained. Kellyn emphasizes the importance of keeping track of the public-facing content we’ve created over time so people know it exists. In mentoring conversations with others about blogging or speaking, what does Kellyn think is the biggest hurdle people have to overcome to actually start? “They think they don’t have anything important to say, and I will remind them that some of my most popular blogs are things that I thought was stupid. Nobody’s going to read this. Nobody’s going to think it’s good. And those are the most popular blogs. I…documented using a Windows Oracle Enterprise Manager and monitoring HP UX targets. I thought, ‘nobody is going to read this. This is only there for me because I’m going to have to support this customer long term….’ That thing gets hit constantly, every single day…. It’s not the things you think will be popular. It’s not the things that everybody else is doing. It’s the stuff that nobody else knows. So just start writing and see what happens. Don’t overthink it.” – Kellyn Gorman, on blogging Kellyn documented building a VM image of a Raspberry Pi to use for STEM classes. People loved it and were downloading it for STEM education. John says we don’t know the purpose for which others will use our problem solving. If we document something for public consumption, people will use it in ways we just can’t know. Kellyn says as people in your community retire, they may take down their blogs. It’s a consideration point. She has some of the only deep command line interface content for Oracle Enterprise Manager, for example, and is committed to preserving it for others. “I can’t ever take that down because if I do, it’s gone. It’s gone forever.” – Kellyn Gorman, on technical knowledge that can be lost when subject matter experts / community contributors 21:11 – A Tale of Two Technical Communities Kellyn does public speaking, has written blogs and books, and has been part of technical communities. What was the order in which Kellyn started doing these things? What came first? Kellyn had attended RMOUG (Rocky Mountain Oracle Users Group). It was the largest regional user group in the country and was closed to where Kellyn lived. “I wanted to start speaking, and the reason that I wanted to start public speaking was I found that my ADHD made it very difficult for me when I was in a public space. People would ask me questions, and I absolutely had the answers. But I would lose access to my brain, and I wouldn’t be able to come up with it at that moment…. Even if I knew the information, it wasn’t accessible for me…. I remember my first talk when I went to RMOUG. I went and did the talk, and I was going to do it on temporary table spaces with parallel processing…. The door closed, and my talk went out the door with it…just was gone…. It was horrible. It was the worst talk ever, but it got better. Again…didn’t give up…be persistent…continue to talk. And now I can talk on anything. I’ve got it down.” – Kellyn Gorman Kellyn would encourage people with questions to talk to her 1-1 at a later time to hide the fact that it was very difficult to come up with answers in the moment. In that first presentation for RMOUG, Kellyn spoke for about 35 minutes trying to go through her slides, but it was a struggle. Kellyn is doing a number of keynote presentations as the Oracle Analytics and Data Summit 2025, Kscope, Scenic City Summit, and SQL Saturday Oregon. Kellyn loves doing keynote presentations on topics that interest her, but it took her beginning the public speaking journey in 2011 to get where she is now in 2025 (14 years). Kellyn went from attending the Rocky Mountain Oracle User Group (RMOUG) to speaking at events. At one point she approached the board members of RMOUG and expressed her interest in volunteering to give back to the community. Other board members of RMOUG immediately suggested Kellyn run for a term as board member, and she did. Once Kellyn was a member of the RMOUG board, she started running the RMOUG Training Days conference. At the time, there were around 1000 attendees. Kellyn recently attended RMOUG Training Days and reports there were only 80 attendees. “It’s heartbreaking to see where the Oracle community is now. Because of so much content that is out there, it’s hard to get people to go in person to events like this. There’s cloud events. There’s everything. It’s very challenging.” – Kellyn Gorman In 2011 Kellyn was made an Oracle ACE. This is a community recognized award. One year later, Kellyn was named an Oracle ACE Director (the highest award from Oracle). In 2014 Kellyn won Women of Tech of the Year for the state of Colorado. Also in 2014, Kellyn and her future husband Tim Gorman were doing keynotes across the world. Being a part of the same community ended up eventually bringing the two of them together. Kellyn stayed in the Oracle community through 2018 / 2019. In 2012, Kellyn attended her first SQL Saturday, which is focused on Microsoft technologies. Kellyn immediately wanted to know how this community was able to get so many women attendees (40% were women at SQL Saturday compared to 7% at Oracle community events). A couple of the speakers at the SQL Saturday event explained the DEI (Diversity, Equity, and Inclusion) and Women in Tech initiatives that Microsoft had. “It made total sense to me. It was what I was trying to bring over to the Oracle side. They just weren’t ready. They just weren’t ready on the Oracle side. And I was just utterly amazed. So, I started going to SQL Saturdays.” – Kellyn Gorman, on discovering the Microsoft community Kellyn worked with SQL Server technologies and had built some expertise in that area. In 2016, Kellyn attended her first PASS Data Community Summit. “I just loved the energy. I loved the inclusivity…everything that they were doing. I just was so impressed…. This is the way user communities are supposed to be. It’s all about you do you and I’m alright with what you do. It was just incredible. That was pretty much my love affair starting with the Microsoft community….” – Kellyn Gorman, on her love for the Microsoft community Mentioned in the Outro Special thanks to former guest David Klee for recommending we have Kellyn on the show! Nick had not heard of the Clifton Assessment before speaking to Kellyn. It’s a great idea to do something like this to help identify strengths that perhaps others do not point out to you. Knowing our strengths can be leveraged when we interview for jobs (part of the career narrative we need to tell in interviews). Kellyn asked people inside the companies she was targeting for her next role for help during the job seeking and interview process. She found a harbor pilot just like we discussed in Episode 317 – Own Your Job Search: Be the Captain, Find a Harbor Pilot. Kellyn’s attitude toward blogging is much like that of Duncan Epping as discussed in Episode 304 – Next Level: Shifting Specialties and Broadening Your Outcome Goal with Duncan Epping (2/2). The purpose is documenting a learning journey that showcases mistakes. It’s ok to be part of multiple technical communities. It doesn’t have to be just one! Kellyn has been part of the Oracle and the Microsoft communities. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YoutTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.

What if your strategy at work was to take on the problems no one else will? For Kellyn Gorman, this is a strategy that suits the way she works and learns best. Kellyn is a multi-platform database professional with 25 years of experience in our industry, and she’s also known as DBAKevlar. This week in episode 320 you’ll hear what it was like to grow up in a perfectionist home as a child with autism and ADHD, the health challenge that forced Kellyn to start over professionally after losing 9 years of memories, and how she went from working at a shoe store to becoming a database administrator. We talk through ways to mitigate perfectionist tendencies by accepting work quality that’s good enough, being kind to yourself, and time calibration. Original Recording Date: 02-21-2025 Topics – Meet Kellyn Gorman, A Perfectionist Environment, Hitting a Roadblock, Pursuing Unexplored Areas to Remove Barriers, Reaching Good Enough by Tuning for Time, Strengths and Weaknesses in Neurodiversity, No Fear in Asking for Help or Giving Help to Others 2:17 – Meet Kellyn Gorman Kellyn Gorman is a database professional who has worked in the technology space for 25 years. Kellyn’s focus has been heavily on Oracle, but she also has experience with SQL Server, MySQL, Sybase, PostgreSQL, and much more. To sum it up, Kellyn excels in multi-platform database administration. Should we have written our questions for this episode as database queries? 3:25 – A Perfectionist Environment Kellyn is the oldest of 3 children and has perfectionist parents. Kellyn is autistic and has ADHD. This is often called AuDHD. See Kellyn’s blog post on the strengths of ADHD/AuDHD. Listen to some of the challenges from Kellyn’s childhood. “So, this perfectionism was always placed upon me to do so much more because I was an intelligent child. But you would get me into most school environments that have a lot of structure…and my brain was like 25 McDonald’s drive-throughs all taking orders at the same time…. And that can perpetuate this idea that you are really failure instead of innovative and kind of doing things very differently than what is that structured expectation of what is fitting inside the box. I did not fit inside the box.” – Kellyn Gorman Kellyn started to get the feeling of not living up to expectations. Kellyn speaks to having an extreme awareness and being able to recognize patterns. She saw the need to structure her own box, which made a huge difference in what being a perfectionist meant. At around age 15, Kellyn told her parents she planned to move far away (and she eventually did to escape what was expected of her). Kellyn’s mother had specific plans and ideas for what success looked like for Kellyn as well as her younger sister. “You comprehend that idea of what your parents may have and their ideas for you and what they think is successful is very different than what you might have decided. By the time I hit about 21 / 22, I was on my own idea and learning how to be good to myself, learning how to do things differently.” – Kellyn Gorman, on the mismatch between her parents’ definition of success and her own definition of it 7:32 – Hitting a Roadblock “I ended up coming to I guess you’d say a complete roadblock in life because that perfectionism was constantly weighing on me even though I was very aware that it wasn’t the right thing for me. I ended up having a medical crisis where I ended up having 5 strokes between 21 and 26. I had to re-learn how to do everything…. I lost nine years of memories. I lost 50% of my visual field. I had to re-learn how to balance a checkbook, how to drive…it was huge.” – Kellyn Gorman Kellyn mentioned she was lucky to have so many others around her for support during this time. Circuit City opened up in Kellyn’s town, and they were looking for people to work in the computer department. Two of the guys working with Kellyn at a shoe store suggested Circuit City hire her. They had nicknamed Kellyn “Kevlar” because they thought she was bullet proof. At the time Circuit City hired her, Kellyn had never worked on a computer (zero experience). She still had a small speech impediment from her strokes then but performed well even on her first day in the role. “And that was my journey into tech. They found out I had a knack for software. I had learned how to fix computers. As my brain healed, this was all coming about.” – Kellyn Gorman Kellyn’s husband was doing desktop support at the time and suggested she give it a try as a next step and kept progressing from there. “What you find out is that a lot of people talk about what they’re going to do. Not many people do…. I remember working in the shoe store and not being able to arrange shoes in size order…. It took me 3 days to do that when I first started. When you come from that place, everything else seems easier. You’re not so overcome by the idea of perfectionism…. It’s just it’s a new challenge and you’re going to take it on, and you’re not scared…you just do. And so, I would take on the things that nobody else would touch.” – Kellyn Gorman Kellyn worked with 14 other people (all men), all of which wanted nothing to do with database software like Sybase or Oracle. Kellyn figured out how to do it. Kellyn tells the story of people from Oracle wanting to know how she was running more than one 16-bit Oracle application on a Windows 95 computer. Those folks later told the company CIO that he needed to make Kellyn a DBA (database administrator) and encouraged sending her to certification training. Kellyn’s first official DBA role was at Duke Energy. She inherited a massive SQL Server cluster that no one else wanted to touch and had no experience working with it at the time. Kellyn had to learn about it without Microsoft’s help, but she figured it out. “So, I just kept doing that wherever I went because I found that people remembered your successes. They didn’t remember your failures…. The whole idea that you were Kevlar or you were bullet proof or that you were perfect had more to do with that you were doing and just did one more time past the failure…fall down 7 times, get up 8 kind of thing…. You could fail all you want as long as you were trying.” – Kellyn Gorman 12:04 – Pursuing Unexplored Areas to Remove Barriers Did Kellyn’s learning process as she recovered become something she learned to apply to anything? Kellyn thinks yes and says she was no longer afraid. What we see on television about amnesia is not like what it really is. Kellyn remembers her brain “unfogging” around 5 months after her last stroke. Doctors realized after extensive testing she was missing 9 years of memories. All of Kellyn’s adult memories, including her college education, were gone. She could not perform her duties as an accountant and needed to start completely over. “My mindset was this is where we’re at. Wipe off the dirt. Pick yourself up. Start moving…. I just stopped being afraid of falling on my face because I was already down there.” – Kellyn Gorman Kellyn has never been afraid of making progress in a new area little by little as a result of everything that happened. She’s never been afraid of taking on difficult tasks (which might be an ADHD thing). “I think that I figured out what was the trick of me getting from the starting line to the finish line and continued to kind of build on that and doing that every time when I was going somewhere and perfecting it…. It’s served me very well.” – Kellyn Gorman This reminds John of a pattern he’s seen in his own life and in the lives of others called Smart Kid Syndrome. When people start to say you’re talented in certain areas, one might get focused on being perceived as being really good at certain things and shy away from things that are difficult or that are new. Because of Kellyn’s situation and the loss of memories, she didn’t have any choice but to take a beginner’s mindset and a growth mindset. “You don’t miss what you don’t remember…. And it may be a little bit ADHD again in me that they joke about out of sight, out of mind with us. For me, it’s very much like that. I don’t remember those 9 years, so I don’t really miss them.” – Kellyn Gorman Kellyn says she has some memories of memories and reinforces that amnesia is not the way it is portrayed on television. Listen to her describe what it was like. Part of what motivated Kellyn to pursue the areas others didn’t want to touch was that it allowed her to learn things in her own way without any barriers. Kellyn sees herself doing this even today for 2 reasons: When other people know a great deal already, Kellyn doesn’t feel she can contribute as much. In these areas, Kellyn can learn at her own pace and do things the way she wants to do them without being bothered. Through experience, Kellyn knows the ways of working that suit her best. She doesn’t do well being micromanaged, for example. “…I know that I’ll be able to be my best me there, that I’ll be able to do things, and no one will be interested in any part of it…not until I’ve turned it into something really, really big and special. Then everybody gravitates to it.” – Kellyn Gorman Kellyn is also preparing herself to do something / build something special and then lose it. She cites this as the biggest hurdle for which she has to prepare. Nick thinks focusing on the doing and the areas that other people aren’t interested in or don’t care about removes the shame of messing up. Kellyn says the hard things come easy to her. It’s the silly details she ends up missing. Kellyn tells the story of a conversation with her son when he was a teenager. He said something about Kellyn being perfect and never messing up. “I always mess up. I don’t give up.” – Kellyn Gorman, speaking to her son Kellyn realized her kids only saw the end product, and most people see her that way too. “I didn’t realize that what people see, even though I talk about the stupid things I’ve done and talk about the challenges that I’ve had, nobody seems to remember that. All they seem to remember is ‘you wrote all these books and you’re doing this, and you designed these systems, and you did Oracle on Azure….’ I don’t think we see ourselves like other people see us. I think we’re much harder on ourselves.” – Kellyn Gorman John says people see the output and don’t see the process, which may be a cognitive bias in humans. We can’t always control the output or the outcome but often want to judge based on these. We can control the process. Maybe when we say we’re trying to control perfectionism what we’re really talking about is an obsession with progress and not giving up. Kelly says it’s also about being satisfied with your output. She recalls walking away from situations that didn’t go as planned but knew she tried her best. In these situations, Kellyn is kind to herself. “If I didn’t do the best that I could have, that’s probably when I’m going to be more persistent and say, ‘you need to try again.’ But there have been situations where I’ve done that, where I’ve just said, ‘you did the best that you could. The output isn’t what you hoped, and you’re going to have to let this one go….’” – Kellyn Gorman Kellyn has seen people she’s mentored and many she admires be very hard on themselves in certain situations despite doing the best they could in the situation. “That’s when perfectionism I think really comes back and bites a person. It really hurts them and harms them…when they don’t understand, ‘you do not control the entirety of this world. You can only control yourself.’” – Kellyn Gorman John thinks when Kellyn is kind to herself or critical of herself, it’s about the process and not about the outcome. For those who are not kind to themselves, the thing they can control and improve is their process. Preparation and interaction with other people are part of process, but we don’t control everything, including how much time we had to do something. 23:05 – Reaching Good Enough by Tuning for Time How do we start to design our processes to accept a quality of output that is good enough? Or does perfectionism force us to think our work must be of the utmost quality regardless of other constraints? Kellyn likes to break things into bite size pieces and determines the level of quality she can produce based on the time she has for that piece. If there is more time, she can revisit and increase the level of quality. Kellyn shares a story of getting asked to do a presentation at a conference the evening before the presentation was to take place. Kellyn wrote the abstract and then worked on the slides that evening for 2 hours and was able to say they were good enough. The next morning Kellyn worked on the slides again to the point where she was totally satisfied with the quality. “But if I didn’t have that time because I was not awake…I would have let them go. I would have been satisfied either way, but I was saying, ‘if I have more time, I will allocate to that. But I would have been happy either way because understanding there were time constraints…this was a last-minute request from somebody. I’m going to knock it out of the park no matter what because I know the topic, but my slides may not be of the pristine level that I like. So that’s kind of how I approach it.” – Kellyn Gorman Kellyn says in this case she did a great job with the presentation and was very happy with it. She focused her topic to fill a gap in content that wasn’t discussed at the event. Kellyn’s story made Nick think that in any given situation there are layers in which we might need to make good enough. Kellyn knew the topic well. That part was of the upmost quality. It was the slides that might have turned out to be good enough based on time constraints. This mirrors decisions Nick has to make when producing the podcast. Kellyn says this comes down to priority also. “What are the things that must be done? What are the things that could be done, and if I have time I’ll allocate more? What are the things that just don’t matter? …I am very much about time management for thigns that are valuable.” – Kellyn Gorman Kellyn does not like having her time wasted and likes to allocate time to only things that are useful or valuable. How did Kellyn learn to delineate efficient uses of time to help herself prioritize? Kellyn feels she’s always been this way. When she works on optimizing database environments, nothing is off the table – the application, the database, the network, or the hardware. “There are reports that you can pull from Oracle that tell you all about what’s using CPU, what’s using I/O, what’s using memory…. I’m always looking at elapsed time…because you tune for time, or you’re wasting time. It’s all about time. What is consuming the time? That to me is efficiency. I think that’s extremely important when you look at all aspects of life. What can I do that is efficient use of time that can provide valuable output, and if it doesn’t provide valuable output, it is a waste of time…. I have to have proof that shows what I allocate time to makes sense.” – Kellyn Gorman Kellyn thinks this is part of AuDHD. People who are autistic understand social cues well but do not accept social cues that don’t make logical sense. The autistic brain also has an insane sense of justice, and these qualities apply to all areas of life. “If it doesn’t make logical sense…if we cannot put order to it, we’re not going to be able to be supportive of it…. Because I see patterns and I see output, I should be able to track it and say, ‘this is an efficient use of my time. There will be productive output of this at the end, and yes, I will do it this way.’” – Kellyn Gorman, on the AuDHD brain Kellyn shares a scenario of co-workers pointing at something specific causing a performance problem in a database environment, but they had no data to back up their claim. John says this sounds like following the scientific method. When we as human beings have a hypothesis, there’s a cognitive bias toward searching for anything that supports what we think might be true. Maybe fighting this bias is a skill? Kellyn does a pretty good job at fighting the bias. “I would not be doing my job if I didn’t request that we have some data behind this before I spend time on it.” – Kellyn Gorman, as a response to colleagues without data backed assumptions of what might be causing a problem John suggests this is coaching and trying to help people get better at their jobs, encouraging them to gather data on their hypotheses. Listen to the story Kellyn shares of being in a meeting where someone just wanted her to agree with them without data. 32:22 – Strengths and Weaknesses in Neurodiversity John highlights Kellyn’s attribution of some of these things to AuDHD. He shares being diagnosed with ADHD as an adult and wishes it had been earlier. John loved spending time on things that were interesting and hated spending time on things he perceived to be unimportant, a waste of time, or just not interesting…regardless of whether the task or tasks would help him make progress on a project. John says he does not feel it is an aspect of his ADHD to hate wasting time. Kellyn says when she is trying to address something tedious, the activity level in her temporal lobe decreases, making it harder to focus. The way Kellyn would compensate for this was to pair up with someone neurotypical. “I could handle this monstrous 95% workload, but he’d come in the last 5% and clean it all up. And then he could go back in the corner and code like he loved to. That’s how I work best…. Little tiny things, tedious little silly things could get away from me. Understanding that and accepting that and accepting those weak points but understanding that I had these massive amount of strengths…this is alright. These weaknesses are alright. How do I find people who can help me to make sure they don’t become an issue? And that’s how I address my ADHD as an adult.” – Kellyn Gorman, on finding people to support her weaknesses John mentions compensating behaviors like staying organized also help him. Kellyn likes to switch between tasks constantly to keep activity up in her temporal lobe so nothing becomes boring. Kellyn asks managers to load up her task list and clearly communicate the deadline for different items. Then she can start working through the tasks in her own way (and finishing all of them). “It’s the way that I work. Because I know that way it can’t become tedious if I’m constantly task switching and moving about different things. It works wonderful for me. It’s not for everyone, but it does work with my ADHD.” – Kellyn Gorman John has a little bit more hyperfocus, and he mentions there is one label of ADHD that applies to many executive functioning issues. 36:08 – No Fear in Asking for Help or Giving Help to Others John asks about being self-taught. When we’re teaching ourselves something and just starting, it can seem overwhelming with so much material to learn. Did Kellyn combat perfectionism when learning new things through time calibration or using some other tool? Kellyn says it’s partly that she’s not afraid to ask for help. Going back to that first SQL Server she inherited (which we referenced earlier), the database team was not on speaking terms with the application and user support team. “So, for 3 weeks, I banged my head against a wall trying to figure out SQL Server, trying to figure out how to do this; and I was incredibly overwhelmed. I finally said, ‘that’s it. I’m not doing this. This is not a smart idea.’ So, I walked into the manager of that entire team (development as well as users), and I said, ‘so I hear that the DBA team and the…team are not on speaking terms…. I’d like to change that right now, right here.’ I was a brand-new DBA. I had nothing to lose…. I could not have done that job without them….learning from the application developers, learning from the people who used this application every day, understanding the data…. I had to go them, show weakness…and I learned a lot. They knew I was willing to put in the time to understand and learn SQL Server.” – Kellyn Gorman This database contained all pipeline data for the western US for Duke Energy. Kellyn had never worked on SQL, never managed databases, and was suddenly responsible for managing all of the hourly and daily data. To learn SQL Server scoured documentation. She also learned how to calculate lock escalation for database tables (which impressed Microsoft). Kellyn is giving back to the people on her team now, recommending O’Reilly books by specific trustworthy authors. Kellyn has followed these authors and their content for years. She knows whether what they write is valuable, and this is a critical skill in a world where some of the content out there is written by people who don’t truly understand the subject matter. Kellyn shares a discussion she had with someone else in the Oracle community about being part of the last generation that will understand Oracle. Things in the cloud are black boxes, and no one is talking about the internals (architecture, diagrams, etc.). “For my folks that I’m working with right now teaching them Oracle I have written in 4 months 250 pages, and I told them I’m going to turn it into a book. And I’m going to call it ‘All the Documentation Oracle Forgot to Write….’ This is why they can’t get the answers. There are no answers out there. It’s really interesting that we are saying everything is a black box. Nobody needs to know how it works. And the truth is if you don’t understand how it works, it’s really difficult to develop for it. It’s really difficult to troubleshoot it…. It’s really challenging as folks are trying to learn, trying to become more, and some of the old ways…it always returns to us as being the most valuable…. The way we taught ourselves, we had to really work with it…. We were building out real application clusters manually across networks that couldn’t handle it, and it was amazing. It was amazing what we were able to comprehend from that where now you can just go out to the cloud, and it does it all for you with a couple clicks.” – Kellyn Gorman, discussing that being self-taught today is different than it once was Mentioned in the Outro Special shout out to former guest David Klee for recommending we have Kellyn as a guest on the show! Through this interview Kellyn is modeling that we should be sharing our mistakes and challenges so that people don’t think we’re perfect or that everything we do succeeds. Going where no one else will go looks like bravery on the surface, and it is very brave. But at a deeper level, this is a strategy that works for Kellyn because she knows herself and how she works best (the type of environment to be in to succeed, desired level of autonomy, etc.). Learning and the building of expertise are natural byproducts of executing on the strategy of going where no one else will go. Getting to good enough in the output of our work requires being intentional about which aspects are good enough and which are of a higher quality based on how much time we have. This advice is very much in line with advice from Finish by Jon Acuff. Acuff talks about choosing what to bomb or what you will be bad at to save time. We did a 4-part book review with guest host Jason Gass which you can find in the following episodes: Episode 272 – Book Discussion: Finish, Part 1 – The Day after Perfect and Cut Your Goal in Half Episode 273 – Book Discussion: Finish, Part 2 – Deliberate Time Investments and Avoiding Distractions – this episode discusses the concept of choosing what to bomb Episode 274 – Book Discussion: Finish, Part 3 – Get Rid of Your Secret Rules and Use Data to Celebrate Your Imperfect Progress Episode 275 – Book Discussion: Finish, Part 4 – The Day before Done and Perfectionism’s Final Roadblocks We ended this week’s discussion on the topic of our industry and the difficulties of learning how everything in the cloud works at a deep level. Good documentation and good sources of information (which Kellen is both recommending to others and building herself) are essential in becoming a good troubleshooter. David Klee spoke to this in Episode 315 -A Love for Troubleshooting: Skill Development through Documentation with David Klee (1/2). Remember to check out Kellyn’s blog – DBAKevlar. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YoutTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.

If you think the job of a manager is to serve their team, think again. This week in episode 319 Richard Russell returns to make the distinction between how to manage well and the specific job of a people manager. As part of our discussion, Richard shares his transition into people management and how he later determined it wasn’t the right fit, his decision to pursue consulting, and the way he landed on coaching. We also highlight the importance of determining the definition of success in your work and finding the space that fits you. Listen closely for tips on how to find the right coach who understands your world. Original Recording Date: 02-17-2025 Richard Russell spends most of his time coaching leaders who work in scale-ups, big tech, and other corporate environments. If you missed part 1 of the discussion with Richard, check out Episode 318. Topics – Pursuing People Management, The Job of a Manager is Upward, A Transition to Coaching, Comparing Coaches and People Managers, The Space That Fits You, Finding the Right Coach, The Greater Context 3:02 – Pursuing People Management Once you become a team lead you can go to maangement, stay team lead, or just be an individual contributor again. What made Richard want to move into people management? Richard’s biggest realization was that people who were really good at specific technologies were better than him and getting even better at it faster than he was. “Relatively speaking to people in my peers, I’m going to continue to fall behind, and the reason for it is because I’m not actually that interested enough to get really good at it…whereas they are…. I followed things that I was interested in, which was people.” – Richard Russell In his early days, Richard was quite interested in Linux and programming ang got very good at it very fast. But then he lost interest in it because he got interested in other areas like business strategy, how people think, what management is, etc. Richard remembers a teacher in high school commenting that he was a natural leader people would follow. Richard didn’t see himself in that light at the time because he was “the nerdy one.” Over time, as Richard was able to influence people (even before his role as a people manager), he began to recognize it was the result of an interest and care for people. Richard shares a story of what motivates him using the example of a colleague he was able to help improve. “These things stick in his mind – that care, that coaching, that attention that he got…the explanations that he got that were patient…and the trust that I had in him then moved him…. That interaction, that fundamental interaction with a human is the thing that continues to motivate me.” – Richard Russell, describing his impact on a colleague Richard is always interested in technological bits and pieces, but eventually he will lose interest and move on to something else. When it comes to people, he’s never lost that interest. Richard went into people management because he felt the topics related to it were and would be deeply interesting long-term. These interests might include topics such as people and how they think, how to influence people, how to solve communication challenges between people, aligning people with a business strategy, how to create value, what a good product is, etc. How did people look at Richard’s experience as a mentor and team lead when he was trying to move into people management? Were those experiences as relatable as we think they are? Richard was a team lead at Deutsche Bank. He then became an individual contributor at Google with roles as a Technical Account Manager and Sales Engineer. The first people manager role came 4-5 years after he began working at Google. “In various situations you express leadership in formal or informal roles,” – Richard Russell At Google Richard did a number of things that were acts of leadership, such as: Running an event called TGIF and doing some public speaking / discussion moderation Working closely with a team of engineers in India to develop software to get public transport data into Google Maps (not formally responsible for the effort but providing leadership and guiding people) If Richard were interviewing someone now for a manager position, he might ask the following: Tell me about a time when you got results from people, got them aligned on a problem, or solved an interpersonal problem with people Examples of mentoring and growing junior employees Tell me about a time when you got a group of people headed in the wrong direction to go in the right direction. “A lot of this work is about people influencing and connecting the people to needs of the business and management. To answer it, yes, all of that work as a technical lead or a team lead or whatever it was in various situations…it’s all massively relevant.” – Richard Russell 8:07 – The Job of a Manager is Upward How can listeners decide if people management is the right choice? There is a debate about whether leaders are made or born. Richard thinks anyone can learn the skills of people management, but it’s important to consider your interests and motivations when thinking through it. Richard made an error when going into people management that he sees a lot of people going into people management make now. “The error that I made…in fact, I alluded to this earlier…the error that I see a lot of people making is they see people management as being going to bat for my team. My job as a people manager is to look after my team and to defend my team and to be a servant leader. But often we look at our managers and think they’re not quite defending us enough or they’re not representing us well enough…or all the problems come downwards and so on…. So, I’ll do it differently. And I’ll get up there, and I’ll make it better for my team. And that’s a good thing in many, many ways. However, the job of manager is not to serve the team. That’s the how. That’s how you do it. That’s how you do the job. That’s the best way to do the job. But the job is to provide value for your business, your organization, and your management. The job is upwards….” – Richard Russell Technical people especially who go into management may disregard the fact that the job is upwardly facing. At one time Google questioned whether managers were even needed, and when they tried operating without very many and it failed miserably, they started to look at what was really needed from managers and overhauled some of their management theory. Servant leadership, mentorship, and guidance are certainly part of it. Managers need to understand what the business really needs so they can help their team understand what the business needs and get the results. “This is the big thing which I think is the misunderstanding I think a lot of first-level managers, especially in technology have – what the job is.” – Richard Russell, on the job of a manager What is the difference between a first-level manager and a second level manager’s job in terms of providing business value? First-level managers can make the mistake Richard highlighted, but in most companies, this will not get you to second level maanger. The second level manager is responsible for providing value but also for developing first-level managers. Some of this development is helping the first-level managers re-orient from previous experience as an individual contributor to focus upward. In addition to helping first-level managers learn to be upwardly focused, second level managers need to be even more upwardly focused. “Management is primarily an upwards focused job. This may be counterintuitive, and it may be controversial among some people. But the job is not to serve your team. The job is to deliver the value, and the how is to serve your team…because you don’t get results unless you do that. That statement is the reason. It’s not because it’s a good thing to do. It is a good thing to do. It’s not because it’s the right thing to do. It is the right thing to do. But it’s not because of that. It’s because as a business, what businesses do is they make money, and they provide value to customers. And they sell things, and that’s what defines a business. You’re hiring people in order to eventually make more money and sell more things to businesses and have your teams create more value. And, if I want to do that with knowledge workers, I’ve gotta have managers who serve them well and do well. But it’s so that we can make more money so that we can run a business.” – Richard Russell Richard says in the past, people managers didn’t really understand the “how” of the job and didn’t care about teams. There has been a big movement toward servant leadership over time. Nick says it sounds like there is a difference in the overall goal and mission of a role and how someone performs the duties to fit that. Richard says this is not a subtle point. The manager’s job is managing situations to get the best results and not necessarily to make the team happy. It’s a tradeoff that can at times be difficult to navigate. Sometimes a manager will need to be unpopular, even if trying to serve their team. Richard gives the example of putting a poor performer on the team on a performance improvement plan or getting them off the team. 13:29 – A Transition to Coaching Did Richard want to keep going to higher levels of management after his experience as a first-level manager? Richard had ambitions of being a founder, a CEO, or some kind of executive after stepping into management. At the time, his definition of success was actually what other people expected of him or what he thought other people expected. It took a long time for Richard to realize these were not the things he wanted to do or where his energy came from. We said management is about providing business value to the company, and this is something which is very important to Richard. There are 2 things Richard struggles with as a manager: The first is putting the value delivery ahead of the people. Richard is very motivated by and cares about people, and it makes him a soft manager. He would rather primarily be developing people. Secondly, Richard finds some aspects of delivering results very difficult such as delivering projects, plans, or documents. “What I found is that when I was a people manager, when that pressure comes down on me or the team…I am not a good people manager in that I can’t care for my people. I can’t do that well. I can’t be the servant leader when I’m under pressure. I did not have that capability…. My shift first of all from being a people manager and wanting to be an executive to realizing I’m not sure I’m motivated to do that. I’m not sure I’m capable of doing that – deliver results through people and put the results first and still care for people…. I think the best way of delivering results is to care for people. That’s one of the best mechanisms to do, but when I’m under pressure, my way of dealing with pressure in those situations…I don’t have the capability to do the caring for people that’s going to get the results to deliver them. And that’s a characteristic about myself that I’ve learned that I’ve found very difficult to deal with because I fundamentally deeply do care about people. And when I’m under pressure in that management role and I’m pushing that pressure onto my team or doing whatever I’m doing, I’m not getting the results. And I’m not making them better. And I’m not happy. And I’m stressed. It’s not a good place for me.” – Richard Russell When Richard realized management was not the right place for him, he went down the path of doing consulting. It was a lot of teaching, helping people solve problems, and doing some delivery work. Based on his characteristics, Richard found consulting was still too far down the path of delivering results. “That’s why I’ve moved to being a coach because actually my job is to care about people…. I can do tough love when my job is to care about you and to help you grow, and I can do that really well in those situations because I don’t have the stress of making sure you’re delivering a result that I need for my success.” – Richard Russell Richard’s success as a coach is aligned with the things he actually cares about. He cares about his clients and helps to develop them into better managers and leaders (i.e. clients get better results, are more capable as managers, have happier teams, etc.). Richard gets a great deal of energy from these conversations, whereas being tasked with delivering a strategy or a plan makes him stressed. “I’m quite passionate about this for people who are listening. Where you get energy from and what motivates you, if that’s really lined up with what success in your job is, that’s a wonderful place to be. And if when you’re doing these things you are the person you want to be, that’s great. If it’s not, maybe look at what change needs to happen. Quite a lot of people I know are just deeply motivated by operating and by building things and by creating things and solving technical problems. And that’s their motivation. …That’s fantastic. And if you can do that and you can care for people and you have those skills of managing and leading people and influencing people and understanding the business…then you’re capable of being an executive. You can get to any level, really. And that might be great for you. That might be the right thing. If you’re the kind of person who doesn’t care about people, you can still get there. You’re just going to cause a lot of pain along the way for other people, and it’s not going to be good. But you can get there…. I wouldn’t recommend it.” – Richard Russell 18:39 – Comparing Coaches and People Managers We’ve spoken with others about coaching and being a people manager and some of the similarities and differences. What does Richard think the comparison looks like based on his experience? Richard believes each person who wants to be successful as a people manager needs to be a great coach. This is non-negotiable. There are 2 main differences between coach and manager according to Richard. The first is relationship – people managers coach their teams in certain situations and during 1-1 meetings, but there is a manager employee relationship still in place. The same manager who is coaching you is assessing you and doing reviews of your performance. A manager can support a promotion, a transfer to another team internally, and make the call to end your employment if that needs to happen. “There’s a whole lot of perceived agenda. A good manager…can coach in those contexts without agenda. It’s about the person and developing the person, and I have had great managers who’ve been able to coach me and help me figure out what’s going on / find the right place while also not holding that as a threat or having that affect their assessment of me. It’s hard to do, but it’s possible. Being a great manager, you need to be able to do that, and it’s really, really important.” – Richard Russell The second difference is that a manager’s job is to deliver results. Part of delivering results is developing a competent team. If a manager has a team member who would like to transfer to a different team, it creates a conflicting agenda. The manager still wants to deliver results and may be losing top talent, but they also want to support what is best for that team member. Richard says good managers should support what is best for a team member, even if that means leaving the team. “If you’re really good as a manager, one of the things you do is you develop a reputation for identifying, hiring, attracting good people and developing them and seeing them move on to greatness. And then people will really want to come to you as a manager. Then you get the best people…. When you have these great managers in big companies and they move around, the first thing that happens is they bring along 4 or 5 or 10 of their best people from around the company and gather them together…. There’s a massive talent in that, and that’s partly about coaching and how you invest in your team and how you invest in their skills…so coaching is super important as a manager. And it is in many ways the same set of skills except that it’s in a context which is different.” – Richard Russell Developing a good reputation for fostering talent as a manager can be helpful in companies of various sizes. This is partly about how you coach and develop your people and invest in their skills. As a coach, Richard’s only loyalty is to his client and their interests. The only real conflict that could come up is if Richard as the coach had a moral or ethical qualm with something the client is doing. Richard works with his clients to improve what they are doing, which can mean the person wants to get promoted, for example. Richard is there to help the person do that and thrive as a person. “Everyone I come across…it’s never just I want to get a promotion, or I want to get more money. There’s a deeper why…. Figuring out how to get people in touch with that and what’s going to make them happy in their careers is really important.” – Richard Russell Listen to Richard tell the story of a fisherman who gets an unsolicited suggestion for creating a fishing business from a banker visiting the area. But creating and selling a business (what the banker thought success would be) wasn’t the definition of success the fisherman really had for his life. Richard once defined success as being a successful executive. At one point he had a team of 100 people reporting into him. When Richard told a friend of his from Google about having a team of this size, his friend said, “wow, you’ve really made it.” Richard would later come to realize the role was not for him, and it was not who he wanted to be. “Can you not create something that’s more like that now? Can you get more control over your life now about your work life balance? You’re traveling 4 days a week. Is that what you want to do?” – Richard Russell, on uncovering the deeper why behind what his clients want to do Richard uses the example of his wife. For her, is a promotion really the right thing? A promotion involves more travel, more pressure, and more stress. “I think most people, myself included, adopt definitions of success and failure from our context and our environment and from other people, and we internalize them. They’re not always beliefs that serve us. The people I’ve seen who are the happiest in their life, most fulfilled, and most successful in ways that matter are people who’ve managed to figure out what success means to them.” – Richard Russell Some define success as the ability to tinker with hardware and software without the need to have direct reports or manage a team. Richard gives the example of an extremely talented individual at Amazon in this category. While we might say the person could be way more successful, the life this person has is the one he wants / chose. It goes back to how this individual defines success. Does the coach have the ability to be more transparent with someone than a manager can be without feeling conflicted about the level of transparency? Richard says yes because there is usually only one agenda. It might seem like a conflict of interest if Richard wants a case study or referral or testimonial, but it’s fundamentally aligned with what a client wants. Managers have things which can pull them in other directions like HR rules, employment laws, corporate risk, etc. A manager’s need to deliver results and the desire to retain someone on their team (even if the person wants to leave the team) creates a conflicting agenda. Richard says it is possible to not be conflicted about these things, but it is difficult. It requires courage, confidence, and experience as a manager. 28:11 – The Space That Fits You What are some of the interesting conflicts or interesting differences between being the owner / entrepreneur of a coaching business and actively coaching clients? Conversations with coaching clients are very personal and confidential. If these could be shared, they would make great marketing materials. Any kind of marketing materials must be sanitized / obfuscated so as not to be personally identifiable. This seems like a conflict of interest, but one can simply learn to develop marketing materials without violating client confidentiality or trust. Doing marketing, administrative work, and content creation is a different kind of work. Richard made a shift in his business over the last few months (which is how he and Nick connected originally). He was spending a lot of time on LinkedIn producing content for brand awareness of his business and at the same time doing consulting work, and he found it to be consistently difficult. “Let’s try and move my own marketing to things that I feel are more natural for me and more energy productive, so I spend more time on longer form content on Substack. I’m creating something that I think is valuable for people, so I’m motivated to do that…. Now sharing it becomes not such a piece of hard work.” – Richard Russell Richard also likes to be a guest on podcasts like Nerd Journey. He feels engaged in these kinds of conversations and does not feel the need to produce a sound byte. It’s about providing value and making the audience think. Richard is also interviewing people for his own podcast. He finds it interesting to learn from the stories of others and share them with other people. The realignment of Richard’s efforts makes the work easy because they are aligned with who he is and what he wants to do. “When I’m doing good marketing, I’m kind of doing the stuff that I’m doing when I’m doing good coaching. It’s the same stuff with a slightly different context…. That’s really deeply aligned with what I believe in as a coach and what I want to do for my clients and how I want to help them.” – Richard Russell Nick likes the process of continued iterative alignment with Richard’s interests and the things that give him energy. The ADHD brain can drop things once they become uninteresting. But once Richard got interested in people, he never found it boring. The focus remained. Richard has always been interested in people as well as business, strategy, and marketing. A topic can be very interesting (business, strategy, marketing), but the work of producing the value in that area can be quite difficult. Richard will continue to find these topical areas interesting, but he realized the need to ensure the production of value is in way that gives him energy. Producing a book, a training course, a project plan, or some other thing that requires very long periods of intense focus can be difficult for Richard. He loses interest in the thing he’s working on but not the topical area in which it resides. Richard tells us some of the realizations he has shared came from working with his own coach. When originally asked about what gave him energy, Richard wasn’t sure how to answer. He needed to think deeply on it and iterate a little bit. “I was quite convinced that being a consultant was the right path, and solving strategy problems was the right thing to do. But I realized after a while that what gets me going there is those conversations, especially helping them get a breakthrough themselves…not producing a piece of strategy or teaching them how to do strategy or creating content that helps them do that. Maybe consulting is not for me because if I do that…the more successful I am the less energy I have. And I’ll get down about it.” – Richard Russell, on why consulting isn’t the right path Listen to Richard describe the process of obtaining and helping a consulting client and which things gave him energy compared to those that drained his energy (writing proposals, setting up meetings, producing an artifact as a takeaway, etc.). Richard talks about his original move into systems engineering and how getting trouble tickets gave him energy. They were problems he would get to solve. Nick says it sounds like Richard is encouraging us to break things down to a task level to analyze what gives us energy, but we should keep in mind the topical areas that get us excited. For Richard, it seemed like it was the intersection of people, business, and technology. “You can’t always be 100% on I only do things that energize me. There’s always washing to do…. There’s always some of this. I do think that figuring out where your fit is is partially about…you’ve got to be realistic about what people want and what demand there is…. Figuring out what demand is and figuring out what I’m good at and where I get my energy from…that’s the whole Ikigai thing, right? What people want, what the world needs, what I am good at, and what I enjoy doing – in the middle of that is…your sweet spot.” – Richard Russell Richard remembers going through school and choosing his degree / looking at the careers guide. It seemed like making a selection was putting himself in a box that would define who he was for the rest of his life. It took Richard a long time to realize it’s about his ability to relate to people and how he makes people feel which is in the intersection of all the areas we discussed. Richard came to realize that what he does with people is valuable. “It’s not everyone who does this. And not everyone has this motivation. And not everyone is interested like that…. I find it interesting, and I find it motivating…. I get value from it. Just getting comfortable with who I am and where value really is, and it’s no longer defined by phrase on a paper or degrees or doing things that people think are clever. It’s a really big change. For different people it’s different…what fits you but finding that space is really important.” – Richard Russell Nick believes it takes some sampling and iteration to understand where you need to be. What Richard has found is similar to the concept of area of destiny. Richard felt like early on he was in a technical box, and he was proud of it. He encourages us to be proud if that is the box where we fit. Over time, Richard met people whose background might be different than what they were doing. He cites examples like a systems administrator colleague with an arts and music degree, a doctor who became an agile and scrum trainer, etc. Seeing people make these changes and shifts helped Richard understand he no longer needed to define himself the way he had been (in a specific box). “I don’t need to define myself by that box anymore…. You can move boxes, and it’s fine. And there’s lots of value in lots of different boxes or spaces or whatever you want to call them.” – Richard Russell 39:26 – Finding the Right Coach How would someone recognize they have found a coach who can help them? Richard says see if they help you. For context, his sales calls are coaching calls. Part of this is determining if you and a potential coach can speak the same language and understand each other. Richard remembers meeting some coaches who didn’t have the right background to help him. “I can’t feel like I connect with you because I don’t feel like you’ve been where I have been or anywhere like I’ve been. I don’t think you understand my world. I’ve had other coaches who haven’t had those lists on their CVs. But at least they speak the language, and I understand that they’ve had the exposure to other people to figure it out.” – Richard Russell, sharing thoughts on coaches who were not right for him Richard’s background helps him connect with product and technical people. He has been in big tech companies and in startups and can speak the same language as others in them now. No one needs to explain what a sprint is to him, for example. When you know the person coaching you understands where you are coming from it creates trust. It fosters a conversation about a problem so a coach can help you work through it. Richard says there is a blurry line between coaching, advising, teaching, and consulting. The coach has to caution against giving too many answers. Coaches can give some answers, but part of the work is understanding the person and what they are trying to do. “Did I get value from this, and would I want more of that? Do I trust this person? Do I feel like they understand me in a way that matters to what I need to do? And, are they helping me? …Did they help me come up with answers? Did I get the change that I want? Do I feel like I’m making progress on these things? If it’s literally just they told me things and they answered questions, it’s probably not going to be deeper change for the long term. But at the same time if there’s none of that, do they even know my world? Do I trust them? You have to have a bit of both of these things.” – Richard Russell, on how to determine if a coach is the right fit for you This brings us full circle back to building trust. Some of the things Richard shared in finding the right coach could also be things we use to determine if working for a specific people manager is right for us. Richard feels like technical managers need at least some context, even if it’s not the same degree of experience as the people they manage. Richard shares the story of a manager he had who came from marketing and law. This person asked all sorts of questions when he onboarded and wanted to understand what systems did and how they interact. Knowledge of the systems and their function empowered this manager to have conversations about them in an effective way. 43:41 – The Greater Context Nick feels there is a nuance to communicating with executives that technical people do not always understand. Richard says this happens with people who are functionally skilled in whatever function it is (technology or some other area). “Your manager may not know the same level of details that you do about things, and that’s normal and that’s ok…. Some of their judgements might not make sense to you…. The real thing is to spend the time to learn how they think or why they’re making decisions…how they’re thinking about something, how they’re prioritizing…. Largely this is about understanding the broader context that they have because by nature of the position in the organization they have broader context. They have much more connection with up – with managers above and across as well…. They should be able to help you understand at least the pieces of that broader context that you need to know. When you’re relating to them, whatever level you’re relating to…first of all spend time to understand their needs and what’s going on and what they need from you. I made this mistake early on in my career with my own manager of basically not having interest in what he wanted and having my own opinions on everything.” – Richard Russell Richard says it’s important to understand the metrics and how your manager prioritizes things. Be open to learning the greater context. It is extremely important to be coachable and open to learning. Richard shares the story of a CTO who would ignore non-technical topics in executive meetings. Richard then encouraged this person to pay attention and ask questions when other executives were speaking about their own functional area (i.e. when the Marketing person was presenting their plans, etc.). As it turns out, the CTO knew about an upcoming software release that could help a marketing initiative, and because he was engaged in the conversation and willing to understand the greater context, both executives built trust and benefited from sharing their respective knowledge. Richard encourages us all to take the time to understand the context from areas outside our own. “This is the big difference between executive and junior, and this is the thing that executives notice about juniors. You’re paying attention. You actually care about the context in which you’re working. The thing that defines the value of what you do…you’re caring about it. You’re someone I can teach.” – Richard Russell Much of the job of an executive is getting the context and figuring out how to communicate it downward in a meaningful way. A CTO, for example, has to build a competent technical team and then has to give their team enough context to be able to make deicisions that are useful. The CTO would be the main communication conduit for this team. “Somehow through the mechanisms that you use to communicate with people in this larger organization, you have to give them enough context such that they can then be empowered to make decisions without then having to come back to you…. So, this is all about empowering people, and this relates back to that whole topic of servant leadership and doing it well by serving teams…giving them enough context so they can make a decision and then coaching them to make better decisions. And, then understanding what misconceptions or errors are they making and where and why and then figuring out…how do I influence that? What other context do I need to get, and how do the decisions they’re making actually fit into the rest of the organization? And where else do I need to influence? …This is about empowerment. You can’t be empowered unless you have the context. And in fact, the context in some ways constrains you, so you have to give the constraints. And that empowers people.” – Richard Russell Managers must learn how to communicate context. Nick loves the fact that Richard’s illustrations show that we all have gaps and need to get better. If you want to follow up with Richard… Visit his website Visit his YouTube Channel – @richardarussell Visit the Scale Up Leaders Substack If you need a coach, Richard is currently taking clients! Contact him, and tell him you listened to this episode. Mentioned in the Outro This episode pairs nicely with the following past episodes: Episode 308 – Probe and Discover: Coaching for Impact with Ramzi Marjaba (2/2) Episode 228 – The Displacement of Joy with Scott Egbert (2/2) [Episode 269 – Monetize Yourself: Leveraging Your Most Valuable Knowledge with Erik Gross (3/3)](https://nerd-journey.com/monetize-yourself-leveraging-your-most-valuable-knowledge-with-erik-gross-3-3/ There was a mention of Ikigai in this episode, which is a state of wellbeing that arises from devotion to activities one enjoys, which also brings a sense of fulfillment. It can be simply translated as a reason to get up in the morning. This idea seems similar to our discussion of area of destiny.

Have you ever felt a work task was boring or a waste of time? It might be because you didn’t understand why you were asked to do it in the first place. Richard Russell, our guest this week in episode 318, struggled with this in his early role as a programmer. All he wanted was to understand more about the business problem his work was intended to solve. In that role, however, Richard never got those answers, and he would later move into systems administration. Richard has developed a pattern of pursuing the things which he finds interesting – a pattern that began in college and has continued over the course of his career as a programmer, a systems administrator, and as a consultant. Each of these roles combined with his interest in the business prepared Richard for the role of team lead in the banking industry. Join us as we explore the team lead role and why Richard progressed to it, how he built trust as a consultant and as a sales engineer, and his genuine interest in people. Listen closely to learn strategies that will increase your ability to influence others, ask the right questions, and build strong working relationships with colleagues and customers. Original Recording Date: 02-17-2025 Topics – Meet Richard Russell, An Interest in Mathematics and Computer Science, Moving from Programming to Systems Administration, Consulting and an Interest in the Business, Combatting Ego and Building Trust, Sharing Your Priorities, Progressing to Team Lead 2:43 – Meet Richard Russell Richard Russell spends most of his time coaching leaders who work in scale-ups, big tech, and other corporate environments. Most of Richard’s clients have some executive responsibilities and come from a product or technology background. Many times, these clients are transitioning into product / tech leadership roles or CEO / founder roles. Richard made the relatively recent transition from doing consulting work to focusing on coaching. Richard resides in Luxembourg with his family. 3:29 – An Interest in Mathematics and Computer Science What prompted Richard to study math and computer science in school? Richard’s father was an electrical engineer and was very enthusiastic about that career path. Richard had a Commodore 64 as his first computer and tinkered with various others over time, even getting into programming. In high school, Richard did very well in the hard sciences – math, physics, and chemistry. When forced to choose a non-science course during his senior year, he chose economics because it seemed the most mathematical. Though he did start out studying engineering in college, Richard made some changes to focus on the things he found most interesting – mathematics, computer science, philosophy, cognitive science, theology, etc. Richard found applied mathematics quite boring at first (just solving differential equations, for example). It was more interesting to him when physics and engineering teachers taught mathematics because there was a need to solve a problem. Richard later went into pure mathematics and found it the most interesting of all. Richard says computer science was something he got into primarily because of his talent in mathematics. Nick remembers hearing physics majors in college echo the same sentiment as Richard. They learned more mathematics in physics courses than in their respective calculus courses. To Richard, initial learnings in calculus seemed to be solving complicated problems that were not applied to anything, and it was a sharp contrast to the way problems were presented in physics or engineering. In the sciences, Richard had an interest in the practical need. In pure mathematics, he had the interest in learning anything within that discipline. Richard started wanting to learn more about the applications of mathematics and became really interested in the abstract concepts of mathematics. Was it a similar pattern when Richard learned programming? Richard says he gets interested in topics, and he wasn’t interested in the complications of applied mathematics (i.e. doing integrals, for example). When it came to computer science, Richard was interested in how things worked and some of the theory behind it. He also liked the ability to express creativity and control what appeared on the screen through programming (which required no artistic talent). Richard later became interested in businesses and how products are built. He had no background in product management and wanted to build games. “The mathematics behind, especially graphics, was very complex, and it was exactly the stuff I didn’t like doing. Whereas the business games and business side of applications or programs or websites and so on…they are quite simple in many ways. The complexity is really about…what do I actually want to achieve as opposed to how do I achieve it. And so that became much more interesting to me. A lot of that is related to my interest in product management as I went on further and in business generally. I have this habit of obsessing over topics, whatever they are, whatever I’m interested in…so I got deep in whatever topic it is.” – Richard Russell 9:40 – Moving from Programming to Systems Administration Was Richard still obsessed with programming once it became his job? Richard tells us within the last year he was diagnosed with ADHD. “I tend to just find things interesting and obsess over them. When it’s work it’s not necessarily interesting inherently. It could be. It might not be. The decision on whether it’s interesting or not is independent of whether it’s work.” – Richard Russell In his first job, Richard was doing software development but worked on a product that was very boring to him. The product was internally facing administration tool that did asset tracking for national parks. The product had only 6 users. Richard would be given a user story and have to build something from it (a web page, etc.). “I remember thinking…why are we doing this, and what problem are we actually trying to solve? Why haven’t I met any of these people who are using this thing? Why do I not understand what they’re trying to do? Is this even a good way of doing it? It’s just like we’re taking an old database system and turning it into a web application because that’s the thing you do. The whole thing…it was fundamentally…on a deep level boring because I wasn’t talking to the people who were having the problem. I didn’t know what we were solving. I didn’t know why we were doing it. I was just producing web pages.” – Richard Russell Richard then shifted from programming to systems administration. The goal was solving problems, and there was a person who had a problem, which made it interesting. Sometimes Richard would need to go and talk to someone to solve a problem. But if a system was down or not performing well, Richard understood the impact to the user base. He was motivated to solve the problems because they impacted people who would then appreciate that the problems were fixed. Richard also worked on patching for Solaris servers (again, a problem to solve). Richard contrasts the work in systems administration to his work programming and building web pages. It would take a long time to create a release, and once the release was live, he would never find out if what he did was of any value to anyone. There was no feedback or ability to see the impact of work completed. In his role as a programmer, did Richard express his feelings to his manager that the work was not making an impact? Richard says he kept his feelings to himself but also does not believe he was aware of what was specifically frustrating him. In that environment, developers were basically handed something to build and told to go build it. It was not obvious that developers would have an interest in the business. This has changed over the last 25-30 years, however. What were some of the challenges of moving from development to the systems administration side? Richard thinks his advice for someone looking to do that now would be well dated. But at the time, Richard had worked with Linux quite a bit and even ran a Linux Install Fest. He also tried to start a startup based on systematic remote administration and patching hundreds of Debian Linux servers. Richard mentions he had played around with Linux in his spare time because it was interesting. It became a hobby. Richard feels that today software development is more connected to the business, while systems administration is somewhat removed from it. Richard built a lot of computers earlier in his career and mentions people have moved up the stack. Doing this same thing now is an increasingly niche area (i.e. the hardware portion). “From my own personal interests, I found it much more motivating to be with people and businesses influencing people and understanding how and why people buy things and what kind of things people buy. That’s much more interesting to me now…. Sysadmin type work is very much a service. If you look at any business, sysadmin or anyone doing IT infrastructure…it is a cost center. It will always be a cost center…unless you’re in a business where it is a business where it is the profit center, which is very rare. In most cases it’s a cost center. When you’re in a cost center you’re always one of the people who gets secondary importance in the organization…at best.” – Richard Russell Nick clarifies that systems administration could mean hardware, software, the hypervisor layer, the virtual machine layer, the operating systems, administration of the pipelining tools that development teams use, etc. Richard mentioned he’s not hands on with most of these things any longer but that levels of abstraction continue to rise. Ideally people would want to be in an area that has some demand for the specific type of work (i.e. a growth area). Think about businesses who make money from doing what you are doing as opposed to businesses where what you do would be a cost center. 19:15 – Consulting and an Interest in the Business How did Richard’s early consulting experience fit into the story? After moving from developer to systems administration, Richard chose to go independent. He provided systems administration services to a number of small businesses in his hometown. Richard refers to it as freelancing. Did Richard like working with multiple customers instead of just working in systems administration full-time for a single customer? One characteristic of ADHD minds is the desire to have variety. Richard likes having variety in his work and the ability to learn something new. Richard knows not everyone feels this way, and he’s had numerous colleagues who would rather go deep into something, own it, and build it over the long term. When consulting with small businesses, you work as a peer or expert along with the people who have the business need, and in Richard’s opinion, the conversations are more interesting. Richard was able to discuss the business problems with his consulting customers and make a recommendation for a solution only after he understood what they were trying to achieve. When working inside a large organization on a team of systems administrators, he was removed from those decisions and focused more on task completion to solve problems, but the systems administration work was still more interesting than his work as a developer when given a spec to build. The human relationship aspect was also very interesting to Richard. It wasn’t just working with colleagues but meeting people who were not experts in the same area and translating their need into the right technology recommendation. Nick feels like Richard’s move into consulting is a mirror of his move from the application of mathematics in the sciences to focusing more on the abstract concepts of pure mathematics. Solving a system problem could be thought of as the application part, and the business problems and challenges and translating back to a solution could be thought of as the more abstract part. Nick feels many people don’t naturally know how to ask the right questions to discover business problems and map them to technology solutions. Did Richard know how to do this or have to learn how to do it? Richard says he’s always had an innate interest in these types of things, and this is the reason for his decision to study philosophy and psychology while in college. It takes time to develop deep expertise in mathematics and engineering topics to be able to have an intelligent conversation about it. Richard also had an interest in marketing and business but felt they were magical areas he didn’t understand well, usually feeling he was the one who knew the least about them in any room. But the interest in these areas drove him to keep asking questions about them. “So over time I kept asking questions and learning stuff and eventually figured out that actually, it’s not that complicated. It’s not that hard…. I have a voracious appetite for reading books…and I read books about marketing and strategy and influence and psychology and management…. So, I’d read a lot of things and pick things up there…. It took me a long time to realize that…actually I do know quite a lot about this stuff now, and I don’t need to have the degree in that topic to be something of an expert in some of these topics. But I certainly learned from these books and from other people how better to go about certain types of questions….” – Richard Russell Richard cites reading The Mom Test as extremely helpful in learning how to understand what types of problems people really have as opposed to the problems we might want to solve. When someone says they have a need or a problem, Nick says we often go to solutioning / presenting a solution before truly asking enough questions. Are people bothered less when asked more questions than we might think they will be in these cases? Richard shares a story from his time at Deutsche Bank. He had moved from Australia to London to take the job and worked with a team who was developing software for trading foreign exchange (traders in banks would use it). At the time, he had little understanding of foreign exchange, banking, or finance and sought help from co-workers to understand the terminology. “I did a little bit of analysis…. Looking at this…that means that every week we trade 2 Australian GDPs. That’s a lot of money…. So, I talked to my business analyst on the team…just asked him, ‘can you teach me about this stuff?’ …He just sat down and explained to me who is doing this, why they’re doing it, and so on. I remember looking at these things and thinking, ‘why does anyone want to buy that thing, this credit default swap?’ …It’s really interesting the way these things work. So, I learned all that from this guy who was a business analyst. He had been in banking for 30 years…. When I asked him, he was like, ‘cool – I get to explain my area. I get to explain what I know.’ …Most of the time…people are willing to explain to someone interested.” – Richard Russell, on learning the banking industry from an analyst colleague The analyst above helped Richard understand the need for liquidity, why certain types of products and systems existed, why some customers wanted to buy specific products (i.e. balancing risk and reward, etc.), and why other companies might not be building the same thing as the bank. We should not be afraid of asking questions within our own company to better understand the business. Richard says this was the exact opposite of his work building software. He remembers going to the trading floor to ask people what they do each day and why there were 9 different screens displaying information, for example. Nick recently heard a personal development teacher talking about learning who recommended telling people we don’t have enough information to understand something yet when asking for clarification / explanation. Richard says one of the worst things we can do is be shy about asking the seemingly dumb questions. Ask why something is being done or why people want a certain thing. These types of questions have an interesting nuance. “Often, people are too shy about asking questions that sound like that. You never learn, and then you never have any idea…. The person on the other end can kind of figure out if you really don’t understand it, and what they want is for you to ask the dumb question so that they can go, ‘cool – now I get to explain the basics to you so you’ll understand. And now that I’ve explained it to you, I now trust that you understand it. Now I trust you more because you’ve asked the question.’ I often find in most of my work these days asking that question really helps.” – Richard Russell Richard will sometimes ask questions he knows the answer to in order to get people to explain something to him in a way that they believe he understands. It’s a little counterintuitive, but then the person will trust him. 31:11 – Combatting Ego and Building Trust Do most people have to get past their own ego when asking these questions? Richard says yes, especially if you come from an intellectual / academic kind of background. He came from an environment where it was important to be right. This comes out in two specific ways for Richard – 1) when someone asks him a question and he doesn’t know the answer and 2) asking seemingly silly questions to get more information on certain topics. In the early days when asked something for which Richard did not know the answer he might try to improvise or make something up (which did not add value). Richard tells the story of getting some coaching from his manager when he was a sales engineer at Google. The advice was to admit he did not know but commit to finding the right answer for the customer. Also, Richard would share with the customer that his company has solved the problem for organizations with similar setups in the past. “What I was doing in that situation as a sales engineer…is first of all acknowledging that I don’t know…but then also building their trust in our organization and my ability to navigate our organization and our ability as an organization to serve people like them…that they will get the result that they want…. I realized my job in that role is not necessarily to even answer the questions. It’s not to give information. It’s to create trust. That was my role. Some of it was about influencing and getting data and changing things…but most of it was about creating trust. Part of that was about learning that I have to create trust in my client…when I don’t know the answer…. There’s a great deal of pride in not knowing and saying you don’t know…very hard to come to terms with ‘I don’t know but trust me.’ But in a sense that actually does make a difference and it does help people, and it’s not misleading because we will figure it out and we have done it.” – Richard Russell Richard recalls a different scenario not so long ago when he was speaking to a group of business and marketing leaders. At that speaking session, someone introduced Richard as one of Europe’s leading marketers just as he walked up on stage. He initially did not consider himself an expert and had to get over the impostor syndrome in that moment. Much of the knowledge gained for that talk came from asking those questions that seemed silly at first. “When you do ask the dumb questions about whatever they are, you’re just getting people to talk about stuff that’s their expertise…. I don’t have much fear of asking silly questions anymore at all. I used to have a massive fear of it. I think just these various experiences of realizing that most of the things that are going on are not about whether I know or not. It’s about can I figure out the answer or can we find the answer or can someone find the answer…what do we need to move forward in whatever we’re doing? And how do we get that thing?” – Richard Russell 34:44 – Sharing Your Priorities Nick says when you tell someone you will find the answer and you go find it, you are developing a reputation that others can count on you to find answers. “Funny enough also…a lot of these questions…they don’t actually need the answer…. Sometimes the question is a mechanism to find out ‘can I trust you?’ Sometimes they’re worried about something that they don’t actually need to worry about, and they learn something else along the way – they don’t need to worry about it. This is especially the case with e-mails. You have these e-mail requests that come in, and sometimes some of them come in and they’re urgent…. And sometimes, you ignore them, and they go away, and it doesn’t matter. Judging which ones are the right ones to do that with can be hard…. There’s a lot of things that come in that aren’t actually important.” – Richard Russell Another aspect of getting back to someone with an answer is understanding why they need the answer. Richard likes to share the list of things he’s been working on to get answers for with someone and then ask if the person still needs them. Sometimes the answer is no because trust has been developed. This can be applied to e-mails by responding to ask if something is still needed (usually after a decent amount of time has passed since the request came in). It might save you time spent on something which is not necessary any longer. By asking if someone still needs something we are showing that we care, that we remembered, and that we were listening to what the person had to say. When something is deemed as still important, you can let the requestor know where it ranks on your priority list and then ask again how important it is / whether it is more important than other items. “Having that active conversation about ‘how important is this’ is a really useful tool to figure out what the most important thing actually is.” – Richard Russell This can work with managers, directors, customers, or other stakeholders. These individuals may have many requests but actually only care about a few of them. We can do the prioritization and bring it back to them to help us decide if something should take prioritization. Nick says we need input on priorities from others and that we should not be ashamed when we ask for guidance. “What I recommend doing, especially as you get more senior, is literally just maintain your own priority list…whatever you think is right. Use your own judgement on that. You might be wrong. And then share it with your managers or your stakeholders and say ‘here’s my priority list, and here’s my capacity. I’ll draw a line under what I think I can get done this week….’ And, have a conversation about it. It’s an opportunity for at least a good manager to educate you on how to make priority decisions…or for your stakeholders to explain ‘this is way more important than that because of…’” – Richard Russell Sometimes the conversations about priorities and how long something will take can be very helpful. Richard tells the story of a project he felt would take him 2 weeks just to develop a plan. Someone coached Richard that 2 weeks might be enough to finish the entire project and coached him on the way in which he was approaching the project. Richard said it helped him realize the project was not as challenging as originally expected. Something similar happened on a large project when Richard worked at Amazon. Something that was expected to take 6 months only needed 2 weeks of time to complete, but the team only came to the realization after truly understanding what they needed to accomplish without letting the scope creep too much. “But having that conversation and clarifying what the real need is, why it’s important, how you’re going about doing it…it was a bit of coaching, a bit of context setting, a bit of…just brainstorming together, a bit of collaboration…and presto – 6 months of work turned into 2 weeks…of a team of 4 or 5 engineers.” – Richard Russell 39:48 – Progressing to Team Lead One step between an individual contributor and manager can be team lead or technical lead. What would Richard say the team lead role really is and is not based on his experience as team lead for the bank early in his career? The team Richard was on was somewhat like a DevOps type of team today, but at that time it was a mix of DevOps, 3rd level support, and systems administration. There was a team of 6-7 people with variable levels of skill. Richard was among the most skilled on the team but in his opinion not the best. “The reason why I got that role was because the people who were more skilled than me or better than me were number 1 not interested in it, number 2 quite difficult to deal with…and demanding and critical of other people when they didn’t get it right. And then thirdly, they weren’t that interested in the business, the customer. …My counterpart at the bank would say…the reason why they wanted me to be the team lead was because I’m the only one in the group that really cared about the business and asked questions about their business…. Everyone else was just doing work, whereas I was interested in understanding it.” – Richard Russell Being a team lead isn’t just about rallying other employees, helping them focus, or coaching them. This is only a part of it. All of this is for one purpose – delivering value to the business or the customer. “To me the difference between a team lead and a manager is probably more about the formal responsibility of performance reviews and the administrative kind of people stuff. The team lead is kind of like that person who is…doing the leading part and getting people in the right direction without necessarily assessing individuals’ performance or hiring and firing and doing performance reviews and so on. That was what my role was anyway.” – Richard Russell, on being a team lead Richard was the person they felt they could trust for the business. His manager and others felt like the team respected him. Richard would coach the junior people and get the senior people working in the right direction. He calls the job “an influencing thing.” Richard thinks being placed in this role kind of happened naturally. A specific dynamic formed, and then there were conversations about formalizing the role at some stage. Richard calls it more of a practical role more so than a formal role. It was about caring for the client’s needs (the business) and being able to influence / coach people. “It had nothing to do with me having the best technical skills. I was good, and I was able to teach people…able to coach people…. It had nothing to do with me being the best technical decision maker.” – Richard Russell Richard mentions a member of the team who was extremely technical (more so than Richard) and was developing an architecture to solve a problem. Richard would help him understand the need for simplicity and getting things completed faster rather than engineering the perfect solution. It was about delivering short-term value. What was Richard’s interaction with his manager like when he was a team lead? Their conversations were more about how well the team was working, how individuals were doing, and if they were the right kind of people to put in a client-facing role. Richard had input on hiring / firing decisions as well. Richard also acted as the main point of contact with the client to stay aligned on what the team was trying to achieve and why, communicating this in both directions (to / from client and to / from the team). “The conversations in that role became much more interesting because I’m interested in the business and the people.” – Richard Russell Mentioned in the Outro We talked about Richard’s progression to team lead in this episode. As a late celebration of International Women’s Day, go back and listen to advice from some of the ladies of Nerd Journey to get different perspectives on the role of team lead. Episode 279 – Change Management: The Hardest Leap and Developing People with Marni Coffey (2/3) Episode 246 – Learning to Lead and a Culture of Excellence with Dr. Sirisha Kuchimanchi (2/3) Admitting we don’t know is something we can learn to do. It’s learning humility, just like when you ask those seemingly dumb questions about things you don’t understand. Do you still need this? This can certainly be great to help manage priorities. It could be a way to get someone to say they don’t need something as Richard mentioned. Asking this question could also be a way to discuss urgency and deadline if those have changed or just were not communicated. To learn more about what Richard does in his coaching business: Visit his website Visit his YouTube Channel – @richardarussell Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.

Cruise ship captains rely on the expertise of a local harbor pilot to safely dock the ship at a port. What if we as the captains of our careers sought the expertise of a harbor pilot to help us navigate a potential employer and their processes? Not sure how to find one? This week in episode 317 we explore this analogy of the captain, the harbor pilot, and how the collaboration between them makes for a safe docking event. We’ll talk through what a harbor pilot might look like, how you can be a harbor pilot for others, and how you can find one for yourself. Original Recording Date: 02-20-2025 Topics – A Topic Idea from Taking a Cruise, Common Mistakes of the Captain, Understanding the Harbor Pilot, Finding a Harbor Pilot, Wrapping Up 1:01 – A Topic Idea from Taking a Cruise Today’s episode is just John and Nick. We’re taking a break this week from having guests and want to share a topic based on a personal experience Nick had recently. Nick and his wife like to take cruises, and on a recent cruise he attended a special panel discussion with the captain and other senior officers. After some discussion about the jobs and careers of the captain and his senior officers, someone asked a very interesting question, and the answer to it gave Nick the idea for this topic. Here’s the question: What is the role of the harbor pilot that boards the cruise ship before we dock in every point? The collaboration between the captain of the ship and the harbor pilot is what allows safe docking of the ship at a port. This concept gave Nick an idea of how this can apply to searching for jobs. The captain in this analogy is the job seeker. The harbor pilot is a person with expert knowledge of a company who can guide you (someone who knows where you’re headed). What is the split in responsibility of the captain and the harbor pilot? The captain knows everything about the ship / vessel and is in charge of all operations. They know the capabilities of the ship. The captain knows the ship’s planned course of sailing and the approach planned for docking at a specific port. There is an entire bridge team working to operate the ship, and all are accountable to the captain. The harbor pilot has expert knowledge of the port. They know the weather patterns. They have worked with many different ships and are there to help the captain dock the ship at a specific port. Regardless of what the harbor pilot says or brings to the equation, the captain makes the final decision on what will be done. Even though their collaboration is a partnership, the captain has to be the one to give the orders. A captain has to take in the guidance from the harbor pilot through the lens of what the ship can do. The captain may choose to follow the harbor pilot’s advice or go against it in some cases. John sees many implications here: Am emphasis on collaboration between the 2 roles The captain has ultimate responsibility for the outcome of the ship regardless of who they collaborate with. The captain has to own the decisions. “You’re the captain. You’re ultimately responsible…just like if we are job seekers or managing our own careers, we are ultimately responsible for the outcome of that career.” – John White 4:55 – Common Mistakes of the Captain What are some common mistakes that a captain (or job seeker) might make? John thinks of not taking responsibility or just handing over responsibility for docking the boat to the harbor pilot (i.e. becoming a passenger and just doing what you’re told rather than being the captain). What does that look like in greater detail in a job seeker? Nick says maybe it is going wherever the wind blows you or only considering opportunities that come to you. This could also mean you didn’t do any planning. The captain has to chart the course for the entire voyage including the selection of routes to take and the order in which the ship will visit ports. Have you researched the company to learn as much about the culture as possible? Are you prepared to answer technical or other kinds of questions? Have you thought about the questions you want to ask in an interview, and do you know how to ask questions that suit the way you like to work as discussed in Episode 314 – Make Goals Inevitable with ADHD: Stressors and Entrepreneurship with Skye Waterson (2/2)? “Here’s the part of the sea that I’m in. These are the potential ports, and I need to know if my ship is appropriate for that port. That’s some of the deep research, And then, once we decide as captains of our careers that we actually want to do some much, much deeper investigation of a specific port, of a specific career branch or an organization to go to…we need to actually navigate how to dock….” – John White Other examples would be blindly applying to a company without doing any research or relying too much on a recruiter to help you navigate the opportunity (i.e. being too passive and not following up when a recruiter doesn’t respond in a timely manner). At some point, the captain has to make a decision whether to take advice as it’s given by the harbor pilot or to adjust it / go against it because the captain knows the ship better than anyone just as you know yourself better than anyone. Maybe a harbor pilot is used to more container ships, and a lot of the advice you get is geared more toward other types of ships. You as the captain have to know your unique capabilities and take customized action based on the advice. Listen to Nick’s example of this scenario from a recent cruise. The captain knew the ship had a particular type of propeller that could be rotated to hold the ship close enough to the dock / pier so passengers could safely enter / exit after someone had parked a small boat in the path of the cruise ship. “As the captain…the outcome that you need is not just docking, but you need…a way to get your passengers on and off…. It’s not just landing at the company. It’s landing with the right role with the right team.” – John White Nick says an obstacle in your way at the pier may require a different approach like we discussed to dock safely, but in a different scenario it could also be a red flag indicating you (the job seeker) don’t visit the port at all. John gives the example of very non-standard job roles being a red flag at a company. The other end of the spectrum would be ignoring all the advice about the port (a company) or not seeking advice in the first place. This assumes you are the expert but have also ignored local knowledge and local context. How many times has the captain even visited that port compared to their overall time on the ship? Nick argues that we can’t be experts at the port where we’re trying to dock the ship. The harbor pilot helps ships dock at this port on a daily basis. John feels like he has made this mistake before. About once per half, if a recruiter reaches out, he has a conversation with them to understand a specific role and practice interviewing skills. John stresses the importance of our need to maintain interviewing skills. At times John has approached these conversations without the same level of preparation as when he is seriously interviewing (i.e. not even looking for a harbor pilot). Nick has made a similar mistake. Sometimes recruiters have reached out with an interesting role, and he was just too busy to dig deeper other than saying thank you. That’s kind of like disregarding the port as a possibility. 13:35 – Understanding the Harbor Pilot We said the harbor pilot has expertise on the port itself. What might the harbor pilot look like at any given company? This could be anyone who currently works at a company or who has worked there in the past. This person would understand how the company runs internally and details of what a role is truly like. Nick says connecting with a harbor pilot can help us set the right expectations when considering a job at a specific company. It sets expectations about docking the ship at this specific port and how you might do it safely. John says the person acting as a harbor pilot may understand internal priorities and how to navigate those. It could even be someone who has gone through the interview process at the specific company for a similar role, even if they don’t work for the company currently. People who have gone through the interview process at this company in the last 6-12 months will be more helpful than those who went through it 5 years ago, for example. John thinks the harbor pilot could be people at the company who interact with the specific role you’re targeting. If you’re looking for a role in sales engineering, maybe you seek out someone in professional services or technical account management. If you’re looking for a role as a cloud engineer, consider people in IT Operations, architecture, networking, or perhaps even cybersecurity. If the company provides goods and services, what about finding someone who is a customer of that organization? Ask the customer how their interactions have been with that company just in general. If the customer works with representatives of a company on a regular basis (i.e. like working with representatives of a technology reseller), it provides insight into the responsibilities of different roles at the company. Customers who are part of a formal advocacy group for a vendor’s technology solution may have even greater context to share on the roles and responsibilities of people at that vendor and the overall company culture of the vendor. Advocacy program members may also have good relationships with employees at the vendor and could be willing to connect you with someone to have a deeper discussion. Loving the technology being used at a company (regardless of the role you are seeking) is one sign it might be a nice place to dock your boat (but not the only sign, of course). Nick thinks we would turn to our immediate professional network first. Hopefully we have kept professional connections warm over time. Ramzi Marjaba had some great suggestions in Episode 307 – Sales Skills: Professional Networking and Continued Practice with Ramzi Marjaba (1/2) even if you haven’t. If you reach out to someone, be honest about what you’re trying to do and the help you need. All they can say is no. John realizes he has acted as a harbor pilot to others who have reached out to him in the past. Nick re-iterates that John was his harbor pilot for a particular job in the past. Several years ago, when John was a harbor pilot for Nick…he referred him, explained the process, shared some of the expectations of the role, etc. But, in this case, Nick was still the captain. More recently, when people have reached out to John, he has offered to have a conversation with them. John will provide context to the person on the organization, even if the open role is in a different group from where John works. A harbor pilot might be able to give insight into the skills required for a specific role and how it has changed over time as a result of the company’s direction. Nick refers to this as some of the stuff that might not be in the job description. John says the words on a job description may mean a very specific thing within the context of a specific organization. When he was at Google, one of the interviews was to determine how “Googly” a person is. It meant something very specific. To take another example…if a company says it is looking for people who can embrace change, what does that mean for that organization? Does it mean job responsibilities might shift every 6 months, you have a different manager each year, that you might have to relocate, etc.? You need a harbor pilot to tell you. The harbor pilot has more context on where you’re going. Nick thinks a great recruiter could be your harbor pilot. He remembers in times past working with excellent recruiters who helped and guided him through every stage of the interview process. Nick says some of it is going to be determined with how much rapport you have built with the person you want to be your harbor pilot. With good rapport established, people may be willing to introduce you to others they know perhaps without you needing to ask them to introduce you. John gives the example of having systems engineer in your title. Sometimes you might be contacted by a recruiter for a role with the same name but in an industry that uses the term differently. In manufacturing, for example, a systems engineer may be responsible for integrating the hardware manufactured with the software. John will usually take the time to politely explain to a recruiter what his experience has been as a systems engineer (in this case working inside a sales organization) so the person understands the nuance in the role across different industries. Even this exercise builds rapport and could lead to future opportunities down the road from the same recruiter. Recruiters in California are not allowed to ask candidates about their current salary. In addition to sharing that he is not interested in a role or that its pay range would not be enough to want to change jobs, John can make the recruiter’s life easier by sharing his salary requirements. “The more vested a recruiter is in landing you, the better…harbor pilot they are going to be…. When they feel like now they’re a little bit more invested in you, that’s when they’ll be way more communicative.” – John White John has also had recruiters give him additional context about why they reached out to him over others (i.e. a need for specific skills / experience, etc.) which might step beyond what the job description says. The key recommendations from John on this are building rapport, being open and transparent, and continuing with a conversation. Nick reiterates that we shouldn’t discount our own ability to be the harbor pilot for someone else. “Wherever you work, whatever you do, whomever you know…you could be this for someone else seeking a job. And perhaps, if you have done that for somebody else and they get the job or they have a good experience…you’ll understand the flip side of that coin.” – Nick Korte, on being the harbor pilot for someone else John says we might reflect more on it if someone for whom we have been the harbor pilot gives us feedback on their experience and the value we provided along the way. 26:31 – Finding a Harbor Pilot There are many people who could be a harbor pilot for you, but how do you find them, engage them, and get them to help you? The harbor pilot has a vested interest in your success. Crashing the ship can also be a poor reflection on them. We mentioned it earlier, but immediate LinkedIn connections are one option. Try looking through job descriptions for the top technologies listed as required competencies. Look for community groups centered on these technologies (on LinkedIn or otherwise) in your area (or even outside your area). Finding and connecting with these community group leaders might be helpful to gain insight as to what types of companies use specific technologies. Community group leaders may even know someone at the company that has the job opening or help you make a connection that could help in some way. John doesn’t recall looking for a Nutanix User Group or even a virtualization user group when he was interviewing for his role at Nutanix. He could have tapped the community to get their point of view on Nutanix as technology vendor, etc. If you’re in a role at any company and deal with vendors or technology resellers, try asking them if they have worked with a specific company to get a perspective. Don’t do this using your work e-mail account, of course! Resellers of a specific technology can speak to interactions they have had with employees of different vendors. Perhaps the vendor you work with could introduce you to someone they know at a specific company who could help (i.e. someone who would be willing to do an informational interview). We discussed informational interviews with Mike Wood in Episode 169 – A Thoughtful Personal Sabbatical with Mike Wood (2/2). John has both given and asked for informational interviews in the past. The purpose of them is to gain more information on the company and not an expectation of it being a formal interview with the hiring manager. John tells the story of having a good conversation with a friend of a friend at Nutanix before he joined that was extremely helpful. Try to think through who to reach out to through the lens of what is most important to you in a job / employer. Is it company culture, being paid well, great benefits, what managers are like, etc.? Your priorities might help you choose who you know that could speak to these points. GO back to the Must Have List created by the hosts of Real Job Talk. If you are actively managing your network and genuinely listening to people over time, you will understand what different people in your network care about. If they care about the area you want to know more about, ask them if they know anything about the specific company where you’re interviewing (or even its competitors) that can help you. John finds the analogy exciting and is starting to view some things we have discussed in the past through a different lens. We’ve been discussing actively managing your network, reaching out to people, and the importance of getting people to help us navigate situations and organizations. We spoke about being a harbor pilot for someone else. What if we reverse engineer that situation where we are a harbor pilot to someone else? Think about the connection the person who reached out had to you. Understanding the connection might help you identify ways to find your own harbor pilot through similar connections. Maybe that’s another outside the box way to help yourself find a harbor pilot. Be curious as to how people found you and why they reached out if you’re giving an informational interview. You might have a blog, a podcast, or something in your LinkedIn or social media profile that makes you more approachable because your work is in the public eye. This applies to others you could reach out to for help. Asking some questions of the people who reach out to you for help will make you a better interviewer and sharpen questioning skills for when you are in a job interview situation. By asking you for help, the person asking is interviewing you. Taking the time to have a conversation allows both them and you to practice interviewing. One of the best books Nick has read in the last year is called Talk to Me by Dean Nelson. Nelson is a journalist who wrote this book about asking better questions and being a better interviewer. Nelson breaks down popular interviews and the questions asked, and it is fascinating. The concepts discussed in this book apply broadly across many fields. Reading this and internalizing the lessons will make you a better job candidate and a better job interviewer. 36:30 – Wrapping Up You are the captain. You make the final call, and you have to own the decisions. You should know everything about your ship (as much as can be known) and have a willingness to take advice from the harbor pilot. Seek expert guidance from a harbor pilot, and have a true collaboration with them. Accept that they are experts at something you can’t be an expert at (your ship at their harbor). We discussed what the harbor pilot might look like and how to find them. Maybe acting as a harbor pilot for others will help you find a harbor pilot in the future. In the maritime world, the harbor pilot has to come help the captain of the cruise ship. It’s mandated by law. In the case of the job seeker, it is going to take some work to get the harbor pilot onboard. It likely will not be given to you. The responsibility and planning have to be there if you truly want a harbor pilot to help you dock. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.

How prepared are you for a career emergency like losing a job? Disaster recovery plans for your career, just like troubleshooting, start with good documentation of technical and business accomplishments. David Klee returns in episode 316 to share the prep work required for building and testing a disaster recovery plan for our careers. You’ll learn how to use David’s technique of looking in the mirror (inside yourself) and out the window (out into the world / greater technical community) to quiet the fear and document and identify transferable skills that can be listed on a resume, on LinkedIn, or shared in a job interview. As we talk through each topic or recommendation, David shares concrete examples from his experience to illustrate how they apply. Original Recording Date: 01-20-2025 David Klee is a returning guest and the owner and chief architect at Heraflux Technologies. If you missed part 1 of this discussion series with David, check out Episode 315. Topics – Keep Your Eyes Open with the Mirror and the Window, Accomplishments as Repeatable Processes, Transparent Outcomes and the Hero’s Journey, Avoiding the Cold Start with Prep Work, Testing a Career DR Plan 3:28 – Keep Your Eyes Open with the Mirror and the Window We all have intentions of keeping disaster recovery plans for our careers and lives up to date, but we fall short. “The tech side is arguably the easier part. DR for the career, especially in this day and age…if you get cut today…what are you going to do? What’s the next step? Are you ready to take an unplanned detour in life? Who do you know? What do you know? What have you done that you can talk about or reference to help you get the next leg up? What have you done that’s so proprietary that you can’t mention a spec of it or it’s so proprietary that it doesn’t transfer out of that job?” – David Klee, on disaster recovery for your career David talks about his first job in college working for a market research firm. The firm had a platform with its own scripting language that could be used to build websites or surveys. David acted as an intermediary between the team that built the platform and the team that used it. “I spent three years there. What did I learn? I learned how to script in a language that does not leave that company borders. That’s not a good career builder unless you intend to stay with that company for your entire career, and this is the 2020s. Good luck with that.” – David Klee John says this could be something we could ask about in an interview. A company is basically asking for an employee to be a captive of that group because of the proprietary nature of the language. David says in most cases like this an employee will not know it until they are in the situation. "It takes keeping your eyes open…no matter how much you enjoy your job…is the captivity of this job worth it? Is there job security? Do I enjoy what I’m doing? Am I growing, or am I just moving laterally? What’s worth it? " – David Klee In this job at the market research firm, they found out David was a good troubleshooter, and they wanted him to fix bugs on the platform others had built. Even when David proposed that it would be faster to rebuild the platform on newer versions of software, they insisted he focus on patching the existing platform. What does David mean by keeping your eyes open? “Keeping your eyes open involves looking at yourself in a mirror. And then, look out the window.” – David Klee David says to look in the mirror we should think about what we want to do, what we enjoy doing, and what we do and don’t like about our current job. Early in his career, he wanted to break out of just being an IT worker. He wanted to be a business driver rather than part of a cost center. “Look at your value to the business. Am I there just keeping the lights on? And what about that do you enjoy?” – David Kleep Looking out the window involves thinking about what you’re doing, what you’re getting paid, and how much you’re appreciated by the business. What are you doing that can be transferred to another business of any size, and how much satisfaction of doing your current job would be retained in making a move? “You don’t have a lot of answers when you’re just starting out, but that’s where you start talking to people. Find people in that area of any specialty, be it IT or whatever, that you enjoy, and there’s probably a community around it. I got lucky. I found the SQL Server community in 2008…. Here’s a room of 50 other people that enjoy the same exact thing. This is cool, and I can talk about it with them.” – David Klee Someone David knew well started a SQL Server user group in Omaha, Nebraska. David found out about the group and was there for the very first meeting. David got to know the community around a specific technology. He would ask people where they work, what they did each day, what they did and did not like about their job, what they wished they could do more of, etc. “You’re getting paid twice as much…interesting. So, there’s less that I don’t like in that role. There’s more of the stuff that I like, and your company gives you time to focus on the stuff that you like to do. Ok, let’s talk. Who do you know, and do you have an opening in your company? …or, I’m not there yet qualification-wise to be able to get that job, but hey, you do this stuff day in and day out. What can I do to learn more? What can I do to push myself? If the company that I’m at is just focused on keeping the lights on, what can I do on the side to grow? …it’s that want to grow and do more that not everybody has…. How can I learn everything that I need to know to go beyond an IT Operations lightkeeper kind of role? What can I do to help the company see the value in IT to invest further in it?” – David Klee, giving examples of what we might talk to others about at a community meeting David considers himself a lifelong learn who wants to know as much about everything as he possibly can. 9:41 – Accomplishments as Repeatable Processes David talked about being a cost center compared to being a business driver. John says at the individual contributor level, the delineation may come down to what you’re working on. Are the systems for the company or a specific product that is customer facing? David says think about how much money the business makes per day because you kept a system up and running. When David worked for a performing arts center, he saw the business need for improvement in volunteer management for each show. David also wanted to learn how to program in .NET and took it upon himself to build a volunteer management system. He knew nothing about .NET and worked on this project outside of his normal work week to beat the deadline for the next season opening. “I built a volunteer management system. It integrated with the ticketing system. The house managers could hit a button, open a show directly from the ticketing system. It pre-filled and populated everything. They had templates for all the positions they needed…. The first week it went live it saved 55 staff hours between 2 people. That was cool…. That’s the resume builder right there, and that actually enabled me to get my next job…. That’s the resume builder because not only did you learn a tech skill…but it showed that you can think about the business and not just a tech feature.” – David Klee, describing the outcome of his work building a new volunteer management system John emphasizes the need for quantification so the next person looking to hire you can understand your value to the organization. Saving that many staff hours per performance translates to dollars. David says this allowed 2 people working 80-hour weeks to work only 50 hours per week. Nick highlights an irony. Many companies do not have enough systems documentation to troubleshoot effectively when there is a problem. When we are applying for a job, we need documentation that indicates our expertise level to be deemed competent enough to go and work on a system which a company may not have documented well. But, if we do not document our own experience well, we have a problem! We have to be able to prove our competence and experience to another company. We might be able to succeed in a technical interview by answering questions, but we need proof of our expertise. Companies may want us to do and not document, but around performance review time documentation becomes critically important. This is at odds with the overall culture as it relates to documentation. “And the documentation onus is on you. They’ll never give you the time to document your successes because they don’t want you to jump ship and bring that list of successes with you. So it’s on you. How much time do you have nights and weekends to keep up on this stuff? You have to make the time.” – David Klee, on documenting our accomplishments / successes How detailed should the list of our own successes / accomplishments be? David says it should be detailed enough to make it repeatable, keeping in mind we cannot take proprietary information from a company. David says the knowledge of building a volunteer management system has stuck with him over time. He has built web applications ever since. “The framework has changed. The foundation has changed. But the knowledge of how to take a business challenge, justify and quantify the impact of solving it technically, implementing it, and then measuring the outcome…if you can document that, that’s what you need for the proof…. What did you do and why did you do it? Give me 3 sentences on how you did it and then tell me the outcome.” – David Klee, on documenting accomplishments According to Nick, getting the refined outcome statement for your resume for an interview takes writing down your accomplishments a couple of different times. Document everything in a brain dump format, refine it a time or too, and pull out those impact statements that are most relevant for a specific role. David says we have to make the time to do it so we can stand out. He also shares the kinds of questions he asks a current mentee. The guy David is mentoring mentioned he had built a web application to help track household finances. It was a PHP front end with a SQL Server back end that ran in his home test lab. QuickBooks may have been easier, but David’s mentee wanted the experience of building the application himself. When asked how much time it took, David’s mentee said it took him longer than it probably should have, but he wanted to learn how everything worked. David will often give his mentee new ideas for things to explore, and the mentee will spend his weekends tinkering. “The tech side of this is easy. Even just a lateral move in the business…how do you justify that you’re going to actually solidify a business need to fill a role? If it’s a promotion, how do you justify that? You have to keep track of those.” – David Klee David gives examples of the outcomes of some of his consulting work – saving an airline over 30 million dollars in database licensing, added 500 million dollars to the valuation of an electric vehicle startup, worked with 4 of the 10 largest hedge funds in the world, migrated 140 terabyte SQL Server database across the country in 18 seconds, etc. To go back one step, David has multiple sets of documents – business accomplishments and technical accomplishments, stressing that these are two different things. He spends one Saturday morning per month making notes on his accomplishments. “And to be able to just rattle that off and say…we did that, and we can do it again. Not only did we have a good outcome with it, but we documented the process. It’s a repeatable process…. Anybody at that company could follow that process and not call me again to do that. And I’m happy for that.” – David Klee, speaking to the success of migrating a very large SQL Server database which came from not only doing it but training people at the company to do it next time The above migration / process or recipe can easily be applied in a quick, useful way to help another company. 18:37 – Transparent Outcomes and the Hero’s Journey David shares the story of one of the most successful troubleshooting experiences that came from a SQL Server migration project with a 2-week timeline to get it onto new hardware after the SQL Server had been running for 8 years. There was no documentation of the environment, and no one at that company who had tried the migration previously could figure it out. “We got this running 3 hours and 10 minutes into a 4-hour maintenance window. I didn’t sleep for a day after that because I was so jacked from nerves. But it worked. And the next morning, because I couldn’t sleep…I’m on a laptop on the couch documenting every single thing that I did and took all the screenshots that I’d been taking through the entire time, stitched them together, and built them a how-to document. They didn’t ask me to do it…but they now have the how-to for how to do this again down the road…. Nobody there had bothered to look into why the system stayed up and running those 8 years.” – David Klee, recounting a very difficult troubleshooting exercise Because David knew infrastructure and coding, he was able to dig into all the right areas to make the project a success. David documented the technical outcome and the business outcome from the troubleshooting session. He also did a post-mortem to explain why the business should have invested time and resources to understand that system before they attempted a migration. He also recommended they re-write a specific application because they no longer had the source code. Nick says the technical and business outcomes David generated from his brain dump are evidence that he’s a good troubleshooter. “The hilarious thing is that at the end of the day, for the business, nothing changed. That platform that they used thousands of times a second was still up and running, so literally sometimes the business outcome is transparent. To be able to tout that to the right people, they get it. But to the non-seasoned recruiter, they don’t know. So, you have to be able to spin that…. You don’t have to embellish anything, but you have to know what to bring to the surface to get them to actually understand the significance of what you’re talking about.” – David Klee John wonders if the right outcome for the business is that nothing went wrong? David says this is how he got into virtualization. Nothing went wrong when he moved systems for the performing arts center from physical to virtual during a time when tickets were on sale. Not crashing was the success. In other cases, database migrations for large companies have been minimizing downtime and disruption of the business (i.e. fitting into a tight maintenance window). Technical outcomes in these situations were things like completing a database upgrade, moving to newer hardware, successful patching, reducing future problems, etc. The business cares about uptime alone. A business might not understand a system is critical because of underinvestment, and they may not see the value of the system’s uptime as a result. When someone puts forth a ton of effort to reduce downtime for a specific system, people might not care because they don’t know. David doesn’t have it in him to let problems / systems crash and burn. Not everyone operates at this level of moral standard. John says a business demonstrates what is and is not important based on budget, time, and attention. It’s difficult as an employee to go on a hero’s journey and fix a problem (potentially sacrificing mental and physical wellbeing) for no recognition. “I’m with you to a point. But at the same time, if the hero’s journey to fix something for no recognition means I’ve grown as a technologist with a transferable and portable set of skills that will elevate my next step, is it worth it? And in some cases no and in some cases yeah. That volunteer management system at the performing arts center…that was 600 hours of work in 4 months outside of an 80 hour a week job. That was a lot. But that skill showed that I can build tools to solve business problems. It gave me a more modern framework to implement that skill, and it gave me an industry standard means to demonstrate it. Maybe I’m a glutton for punishment and a workaholic, so I come at this from a rather jaded perspective. But if your home situation and family situation allows you to do it for bursts, I claim it’s worth it. You don’t have to do it all day every day for 25 years, but to do it in bursts to hit a marker that you give to yourself…you’re not running an ultra-marathon by training for 20 minutes a week. There’s work that comes along with it, and there is sacrifice in a lot of this stuff because the knowledge isn’t just going to pop into your head. And work’s not going to give you the time to learn this stuff. They’re just not…not unless you have a truly special organization…. You’ve got to push yourself. It pushes your career. It pushes your ability to prepare.” – David Klee 27:25 – Avoiding the Cold Start with Prep Work What if the business you work for goes under / goes out of business? What will you do tomorrow? David says this has to be in our minds. From a business and technology perspective what do we do? How can we make the next step easier? Nick thinks we would need to know Where all documented accomplishments are (if that’s been completed) Who to call and network with about job prospects Understand / have a tight handle on our finances “It’s a hard one, and that goes back to the loop of personal troubleshooting and documentation. Say you do a job for 5 years. Your last day on the job…are you going to remember all the accomplishments that you had during that 5-year tenure? No. Are you going to remember that monthly? Sure. Take a Saturday morning. Sit there with a good cup of coffee or something, and just write. Throw it in a Word document. Throw it in Dropbox or OneDrive or wherever…. It doesn’t have to be pretty…. What did you enjoy? What wins did you have? What problems did you solve? What did you learn? What did you do for the business? What did the business do for you? If the business did something cool for you and you liked it, maybe that’s a pre-requisite for hiring at your next job. A couple of the companies I worked for…they were nice enough to send me to some conferences. I learned a ton. Document it. Take the time. Yeah, it’s time out of your week. It’s not fun. It’s not enjoyable. But at the same time, it gives you a foundation to say, ‘I did this.’ And if you’re looking for another role, and if it’s a role dissimilar to what you’re doing today, how can you adapt what you’ve done to the new industry or the new role or the new vertical? And that’s a hard one for people to wrap their brain around. All this stuff applies. You just have to spin it the right way.” – David Klee David shares that his brother finished a career as a music teacher at a high school and became a police officer. Transferable skills were things like working with crowds, training and educating, getting people to work together, etc. David mentions a friend who worked for a database monitoring company and built software and tooling for that company. This friend later moved to the financial sector. Though the database being monitored might be different, the framework and the foundation for documentation / monitoring / quality assurance testing / user acceptance testing all still applies. John says the typical scenario is someone losing their job and needing to come from a cold start. The person has done no disaster recovery planning and needs to run their disaster recovery plan. “Clear your mind, and start thinking. Give me the top 5 things about the current job that you really enjoyed, and then make a beeline and run…. If you like infrastructure, look to see who’s hiring in your town. Look for those user groups…. It doesn’t take more than a meeting or two if you’re comfortable around people to actually get to know some of these folks…. Dig in your heels. Get yourself out of your comfort zone and go to these things and start talking to people.” – David Klee David mentions meetup.com and the Azure Data Community as great places to find technical user groups. Don’t rule out business user groups as well because it doesn’t have to be tech focused. David says we don’t have to be way out of our comfort zone to say hello to someone at a user group, tell them what you do, and ask what they do. Nick says we can even ask people if there is someone they know that we should meet. “The worst thing you can do is nothing. Nothing will not move you forward. Even a basic conversation, if nothing else comes from it, you’ve still talked to somebody. You’ve still got a connection now.” – David Klee John says many of us have critiqued an employer for a lack of disaster recovery planning or business continuity planning, but at the same time, we haven’t done that same kind of planning for our own careers. We have to take accountability for that in our own lives. “Nobody is going to hand you a new career or a job promotion on a silver platter…. It just doesn’t happen. And for all of the folks that sit around waiting and they just think that better things are around the corner…the odds are, if you don’t push, better things are not around the corner. It may not be any worse, but it’s probably not going to be any better Career paths in IT with a company that’s willing to invest in you are rare these days. They want you to do a job, and that’s what you’re there to do. There’s not a track for promotion or advancement. So, the convention in the US is to quit your job and find a better one to get that promotion. I hate to say it. I’d love to have career paths. It just doesn’t really exist all over the place, so it’s on you. What are you doing?” – David Klee For David, his action was going independent and working for himself. It gives him the freedom to select technologies that have business value and learn them to the depth of being able to tell other people how to use them. This choice (business ownership) allows him to be flexible and change direction when needed. If the world changes or shifts, we can pivot our careers. David was an infrastructure admin who became a software developer, a database administrator, a consultant, and a consulting firm owner / nerd of all trades. “You can pivot, and it all just builds. And that list of accomplishments, that prep that you’ve done to build the foundation to make essentially disaster recovery for your career easier. Failing over a database to a different site that’s already been replicated is a right-click go kind of operation. If you’ve pigeon-holed 20 years of your life on a system that is totally proprietary and non-transferable, what are you going to do?” – David Klee David tells the story of a friend from one of his first jobs who was laid off after 25 years of working on proprietary systems. The friend had not done the prep for career disaster recovery. It took 7 months to figure out what to do after that for a job with half the pay. “The prep wasn’t there. It drives me nuts because the prep needed to be there.” – David Klee, commenting on the lack of preparedness of a friend who was laid off 35:47 – Testing a Career DR Plan Even for those of us who agree we need a DR plan for our career or have some form of one, what elements might we not be thinking about? What are some of the unknown unknowns? David says if we were to take our company’s IT systems and fail to DR right now, something will not work because of an undocumented change, a software update, etc. “No DR strategy is perfect unless you test it, and who wants to test a career DR strategy? …It goes back to…can you troubleshoot? Can you identify the things that are missing now that you’ve failed over and what isn’t working? …Go through the feedback loop. Can you improve and clean up and fix? And, arguably, don’t make it equal to where you came from. Make it better. Because then, the bar has now risen, and it’s just an uphill climb after that. There’s no downhill slide.” – David Klee The only way Nick can think of to test a career DR plan is to follow the documented plan you have to see how fast you could get an interview and into the final round. David says even if you’re content where you are, go look for another job. If you get an offer, that’s a pretty good DR plan if the job you looked for is something you want. If you try this and can’t make it past sending in a resume, you have a safety net because you do not have to leave your current job. “You can start to look at the mirror. What am I not doing that’s making me less marketable to these folks? And that’s a hard pill to swallow…. If you’re not intent on leaving your current job, there’s really no harm in it….” – David Klee Nick cautions about burning bridges. If you are going to interview for a role, really consider it. Be kind and courteous to recruiters and the people you speak to during the process, especially if you have to turn down an offer. David says if you have a job and you’re looking for a new one, there is nothing wrong with taking a job that will better your situation. “There’s a certain number of hoops you have to jump through to get a job. Have you even written a resume recently? Have you written a cover letter if you think that’s necessary? Have you submitted a job application and gotten a recruiter to call you back? …And, have you been able to get past that…recruiter screen to get to talk to whatever the next level is…? And if you are consistently getting to hurdle 5, maybe you don’t need to worry…. The vast majority of people don’t even start because they think about that last hurdle – what if they offer me somehting and then I need to make a decision about whether to leave or not? Well, that’s not the situation that you’re facing yet.” – John White John mentions chats with hiring managers, skip level leaders, vice president level personnel, and even technical presentations as hurdles and levels in the interview process / road to getting a new job. Not taking that first step in the process is the mistake everyone is making. As a consultant, David does consistent job interviews (5-10 times per week probably). He’s had a lot of practice. “It takes some experience, so start the process. Because if you are just jittery, nervous, can’t speak a sentence to these folks…how are you going to make it to that next level? How are you going to get to the point where they’re extending you an offer? It’s hard. It takes time. It takes experience. It takes a feedback loop of improvement in yourself to understand how to approach those things. And I’m not saying just interview to waste somebody’s time, but if you are seriously looking, interview for things that may be tangential to what you’re interested in in the hopes that they may actually be better, a better fit, a better path…because the more experience you have with it the better.” – David Klee, on interviewing David got a job as a database administrator (DBA) because he knew a lot about infrastructure and had some SQL Server experience. They made him a DBA, and David really enjoyed it. A business doesn’t refuse to investigate disaster recovery because the disaster recovery target might be better than the existing infrastructure and present a difficult decision. John reminds us that people make similar statements about their career disaster recovery every day. “If the poop hits the fan, what would you do today? What would you do tomorrow? What would you do next week? What professional network have you built up? What proof do you have in the industry of what you’ve actually accomplished? Who can you call to vouch for you? They always ask for references. What can you do? What can you reference? What can’t you reference? What can you make veiled allusions to? …I hate the phrase ‘brand awareness…’ but to have visibility and verifiable proof that you’ve actually done something – that’s powerful. You need to have that, and it goes back to the prep. Push the fear aside. That’s the hardest part. A lot of folks are afraid of the end result. A lot of folks are afraid of the process. A lot of folks are afraid of the act of change…because it puts you out of your comfort zone.” – David Klee John thinks all of these fears are stand-ins that prevent us from facing the fear that losing our position is a very real possibility. Facing this fear of the possibility of losing your job could produce crippling indecision too, so people decide not to think about it (the worst thing you can do for disaster recovery). David takes us back to that SQL Server User Group meeting in 2008 and says back then he did not like speaking in front of a crowd. He would help coordinate things from time to time but was always the guy in the back. People at the user group knew the kind of work David did each day, but he didn’t think much about it as something to share in a presentation. In 2010, they decided to hold a SQL Saturday event in Omaha. When a speaker backed out at the last minute, one of the leaders asked David to speak on SQL Server virtualization instead. David agreed to do the presentation and really enjoyed it. There was someone sitting in the back of lthe room during David’s presentation that day, and it just so happened to be the author of SQL in a Nutshell Kevin Kline. Kevin e-mailed David 6 months later to ask him to co-present on the same topic at a very large conference. In November 2011, David delivered his first big technical presentation at the conference. “I figured there’d be 30, 40 people in the room. No. They closed the doors 30 minutes before the presentation because they hit the 500-person fire marshal limit. And we give an hour-and-a-half presentation in front of a packed room, and it turns out his role in the presentation was to be comic relief between sections and he wanted me to give 95% of the presentation. That was, right there, what let me get into consulting for myself…. That was the thing that showed that this thing that I leaned how to do on my own is something that not everybody could do, and it gave me te confidence to be able to run with it – both from a tech presentation perspective and a career perspective and literally make it work…. It was a topic that I knew. It was the unknown knowns. And from telling people about it I had the experience of being able to share it in a way that they could understand even though the topic was foreign to them back then. And it worked. It clicked. I would say that was the career disaster recovery to a better infrastructure. Things just skyrocketed after that. I spoke at 118 SQL Saturdays after that. It set the awareness in the community of what I could do so that in 2013 when I went independent as a consultant…we got our first customer day 3 all from somebody seeing me at a SQL Saturday event talking about this topic…. So unbelievably cool…it’s everything that accidentally came together in the whole career DR except I would say this was a proactive career failover for disaster preparedness…. We’ve been in business now 11.5 years…. I look at tomorrow. Where do I need to add stuff to the career? Where do I need to add more awareness to any of this stuff? Where do I need to be so that if the world shifts in a year, I’m ready? Every day I look at the mirror. You have to…because if you don’t, you’re going to be caught off guard. It’s the last spot you want to be in both for you and your family.” – David Klee David still has the photo from that conference that someone took looking from the stage to the audience during his session. David put himself in a position to be lucky by going deep in multiple areas, sharing his work, and learning in public. “That one presentation in 2011 was 12 years in the works.” – David Klee, on all the events that led to the presentation that changed everything…or as John says, David became an overnight success 12 years later David’s business is still running strong despite the pandemic, and he doesn’t have to market. The work comes to him because of the brand awareness he developed. For this, he is very thankful. And the accomplishments are documented in the public eye. To follow up on this conversation with David: Visit davidklee.net or heraflux.com (the home site of David’s consultancy, Heraflux Technologies). You can also contact David on LinkedIn. Mentioned in the Outro Can you see the loop of personal troubleshooting and documentation now? After listening back to this discussion with David, Nick was reminded of Episode 284 – Draft Your Narrative: Writing and Building a Technical Portfolio with Jason Belk (2/2). We never used the word narrative in this discussion, but that’s what we’re building by doing the documentation. Documentation is an input to having a narrative in the first place. We have to take the time to do the documentation of our accomplishments to avoid the cold start situation of needing a job having done no prep work. There were so many questions David suggested we think through as we document. David says we’re documenting repeatable processes. But it turns out the documentation process itself is a repeatable process that we can use for our work solving a problem and for our accomplishments. After listening to this, is the documentation of your technical and business accomplishments up to date so you can share them in interview discussions, promotion discussions, and even in conversation in community groups? Look in the mirror and out the window, and find the communities that can help you learn! Special thanks to David on suggesting the topic and collaborating with us to create a create a great discussion. If you have an idea, please e-mail us or contact us on LinkedIn. Let’s collaborate and create a great show! Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.

Can writing documentation beef up your troubleshooting skills? This week in episode 315 David Klee returns to explore the connection between effective troubleshooting and documentation. We’ll discuss appropriate levels of detail for documentation and explore it as a skill building exercise. Listen closely to hear why good documentation can make all the difference in a regulatory compliance audit as well as in emergency situations. Also, we’ll talk through some interview questions you can ask to determine the value of good documentation within an organization. Original Recording Date: 01-20-2025 Topics – An Exploration of Troubleshooting, Pre-requisites for Effective Troubleshooting, What Should Be Documented, Forms of Documentation and Emergency Preparedness, Interview Questions and Employer Perceptions 2:32 – An Exploration of Troubleshooting David Klee is a returning guest and the owner and chief architect at Heraflux Technologies. If you missed the previous discussions with David, you can find them below: Episode 119 – Tinkering into Specialty with David Klee (1/2) Episode 120 – A Time to Build with David Klee (2/2) Episode 309 – The Consulting Life: Managing Travel and Becoming a Better Communicator with David Klee (1/2) Episode 310 – Finding a Better Way: Contracting, Independence, and a Consultant’s Reputation with David Klee (2/2) David approached us about an idea for another topic to explore. After many years in the industry (11 of them as a business owner), David began to think about patterns he has seen and what has made him and many others successful. “What has actually made this work? And it’s the art and the science and the luck of troubleshooting…. What makes some of the best technologists arguably some of the best troubleshooters in the world, and then how do you apply that to life? …There’s a lot more than just knowing a technical feature or two or being able to Google faster than the person next to you. I have a lot of fun with this topic.” – David Klee, framing our discussion Philosophically, David believes troubleshooting is as much an art as it is a science. There is a foundation one needs to be a good troubleshooter, and David tells us this stems from our childhood curiosity about why things do what they do. David tells the story of learning to use a screwdriver at age 5, taking the family’s VCR apart, and successfully putting it back together again (which may or may not have landed him in trouble). Over time some people have a constant need to know why something is what is / why it works the way it does. David sees this present in some people but not all people. “When you look at those that are truly great at an industry…they want to know why, and they don’t stop until they know why.” – David Klee David mentions the Dunning-Kruger Effect, which speaks to breaking up the things we know and don’t know into 4 quadrants: Unknown unknowns are the things that get people into trouble because they think they know these but do not Known unknowns – David considers this area enlightenment in IT and a way to know where the boundaries are “Unknown knowns are the things that I consider you a master at a technology or a topic of anything because what you know becomes so integrated into your frame of reference and your being that you don’t know that you know it. You just do it. And, when you hit that point of a mastery of something…you may not be able to explain how you do it or you may not be able to tell somebody the steps to do it. But it’s just muscle memory. It’s just go. You do, and it works…. The truly good educators are the ones that can actually take what they know and dial it to the level of the people that they’re talking to. Some experts cannot do that, but they are so good at what they do. Others can. It’s fascinating…. It’s the unknown unknowns that gets people into trouble. It’s the unknown knowns that really separates people.” – David Klee We did not mention known knowns, but it would be the final quadrant. John says it’s the idea that you can master a skill or process but not have mastery of teaching or explaining that skill or process. Doing ang teaching could overlap, but they do not always overlap. David comes from a family of teachers, actually. His parents were traveling road musicians who fell into education, but they have always continued some sort of musical pursuit on their own. “It’s neat…to be able to explain to somebody how something works and why. I love it.” – David Klee When Nick thinks about troubleshooting, he thinks about both high pressure and low-pressure situations when we’re trying to figure out why something is not doing what it’s supposed to do. David says we’re trying to determine why there is an unexpected outcome and what we need to do to get to the expected outcome. “It’s a formal methodology or informal methodology for understanding why something does not have an expected outcome and working through the process that is an iterative process – either elimination or identification. And you end up with essentially identification, review, remediate, rinse and repeat until you get the desired outcome. That’s about as formal of a definition as I can give you.” – David Klee John thinks this may disguise the art in the troubleshooting process of knowing what issues may be more likely than others. People might discover something is not working and change 10 things. If something then starts working again, how do we know which change (or combination of changes) actually resolved the problem? We are far less likely to undo the changes once something begins working again. John mentions being good at troubleshooting in areas in which he has lost the fear of something going wrong. While John feels comfortable troubleshooting computer systems and software, he’s not good at troubleshooting car problems due to limited knowledge and a feeling of high stakes. Someone with a better knowledge of cars may perceive the stakes to be far lower when making a recommendation for fixing problems. David says it depends on what you are troubleshooting. There is a risk qualification element that needs to be considered with the process used in troubleshooting. David shares the example of troubleshooting a payment processing system with a group of folks who didn’t know what they didn’t know. The process they had developed to troubleshooting ran the risk of preventing payment processing for the entire company. David describes determining the need to speak to the group of people who built the system in order to troubleshoot the system safely. 11:43 – Pre-requisites for Effective Troubleshooting Nick mentions we highlighted a pre-requisite for troubleshooting being knowledge of the systems we’re troubleshooting. What is the correlation between how good a troubleshooter one can be and how well one knows the systems involved in troubleshooting? If we know our systems well, we know what is / is not possible within a given set of constraints. One example is knowing the ramifications of changing different database settings. “You know what’s going to happen because you know the platform and you know your environment, and you know how they come together. If you know this stuff you can resolve these issues a whole lot quicker.” – David Klee Knowledge of the platform and environment would mean we know the systems which interact with the one we are troubleshooting, the impact of the outage, the right person to call for help, and the questions you need to ask them. It can be much harder when you inherit a system someone else built and no documentation on why it was set up the way it was or how other systems communicate with it. Likely you also don’t know what types of changes have been made to it over time (whether they were band aid type fixes or some other kind). John mentions we’re highlighting domain knowledge of a system and its specific failure modes combined with what has happened in the past to diagnose and fix those things. A resilient system should have these things documented. David says the flip side of this is being someone coming in from the outside who has never seen this machine before. Think about the scenario in which you are asked to troubleshoot a system which people with all the domain knowledge can’t fix. As a consultant he runs into this pretty regularly. It can be challenging, but David says it keeps him sharp. Someone troubleshooting a system like this has to keep track of what’s already been done, what should have been done, and what questions need to be asked to extract domain knowledge from others when information hasn’t been documented. One must also know the platform well enough to successfully understand a system’s current state (which might be different than what people tell you). “Perception of a system’s state might be entirely different than the reality of the system’s state. That’s a hard, hard art to master right there.” – David Klee John says someone who doesn’t know a system may have a better chance of doing effective diagnosis. The person who knows a system well is going to make assumptions someone who doesn’t know a system would likely not make (i.e. the database is running great, etc.). David stresses the importance of quantifying performance when we’re troubleshooting. Preconceived notions about an environment might lead to subjective explanations. When he walks into an environment to troubleshoot a problem, David wants to look at the raw data. This data can help provide the true nature of a system’s state and perhaps prevent finger pointing between teams. “Show me the data. Show me why you think this. And most of the time, people cannot produce that data.” – David Klee Even trend information on how past issues of a specific kind were resolved counts as data and may provide a nice starting point for troubleshooting. David tells the story of a database administrator and a storage administrator getting into a shouting match over a specific problem. Each of them wanted to be right, but neither had data to back up their claims. In the end, both were right – the problem was somewhere in between the database and the storage in the network and operation system layers. Listen as David describes it in detail. “But it’s ‘I’m right. You’re wrong.’ There was no ‘I understand that my telemetry is showing me this, but your telemetry is showing you something different.’ Put the data together, and draw a line between them. It’s the why is this showing 2 different things.” – David Klee on troubleshooting telemetry data from different systems 18:29 – What Should Be Documented What type of documentation would be helpful to have in situations like the one David described (the network and database administrators getting into an argument)? David says it would have been ideal to have a diagram of the entire environment that highlights the data communication flow between systems. “If we were able to literally have every single hop there, then you essentially start at both ends, and you start collecting the data until you meet in the middle. If you know the pieces involved, you can collect the system state and the telemetry behind it. That’s the easy part. You just have to know how to draw that line.” – David Klee Should each hop in the flow of data be instrumented from the beginning or only when there is a problem? David says you need data to baseline for good performance, and when there is a problem, you have to compare the telemetry for each part of the path to that of the baseline. David feels like he spends 25% of his week benchmarking and baselining things for people and has developed methodologies for different types of systems across technology stacks. “How can you tell me it’s running slow if we don’t know how it was running when everything is fine? You have no objectivity to gauge it’s slow.” – David Klee John highlights the challenges of diagramming these types of systems or applications. We need to represent physical connections, virtual connections, and even API calls for example. There are many layers involved, each of which can change. David thinks of a system he might be troubleshooting as an ecosystem rather than something static. He gives the example of a desktop computer and how a single software update can change everything. “To me it’s document what’s in your domain. Document it the best you can. Imagine you get hit by the beer truck, and somebody else has to come along and follow you…. I want you to know everything there is to know about why this machine was setup the way it was, what it took to get this thing running stable including custom tweaks, the raw architecture behind it, the configuration, everything I can possibly think of…mostly because I’m probably going to be the one to upgrade this thing in 4 or 5 or 6 years. I want to know – what did I do to stabilize this thing? Why is it setup the way it’s setup? And if somebody else needs to come along and support this…” – David Klee, on the purpose of good documentation David gets calls from customers during problem situations asking why certain configurations were made, and when this happens, he will send them the same, extremely thorough set of documents he produced and shared with them when the system was originally built. David has high expectations for what good looks like when it comes to documentation. The output from a SQL Server and infrastructure health check provided to customers will be around 250 pages on average. The spirit behind this is so customers have the what and the why. David highlights some big successes from producing thorough documentation for customers. David’s company saved a customer over $30 million in SQL Server licensing because of effective tuning, and due to this work, the firm later won a massive SQL Server migration project as a result. “They liked the documentation. They liked the why and not just the what.” – David Klee, on thorough systems documentation as a differentiator of his business John says people often don’t want to document things for the next person, but many times the next person who comes along is you 6 months later. These things need to be documented well or perhaps put into a knowledge management system. David documents things so he isn’t forced to recall them from memory months or years in the future. He could be documenting a quick change or something that took 40 hours to find in the process of solving a problem. When making a change to something weird or nuanced, David will document it and make sure he and his customers have multiple copies of it. “There are things all over the place with the kind of tuning that I do. If you didn’t know it was there, you’d have no clue. You’d just have weird symptoms here or there, but these things are so nuanced.” – David Klee How can we balance thorough documentation with the need to make progress and not impede it? An organization has to be on board and allow technologists the time to document properly. If this doesn’t happen, the entire IT organization suffers. The technologists who made changes to solve a problem will forget what they did very quickly when forced to move on to the next fire immediately. “I think that’s why I run into a lot of the states that I do out there…. Something broke. Nobody’s had the time to think about it or look at it or document it or review it…. Here, you figure it out.” – David Klee 25:25 – Forms of Documentation and Emergency Preparedness Is the documentation we’re talking about something kept in a change control system, a wiki, and asset management system, or just some large document somewhere? If enough history is provided, David tells us the format doesn’t matter. Some places use a formalized change control process with tickets and platforms like ServiceNow. It’s a process that works for those organizations. Some organizations treat infrastructure as code and leverage JIRA tickets for tracking changes. “As long as I have a list of what has changed and when and why and a reference document that shows why the system is configured the way it I, any nonstandard change, any reason why the system is in use, anything. What’s it talking to? What’s placed on it? What firewall exclusions, routes…? If I have that, I know 90% of what I need. It’s that last 10% that’s always…specific to a given machine. But if I know the why, the what, and the where…you can figure out the how.” – David Klee Make sure your documentation is retrievable even if a system or platform or datacenter is offline! David has one customer who prints out the documentation once per month and puts it into a fireproof safe to take one example. There are many ways to ensure the documentation is retrievable in a critical situation. We need to make sure it’s available offsite somewhere (digital or printed copy). Who should have access to the documentation? David says more than one person for sure. Things can happen to people like getting hit by a beer truck or being in a natural disaster. “If you have one copy…single point of failure; I don’t believe in that. Two, three, four copies – park it on a USB drive at a bank deposit box. Park it in a public cloud that key members of IT can get into. The odds that that goes down…slim.” – David Klee Nick mentions the access to documentation (i.e. the run books) would need to be part of onboarding and offboarding new team members. David tells the story of helping a trucking company build a DR plan several years ago. The company was in tornado alley and had around 800 virtual machines. Due to regulations in the trucking industry, there is a requirement for constant telemetry feeding back to corporate systems from the trucks themselves. “I don’t believe in just testing a handful of pieces of DR every once in a while. We fail over and run from DR for 1 week out of every month…. They fail over the first Friday night of the month. They fail back on the second Friday of the month. Half of IT gets off the 3rd Friday of the month, and the other half gets off the last Friday of the month. I think it’s great. They love it…. Anybody in the room can fail over the entire company with the run books that are provided and maintained by every member of IT.” – David Klee, speaking to a DR plan for a company he helped architect In this scenario, the company’s CIO chooses 4 random members of IT staff who cannot be part of the DR exercise (i.e. simulating that they died). If any member of the team has to call one of those 4 team members during the fail over or fail back, the DR exercise fails. The company we’re talking about not only says they have DR. They demonstrate it to insurance companies and auditors, and their insurance is much less as a result. The full failover to / from DR takes about 43 minutes. The process took about a year to get right because of so many moving parts, but it works very well. How detailed should a company’s disaster recovery or business continuity plan be for the purpose of audits? David says there are varying degrees of detail. Some auditors may be checking a box, only looking for backups and offsite copies of data. Good auditors would ask to see the detailed process of how things failed over and how long it took. Some companies do disaster recovery and only fail over one system (maybe even without all the dependencies). “The good auditors are the ones that ask how long, when, not just what. Those are the auditors that most people in IT hate.” – David Klee David shares the story of a database administrator friend of his who was, in an audit, asked about the disaster recovery process and if he could demonstrate it. The auditor then noticed a 400-page book about SQL Server backup and recovery that David’s friend had written. David’s friend mentioned the book was the genericized process, but he then produced a specific document of the process at that specific company. It answered the auditor’s questions in 5 minutes. 33:12 – Interview Questions and Employer Perceptions John is wondering if we may have uncovered some good screening questions for job applicants to use in interviews related to this topic. We could ask about the company’s knowledge management strategy, the way they document how systems work, or the level of importance placed on documenting disaster recovery / failover processes. David says the employer should have an immediate answer for this. If they don’t, it’s a red flag and may mean you are the one who has to do whatever it takes to get stuff up and running again. Different parts of the business might document things in different ways (all of which could be effective), and processes might have different levels of importance when it comes to business resilience. John gives the example of documenting an employee onboarding process and where that ranks in overall priority compared to other things. David shares the story of a company whose disaster recovery plan includes helping the families of the IT professionals who need to engage because of an emergency situation. This includes transportation, housing, and much more. What types of questions might David ask a prospective job candidate on this topic? David would ask how someone documents why something works. David also asks for a 5-minute technical presentation covering a facet of what they are working on and why they enjoy it. “It’s an interesting twist because it tells me…can you talk to somebody who knows something about what you’re doing? Can you convey it in a way that people can understand? And it helps me get into their brain. Why do you like doing this?” – David Klee These types of questions help David understand how much someone enjoys working in the technology field or they are in it solely for the money. Do most employers see value in a prospective employee having the experience in writing detailed documentation or disaster recovery plans, or is it a mixed bag? “The company should love it. I can’t say they always do.” – David Klee Some employers may think you are too deep in the weeds or that you spend too much time on paperwork and process to effectively get things done. Companies could be solely focused on getting things done, which can be a problem. Companies too focused on process may be very inefficient. David says it’s an interesting balancing act and sees this play out differently inside different organizations. The approach may depend on the type of business and what they are trying to do. “If a person’s process behind this stuff doesn’t line up with the company, you may not be a good fit.” – David Klee John mentioned the good and the bad of systems being designed to prevent change. “Database technologies are very evolutionary. I see people that can’t embrace positive change to be as big of a detriment as people that embrace negative change too haphazardly.” – David Klee David highlights an example. This company needed a more highly available database environment but was too reluctant to migrate to one. The change was too much for them to embrace even though it would provide a great benefit. This isn’t about a poor value statement for the change. No one wants to put their job on the line if something doesn’t work. David mentions a mandate from the top of a company for availability, but no one at lower levels is willing to make changes to achieve it. This is a case of a mandate not being enforced. “It’s we’re willing to sacrifice what we know to move into unknown territory carefully, cautiously, one piece at a time…and they can’t start the process.” – David Klee John says this may be due to cultural or political undercurrents not visible to someone on the outside of the system. David references a previous conversation we had on the show about consulting and the level of exposure to politics. David reiterates one of the reasons he loves consulting – because he does not do well with politics. Are consultants brought in because of company politics? The fun part of consulting according to David is when a company brings you in to tell them what they need to do. When a company brings you in and tells you what to do as a consultant, you have the ability to say no if asked to take an improper or incorrect approach (another reason David loves consulting). In environments where detailed documentation is seen as valuable, can this get someone a promotion or perhaps even save their job? The answer is 100% yes. David gives the example of a company which had a security incident last year. The database administrator was seen as someone who always said no to things, wanting to look at code before it was released to production or have changes happen during normal working hours, etc. After the company was hit by a ransomware incident, the database administrator (or DBA), recovered the machines in 7 hours. It took 2 weeks for all other systems that used the database to get back up and running again. The database servers had proper change control, use of service accounts, firewalling, etc. and were the most resilient because of that. “Data was up all because…questioned everything, didn’t trust a bit. I trust you, and I trust your intentions. But prove it.” – David Klee, on the mindset needed for resilient systems Mentioned in the Outro When creating system or change documentation, remember that one person you could be writing the documentation for is you in the future. You can also take the attitude of providing the right level of depth in documentation so that others can fix the problem without needing to call you. Having appropriate levels of documentation in a place where everyone can find it can make it easier for team members to rotate in and out of certain areas and support taking uninterrupted vacations. If your company or team isn’t documenting systems or changes at a deep level, maybe you can be the one to start the trend or help operationalize it for your team. Try speaking with your manager or team lead about the value of better documentation and ideas for getting there (maybe differently than it has been done in the past). Even making small improvements is progress, and it could be the kind of progress that helps you progress to team lead someday. For additional interview question ideas related to documentation and knowledge management, check out Episode 293 – Enterprise Knowledge Management: A Consultative Approach to Solving the Right Problems with Abby Clobridge (2/2). Troubleshooting is about drawing a line between two points and checking telemetry at every point in between, but when we are troubleshooting with others, it is an opportunity to show empathy, to collaborate effectively to solve a problem, and to learn from colleagues. Maybe you can learn from the way colleagues on other teams document their changes and see how it compares to the way your team is doing it. Documentation lends itself well to ensure we are prepared for a business emergency Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.

Does the ADHD brain experience stress differently in situations like being laid off, for example? According to Skye Waterson, ADHD coach and our guest in episode 314, stress actually has the potential to hit you harder after a crisis. In this discussion, Skye shares practical tips for setting achievable goals as a job seeker or an entrepreneur and the importance of taking a long-term view throughout the process. We talk about the strengths of the ADHD brain in the tech field and how to determine if a work environment is the right fit when you’re interviewing. Skye also shares the reasons she decided to walk away from academia to start a business and some of the lessons learned along the way. Original Recording Date: 12-29-2024 Skye Waterson a former academic turned entrepreneur and ADHD coach. If you missed the first part of our discussion with Skye for a slightly different perspective on the ADHD brain, check out Episode 313. Topics – Stress and the ADHD Brain, ADHD Strengths in Tech, Setting Goals and Maintaining Accountability, Walking away from Academia, Reflecting on Entrepreneurship, Job Interviews and Finding an Environmental Fit 2:34 – Stress and the ADHD Brain Nick suggests we talk about stress in the context of the current job market. We’re seeing layoffs across tech and other industries continue. How do these stressful and traumatic situations affect the ADHD brain differently than perhaps those who do not have ADHD? “There’s no conclusive thing that I can think of in the research that I’ve done that we experience stress in a different way…. What I would come back to with ADHD is that we have impulsivity struggles and we have executive functioning struggles. And so, it comes back to this idea that you’re ADHD all the time. When something stressful happens to you when you have ADHD…you have to deal with all of the emotional regulation, all of the thinking…all those things can mean it hits harder.” – Skye Waterson People with ADHD can struggle with rejection sensitivity and self-criticism. Self-criticism could be partially due to receiving a lot of criticism when younger (positive or negative). Stressful events can hit harder as well if you have PTSD or other mental health struggles. Skye gives the example of getting into a car wreck. After it happens, you have to call the insurance company, figure out what to do with your car, and do many other things. “And especially once the dopamine is gone…you might be good in the crisis, but post-crisis, you now have to pick up all of this executive functioning task work and do emotions. So, you might be struggling way longer than somebody else might be struggling…because now you have to deal with all this actual admin work as well.” – Skye Waterson, on experiencing stressful situations with ADHD If we put that same set of challenges in the context of someone losing a job, someone would need to figure out how to spend the time they have left at a company (could be some or none), update their resume, update LinkedIn, and decide what to do next. “I’ve worked with a lot of people in that job space…. Essentially what you’re doing is you’re starting a small business called finding another job. It’s really complicated…. Really it does have to be a system that you break down…. What is my goal? My goal is to get this job. What are the steps that make this goal inevitable in a day? …Make it an achievable goal for you to hit those things and focus on that and give yourself dopamine for that rather than…my goal is to wake up every morning and try and get a job. That’s very, very difficult and not very fun from an emotional point of view.” – Skye Waterson Some of the people Skye has worked with chose to begin a small business on the side after being impacted by a layoff. It’s certainly one option for people but not the only one. Part of the system might include a specific number of people to message per day, a specific number of resumes to send per day, and a specific number of jobs to check in on. These goals should be achievable for you. Would the amount of dopamine required to work toward getting another job each day be even higher because of the compelling event that put you into a stressed state? Skye says yes but you also do not have to start immediately. We can sometimes go into crisis mode and use the dopamine of stressful events to push us forward. It can seem like a crazy burst of energy that propels you until you crash. “In the moment when it happens…and if you knew that this might happen it can be good to prepare this in advance…you want to go ahead and do something grounding. Things you liked as a kid are very helpful. Give yourself Chinese food, watch a movie with a friend…things like that could be really good. But have a time in your calendar that you’ve blocked out that is ‘plan to find another job.’ Give yourself a 2-hour window. Put it in your calendar like you’d put a doctor’s appointment. Take yourself to a coffee shop if that’s going to help you stay motivated to do it, especially if you’ve been used to a working environment, and once you’re there, give yourself a really nice cup of coffee (maybe a chocolate biscuit with this one) and then go ahead and plan it out.” – Skye Waterson Skye recommends an AI-powered app called Goblin Tools to help with planning / breaking down things into steps. This app is free and is designed to help people with ADHD. You could search for “find a job in X industry in X country” for example, and the tool will break it down into steps that you can convert into a daily rhythm (focusing on the input and not the output) and overall system for finding another job. With ADHD one of the struggles with executive function is working memory. It can be hard to break things down into subtasks once you have a high-level task or goal. Skye likes to use the example of buying a new rug to show all the subtasks required (measuring, finding a new one, going to get it, deciding what to do with the old one, carrying it upstairs, etc.). Nick has seen the challenge of breaking things down into steps firsthand through working with his daughter. It’s like there are dependencies that are missed. But once Nick’s daughter has the list, it’s easy to move forward and make progress. “A list, a daily routine, a reward,…making it a realistic thing….” – Skye Waterson, on the elements of a good system for a job search Goblin Tools can also provide a rough time estimate for tasks. They probably are not really accurate, but it can help you understand everything will not happen tomorrow and that it will take time. Is it easier for the ADHD brain to find closure after a stressful event (loss of a job, death in the family, etc.)? Skye has not seen any evidence to suggest this is the case. “It’s more the case that the admin of all of these things can tend to linger for a lot longer for people who are neurodiverse. So, they might still have boxes of things that they haven’t organized, for example, for years after other people would have organized them.” – Skye Waterson Part of the reason Skye recommends using the prioritization filer we discussed last week was to account for things which might be lingering in someone’s mind for a long time (like things that have gone unorganized). Some of the strengths of ADHD are creative problem solving, original thinking, etc. 11:53 – ADHD Strengths in Tech How might the strengths of the ADHD brain play out in the world of technology? Nick mentions a great discussion from the ADHD Skills Lab podcast with guest Lisa Ballard about working in technology sales with ADHD. “There are a ton of strengths. When I work with people who have ADHD it’s really about how do we mitigate the struggles so we can focus on the strengths. We’re not living a life of just mitigating the struggles, and sometimes people think that…. We know from the research that we’re original thinkers. If you give a person with ADHD a task and an example of the task, people who are neurotypical will tend to iterate around that example. People who are ADHD be fully left field…and completely originally redesign this thing…. You can sort of see how that would work well if you were in a workplace and you were solving a problem. One of the best things about ADHD in the technology space is that we are out of the box thinkers. We love pulling a solution to a complex problem out that no one else has seen before. And we’ll usually have an original perspective on why it exists, what we should do about it…. They’re great people to have in the room when you are ideating, when you are problem solving, when you are bug fixing even…all of those spaces.” – Skye Waterson, on ADHD strengths and how they play out in tech Would this support the theory that many entrepreneurs have ADHD? Skye says ADHD is so common in entrepreneurs that people just assume entrepreneurs have it instead of the other way around. Skye mentions two types of entrepreneurs: The first type would be someone who has ADHD, never really worked on it, managed to focus without burning out completely, and became a very successful business owner with multiple employees. This person has not sorted out their own ADHD. The second type is the entrepreneur with ADHD who is struggling (and maybe burning out) who seeks out strategies and support. “Sometimes people will say ‘I have ADHD, but it doesn’t affect me….’ You should talk to the people in your office. It might.” – Skye Waterson 14:43 – Setting Goals and Maintaining Accountability How can the entrepreneur stick to the business they have chosen and focus on it without getting distracted or losing interest in it completely? One of the ADHD traits is losing interest in things after a time and abandoning them. Skye says it’s very hard, and she’s spoken to other entrepreneurs with ADHD about this. One way to combat this is to only do things that add to what you’re already doing. If you only help people in the technology space, you should only decide to do things that help people in the technology space. Another way is to set a very long-term goal for your business (possibly a 25-year goal) and then smaller, shorter term goals or targets you’re working toward along the way (i.e. where you might want to be in 5 years or even 1 year, etc.). Ng Having an EA or executive assistant can also be very helpful to hold you accountable and to be honest when you have added too much to your plate. External accountability can be very helpful. Can we have people hold us accountable in a way that we don’t feel the shame of not accomplishing a goal or abandoning a goal? With the challenges in emotional regulation that come with ADHD, does the sense of shame become greater? Skye says yes it can be greater. But the problem may lie with the goal you have set. In business, we often talk about the idea of a BHAG or big, hairy, audacious goal. It can be easier to not feel shame if the goal doesn’t have a strict timeline. When working with an executive assistant, ask them about their goals to ensure their goal fits within yours. Skye gives the example of having a goal to create a business that eventually becomes a media empire but at the same time is sustainable and will support balance with family life. “If you said to somebody, ‘that’s my goal,’ and maybe part of that, because we do want some kind of measure, is ‘I want my business to hit 6 figures by the end of the year. That’s my goal.’ If you don’t hit 6 figures by the end of the year because something happened, it doesn’t super matter because you’re working toward a 25-year goal…a media empire 25-year goal. This was just a bit of a valley year. And so, you’re still going toward the goal but you’re just adjusting the goal posts when you get there. Don’t adjust them prematurely….” – Skye Waterson Skye is advising us to take a longer-term view of our goals and to remind ourselves of the progress we have made, even if the progress was not as much as we wanted. Don’t think about missing pre-defined targets as failures but rather as puzzles to solve while you make progress. “This is a lot easier to do when you get out of the ‘I need to make enough money to survive’ part of business. But usually, when you’re in the ‘I need to make enough money to survive’ part of business, you have enough dopamine. It’s that middle piece that can sometimes be the problem when you’re scaling, you don’t yet have the finances to bring other people on to support yourself…to be able to get out of the things that you don’t love. You’re starting to do that, but you’re in that…complicated middle space.” – Skye Waterson, speaking to the dilemma of the solo entrepreneur Nick says at this point effort has to go up because you are not quite big enough as a business. “There’s that bit where…there’s no one, there’s no money, and it doesn’t super matter what the goals are because you’re just starting. No one will really notice. You can sort of play around in that space and figure it out. And I did this for years…. The middle piece is often where people find themselves stuck. They’ve got something. It’s making money, but they don’t know how to hand off those tasks and in what order and how to focus to do the thing.” – Skye Waterson When you reach the point of being able to hire someone to help you, that can come with its own set of unique challenges according to Skye. Before starting Unconventional Organisation, Skye helped her husband run a frozen foods business during which she learned a lot. 21:43 – Walking away from Academia Why did Skye become an entrepreneur, and how has she seen the challenges and strengths of ADHD play out during that experience? Skye originally wanted to be an academic. Being part of that world involved a lot of short-term contracts and grant writing. It did not seem as stable or as free as she would have liked. “I didn’t really know what to do about that, but I did start looking at entrepreneurship at that time.” – Skye Waterson Skye loved art and tried to sell a few paintings, but that didn’t really work well. She continued experimenting. Skye’s then boyfriend (and now husband) who also has ADHD was starting a business selling frozen food in New Zealand. Skye helped him with the business and gained some experience, but the business fell victim to COVID shutdowns. “It taught me a lot…. The thing I love about business is no one tells you no…and this kind of goes back to the idea of getting let go…. When you’re in a workplace, you can do your absolute…best, and you can still get fired, or you can still not get the promotion. There can be politics. There can be other things. When you are running your own business it’s sort of like a big giant puzzle. Yes, someone can say no to this thing, but maybe you just need to rethink what you’re doing, or maybe you need to talk to a different audience…. There’s often a solution. There’s something to do. And that for me was very good.” – Skye Waterson When Skye started as an ADHD coach, she did not anticipate it becoming a large business, but she did hire a business coach. Skye knew from her previous experience how important this would be, and she also hired an executive assistant for a few hours per week. Skye highlights these two decisions as helping her grow and develop tremendously. Skye would eventually decide to leave her PhD program and tells us it was one of the most difficult decisions she’s ever had to make after spending so much time pursuing that path. Skye found that her PhD supervisors / advisors were supportive of her decision to start a business and leave the program. Skye is still involved in research and has a researcher on staff. Skye’s podcast, The ADHD Skills Lab, is a platform to discuss the current research which she can then turn into helpful teaching tools. “In that way, it’s been great because businesses are like this little interesting engine that you can craft to however you want to work…. I still do the things I want to do. I just do them in a slightly different way.” – Skye Waterson Nick thinks Skye has taken the things she enjoyed from academia and put them into a slightly different context. Skye was at the dissertation stage when she left her PhD program, having already done the research that just needed to be written up. She also had a small baby at the time. Skye said she was going to pursue a PhD and then didn’t finish it, but it’s ok that she didn’t finish. There is no shame in it because that was a small step in a much longer-term journey or goal. Skye is modeling for us that her own focus is on longer-term goals. 26:56 – Reflecting on Entrepreneurship What are some of the things Skye wishes she had asked about being an entrepreneur that she had to learn only after becoming one? Skye wishes she had asked how to make money. That was definitely harder than it looked. It wasn’t until after building a 6-figure business that someone told Skye how to do sales properly. She mentions she had been order taking rather than making sales. “At the end of the day the number 1 thing you want to do is sell. Sales is super important, and I’ve had amazing business mentors throughout my career. That’s been the thing that has been most helpful. Do you know how to sell something to someone? …I knew how to do academia. I could talk for ages, but I didn’t know to sell something. That was big.” – Skye Waterson, on learning how to sell Skye would highly recommend the book Spin Selling. Skye has also found putting on her psychologist hat really helpful within the context of selling. People have a problem, and you may have the solution to that problem. But you need to understand the problem before proposing a solution. “So, if somebody has this problem and you have the solution to this problem, then it’s…your job to make sure you understand all the objections to the problem…. I did clinical psychology in my undergrad, so if you think about it from that perspective, I find that much better than sales.” – Skye Waterson When selling a product or service, in many ways it’s like a bi-directional job interview. The entrepreneur can say no to the wrong kind of client / customer. Skye tells us she has said no to potential clients before and that there is a qualification process one has to go through before working with her. Often times saying no to someone is because the person may need more intensive mental health support. Skye only supports clients (business owners) who do high ticket, high value products. Skye mentions most of her work being centered on helpful content creation and development. Some people who have found the content helpful are potential customers and can then be taken through the qualification process to determine if they are a good fit for the product or service. Skye says in this way, it feels less like what we expect traditional sales to be, but in reality, this process is what high-level salespeople are actually doing. One of the patterns we’ve seen in the careers of previous guests is using content creation / public proof of work to stand out in the job market. Just as it helps entrepreneurs like Skye sell a product or service, it can help individuals land a new job opportunity (even if it’s unexpected). 31:41 – Job Interviews and Finding an Environmental Fit Within the context of a job interview situation, what are some of the things the neurodiverse individual can ask to pinpoint any red flags in a potential work environment? The number one thing for Skye is to understand the options for flexibility in the workplace. When you are given the chance to ask questions, consider asking: What are your different workplace options? What are the different ways that people in your office work? “Often times with ADHD the thing we’re looking for is an environmental fit…. What we want to know is are you going to get dirty looks every time you put your headphones on? …If you just said, ‘I’m really curious about the different ways people in your office work. Is everybody at their desk? Do people have their own offices? Do people work from home? What are the different options?” – Skye Waterson, on environmental fit in interviews Some environments may have flexible working hours as well. If the options for working sound like a fit, Skye would also recommend (if you can) speaking to someone else who works for the company (in the office or remotely) to get the inside scoop on what it’s really like. Ask about whether the work is project based or repetitive. Will there be clear deadlines, or will new tasks come from multiple different departments every day? Either can be fine, but it depends on what you as the job seeker with ADHD want. Should someone share their neurodiversity openly during the interview process? Skye says this is a very personal decision and that many people choose not to share it in an interview scenario unless it will have a big impact on the workplace. It is more likely for people to share their neurodiversity once others get to know them as a person. This helps avoid stereotyping from others. “Instead of saying, ‘I have ADHD,’ you might say, ‘by the way, I work best in these environments.’ So, you’re giving them the context, the information about what ADHD is without saying, ‘I have ADHD….’ You might say, ‘I have these characteristics,’ whatever it is that is important to you about expressing from the ADHD.” – Skye Waterson You could say that you like strict deadlines, for example. Nick suggests expressing what you want to express to multiple people throughout the interview process (recruiter, hiring manager, others on the team, etc.) to gauge responses. Even though a company may not advertise the flexibilities an individual with ADHD might be looking for, the right manager and the right team could be the fit needed. Skye says one challenge of the workplace is that it is team based, and different department managers may have different rules. To reach out to Skye or learn more about her work… Visit the Unconventional Organisation website, and be sure to check out the blog section. Contact Skye directly on Instagram @UnconventionalOrganisation Be sure to check out The ADHD Skills Lab Podcast where Skye and others interview amazing people with ADHD like Lisa Ballard and share research recaps to educate the greater community. Skye is currently working on a book called Focused, Balanced Days with ADHD that you can read on Substack. Mentioned in the Outro Nick loves the idea of making your goal inevitable within a day or setting yourself up so it is a given that you will hit your goal. It does involve breaking things down into smaller steps and chunks that are parts of systems and processes, but it sounds a lot like we need to develop a routine we can use to work toward our goals (like finding a new job) during the time slot we have! Have you tried Goblin Tools yet? If so we would love to hear how you use it! Send us an e-mail. This development of a routine can translate to preparing for the interview process. For example, we can develop the go-to questions about the type of work environment that best suits our brain or working style. We’ve had a number of discussions with guests about deciding to stop doing something that once took a great deal of time and effort. Skye decided to walk away from her PhD, but taking the longer-term view helped her gain perspective on that single step in the journey toward something else. Nick feels like he heard an episode of the Truth, Lies, and Workplace Culture Podcast that discussed the idea of no experience ever being a waste. That experience in academia wasn’t wasted for Skye. She uses many of those same skills and more as an entrepreneur and business owner. Seth Godin as said deciding to stop doing something is a gift from our past self to our future self. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.

Are push notifications directing your day? While useful in some ways, push notifications can also become a huge distraction, especially for the ADHD brain. This week in episode 313 we’re joined by Skye Waterson, a former academic turned business owner and ADHD coach, to discuss practical strategies for staying focused in your work. Since dopamine levels affect our motivation, we might need to make adjustments to our dopamine levels to help increase our focus whether we work in an office or from home. Skye will explore some of the unique challenges of working from home with ADHD, thoughts on the ADHD brain’s struggle with procrastination, and the importance of clarifying our daily priorities. We also discuss the purpose of developing daily routines that will decrease stress and support working memory. Original Recording Date: 12-29-2024 Topics – A Different Perspective on ADHD in Our Careers, Baselining ADHD and Work Environments, Motivation and Dopamine at Work, Working from Home and Managing Distractions, Developing Purposeful Routines, Communication Preferences and Managing Push Notifications, Procrastination and Prioritization 2:11 – A Different Perspective on ADHD in Our Careers Skye Waterson is a former academic who found out she had ADHD at the beginning of pursuing a PhD. As a result, Skye decided to focus on ADHD research. After doing a bunch of research on ADHD, Skye posted her findings on the internet. Once the pandemic hit, Skye began coaching and loved it. She has grown her coaching practice into a 6-figure business and recently transitioned to working with business owners who have ADHD. We’ve discussed ADHD on the show previously with guests Jon Towles and Kristen Carder, but this time we’re going to approach it from a different angle. Here are the links if you would like to go back and hear those discussions: Episode 129 – The Challenges of a Superpower with Jon Towles (1/2) Episode 130 – The Excellent Advocate with Jon Towles (2/2) Episode 216 – Experiencing a Neurodivergent Diagnosis with Kristen Carder (1/2) Episode 217 – The Vulnerable Parts of ADHD with Kristen Carder (2/2) 3:15 – Baselining ADHD and Work Environments How would Skye define what ADHD is and is not? ADHD is a persistent and pervasive struggle with executive functioning (an area where Skye is heavily focused), impulsivity, and emotional dysregulation. This comes from shifts in the brain as seen in the neuroscience. Skye tells us the DSM-5 is most commonly used for diagnosing ADHD. The DSM-5 is a set of criteria and questions one would get asked by a professional (usually as psychiatrist but could be other professionals depending on your country) to diagnose ADHD. There are slightly different criteria to diagnose ADHD depending on whether you’re a child or an adult. When diagnosing adults, professionals are looking for whether your struggles have been pervasive over time. There are two primary types of ADHD: Primarily Inattentive – it may not show up, but this usually means you are distracted Primarily Hyperactive – driven by a motor internally / difficulty sitting still There is also a combined type (which happens to be Skye’s diagnosis type). These types are going to play out in our careers. What might ADHD look like for someone who works in technology? Skye says this can look like many different things. Work environments can look like Google, a place where there is a lot of flexibility and freedom. Environments like this also force you to manage your own time. Doing technology work for the government, for example, may not allow flexibility in the applications you get to use. In some cases, Skye has worked with clients who were employed by a government and were not allowed to use their phones at work. Overall, it depends on the level of flexibility your work environment will allow. “Mostly we’re thinking about how do you focus on the work you have to do? How do you prioritize that work when new things are coming in all the time? And how do you stay motivated to keep doing it consistently?” – Skye Waterson 6:17 – Motivation and Dopamine at Work Motivation is something we all need. What are some of the motivation challenges for the ADHD brain when hit with something that is not very exciting? Skye tells us neuroscience and ADHD are areas of current active research. The neurotypical individual, when starting a task, usually has some type of spike in the brain’s reward center for starting a task (i.e. a spike in dopamine). In the ADHD brain, however, this spike doesn’t really happen and might need some help. Skye says people with ADHD will say they feel lazy as a result of this. In reality it is the brain doing different things in different ways. People with ADHD need to add some dopamine to get to the same place. Skye equates this scenario to being underpaid in rewards. Adding dopamine certainly can help the ADHD brain with motivation, but it can be helpful on a wider scale as well. But how? Skye worked with the New Zealand Intelligence Services and the District Health Board. After providing some strategies to help personnel with ADHD, these organizations recognized the strategies could be helpful on a much wider scale internally. “Everyone has a down day like you said, but we struggle with it the most.” – Skye Waterson, on the ADHD brain and motivation Skye took all of the research she’s studied and turned it into a program called Focused Balanced Days. The intent is to help people move from inconsistent to consistent. Skye says at a high level we can add sensory things and stack them. It’s not about just rewarding ourselves with something to eat because taste is 1 of the 5 senses. We can often be understimulated across the 5 senses rather than overstimulated as many might think. “If you’re talking about a workplace, for example, you might say, ‘ok, what can I bring to work that I can touch, that I can taste, that I can smell, that I can see that’s going to help…raise the level of stimulation to help me stay focused at work?” – Skye Waterson If we take working in an office as an example, does strategically planning to get coffee from the break room help? This is a start, but Skye would encourage us to think about what we can have at our desk in an office. This can be a little tricky. Could you bring a fidget that looks like a key ring or even a Rubik’s cube? Note taking can allow fidgeting also because it allows switching between doodling and taking notes. If there’s a blank wall around you at the office, can anything be added to the wall? Likely we cannot do much about smell in an office. Can you use / wear headphones at the office? They can be used for noise reduction, adding in some type of different noise / sound, or for listening to something. You could also consider using earbuds and putting in only one of them. This works well when the earbud is Bluetooth connected to your phone. It allows one tap to turn on / off so you can have a conversation with anyone who walks up to your desk. Skye mentions she has leveraged the single earbud strategy at times to provide a distraction from unpleasant things like going to the doctor. She will listen to music or a podcast. What about asking to sit in a different area because the area where you are now is too distracting? Skye says this is definitely worth asking about but can get political at times. It will depend on how willing your management are to accommodate this kind of request. This is something to think about when seeking the right type of work environment for you. Skye would encourage us to align what we want with the goals of the company in order to improve the chances of getting what we want. Sitting somewhere else would help you contribute to the company goals / mission better or faster, etc. because you are less distracted. “You could be in a busy traffic area and just chat to everybody all day and get super distracted. It’s not going to be great for the workplace, so that’s kind of the key.” – Skye Waterson, on moving your desk to prevent distractions 13:48 – Working from Home and Managing Distractions How can we minimize distractions while working from home but also increase dopamine levels / number of sensations available? “This is a tricky one because when you’re talking about the workplace, often you’re talking about external distractions. When you’re talking about the home, we can still be talking about external distractions, but we’re more talking about internal motivation…because everything can feel more important than the work.” – Skye Waterson Skye hears people talk about various tasks that keep them from accomplishing anything when working from home. Examples we discuss are cleaning a room, doing the dishes, etc. At home, we are more susceptible to procrastivity, which is doing something that feels productive to procrastinate on doing something we don’t want to do. Send Skye a message on Instagram with the words “Nerd Journey Focus” in the message body to get a document explaining some of the things we are about to discuss. We have to step into focus at home. Part of this is working through the resistance we feel. At work, there are opportunities for “body doubling,” which can be very helpful to the ADHD brain. But at home, you likely will work by yourself and might have people in other rooms of the house doing other things. Skye recommends having a dedicated space for work. You want to prevent the pull of needing to organize something. You don’t want too much clutter. Skye is not saying you need to organize a bunch of things before you can get work accomplished. Just keep it out of your sight and away from distracting you. Stepping into focus means you’re moving yourself from being distracted and unmotivated to working and focused. Especially when you’re at home, reward yourself for starting (some kind of dopamine reward). Maybe it’s reading an article, listening to music, and having a cup of tea. When people question giving themselves a reward, Skye might remind the person how much less time this will take than doomscrolling social media. Should the music be instrumental only, with lyrics, or does it matter when it comes to stepping into focus? Skye mentions there are a lot of discussions about the idea of a dopamine detox With ADHD, Skye recommends dialing down your dopamine but not turning it off completely. It’s difficult for the ADHD brain to dial down dopamine from 100 to 0. If we start stepping into focus by reading an article, Skye recommends switching to either a podcast or to music with lyrics next. At this point you would turn off any distractions and write down the task you want to complete during this time period (which supports working memory and is a very important step). Maybe then you feel less distracted than when you were reading the article but decide to switch to music without lyrics to prevent distractions while you open an application and start to use it. “I like to imagine it as turning down the dial. You have a big dial, one of those old school dials that clicks, and you’re adjusting the dial…. This is my level of distraction, so I’m not going to suddenly try and sit in silence. That’s never going to work. I’m going to instead try listening to a podcast because I would probably do that. Once I’m more focused I might turn off that and switch to music with lyrics, etc.” – Skye Waterson Check out this menu of ideas to increase dopamine, also called a dopamenu. What about number of monitors / screens? Is having 2 monitors too distracting? Skye likes 2 monitors because of working memory. People with ADHD really struggle with working memory. Switching between tabs can be a challenge (i.e. forgetting what was on the first as you switch to the second). Having 2 screens allows you to have multiple tabs open at the same time and supports working memory. Is changing your environment by going to a coffee shop a reward or too distracting for the ADHD brain? “Some people find that over stimulating. The thing about ADHD I will say is that different scenarios are different levels of stimulation for different people. With ADHD it also depends on the task. My recommendation is have a toolbox of different environments you want to work in and adjust it based on you. But for a lot of people, working in a coffee shop can be really helpful. It can be the difference between getting something written and not getting something written. I know for me, I do all my writing in coffee shops because it’s too distracting to do it at home. But if I’m in a coffee shop and I have a coffee in front of me, I have the stimulation I need to step into focus.” – Skye Waterson This is going to be different for everyone, but if going to a coffee shop helps you focus, Skye would encourage you to keep doing it. The price of the coffee is worth it! Maybe we should approach this with the mindset of experimentation. Would Skye encourage us to journal on how focused we feel when we experiment? When people work with Skye, she asks them to commit to experimentation. The commitment is to try and then adjust once you know what is and is not working. This process is like untangling a ball of yarn / string. It is challenging to experiment when you do not have the strategies and the systems in place to know and understand what went wrong. 21:44 – Developing Purposeful Routines A travel-heavy role certainly may require some experimentation. Travel could be local, regional, or otherwise. What can we do to help ourselves stay structured if we have to travel? Traveling can be tricky with ADHD according to Skye. She suggests keeping your routine and adjusting it when you travel. “I recommend people have routines they can stretch and squish down, so they can sort of stretch it out or squish it down.” – Skye Waterson Skye gives the example routine of waking up, doing some journaling, having coffee, having breakfast, and then getting in some movement. Movement is a great way to support working memory. In a travel situation, Skye might shorten the example routine above to journal only a few words, getting breakfast, and then doing ten jumping jacks. “…so that’s kind of a very squished down version, but you’re keeping the routine. You’re not breaking the routine. This is also really helpful for the holidays.” – Skye Waterson There’s also a planning element needed to avoid being late for things when you travel. “Sometimes when people travel, they…decide to give up all of the ADHD strategies that they’ve learned that work. We’re always ADHD all the time. So, you want to be using those strategies whether you’re at work, whether you’re on holiday…it’s the same thing. You want to go ahead and schedule what you’re going to do in your calendar. And schedule transition times as well because with ADHD we really struggle with transitions. And we love to think we can teleport, but we can’t.” – Skye Waterson Skye recommends planning your prep time as well as your leave time (put time for each on your calendar). This can help prevent being consistently late or consistently too early, decrease stress, and make effective use of transition times. Even if you are never late, feeling like you’re almost late can increase your stress level. Nick likes the idea of having routines each morning or even before certain activities. It seems to be very stoic. What is the purpose of the routine according to Skye? The routine supports emotional regulation, addressing physical needs (like eating / fueling your body), and working memory. It also gives an opportunity to get some dopamine (a dose of fun in the morning). We know from research that movement supports working memory, and this is especially important for those with ADHD. Does journaling increase dopamine as well if it’s part of a routine? There’s a growing understanding of ADHD and emotional dysregulation. Things like relaxing, reducing, grounding, and calming all become important. Skye personally likes journaling, but her podcast producer actually finds journaling stressful and would prefer to mindfully do something else. Skye recommends listeners pursue some form of mindfulness that allows a release or reduction of thoughts in our heads to bring a sense of calm. She would recommend everyone do something for themselves in this way. Personal development guru and high-performance coach Brendon Burchard has spoken about the benefits of consistent journaling for stress reduction. Is there a specific type of journaling the ADHD brain should focus on, like just writing your thoughts (more like morning pages) or perhaps choosing a specific topic? On Skye’s podcast, The ADHD Skills Lab, they frequently discuss research topics, and as of right now, there does not seem to be a specific type of journaling that suits the ADHD brain best. On a personal level, Skye likes using the morning pages system. It’s all just about getting to a place where you have a little bit more distance between your thoughts and your actions. Because when you have ADHD, we are more impulsive…. And so, we just want to take a minute in the morning if we can and just remind ourselves about that separation. And that’s really what the purpose is." – Skye Waterson 28:07 – Communication Preferences and Managing Push Notifications In communication, is there a medium that a working person with ADHD might prefer over others? Is it e-mail, text, phone call, instant message / chat, etc.? Skye says there is no one medium that is particularly good for everyone with ADHD, but most people with ADHD will have a strongly held preference for one particular communication medium. There are other learning difficulties that can be connected to having ADHD like dyscalculia, dyslexia, or something else. This could be part of the reason people with ADHD have a strong preference. Some people will need to write things down, some will need to say it out loud, some will need to hear it, etc. Usually, people will have 1 or 2 communication mediums they really appreciate, but it will come down to the person. Skye often works with people supporting entrepreneurs. If she were coaching someone on how to communicate to a team, consider the following… Slack, for example, allows audio messages to be sent and will include a transcript of the audio messages. Platforms with a transcript option can be very helpful if people who need to receive the message are not auditory receivers. Platforms are making it easier to communicate with different types of people like transcribing uploaded videos as well. Should we expect colleagues with ADHD to tell us their preference of communication medium, or should we get better at asking them what they need? People with ADHD may not be able to pinpoint what works the best for them. Skye says it’s about understanding people and paying attention. For example, does someone never respond to your written messages? We might have to share some observations with a colleague and make a suggestion based on our observations. What about handling push notifications from the applications we use? How can the ADHD brain prevent these from being too distracting? Skye says push notifications are terrible for the ADHD brain, and they should be removed immediately. Overall, Skye encourages people to have a rhythm to their day. The reason Skye concentrates on focused balanced days and focused balanced business growth is to make it easier to remember when things need to be done. “Decide your rhythm for checking things, and then turn off all other notifications except for the emergency contact…. That would be my recommendation when it comes to push notifications…just aggressively remove them from every single app you get.” – Skye Waterson The above applies to checking e-mail (which you might do at specific times of day, etc.) and all other notifications. Even with notifications turned off, you might find you reflexively open a specific app on your phone or computer. To stop yourself from checking it as much, try putting the shortcut to the app in a different place on your phone / computer (i.e. not on the home screen or bookmarks bar). How does the shift to no push notifications look to other people you work with? Maybe some people manage this transition better than others? If you’re planning to do this at work, you may need to have a conversation similar to the one about moving desks. Skye says this is the digital version of moving desks. When Skye works with clients, detailed advice in this area is also about what their job role requires from a communication standpoint. If the person needs to respond to e-mails within 10 minutes, that is going to look different than needing to respond within 24 hours might. For example, being unreachable for 2 hours to focus on a specific task or set of tasks unless someone calls you is probably going to be fine. “The biggest problem you’re actually going to have is that now, the source of dopamine that you were using and justifying, which was checking your e-mail, is now gone. So, you might have to dial down your dopamine. The most stimulating thing you might be doing all day is checking your e-mails.” – Skye Waterson Perhaps you could listen to more podcasts in the background while you work. Once you start checking e-mail less, as Skye and many others have learned, you might realize that checking e-mail or other analytics was your way of procrastivity (avoiding other things). If you spend all your time looking for the perfect app for something, it might be procrastinating! 36:06 – Procrastination and Prioritization “You could almost call ADHD struggles with procrastination. That could almost be an alternative title for ADHD. Because when…you’re talking about the general idea of working memory and time blindness and all of those things…one of the reasons we procrastinate is…the thing is too boring, the thing is too emotionally salient…or it’s too confusing. So sometimes rather than addressing or understanding the reasons I’m not doing this project, we will just go off on a million different side quests and never come back to the project.” – Skye Waterson Skye tells us there’s no formally agreed upon definition of executive functioning. All the side quests mentioned in the quote above make us feel like we’ve accomplished something. Send Skye a message on Instagram with the words “Nerd Journey Prioritization,” and she will send you a doc on this topic. There is a prioritization filter which can be optimized when Skye works with clients as a way to keep them from procrastinating. “I’ve done this prioritization filter so many times with people…. If you have more than 5 things to do today and more than 10 things to do this week, you’re probably not prioritizing correctly. Most of us only have that number. We could have some subtasks maybe, but for most of us that should be the number we’re working at. Ninety percent of people I haven’t seen go over that number once they do the filtering.” – Skye Waterson If your task list seems too full, Skye would advise you to consider the following: What can be delegated? Can something you took on from someone else be given back to that person (i.e. a catch and release)? “What needs to be done today or there will be a significant external negative consequence? And if that’s not the case, it doesn’t have to be done today. It could be done today. It might be that it’s important and you want to do it today. We can bring it back in. But we don’t have to run around with this, ‘it has to be done today or everything’s gonna fall apart’ because it doesn’t have a significant external negative consequence.” – Skye Waterson Skye struggled in this area quite a bit, especially when she was in academia. She tells the story of telling people she would complete things by Friday and then work late into the night on them. When her husband asked who the work was for, Skye began to realize she was trying to complete too many things by Friday that had manufactured deadlines (the ones she made for herself). Nick says some of this could be because we said we would do something by a certain date, and we want to be seen as reliable. “And it’s a real trap with ADHD because we have time blindness, so often the deadlines we’re creating were unrealistic to start with.” – Skye Waterson One of the most effective things we can do in the workplace is put a clock in a visible place so that people in meetings or at their desks can see time passing and be less susceptible to time blindness. Mentioned in the Outro Did you turn off your push notifications after listening to that episode? Skye is encouraging us to manage notifications and distractions so we can have more periods of focus throughout our days. Getting more periods of focus each day aligns with the principles of Deep Work that Cal Newport write about and that we reviewed in Episode 141 through Episode 147. Dopamine hits from checking e-mail and other notifications sound like the hiding places Jon Acuff mentioned in his book Finish. We discussed hiding places in detail in Episode 273 as part of a 4-part book review series of Finish. Remember also the managing of notifications and prioritization filter will depend on the responsibilities of your job. If you need help refining these 1-1, consider getting a coach. The Unconventional Organisation site has a number of fantastic blog articles you can find here. Getting Help With ADHD and Routines Email Management Tips for ADHD Brains Three Tips for Better Communication with ADHD Remember to check out Skye’s podcast, The ADHD Skills Lab. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.

How should we use our influence as technologists? For Julia Furst Morgado, it’s not about increasing followers on social media or hitting some kind of metric. It’s a focus on educating and helping others…being a bridge into a technical community for someone else. This week in episode 312 you’ll hear more about Julia’s role as a global technologist for Veeam. We discuss the realities of traveling heavily for work and attending events while continuing to learn and build community. We’ll explore Julia’s involvement in the open-source community as a CNCF Ambassador and how she overcame impostor syndrome as a public speaker. Part of being an ambassador and a bridge to technical communities is also acting as a technical translator, making complex topics easier to understand. Listen closely to hear the full story. Original Recording Date: 12-19-2024 Julia Furst Morgado is a global technologist at Veeam. If you missed part 1 of our discussion with Julia, you can find it here. Topics – Public Speaking and Acting as a Bridge, CNCF and Open Source, Finding Balance and Focusing on Helping Others, Work Travel and Community Building, Global Technologist and Translator, Parting Thoughts 2:28 – Public Speaking and Acting as a Bridge Did Julia know there would be a large component of her work in the role at Veeam that was public speaking? Julia did not realize this would be a big part of her role at Veeam. She was excited to be offered the job even before finishing the boot camp but had also heard one’s first job in tech can be hard when you are changing careers / coming from a non-technical background. While Julia had a strong professional network already, she knew the role would be an exciting challenge. “I said ‘yes, count me in.’ And I love what I do. I love what I do. My team is amazing. I couldn’t dream to do something different. It was perfect. I couldn’t have asked for something different.” – Julia Furst Morgado How did Julia prepare to give public presentations? Julia tells us she used to be more introverted but learned to get out of her shell and not fear judgement from others. It was the same with public speaking. She tells us being prepared helps us be confident to deliver a public presentation. “The problem for me was impostor syndrome. The problem wasn’t getting on stage and presenting and not stumbling or…forgetting the slides. For me it was impostor syndrome because I never worked in production. Even to this day I never worked in production…. And I’m up there talking to engineers, senior engineers, even CTOs, CISOs…. Who am I to be up there without experience? That’s what really bothered me for a long period, but it doesn’t bother me anymore.” – Julia Furst Morgado, on impostor syndrome Julia says it took some self-talk to shift her mindset going into these presentations. She told herself it was ok to be up there speaking. She may not know everything about a topic but can still present confidently on the topic. If someone asks a question Julia does not know how to answer, she can find the right resource to get the person’s question answered. “But I’m just that bridge. I’m a very good bridge from the technical to the external audience…so communities at conferences and events.” – Julia Furst Morgado John highlights the feeling that people expect a presenter to be an authority. He calls what Julia has done being a gateway to other resources like product management or solution architects. To do this, you have to be honest with yourself about what you know and what you don’t and at the same time be willing to direct someone to the right person to get an answer. “I can tell you about this technology, but if you want to go deeper, I can tell you who you can talk to.” – Julia Furst Morgado Julia isn’t ashamed of saying she may not be the right person to answer specific questions that pop up during a session. Julia considers herself a generalist and tells us she doesn’t want to be “just technical.” Her desire is to bring business value into the technical discussion to become a gateway to CTOs and other C-level executives. 7:09 – CNCF and Open Source A lot of what Julia does is organizing events. Julia organizes both the Kubernetes Community Day (or the KCD) and the AWS Community Day in New York. She also organizes the CNCF meetup in New York. Julia is involved in the CNCF community and AWS community. She is a CNCF Ambassador, and an AWS Container Hero. Julia also mentions being an ambassador for Google’s Women TechMaker Program, an ambassador for GirlCode, and also an ambassador for Civo. All of these achievements came over a span of 2 years. Many people want to know how Julia achieved so much without having the previous technical background. She is trying to show people they don’t have to be only technical and that they can add value with other skills. Becoming a CNCF Ambassador doesn’t require someone to be a senior staff engineer, for example. What is a CNCF Ambassador expected to do and be? A CNCF Ambassador is a spokesperson for the CNCF and may give talks about some of the open-source projects (a presentation at a conference, a YouTube video, etc.). Julia says it’s like being a subject matter expert on the CNCF. People can come to her and other ambassadors if they have questions about open-source projects. There are certain perks to being a CNCF Ambassador like discounts on certifications, a discount and special room / lounge at KubeCon, etc. An AWS Hero is similar to a CNCF Ambassador. They are experts and thought leaders who create content and try to build community around a specific topic. The CNCF Ambassador program requires people to apply for it. This would be similar to the Veeam Vanguard program. John describes it as being recognized for creating a portfolio of work that you need to keep working on to stay in the program. The AWS Hero is not something you can apply for but rather something you must be nominated for by others. Julia says you can apply for the AWS Community Builder program, for example, but being a “Hero” is a higher status because you cannot apply for it. Where can people begin if they want to get involved in open source in some way? If you’re not sure, you could reach out to Julia or another ambassador for guidance. She says the answer of where to start depends on a few things. Think about how you would want to contribute to open source and how much technical experience you have. What type of technology are you using? Passion for a technology you’re using can be channeled via contributions to an open-source project. Contributing to code may not be something you have the techncial experience to do yet. Try contributing to documentation or translation / localization. Other ways to contribute could include triage or fixing bugs. After thinking about how you would like to contribute and the technology you want to target, you can filter the list of potential projects. Take a look at their documentation. The majority of projects have documentation that tells you how to get started as a contributor. If there is no documentation on how to contribute, reach out to the project maintainers. Often times open-source projects will have their own community within Slack or Discord. Don’t be afraid to express your interest in contributing. Julia tells us all these projects need contributors. “If you’re curious, and you know a project, go for it.” – Julia Furst Morgado, on contributing to open-source projects Julia also has a blog about contributing to open source that can help if you don’t know where to start. She also has posts about how to get started in cloud or just in tech and continues to act as that bridge. 13:22 – Finding Balance and Focusing on Helping Others How does Julia keep herself from getting overwhelmed or taking on too much? Julia isn’t sure she has a good answer to this one. It’s been 2 years, and she has been putting in tremendous effort at a fast pace. Julia is scared of burning out and tries to slow down when possible. At the time of this recording, Julia already has a number of events booked for 2025, including being invited to do keynote speaking engagements and to be on other podcasts. “It’s just really hard because I’m trying to surf that wave, you know? …I can say no, but I don’t want to. I love what I’m doing, and the opportunities are coming my way. So, it’s really hard, that balance…work-life balance.” – Julia Furst Morgado Right now, Julia says things are going well. She is trying to learn how to say no. Will it help? Instead of answering 10 messages about how people can get into tech, Julia wrote a blog post and will send people the link. Maybe in a year or more we can talk to Julia again and see if she has a different answer. What about community interactions and balancing participation in several of them? Julia has friends who are learning serverless technologies and want her to do the same. She tells the story of giving a talk at AWS re:Invent about running containers on AWS. Julia is now working to learn Lambda and serverless. Sometimes Julia wonders if she should keep going or if she is going too deep in an area. “I’m still learning. I don’t know if what I am doing is right, and I tend to try to do a lot, put a lot of my plate, and want to learn everything.” – Julia Furst Morgado Julia also mentions she has ADHD and has lists of many things to learn. John highlights the difficult balance between following everything you are interested in, developing a passion, and burning yourself out trying to do too much. Nick says there are many positive indicators about what Julia has shared. She’s still excited about what she is doing. She is learning the things which are interesting. None of this feels like a chore from the way she described them. Part of Julia’s job is traveling to attend events, and that might be for half of each month. She loves meeting new people and talking about different technologies but also works to prepare demos or write blog posts. The majority of what Julia has to do from a responsibility standpoint is fun, so she has no complaints. John mentions one of the things he noticed about Julia’s social media profile before we conducted this interview was the way she posts on social media at conferences. She often goes to different vendor booths at the conference and interview people. At the last KubeCon, Julia did an interview with people from every booth for an open source project within the project pavilion. Conference attendees can take a tour of the project pavilion (led by a CNCF Ambassador) to learn about the different projects. Many people cannot afford to attend KubeCon, and Julia wanted to record with each project maintainer to educate more people and encourage participation. Julia would like to do more of these interviews at other conferences perhaps related to challenges people are facing or some other topic. Short videos are quite popular right now. It’s a good style, and she will need to select a good topic for the discussions. Julia isn’t concerned about followers or the metrics on views of a social media post. She is focused on educating and helping other people, and maybe this focus is the reason she has not burned out. Many people are only focused on gaining more followers, and they keep posting only for this purpose. Julia knows people are getting something out of her content. They write messages to her with their appreciation. Julia keeps a brag folder (much like Ramzi Marjaba’s mention of a brag file in Episode 308) with screenshots of the feedback people have sent to her on the usefulness of her content. The feedback fuels her to keep going. It seems like Julia has found a community in which she feels like she belongs in the technology industry. Even though she was not exposed to strong communities in law or marketing, was she exposed to community during other times in her life? Julia says no. There are probably marketing meetups, but it’s unlikely they will share a repository to work on a project together as people in tech might. The tech community is very different. John mentions The Cathedral and the Bazaar paper by Eric Raymond about the structure of open-source software (the bazaar) and how it contrasted with the previous methods of developing software (represented by the cathedral). On the surface it may seem like the makeup of the bazaar is many people with competing interests, but the uniqueness comes from the openness and sharing. Law and marketing may not have anything akin to the open-source community because open source is more idea driven than profit or goal driven. Maybe other professions or even multiple professions can organize communities around ideas in a similar manner. But on the surface, the legal and marketing professions don’t seem to have anything like what you see from an open-source community. 22:41 – Work Travel and Community Building How does Julia manage this aspect of the job? Traveling for work is not as glamorous as people might think. Julia does not fly first class. She has layovers and wait times at airports. Arriving early somewhere requires her to wait to check in. Julia is grateful to have the opportunity to travel and doesn’t focus on the hardships of that travel. Other people working in developer relations may complain about the need to travel, for example. John mentioned the goal of teaching the people following behind you as a mitigating factor against the travel required for a job. Many people think a role in tech marketing or developer relations is glamorous because you become “nerd famous.” John says people might aspire to obtain the “nerd famous” part of this not understanding some of the things that can get you there – the drive to teach, the drive to educate, the desire to give back to a community (all part of investing in other people’s success). “I totally agree with you. It’s about helping others, lifting others up because by lifting others up they are going to come with better ideas and then they’re going to share them with you…. If you’re selfish and you just focus on you, you can definitely build something. But if you share your ideas with others, they are gonna definitely improve that with you. I’m all for uplifting others, helping others, and not just keeping to myself. That’s why I think I’m so good at building communities and engaging with communities.” – Julia Furst Morgado Julia’s intention is also to have interesting conversations and to help fix problems. It’s not about showing up and taking selfies with people. The fame part that may come in this type of role from the type of exposure you get is not the fulfilling part. Julia has people who follow her, see her in person, and may want to take a selfie with her. John mentions likely these are the people who are getting value from the content Julia has created and shared. People can see that Julia is genuine and authentic. She feels like this is the reason people come to ask her for help. When people ask for help, Julia helps them. Other people can tell when you’re doing something just for the numbers to gain influence. “I’m just another human like you. I write that on my blog posts. I struggled as well. If you want to reach out, I’ve been in your shoes.” – Julia Furst Morgado 27:26 – Global Technologist and Translator Julia’s role is truly global in scope. Remember Julia speaks 4 languages fluently (including English). Julia’s mother’s family is French, and she studied in a French school in high school in Brazil. She also spoke French at home. Julia speaks Portuguese because she was born in Brazil and Spanish after living in Spain for over a year. Julia lives in New York but attends events all over North America and Canada. She also supports Latina America (the LATAM region) in her role. Julia’s family now resides in Portugal. She visits them frequently and helps with the local AWS User Group when in town. One of Julia’s proudest achievements is giving a presentation in Monaco in French. Julia has not yet delivered a presentation in the APJ region, but maybe she can do it in 2025. Does the desire to bring more business value into presentations align well with being a part of a product strategy team? As part of the product strategy team, Julia and her colleagues talk frequently about product roadmaps, receive feedback on the functionalities they should add to the products in the near term and longer term, and discuss the business value of the solution. Julia and her colleagues attend meetings with customers as thought leaders. In those discussions, someone like Julia would speak to the business value of Veeam’s solutions (i.e. value of backup, using deduplication and compression, having a disaster recovery plan, etc.). Technical people may not be thinking about the big picture, but Julia and her colleagues bring a perspective on the big picture to customer meetings. Do most members of the community not really know how to communicate with product teams in an effective way? “Technical people, they know how to talk technical things. You have to translate it so product managers can understand and so other teams can understand as well…. Technical people…they don’t even realize that what they write, the way they speak, is too technical for other people…. I think some of my value is translating that into less technical terms.” – Julia Furst Morgado Julia knows people who write very technical content. She shares the story of finding a blog post and not being able to follow some of it because it was too technical. Julia wrote a version of the same blog post breaking down the steps into more detail. Communicating something in less technical terms is about explaining it in a way so that you meet the audience where they are. We can do this for customers, product managers, a beginner in a community trying to learn something new, etc. This is part of the reason Julia calls herself a bridge. Does Julia have a blog post on CNCF projects and the order in which she might recommend people learn and understand them? No, but Julia says it’s a great idea and is something she can work on in the future. Julia loves feedback and ideas from her audience. John provides more context on what led him to ask the above question. Someone had asked John about Falco and Knative, and these projects probably are not where someone should start when thinking about cloud native. Julia’s guidance is to start learning containers, maybe Docker, and then work up to Kubernetes. Tools like Falco and Knative are built on top of Kubernetes. Getting to Kubernetes might make someone think twice about choosing to continue on this path because it is conceptually difficult. 33:21 – Parting Thoughts The best way to follow up with Julia on this conversation is on LinkedIn. But if you connect with Julia on LinkedIn, be sure to send her a message and not just a random connection request. Julia learned this from her boot camp. When you add someone on LinkedIn, you should send a message. It helps you remember where you met that person. Julia is also on Twitter, Blue Sky, and others, but LinkedIn is the best way. You can find Julia’s blog here. And if people are hesitant to jump in and join a community, what advice would Julia give them? “Start with one person. Try to find one person that is in that community…. Got to them and say…‘I want to join. I’m new. What can I do? I’m a little overwhelmed.’ Be honest. Don’t be afraid of being vulnerable…. Try to find one person, and that person will probably help you, guide you, or put you in touch with the right person to get involved in a community.” – Julia Furst Morgado Julia recently re-read a book by Brené Brown on vulnerability, and being new to a community requires a little vulnerability. Find that bridge into a new community! Mentioned in the Outro Special shout out to Al Rasheed for recommending Julia be a guest! I hope you could hear the enthusiasm in that story like we could. When Julia writes a blog post to help answer some frequently asked questions and shares it with people who reach out to her, it aligns with the idea of becoming hard to reach from our discussion of Deep Work in Episode 147. Having a document with the answers to common questions allows Julia to help more people. If you’re looking for more stories of guests being involved in the open source community, check out these episodes: Tom Hatch was the creator of Salt. Episode 154 – Find a Balanced Life with Tom Hatch (1/2) Episode 155 – An Open Source Career with Tom Hatch (2/2) Max Kanat-Alexander did bug triage for the Bugzilla project before later working on it as a contributor and eventual maintainer. Episode 285 – Contribute Back: Embracing the Open Source Spirit with Max Kanat-Alexander (1/3) Episode 286 – Succession Planning: Delegation Skills and Technical Ownership with Max Kanat-Alexander (2/3) Ken Collins is a self-taught programmer who eventually got into the open source community to boost his career. Episode 241 – A Self-Taught Programmer’s Banyan Tree of Knowledge with Ken Collins (1/2) Episode 242 – Modalities of the Staff and Principal Engineer with Ken Collins (2/2) Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.

What would you do with a free pass to a tech conference? Julia Furst Morgado had to decide whether to attend KubeCon without ever having been to a tech conference. After deciding to attend, she came back from the conference with a new perspective and a job offer. While this looks easy on the surface, there’s much more to the story. In episode 311 we’re joined by global technologist Julia Furst Morgado. We’re going to explore Julia’s early career in law, the shift to marketing, and how that ultimately led her to the tech industry. Julia will tell us her reasons for attending a boot camp and how informational coffee chats and “hallway track” networking at tech conferences were instrumental in building her professional network. If you’ve heard the phrase “learning in public” but have never done it yourself, get ready for some inspiration from Julia’s story and tips on how you can get started helping the greater technical community. Original Recording Date: 12-19-2024 Topics – Meet Julia Furst Morgado, Life before Tech, Learn in Public, Pursuing a Boot Camp and Building a Professional Network, Tech Conferences and the Hallway Track, Details on 100Devs 2:37 – Meet Julia Furst Morgado Julia Furst Morgado is a global technologist at Veeam. Julia’s role is as a community-facing technical evangelist. She is heavily involved in the technical community and shares feedback with product managers to improve future product functionalities. When new product releases happen, Julia also gives presentations, hosts webinars, and writes blogs to educate the technical community. Though not directly part of her job, Julia organizes a number of events that benefit the greater technical community. Would Julia’s role be classified as technical marketing? A more appropriate classification would be developer advocacy or developer relations. Julia works within the Office of the CTO, but many times these roles can sit within a marketing organization or even inside a sales organization (which ultimately depends on the company). 4:35 – Life before Tech How did Julia get interested in technology in the first place? Julia transitioned into the technology field about 2 years ago and has achieved a great deal in a short time. Julia is from Brazil and was born in Sao Palo and went to law school there. Julia had a sister studying law, and not knowing what she wanted to do after high school, Julia pursued law as well. Julia later moved to the US after getting a student visa and studied business at the University of California at Berkeley. She went on to work in marketing as a marketing manager at an MSP (managed service provider). Before working for the MSP, Julia never would have considered a transition into technology. Working with the engineers at the MSP taught Julia quite a bit. As the only marketing person at the MSP, she had to do a number of things. “It sparked that want to be more technical. And during the pandemic I got laid off, and I did a coding boot camp. And that’s how I transitioned into tech.” – Julia Furst Morgado, on working for an MSP as the spark that got her interested in tech What did Julia not like about law? Julia describes the law field as a different world. People wear jeans and t-shirts at technology conferences, but you won’t find that in the legal field. People wear suits and are very formal just like we see on Netflix and other television shows. “I worked at an office that was very toxic, and I just decided that’s not what I want. And to begin with, I wasn’t even sure…that I liked law.” – Julia Furst Morgado, on pursuing a career in law Julia then moved to the US to study business, feeling it would open up a number of possibilities for her. What specifically drew Julia to marketing? Julia is a very creative person and recently heard from someone she might have giftedness. During her business studies in school, the marketing classes challenged Julia to find alternative ways to solve problems, and she really liked that aspect. Julia pursued a job in marketing right after finishing her business studies. After starting the marketing role at the MSP, Julia worked with software engineers, IT support, and people in DevOps focused roles. Julia was tasked with rebuilding the MSP’s website, creating white papers, and writing corporate blogs. She also worked with SEO (search engine optimization) and analytics. All of this ended up being relatable experience for what Julia does now as a global technologist. “I had to be in contact with engineers to make sure what I was writing was correct…. Because I’m so curious I would always go to them and ask more questions and research on Google and go down the rabbit hole on something…. My job was…write that blog post. Don’t learn about that technology. Just write the blog post. But I did indeed….” – Julia Furst Morgado, on spending extra time to learn technology even when she was a marketer The extra time Julia spent learning was not wasted. It provided her with a background of knowledge. Learning at a deeper level prevented the content Julia was creating from being superficial. 11:16 – Learn in Public Julia’s job as a marketer was heavily focused on writing and creating content. We’ve advocated on the show for people to blog about the things they are learning. It sounded like Julia was able to do that as a job. When Julia started the boot camp, she learned the term “learn in public” or “learning in public.” She cites a blog post that details the idea. “Whatever you’re learning…share it with others because it builds credibility. One, you’re teaching others. You learn it even better. So I applied this concept, and I would share it on social media. I created a blog, and I also created not one, not two, not three, but four YouTube channels because I speak four languages and wanted to do one YouTube in each language.” – Julia Furst Morgado Julia stresses the importance of being consistent in creating content and sharing it. “I started creating a lot of content, since the beginning, without being afraid of showing…my weaknesses. I think this is important…. Everyone should write or do a live stream or YouTube. It doesn’t necessarily have to be written content. There are other alternatives.” – Julia Furst Morgado People are fearful of showing that they are not an expert in a specific topic area. Regardless of your level of expertise, the content you create can help others who are learning and are not at the same level as you. John references Show Your Work by Austin Kleon. Many times people want to learn from someone who has not mastered a topic but someone who is documenting the journey of gaining expertise over time (starting from novice, for example, to competence and beyond). Documenting the journey can give someone an authentic voice because you are writing for an audience, even if that audience is only you. Perhaps you can also find a community of others from which to learn along the way. Did Julia like to write when part of her job as a marketer was writing blogs for the MSP? She did not like it. The content was marketing and very salesy. Julia did not feel it was authentic. “Nowadays I write a different type of content…more authentic – what I think about the tool, the challenges I’m facing…. Now I write the real deal, the real thing.” – Julia Furst Morgado Julia likes to write about the things she’s passionate about, and it allows her to be more authentic. People may not know what their authentic voice is or the way in which they prefer to write until they are in the midst of the writing process. This is an indirect reference to the phrase “writing is thinking” from Episode 156 with guest Josh Duffney. “You can only find out by doing it. People get stuck in that planning phase, and they never execute. And I’ve been there…. We will only find our voice. We will only find the topics that we want to create content or to write about if we start.” – Julia Furst Morgado, on creating content Julia wants to start a podcast and right now is in the planning phase for it. Julia encourages people to start creating some kind of content, even if it isn’t perfect. When Julia began writing blogs and sharing her content, was there a pressure to keep doing it because it was done “in public?” Julia feels like there is pressure once you start sharing content on social media, especially if people find it valuable. When someone re-shares something you wrote or sends you a message telling you it is helpful, it can make you feel like you should do more. Julia encourages us to be consistent with our content. If you are releasing something once per week and for some reason miss a week, people may decide to place their attention elsewhere. The consistency in creating content needs to be something that is sustainable for you. You don’t need a blog post every day. Julia suggests starting off with a target of once per month. How did Julia’s skills in digital marketing shape the way she approached sharing content on social media? Julia writes with her audience in mind. Her intention is to solve a problem for the audience. She always includes a call to action (or CTA) at the end. This may encourage people to comment, like the content, or attend an event for example. Julia structures her post in a way that people will want to read it. Writing in a single block isn’t as easy on the eyes. People might not read your post based solely on this format choice. Blog posts should start with a “hook” to get the reader’s attention. You should follow this same guidance for social media posts. On LinkedIn, for example, only a couple of sentences show up with a link for people to “read more.” Will your first 2 sentences be powerful enough to make people want to know more? 20:56 – Pursuing a Boot Camp and Building a Professional Network While working for the MSP, Julia was already looking at boot camps in New York City. A boot camp can cost $10,000 or more, which Julia was willing to pay. Julia wanted to learn technical skills and software development. At around this same time she was laid off from her role at the MSP. Julia saw a post on Reddit about someone starting a boot camp in January 2022. It would be live streamed and focused on web development (JavaScript, Node.js, React, etc.). She attended the live stream twice per week for 3 hours. The instructor had office hours and required homework. “The thing is the boot camp wasn’t just a coding boot camp. He said his goal was to get us a job in tech, our first job in tech.” – Julia Furst Morgado, on the uniqueness of the boot camp she joined and the instructor’s goal As part of the homework for the boot camp, Julia and other attendees were required to do coffee chats with others in the industry. They were to reach out to people already working in the tech industry to ask for a 15-minute coffee chat. Julia conducted over 100 coffee chats during this time, and she built a professional network. She kept a spreadsheet to track the people she spoke with and notes on the conversation for future reference. “And I built my network very easily. Because when you’re starting out, and you show people you’re putting in the effort, they will help you. They won’t help you if you just say, ‘I want a job. Can you give me a referral?’ …If they show you that they’re putting in the work, yes, I’ll give you 15 minutes of my day to tell you about how I got here where I am and give you some advice. And that’s what I did, more than 100 times.” – Julia Furst Morgado, on doing coffee chats with other technologists as part of a boot camp assignment How many of the coffee chats ended after 15 minutes? Most of the conversations ended up being longer than 15 minutes. Julia says she was able to find mentors through these coffee chats. Most people were very open to speaking with her. Three of the coffee chats became recurring coffee chats. Most of the coffee chats were with men. Julia advocates for helping and supporting more women in tech, just as she had supporters and many people who encouraged her during this process. “It was great. It was amazing. And I hadn’t seen that in marketing or law. This I think is more particular to tech. Because of open source people want to collaborate and help each other to achieve the same goal. They don’t mind telling you what they did, their path to success…. It’s one more that is going to help the cause or collaborate together. That’s one of the things I love about tech.” – Julia Furst Morgado Did anyone give Julia advice on career options in tech before she attended the boot camp? “No…. I went to the boot camp thinking mostly that tech was software engineering.” – Julia Furst Morgado Even though she had worked with IT Support and DevOps folks at the MSP, Julia thought to say you worked in tech meant you were a software engineer. She learned there is so much more than that under the tech umbrella. In the coffee chats Julia spoke to software engineers, program managers, DevOps engineers, platform engineers, data analysts, etc. from an array of different companies of various sizes (including large companies and startups). During this process, Julia was learning about different job roles and what those entailed. But until she worked with some of the tools needed to do these types of jobs, Julia did not know which one might be best suited for her. Julia tried building websites and decided she did not like front-end work. After working with APIs, she found she did not like back-end work or even full stack work. Julia enjoyed working with cloud technologies from AWS and eventually gravitated toward Kubernetes. It was her network that took her there. Julia shares the story of someone she met on social media in the greater tech community. This person gave her a lot of guidance and advice and then a free ticket to KubeCon. Julia was presented with the free ticket while she was still doing the boot camp. “And by the way, I wasn’t sure if I should go because I thought it would distract me from software development. My other mentors…they said, ‘Julia, go for it. The homework you have for the boot camp…you can do it after or before. But go. This is a great opportunity.’ I went, and I met a lot of people. I saw there is a different world besides software development – DevOps and platform engineering and infrastructure…all of that. The community is amazing there.” – Julia Furst Morgado At the conference, Julia met Michael Cade (a now colleague at Veeam who she knew only from Twitter then) in person. Michael said he wanted Julia to come work on his team. Veeam had a booth and a number of events at the conference. Julia spent a day going to all the Veeam events and talking to a lot of people. Michael wanted Julia to come work at Veeam and put her in touch with the hiring manager. “I had two interviews. They weren’t technical. It was more like a chat. He wanted to get to know me. And I got the job.” – Julia Furst Morgado 29:44 – Tech Conferences and the Hallway Track While getting the job at Veeam might have looked easy, Julia had put in the work to develop a background in advance. Julia’s social media presence and the willingness to learn in public is part of what made others want to invest in her (i.e. the free conference pass). During the second interview, Julia told the hiring manager she had never worked with backup, servers, infrastructure, or hardware. “It’s ok. We can teach you that. But we can’t teach someone this hunger to learn and adaptability. You take initiative. We don’t need to hold your hand to teach you something.” – hiring manager to Julia Furst Morgado Julia calls the above the soft skills. While technical skills are important, soft skills are very important as well. John says learning in public can often be individual and solo. Learning at a conference is learning in a group or learning from someone broadcasting information in a session. What thoughts does Julia have about the contrast in learning styles? “When I go to conferences, I don’t learn a lot. I learn after I get home from conferences because at conferences, I focus on networking…. It’s basically just meeting people and building those relationships.” – Julia Furst Morgado When at home…Julia will study, work on personal projects, read books, or watch YouTube videos. When she is at a conference, Julia will talk about what she is learning and ask people for help if needed. Julia has a lot of friends in the tech industry now. She’s seen them multiple times at events and will comment on their posts. After coming back from a conference, Julia will watch announcements and recorded sessions from the conference to catch up, learn, and put things into practice. At conferences, Julia would advise listeners to focus on networking (or the “hallway track”). You can go to sessions if you would like to meet the speaker in person or ask specific questions. John says some people may have trouble with the hallway track due to introversion, but he has seen a number of people attack the hallway track with some vigor. Julia says this is part of developing soft skills like effective communication. Many people in tech may be shy or introverted. You have to learn to talk to other people by doing it. Julia says we can practice at the grocery store by talking to the cashier. It’s a small step toward meeting new people at a conference. After getting the free conference pass, did someone give Julia advice on how to approach the conference? No. Julia came up with what she did at the conference on her own. “I didn’t know what to expect. I was shocked at the beginning. It was so big. I think there were…around 10,000 people. I didn’t know anyone.” – Julia Furst Morgado Julia went to the booths and conference events. Someone she knew introduced her to someone else, and it went on from there. Julia enjoys talking with people, and it was easy for her to meet a lot of people. By the second day Julia felt pretty comfortable. “I didn’t know what Kubernetes was yet. I was trying to understand, but Kubernetes is very hard. But I knew people and they were willing to help me…. That’s what I love about tech.” – Julia Furst Morgado 36:29 – Details on 100Devs Is the boot camp someone can do on their own time, or does it depend? The free boot camp Julia did was put on by Leon Noel is called 100Devs. See also the main 100Devs site. Check out Julia’s videos on 100Devs below. Her advice after being asked by many people is get started, and keep going. Do not stop when things get hard! Free Coding Bootcamp – 100Devs Everything you need to know about 100Devs. Mentioned in the Outro Special shout out to former guest Al Rasheed for recommending we have Julia on the show! The coffee chats were a great idea for professional networking. In in these 15-minute discussions (many of which went longer than that), you are interviewing the person about their experience, the tools they use, what they are learning, and what their job is like. This goes well with Ramzi Marjaba’s advice on professional networking in Episode 307 – Sales Skills: Professional Networking and Continued Practice with Ramzi Marjaba (1/2). Tracking the coffee chats was a great idea to remember who Julia spoke with and their area of specialty. Talking to many people and getting advice from all of them might make one wonder which path to take in the tech industry. Julia had to do some tinkering with different tools before uncovering an interest in cloud technologies and Kubernetes. Julia decided to learn these in public. Is there something new you want to learn? Maybe it’s something in your area, outside your area, or just something that is interesting. It could be a certification you want to get. Suppose you book a certification test and take a course to help you study (with plenty of time to complete it). But as you work through it, consider documenting the following items in blog form to share as evidence of learning in public: Why you chose this area / what interested you in the first place The notes you took on hard concepts or some of the items you learned in the process Whether your preparation was adequate for the exam / if you would have prepared differently if you did it all over again If pursuing the certification made you want to go deeper in the area or revealed it wasn’t as interesting as you thought Maybe you publish 1, 2, or 3 posts. It’s a small start to learning in public that can help others and help you at the same time. And it’s not a huge commitment to create content. It’s worth thinking about! This is proof of work and proof of learning. It also shows your thinking process. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.

Does a successful consulting career mean you should only work for yourself? David Klee insists you first need to become a skilled consultant with the right kind of reputation. In episode 310, part two of our focused discussion on the nuances of consulting, we dive into the realities—and the pros and cons—of contracting, working full-time for a consulting firm, and the independence of running your own business. These represent 3 of the 4 ways someone could work as a consultant. Building on last week’s conversation about what makes a great consultant, we discuss the importance of developing a reputation and some tips for how to do it. David also shares his approach to assessing consulting talent, highlighting the key traits that make a consultant stand out. And we’ll also hear why, after 11 years owning a consulting firm, David can’t see himself doing anything else. Original Recording Date: 12-18-2024 David Klee is the founder of a niche consulting company called Heraflux Technologies. If you missed part 1 of this discussion with David, check out Episode 309. Topics – Contract Work as a Consultant, Working for a Consulting Only Firm, Starting a Consulting Firm / Doing Your Own Thing, Keeping Consulting Enjoyable 2:25 – Contract Work as a Consultant Another way to do consulting work is to be a contractor. How does this work differently than full-time employment? Full-time employment could be 1 project for 40 hours per week, but it is unlikely. It will more often be a certain number of hours per day working on a few (or even several) different projects. “Things just kind of float to where you’re juggling anywhere from 3 or 4 to 20 projects at the same time. A contract is going to be a tightly defined scope for a block of time for either per day, per week, whatever. And it’s going to run a duration such as 2 months, 6 months, a year…something like that where you’re able to refine what you do. It’s generally speaking going to be a task or a set of tasks, and that’s what you do.” – David Klee, contrasting being a consultant working full-time for an employer that does more than just consulting with being a contractor A project you work on as a contractor is controlled. You know when it starts, what to expect, and when it ends. A contractor has to line up the next project once one ends. Knowing the endpoint can help you understand when it’s time to begin looking for the next project. Contracting might allow focusing or going deeper on the work you are tasked to do instead of getting too broad. David gives the example of needing to build a data warehouse for a specific ERP system within 6 months. David says contract work is safe and sustainable. In fact, one of the first projects after David started Heraflux was a contract engagement which required travel to Connecticut and working 5 days per week at a customer location for 6 months. Where can people find contract job openings? Are these on company websites, on LinkedIn, only available through headhunters, etc.? David says it works best if you can go through a headhunting entity. Companies may post contract positions on LinkedIn or popular job sites, but a headhunter can evaluate someone’s skill set and share a set of projects that align to that skill set. The candidate can then select which projects they would like to interview for, and the interview may be with the headhunter, with the end customer, or possibly both. “It’s a way where instead of you looking (and there may be phantom jobs or people just fishing for who is out there) the headhunter is usually going to be a lot more serious. If it’s through a headhunter, the right might be a little lower than if you would go direct; however, the headhunter might also be able to provide you healthcare…and that goes a long, long way…. There are some benefits like that that really do help.” – David Klee, on contract work through headhunters A headhunting firm could potentially provide the healthcare benefits for 6 months or 12 months while you are working on a project so you don’t have to look for it yourself. The headhunting firm may also be able to handle tax withholdings from your paycheck so you don’t have to handle it after the fact. Contract workers would likely be paid via a 1099 form in the United States. What type of headhunters should people who want to do contract work seek out? Are there big names to be aware of? There are national chains that do this as well as regional and local. Each one will have benefits. A national chain may be more likely to offer you interviews for projects that require air travel to a customer location each week. Regional headhunting firms may have some travel, but you can easily get a feel for their reputation. You can speak to people who have worked with them as contractors as well as companies who have worked with them. This can help you get an idea as to whether the firm is a fit for what you want to do as well as a cultural and a people fit. “The national chains will almost certainly have more opportunities. You may have to travel for it. The regional stuff you’ll be able to get to know them a little bit better, and after enough time they may actually know to call you if they have a project of a certain type…. And there’s no reason to say you only have to work with one headhunter.” – David Klee, on contracting and working with headhunting firms David mentions he has gotten to know a number of good firms in the Omaha and Lincoln, Nebraska area. When a project ends and the headhunting firm you have been working with doesn’t have more projects that fit you, nothing is stopping you from working with a different firm. Working with the headhunting firm can help spread your reputation to multiple end customers because of the reach of the firm. Would a headhunting firm or end customer pay for travel if you are working on a contract basis, or would the contractor need to pay for it themselves? David says it should be that someone else pays for the travel, but this can work in many different ways. Sometimes the headhunting firm may book all your travel arrangements as part of any travel you do. If this happens, beware of getting placed in very inexpensive accommodations. Sometimes you may be given a travel budget, and it’s up to you to figure out how to use it. Exceeding that budget would come out of your own pocket, but if you come in under budget you may get to keep the difference. Some people may do contract work as a side gig in addition to their full-time job in the form of moonlighting. David says you have to ensure your contract for your full-time job does not prohibit you from doing this kind of thing. For some full-time employers, doing extra work on the side is not a problem as long as there’s no conflict of interest. “…The side stuff should never get in the way of the full-time job…. Some companies out there, including some big ones, they’ll let you moonlight as long as you disclose it and as long as there’s no chance that it could ever conflict and hurt the mission of the full-time job.” – David Klee, on doing part-time contract work in addition to your full-time job David says moonlighting is a great way to gain experience consulting, but you need to make sure no one expects you to be available during normal business hours. This can be challenging as many companies might want things fixed during the day. David gives the examples of database index tuning and custom programming that should be fine to work on after hours. But you should always make sure the company you’re moonlighting is ok with your hours of availability. What about the stability and volume of contract work during difficult economic times? Contract work according to David will ebb and flow usually with what the economy is doing. In difficult times, companies will pause projects that involve outside contractors or maybe just slow them down / decrease the hours. David cites a customer he worked with who leveraged contractors and consultants for 75% of the IT workforce. During tough times this company would pause or suspend the projects, making sure they never had to lay off full-time employees. Being on a time-bound project as a contractor does not protect you from difficult economic times. Companies can still pause the project or end it. “A lot of people I knew were on contracts during 9/11. And boom. A lot changed, and these projects were just done. Within a couple of days a whole bunch of stuff changed, and a lot of people were out of work. Now it didn’t last that long for them thankfully. But, there’s always a clause in there that says these contracts can be terminated at will.” – David Klee, on contract work David shares the story of leading some SQL Server migration projects for a large airline and the changes that happened when the pandemic hit in 2020. “I get an e-mail at 10 o’clock in the morning saying, ‘stop what you’re doing. Document everything you can through the end of the day. That’s it.’ …Because the airlines shutdown, it was cost savings panic mode, and every external project with external people suspended immediately.” – David Klee How do hiring managers for full-time roles look at candidates who have done a lot of contracting? David doesn’t see someone doing contract work as a bad thing, but it depends. He would want to know why the person was choosing to go back to full-time work somewhere. Did the person get a poor reputation from doing contract work, or do they just want benefits like healthcare, paid time off, a 401K, etc.? “Those are a lot of reasons why a lot of folks get out of consulting and go back to being an FTE. There’s stability. There’s job security. There’s benefits. If you’re tired of the constant churn of different projects, you now have a controlled environment, and you know what you’re working with there. And there is nothing wrong with that.” – David Klee How is the interview process for contract work different from full-time employment? Is it shorter? David says usually it is shorter, but it also depends. Interviewing for a full-time role might be 5 or 6 interviews because the company wants to make sure you’re a cultural fit in addition to just being a technical fit. When interviewing contractors, people might be more concerned about the ability to get the job done rather than the cultural fit. When interviewing for a contract role proof of competency and ability to get the job done are going to be the most important things. David says the contractor may have 2 interviews as opposed to 3, 4, or 5. Thanks to his reputation for doing good work in the industry, David’s average interview / pre-sales call is 30 to 60 minutes. After that it’s either a fit or it isn’t (on both sides). “People know what we do, and by the time it gets to us, they know we’re qualified for what they’re going to ask us to do. The question is…how long is it going to take? When are we going to start? Thankfully, after being in business 11 years, we’ve finally gotten to that point where we can say…we can do this, and you know we can because you know us.” – David Klee, on developing a reputation 17:14 – Working for a Consulting Only Firm Another option for people who want to do consulting is to work for an established consulting firm (i.e. a company whose sole business is to do consulting). Are there things to look for in a consulting firm to work for? Talk to people in your professional network about the firm’s reputation in the industry. David would also recommend speaking with consultants who work there already (i.e. future teammates). David would advise considering the following questions. Some may be the same as what we have previously discussed, but some are very different. Are current employees of the firm happy? Are projects a “bait and switch” approach or are they completed to meet and exceed expectations of everyone involved (customers, consulting firm employees, etc.)? What is the caliber of the firm’s customers? What size companies are they, and can the client hold up their end of any project? What kind of travel is required? Will you need to serve as part of an on-call rotation? What’s the breadth of customers you should expect to work with, and how many projects should you expect to work on in a given week? If this firm does remotely managed services, for example, you could be working with 20 different customers in a single day. Are you ok with context switching like this? Are you responsible in any way for pre-sales as well as delivery / post-sales? What does the split look like? What will you be expected to do? Is working for a consulting firm in one specific niche ideal, or should someone target a consulting firm servicing many areas? “If a consulting company has a super tight niche, are they changing with the times? It gets really interesting. If the company has enough business to do XYZ and that is all they do and then some revolutionary technology comes out of the woodwork…guess what? They’re done.” – David Klee David shares the story of someone he knew in college who was a talented Adobe Flash programmer and didn’t want to learn anything else. David mentions being on-call 24/7/365 for most of his employers (including holidays). Ask a consulting firm where you might want to work how hard they push this and what constitutes an after hours call. If you take a vacation, will they call you while you’re on vacation? Are you expected to check e-mail on vacation? What will the firm do to help keep your technical skills current? Do they want you to get certifications? Will they send you to conferences? Will you be given time each week for professional development? Some firms might just expect you to keep up with the technology on your own but may not encourage it or support it, while others may be very good in this area. David knows many people in the SQL Server community who would support someone attending a conference or a SQL Saturday and ensuring that person can be present to learn and network with people (i.e. the workload would be covered by others at the firm). “They benefit. You benefit. You’re happier. You’re not going to jump ship to somebody else that’s going to do this.” – David Klee, on training and professional development Could training employees / allowing them to get certifications be looked at as just making them more expensive? David says the firm can justify billing more for a person because the person has increased capabilities. Do consultants have insight into how much the consulting firm is charging compared to how much the consultant makes? David says this is rare. “When I was consulting for somebody else, I would always see the technical details of the paperwork. I would never see the money side. You knew what companies were capable of charging. You never knew what they were actually doing.” – David Klee There is another layer. The company you work for may be a subcontractor to another company. The markup to the end customer of your company’s services can be considerable. Is it a safer choice to work for a company whose main business is consulting (i.e. it’s not just something they do in addition to selling technology)? David says it depends. “If you’re working for a company whose sole mission is consulting, that’s their revenue stream. If you’re working for a company who sells software and then consults on the software, if things slow down, they still have the revenue stream from selling the software…. So that’s the safer route. However, if a company is solely purposes with selling you and they’re good and the rates are reasonable and they know how to market, you shouldn’t be concerned…because they should have enough…to say, ‘if we don’t have a project for you for a couple weeks, it’s ok. We’ve got the money banked, and we’ve got another one coming soon.’” – David Klee Is there a natural progression for the consultant through the options we’ve discussed so far? David doesn’t see people move away from roles at companies that do more than just consulting very often. Usually, those folks who do contract work tend to enjoy it and consistently move on to the next contract without too much trouble. If you are a consultant working for a company that only does consulting, there are a couple of paths forward: Progress through the ranks and outgrowing consulting Those who get tired of the grind will likely go to contracting, to a full-time employer somewhere, or choose to do their own thing / start their own business. 25:14 – Starting a Consulting Firm / Doing Your Own Thing When should you seek to go out on your own? Is it only if some of the other options aren’t possible? “I would say you should do one of the other 3 to prepare you to be a consultant for yourself.” – David Klee Owning your own consulting firm juggling multiple projects means you are responsible for everything – pre-sales, delivery, marketing, paperwork, and much more. Projects may not last as long as if you were doing contract work. You need to be ready for this as a consulting firm owner. David says you have to know how to talk, how to sell, how to deliver, and how to upsell. “You need to know where your next project is coming from.” – David Klee David tells us upselling is not to be taken in the used car salesman sense. It’s about spotting legitimate problems within the realm of your expertise and pointing them out to your customer. “It’s other problems that you can solve that you know how to do, and you have to know how to say, ‘I’m better than the other people at being able to solve this problem. And I already know you. I already know your environment. I’m better suited to solve this because I’m already here.” – David Klee, on upselling When people like the work David’s firm has done, they call them back for return projects. Because he trains people to solve their own problems internally, a customer generally does not call him back for the same problem. This goes back to reputation. “But the hard part is…how do you get the reputation? Consult for somebody else. Get the contracts, and get to know people. And put yourself out there…. The biggest fallacy is that you might be good at something technically. And a lot of people…I don’t know where they get it from, but they seem to think that they can just hang a sign on their front door that says ‘I’m good and I’m open for business’ and that people will just come flooding in…. It unfortunately doesn’t work like that…. That’s what a lot of folks think, and then they go 6 months and they’re barely making minimum wage or less. People run into trouble with that, and it’s tough…. I’m good. I know what I’m doing. Why can’t I get the projects? People don’t know that you’re there.” – David Klee, on going into business when you don’t have an established reputation Doing presentations and going to user groups is good marketing just as we discussed earlier. Nick encourages people who have been laid off to attend user groups to build connections with new people. David mentions he recently won a project because someone remembered a presentation he gave several years ago at a SQL Saturday event. This was about word-of-mouth reputation. If I’m a consulting firm owner who has developed a reputation and needs to expand the firm by hiring more people, is it more attractive to hire contractors or full-time employees? David says it varies. You need to consider your project flow and revenue first. Do you have enough to support bringing someone on board and to train them to do the project work needed? Can you find someone with the skills you need, and can you charge enough to afford the person? Will you have enough to pay for the person if at any point you do not have enough work to keep them busy? “Take whatever you think you make. The employer is paying about 40% more between healthcare and taxes and all that stuff. They’ve got to be able to cover that bill, and some people are not cheap.” – David Klee David has developed a ring of contractors and consultants he works with now (meaning the paperwork is in place to do so as schedules allow). Though the cost is more per hour for these people, he does not have to pay to keep them on the bench as full-time employees if there are no projects for them. David did try the full-time employee approach at first, but people were recruited away. The other side of this is David cannot dictate a contractor’s time like he could a full-time employee. If the projects that you work on are flexible, David tells us there are a lot of independent subcontractors who are really good. But it also goes back to who you know that does the type of work fitting the help you need. What is David looking for in contractors and consultants who work for / with him? “I look for people that genuinely love what they do. It shows in the work.” – David Klee David likes to ask people things like: How much of your free time is spent keeping up with technology? What was the last new technology you picked up and learned, and how long did it take you? And why did you do it? What kind of a home test lab do you have? Name people in the industry who publicize how-tos and training videos and blog posts. “Tell me the last time you did a technical presentation. What was the topic? How many people were there? Did you enjoy it? What did you learn from doing the presentation? What could you have done better on the presentation? And when are you giving it again so I can watch you do it?” – David Klee A video link of you doing a technical presentation is a great thing to have ready to share with someone! How long have you been working in this? Why are you in this industry? Is it something you enjoy? “It’s that want to know, the want to fix, the drive to do better and learn and grow and contribute. That’s what I look for.” – David Klee, on what to look for in consultants he would hire or work with Has David spoken to anyone who struggled to articulate why they enjoy working in this industry or why they work as a consultant? David says yes. “If they can’t tell me why they want to be or stay as a consultant, it tells me they may not be really invested into it. So, they are just there on a 9 to 5 basis. For some jobs, that’s perfectly fine. It really is. If I need an operations person to keep the lights on, keep stuff running, that’s fine. But if I need somebody to say, ‘we’ve always done it this way, but here’s a new way. And it’s a better way. And I figured out how to do this.’ That’s what I want…. Do you enjoy finding a better way? I think that’s the one succinct statement I can say right there that makes a great consultant instead of a good consultant.” – David Klee 35:47 – Keeping Consulting Enjoyable After all of his experience in consulting and now after owning a business for many years, how does David keep the enjoyment despite the stress and all the obligations? David likes doing new things and gets bored easily. “As a consultant, you can choose to spend non-billable time that’s business oriented.” – David Klee When there is an emerging trend or technology, David can spend time learning to deepen his expertise. David gives the example of clearing his calendar for 2 weeks to go deeper in some specific technologies. A full-time employee is unlikely to get this type of opportunity. The consultant can use the learning to widen his reach and to provide more value to customers. “To be able to say here’s a new technology; I think it could compliment what I do and adapt and grow and broaden what I do and sharpen what I do…. The more you know, the more you know the failings and the positive things about the stuff that you already do. Database technologies, infrastructure, cloud…they are more tools for the toolbox. It makes you a better consultant….” – David Klee David can also say no as the owner of his consulting firm. He can avoid accepting projects which are not a good fit or are destined to fail. “The consultant…you can say no. The contractor…you may have to work out the remainder of the contract, but you know it will end at some point. Being an FTE or a consultant for somebody else…you may be kind of stuck…which, that’s difficult.” – David Klee “If you’re willing to put in the effort and work it and it works, you’re doing this for you. You’re not doing it for somebody else…. It’s a massive shift, and it’s not why you want do it. But at the same time, if it works, that is a good motivator…. You’re the one building the reputation for you. You’re the one building the professional contacts that stick with you through thick and thin. It’s for you. And you and enjoy it. And you can’t trade that for anything.” – David Klee Working for yourself means you don’t bring on the wrong person, don’t bring on the wrong project, and you don’t keep customers who are not a good fit for you. “The biggest power you have is you can say no. It’s empowering. It builds confidence. It strengthens your convictions on why you continue to do this. Because after being in business for 11 years and being in consulting for 14, will I ever go back to working for anybody else? No way. I’m having too much fun.” – David Klee David recounts the story of recently saying no to a customer. It can be unexpected and hard to hear. If David could go back and do it all over again, would he still go into business for himself? David says yes – without hesitation. He also might have done it a couple of years earlier. “I’m having too much fun. I know it sounds cliché, but most of my day is solving problems for folks…. Call me weird. I know we’re unsung heroes in IT, all of us. I get a personal thrill out of being able to make that kind of a difference. Even if it’s saving somebody ten grand on database licensing or making this report that they have to run every single day over lunch…to be able to make that run quick…they curse the machine less and they can do more of the job that they enjoy. And that’s fun. I thoroughly enjoy that.” – David Klee David shares some examples of the ways he has made a difference in the lives of his customers -fixing a recent SQL Server performance problem, helping a customer save millions on licensing, making improvements that added to the valuation of a company, etc. If you want to follow up with David on this conversation, you can Visit Heraflux.com. Visit DavidKlee.net. Connect with / contact David on LinkedIn – davidaklee. Mentioned in the Outro The way David assesses consulting talent, especially those he might work with as contractors, was extremely interesting. Asking about why someone does what they do and how much they enjoy the work gives you insight into whether this person is likely to remain valuable in our industry over time. The consulting firm owner wants to work with people who will continue to be valuable over time. Try asking some of these questions of a co-worker. What are they learning, and why are they in this industry? David talked a little bit about upselling. This is not something exclusive to selling a product or service. Full-time employees of any company do this all the time. Think about the last time you added to the scope of a project because it was interesting or you spotted something that needed to be fixed. We might do this to provide more value to the company, to show we’re taking initiative, or something to help you gain expertise in a new area. We might need to sell the idea of spending more time or resources on something to our management, especially if we’re not usually in control of our workload. Remember to provide details on what will be done and the value something will provide (i.e. decrease risk, increase revenue, etc.). If you’re looking for more stories of those who have pursued consulting, check out our website’s consultant tag, or listen to some of these recommended episodes: Tad Reeves had a lot of experience doing contract work and spoke to us about the things he liked as well as how there came a time in which it no longer fit with his life circumstances. Check out [Episode 297 – Consulting and Content Management: Blinking Lights and Big Impacts with Tad Reeves (2/3)(https://nerd-journey.com/consulting-and-content-management-blinking-lights-and-big-impacts-with-tad-reeves-2-3/). Marni Coffey shared her experience as a consultant, spoke to the glamour of consulting, and shared why she didn’t like it. But we also found that this made her a better leader later in her career. Check out Episode 278 – Uncovering Empathy: The Greatest Skill of an Inclusive Leader with Marni Coffey (1/3). Both Dale McKay and Erik Gross shared their respective thoughts on the role of a consultant and how to be successful. Check out these episodes: Episode 289 – Enhance Your Personal Brand: Feedback as a Catalyst for Change with Dale McKay (2/2) Episode 295 – AI and Automation: Repeatable Patterns for Learning, Consulting, and Growth with Erik Gross (2/2) Justin Kelly has experience doing contract work, moonlighting, and is a business owner like David. Episode 271 -Moonlight Business Ownership: Inside and Outside the Hurt Locker with Justin Kelly (2/2) Abby Clobridge was another recent guest who owns a consulting firm. She has some great thoughts on what it means to take a consultative approach in these episodes. Episode 292 – Library Science: Information Architecture and the Synthesis of Details with Abby Clobridge (1/2) Episode 293 – Enterprise Knowledge Management: A Consultative Approach to Solving the Right Problems with Abby Clobridge (2/2) Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.

What does it mean to be a consultant? We’ve explored the consultant role as part of the career path of previous guests, but this episode kicks off a focused two-part discussion on the nuances of consulting. In this first part of the discussion, episode 309, returning guest David Klee shares practical insights for managing business travel, enhancing communication skills, and excelling in the consulting profession. He explains how great consultants adjust the information they communicate (and the level of detail) to resonate with people in different roles within an organization. Whether you’re considering consulting, already in the field, or collaborating with consultants, this conversation has actionable advice that can help. Original Recording Date: 12-18-2024 Topics – David Klee Returns, Focusing on the Consultant Role, Consulting as a Career Path, Job Descriptions and Interview Advice, Travel Expectations and Being Productive, Working for a Company with a Consulting Arm, Presentations and Communication Skills 2:23 – David Klee Returns David Klee is the founder of a niche consulting company called Heraflux Technologies. They do performance tuning and availability architectures for SQL Server and everything underneath. This spans on-premises, in the cloud, virtual, and physical instances. David has worked on some of the biggest SQL Servers in the world. This discussion series is meant to be focused on the life of a consultant. If you missed the previous episodes, we recorded with David that include his origin story in technology, check out these discussions: Episode 119 – Tinkering into Specialty with David Klee (1/2) Episode 120 – A Time to Build with David Klee (2/2) 3:22 – Focusing on the Consultant Role We’ve heard the term consultant used in many different interviews and contexts. How would David define what a consultant is? “I have a whimsical definition of it. A contractor is somebody you tell what to do. A consultant is somebody that tells you what to do.” – David Klee, on the definition of a consultant Hire a consultant to solve a problem you do not know how to fix, engineer something you’re uncertain of, or to handle tasks you may not have the skills in-house to do. Some of these tasks might be routine health checks, platform assessments, etc. We may have worked in an environment daily for many years, but a consultant brings the unique background experience of working across many environments over time. With the right background knowledge and experience, why do consultants get a bad reputation? “There are a lot of really, really good consultants out there, and there’s a lot of really bad consultants out there. And there are a lot of really good consultants out there that charge a ridiculous amount of money for what they do, and there’s a lot of bad ones that do as well.” – David Klee People remember the bad consultants they have worked with more vividly than the good, and this shapes their perception of what a consultant is. People might develop their own persona of a consultant as someone who charges too much, doesn’t do a good job, and then leaves. David tells us this spans across industries and is not unique to technology consultants. When people seek to hire a consultant, they might not know what to ask to vet that consultant’s experience before hiring them. Are references a nice way to do this? David says he gets asked for references pretty often, but speaking to references can be a challenge as well. You might talk to a reference and find out they are related in some way to the consultant, for example. “You just have to be careful when you talk to these folks on the other side of the table…. It’s not that all consultants are bad. It’s just there’s a lot of average consultants. There’s a few bad ones. There’s a few really good ones…same thing with normal hires.” – David Klee A consultant could be brought in to help for a short time, for a medium term, or for a long-term project. David mentions a friend of his who has worked on a block of hours that has renewed for 12 years. In this specific case, the person is basically part of the company and treated like family. This long-term nature of the engagement makes it easy to take time off when needed. How can listeners work better with consultants during the hiring phase and in collaboration with them after hiring? David says it is important to understand and convey what you want a consultant to do or the direction you want them to steer you. We should convey what we want from a consultant in as much detail as possible. Suppose you told someone to build a car for you. The skillset to build a semi-truck is totally different from that needed to build a Formula One car. “If you tell somebody something and their background is building racecars and what you really need is somebody to tow a trailer…if you just say go build me a car, guess what? Out comes some really cool high performance sports car that’s not what you needed. And you’re disappointed. They’re unhappy. Nobody wins.” – David Klee David says plan to give the consultant as much of the detail up front as we have. If you don’t have all the detail, communicate there is some ambiguity, that you need help choosing a direction and filling in gaps. This helps a consultant scope the product and understand what you really want instead of what you say you need (which could be 2 different things). A scope of work defines what a consultant does and whether they perform hands on keyboard work or not. Can people just purchase a number of consulting hours without a clear deliverable? “There should always be some kind of deliverable…. If somebody walks in the door and you say do task X and then they go do task X and then they disappear…if you don’t have a record, do you know what they actually did? And if they get hit by the beer truck, can somebody repeat what they did tomorrow? …The scoping is one of the hardest pieces.” – David Klee Scoping can be challenging and varies by project. David gives an example of a SQL Server migration project. In this case he would provide reference material to help build a new machine. David could build the new machine and show someone how or let them build it while he walks them through it. There are a number of elements of scope in addition to performing the tasks. Scripts might need to be run or problems fixed before a migration can happen to continue the example above. Once the work is complete, David will provide a document describing the new machine, how it was set up, why it was set up that way, and any fine tuning needed to run a specific application. 9:55 – Consulting as a Career Path Why do people pursue a career as a consultant? What makes it attractive? For some people it is not the right choice, but for others it is the clear choice. Consulting might be a good choice for you if… You are bored with the tasks of your normal job You want to do something different There isn’t any training You like dynamic work environments David tells us if you’re pursuing a role as a consultant, be prepared to learn! David likes consulting because every day is totally different. This can also be a downfall sometimes. Full-time employees of a company can end up working in an environment with a boss they don’t like or a co-worker with which they clash. David mentions working a short consulting engagement in a less-than-ideal environment is more tolerable knowing he will move on to something else once it’s complete. Consulting can keep things fresh, allow you to see new types of problems or environments, or give you the chance to do something new. Being a consultant can remove you from some of the politics within companies. David, for example, doesn’t deal with corporate politics very well. If politics get in the way of getting something accomplished it can be frustrating because the roadblock is not technical. The consultant would prefer to just be able to do their job. David, as the owner of a consulting firm, can say no to taking on a project. What can a full-time employee do if they are told to do something that is the wrong approach? David feels the employee cannot realistically say no. David shares an example from one of his first jobs out of college. He worked on a specific application’s programming language and was asked to fix all the bugs. After presenting the people in charge a choice between rebuilding on the latest software version (3 months) or patching the existing version (9 months), they chose the 9 months. It was not the right approach because of all the new bugs that were found which took longer to fix based on that decision. A consultant may have to present options and make a recommendation, but it is the customer who makes the decision on what is to be done. If a consultant feels like it is the wrong approach or not in their best interest and they are empowered to do so, they can decline the project. Does a consultant need to bring a deep expertise in one or more areas into the role, or are there other qualities one might possess that can make up for this? It’s ok to not be as deep, but you must be willing to ramp up to meet or exceed the expectations of the employer. “A lot of people can do the technical work. Can you talk to the people in the business in a way that represents their role in the organization? Talking to a CFO is totally different than talking to an application owner and totally different than talking to an infrastructure engineer or software engineer. That’s one of the biggest things…understanding how to take what you know and interpret it to what you need out of that individual role and convey it in a way that matters to them and a way that they can digest and actually comprehend. It’s a hard art…and I’ve been working on that for a very, very, very long time. It took being placed in a number of quite frankly uncomfortable situations to really understand how to talk to those people easily, naturally.” – David Klee Consultants can learn communication skills over time. David says a good consultant is ok at this, but for a great consultant, it’s natural. 14:46 – Job Descriptions and Interview Advice What types of roles do consultants have before they become consultants? There are many possibilities here – generalist systems administrator, network engineer, storage engineer, etc. David knows people who consult in areas such as: Project management Social media marketing Offering a fractional or virtual CISO (Chief Information Security Officer) Virtualization / infrastructure You don’t have to be the master of all things to get a project, but you do have to be able to deliver. Do job descriptions for consultant roles read similarly to those for full-time employees inside a big company? David says sometimes they do. But sometimes you see job descriptions asking for experience that isn’t possible. David shares the example of a company wanting 5 years’ experience with SQL Server 2016 in the year 2016. David told the company SQL Server 2016 had only been out for a month and that he had worked with SQL Server since 1995. That wasn’t good enough. The person doing the interviewing also was not the most technical. This kind of thing is a red flag in the interview process and a sign that you probably don’t want to work there. How can the consultant better understand what they are about to sign up for before taking the job? Pre-sales discussions around consulting are as much you interviewing them as it is them interviewing you. David likes to ask questions that give him information about how a company or team operates. He might ask about emergency protocols, documentation for their virtual machines, change control processes and records, and scheduled maintenance windows. Can a consultant stay out of pre-sales conversations and stay post-sales exclusively? David feels you should be part of the pre-sales process to validate the project is a good fit. Even when working through a headhunter, it is likely you will get to speak to the end client customer to determine project fit. “You shouldn’t be expected to just walk into a project blind.” – David Klee, on being a consultant If you’re working as a consultant for some kind of consulting firm and have projects passed to you, there should be some kind of a project acceptance process to brief you about what you’re about to walk into. If a consultant comes in and asks a lot of questions that have already been answered by the end customer, it sets the entire project off in a bad direction. Are consultants afraid of being involved in pre-sales conversations? “Think of it like a job interview you do 12 times a week. That’s hard…. You’ve gotta get real comfortable thinking about everything that you know and understanding how to answer what they’re asking you in a way that is not arrogant but confident. And if you don’t know something, it takes a certain level of experience to say, ‘I don’t know, but I’m going to find out… I’m going to get you the right answer.’” – David Klee David said it takes practice to figure out how to answer the questions in these types of discussions. David shares the story of interviewing for a 6-month contract at one of the largest hedge funds in the world. When they asked a specific technical question, David admitted he did not know. David knew where to find the answer and said he would get back to them once he found it. After doing that, David got the job. We should not claim to know more than we do. People with experience can easily detect it when you are trying to fool them. Why is it hard for people to admit it when they don’t know something? David mentions the Dunning-Kruger Effect as one reason. Ego may be another reason. People do not want to be perceived as not understanding. “When you hit a certain point in any mastery of a certain topic, I call it enlightenment because at that point you know what you don’t know. And you’re not afraid to admit it. But because you know what you don’t know and you know enough about the platform, you know how to go learn what they need pretty fast. And that’s the fun part.” – David Klee David has won a number of projects that were similar to other things he has done but not exactly the same. In these cases, he has asked for one week to create the scenario in his lab. After that time, David shares with the potential customer what he did and confirms it is what they are looking for / that this will meet their needs. Listen to David’s story about solving a problem related to SQL Server Integration Studios for a customer by tinkering in his lab. It was a situation where he explored a product he did not know well and ended up solving a problem. 22:12 – Travel Expectations and Being Productive In our previous discussions with David, he mentioned travelling 150 to 250 days per year for 11 years straight. How much travel should someone new to consulting be expected to take on? David has cut back to no travel ever since the pandemic. Sometimes he misses the travel, but he really likes sleeping in his own bed each night. The amount of travel is going to depend on the nature of the work. If you are consulting for someone else and the expectation is that you will travel, someone else is likely paying for that travel. The amount of travel depends on the contract and type of project. If you are working for yourself (like David), it also depends. You might need to be physically on site to meet or get to know people, especially if a customer expects it. You might need to do it to build trust first and transition to more remote work later on once the customer knows your reputation. David says before 2020, everyone wanted him to come on site, and over time it got old. He tells the story of being flown across the country only to sit in a conference room on a Zoom call and logging into a server located across the country to perform a migration. The company wanted him there as an insurance policy. “The means of doing this stuff remotely have been demonstrated and confirmed. It goes back to the company culture at that point. If the culture wants you on site because they want to physically see you, it is what it is, but some companies are a lot more open to letting people work remotely than they ever used to be…. My days are quite busy. Every bit of it’s remote.” – David Klee Should you expect to get paid more if your role requires travel? It will depend on the company, the type of project, and it will depend on whether you work for someone else or are independent. Being independent might get you more money or higher per diem / travel reimbursement. If working for a consulting firm, hopefully your salary takes the travel into consideration. If you were expected to be on site working 40 hours per week, you might be traveling on Sunday night or very early Monday morning. The travel to and from the customer site is not part of the 40 hours. David doesn’t live in a hub city, for example. Because of this it might take him between 5 and 16 hours to get to a specific destination traveling by plane. That would not count transit time to and from airports (time to rent a car or catch a ride share, etc.) or any extra time due to flight delays. After 1400 nights on the road over the course of 11.5 years, David tells us there have been plenty of travel delays. Hopefully the amount of travel required is clearly stated in the job description, but it can always change at any company based on the needs of the role. David mentions a previous role that started as 25% travel but became closer to 75% travel by the time he left. David says the job dictated the amount of travel. “You have to make sure that if you sign up for travel…for just that rate of travel, is your family ready for it? That means potentially missing family events and late nights and early mornings. It’s not just you that has to be prepared for it. It’s them. If you take any kind of a consulting role that requires even a small amount of travel, be prepared for that, and have that discussion with your family just to make sure. Even if they say they’re ok with it, really press hard. This is real. I’m not going to be here for a while.” – David Klee, on preparing your family for travel Your family might not understand that you are going to come home exhausted every week, need recovery time, and then have to do it all over again. David remembers many times when he would get home late Friday night and then be back on a plane Sunday afternoon. “I enjoyed being at the destination. I hated the journey of getting to the destination.” – David Klee How can people use their travel time to be more productive? David says we should understand how we work and if there are things we can do offline (with no internet connection). It’s important to learn how to work on a plane or in an airport and focus on what you’re doing. Can you block out the world / all distractions? David bought an 8" Ultrabook in his travel days to be able to work on PowerPoint presentations on a plane with room for a mouse. It was small enough to fit in his pocket. A Microsoft Surface was too big and would slip off the back of the tray table. “I figured out I could get a lot of quality time working on presentations or catching up on tech material all on this little tiny thing, so I splurged…. And it actually worked well…. If you don’t work well with distractions…if you can’t sleep on a plane…you have to understand those limits before you even try. Just don’t lie to yourself.” – David Klee, on getting the right device to be productive on an airplane. Is the travel involved in being a consultant something that attracts people to the role? David says yes and that this was one of the reasons he started doing it. He had not traveled to a lot of places before getting into consulting. After over 11 years on the road, he has visited 47 states and 13 countries. Through this experience David developed confidence in his ability to get up, pack quickly, travel to a foreign country, get transportation, and go to a restaurant and order food. David learned to do the planning in advance for his travels after a lot of trial and error. There was no executive assistant to do it for him. 30:51 – Working for a Company with a Consulting Arm We’re going to pivot to discussing the different environments someone could work in as a consultant because they are not all the same. Let’s start with being a full-time employee of a company that does more than just consulting. Maybe it’s working for a technology company or a value-added reseller. This was the entry point into consulting for David, joining a company that was doing Oracle consulting. David provided SQL Server consulting services to the same group of customers. David had a lot of fun with this and got to see a number of different environments. He even got to help the company expand into new markets and bring in a lot of new customers. Is this type of environment the optimal entry point for most people? David says it depends on what you really want to do. “If you’re the kind of person where you need to do 1 thing and 1 thing well…where this is your system or your database or your application, I would say that kind of role might not be the best fit…. You may not be tasked with doing one thing well. You may be tasked with doing a bunch of things at more of a higher level or not as deep.” – David Klee, on working as a consultant full-time for a company whose business model is not just consulting For those who like to do just 1 thing very well, you have the option to look at contract work through a headhunter (i.e. almost being a full-time employee through them). If someone is part of the consulting group or branch of a company that does more than just consulting, how much control would someone get over the work they are given? David says most of the time you don’t have a lot of control. It is often based on customer need, the available people, and the skill sets of those people. Someone would be assigning the projects to you as a consultant. If a consultant brings a specialty to the role, should they expect to change it over time based on customer needs? David says yes, and this concept should apply to everyone in IT. He gives the example of people who began as COBOL programmers (which we don’t see much of today). “In IT you should be expected to evolve with the technologies and your own interests. Let’s say AI is just now magically everywhere. What if that’s one of your interests? Take your foundational skills that you enjoy, and bolt on this new technology and explore it. But don’t get rid of your passions…. It’s a logical progression and extension, but you have to go out of your comfort zone to learn something new…. You’re not discarding anything from the past. You’re just building on top of it. But if you don’t do this, you’ll be considered a dinosaur. And you may have a decent job for today, but if that technology evolves to the point where you’re no longer useful and the company is moving past that technology, you’re in trouble.” – David Klee David was an infrastructure administrator who dabbled with databases. He became the database administrator and introduced virtualization when his company did not have enough physical servers to run the systems they needed to run. David expanded his knowledge base from virtualization to cloud technologies (virtualization in someone else’s datacenter with really good automation). David named his company Heraflux technologies because Heraclitus coined the phrase about the only constant being change. “As a consultant of any kind, if you’re working for somebody else, they may pay to give you some training. You still have to keep up. If you’re doing it for yourself, the keeping up is only on you and you have to keep doing it.” – David Klee What can someone ask in interviews to sort out whether this is a good environment for them? David provides some suggestions: Are you expected to be in an on-call rotation? How many people are in the on-call rotation? What’s the amount of travel required? Am I compensated for part of the travel time? What are the policies for the travel itself? For example, do I have to fly standby to keep costs low? Do I have to stay in cheap motels, or can it be at least a Hilton of some kind? David shares the story about some consultants who were given a $20 allowance for dinner in New York City. The rest came out of their own pocket. Am I expected to be on call for products I am not skilled at or don’t want to work on? When David worked for the Oracle consulting shop, he and others were expected to help with Oracle support calls after hours. David did not know Oracle well and needed to know who he could call for help. What are the hours? Is it expected that you be in an office every day? Do you have the ability to take off early if things are slower? Is there some flexibility in the schedule? What are the benefits? How much PTO (paid time off) and sick leave are personnel given? What are the holidays the company takes off? What kind of training opportunities are there? 38:29 – Presentations and Communication Skills Before David became a consultant, David only got to go to a conference because a vendor wanted him to present a session based on a problem he had solved that made their CRM solution easier to use. His first technical presentation was in front of 2200 people! Does being a consultant lend itself well to presenting at a technical conference or user group? David says yes. “As a consultant, the easy part most of the time is the tech. The hard part – showing people around you what you did and talking upwards and laterally to say ‘here’s the value of what I just did.’ So, you have to understand how to present something in a nontechnical manner…at which that person would best receive it. And if you can learn the art of talking to people at the level they are at, be it nontechnical or ultra technical / absolute guru…if you can figure that out, you can do a technical presentation in front of 10,000 people and you’ll be perfectly fine…. And be it a 5-person user group or 2000 people at a conference, the only thing that’s different is can you see the back of the room and are you blinded by spotlights.” – David Klee David has given presentations to audiences of various sizes over time. He says if we know our content and how to speak to an audience in a way that “clicks” with most people, it can be a lot of fun. David says the presentation to a very small group compared to a large group is not that different. You likely will get more nervous speaking to the large group but are talking about the same topic. The visual aids / slides might be more polished for a larger audience. “But the core flow of the presentation doesn’t have to change just based on the size of the audience. You still want to do a good job even presenting to 2 or 3 people.” – David Klee In part, a presentation will sell the value of what the consultant has done on a project or sell the solution that best fits a problem. “If you’re confident in that, they won’t question the fact that you know what you’re doing. They won’t question the what and why. They’ll just question the how.” – David Klee Nick thinks the biggest difference in being on a conference call compared to being at a technical conference is that the conference talk can make it more difficult to be interactive. Nick likes to get feedback from the audience during a presentation when possible because it helps calm his nerves. David says you can still make it personal for the audience and make eye contact with them. David shares the story of arriving an hour early for a presentation and answering questions. It might not make more people ask questions during a presentation, but it could encourage people to continue the conversation with you after your presentation. For the consultant listening to this, consider doing a presentation at a user group or conference. David suggests doing a 5-15 minute “lightning talk” on a topic of interest. It does not have to be unique and can be something you put your own spin on when you give the presentation. “You can enjoy it. You can have fun. People will benefit from it. And if you can learn presentations like that, it makes you a better communicator…because the tech side of consulting is arguably the easy part. It’s the people skills, it’s the communication that’s arguably one of the biggest things you need to be comfortable with. You don’t have to be good at it. You don’t have to be perfect at it. But if you can be comfortable with it, it makes you a better consultant.” – David Klee How do we tell how comfortable someone is with communication skills during an interview? Pay attention to a person’s body language and whether they look you in the eyes. David would encourage us to watch their face as they think through the answer to a question. If the person is sure-footed in their answers and overall communication, it can help the interviewer understand the job candidate’s level of experience. Mentioned in the Outro Learning new things to add onto our body of knowledge is a great thought David proposed. Looking at what we are interested in keeps us engaged motivated to continue learning. Great consultants are also great communicators. A lot of this comes through interviewing – customers interviewing a consultant before hiring them, consultants interviewing customers to get more detail about a problem and the customer’s environment, etc. When you are interviewing someone or they are interviewing you, someone is doing discovery like Ramzi Marjaba spoke about in Episode 308 – Probe and Discover: Coaching for Impact with Ramzi Marjaba (2/2). Maybe great consultants are really just great interviewers! If you want to hear more episodes about consulting, try searching for episodes based on the consultant tag on our website If you’ve been a consultant, what do you love about being a consultant? Send us an e-mail or share this post and tag us on LinkedIn. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.

What does it mean to coach someone? Is that the same or different from being a people manager? Ramzi Marjaba is back to delve deep into the process of coaching. This week in episode 308, we discuss the roles of mentors, managers, coaches, and how their skills might overlap. Ramzi will share the reasons he is passionate about coaching others and the qualities of an effective coach. We also talk about how making tasks look easy can mask the hard work behind them. Original Recording Date: 12-07-2024 Ramzi Marjaba is a returning guest and the man behind We the Sales Engineers. If you missed the first part of this interview with Ramzi, check out Episode 307. Topics – Making Things Look Easy and Keeping a Brag File, Defining Coaching through What Coaches Do, The Skills of a Coach, Managers as Coaches, Parting Thoughts and the Future of We the SEs 2:51 – Making Things Look Easy and Keeping a Brag File A software developer would practice building software every day. A sales engineer, on the other hand, is not practicing doing demos every day. They might do a dry run before a customer meeting to prepare, but that is likely it. Ramzi shares a story of preparing a customer demo to illustrate how salespeople and sales engineers might not truly understand each other’s roles and the work each requires. A salesperson scheduled Ramzi to do a “quick and easy” demo to show interoperability with other solutions a customer was using. Ramzi met with the customer before the demo happened to make sure he understood the customer’s expectation. “I went in. None of their products worked. So, if we’re doing an interop, and their product doesn’t work in the middle of a demo, whose fault is it? The sales team, more specifically, the SE.” – Ramzi Marjaba Ramzi did some interoperability testing with the customer, and they decided Ramzi would do a demo just to show how the product works and ignore the interoperability part. Ramzi prepared a demo based on the prep done with the customer, and it went great. On the way out of the meeting where Ramzi did the demo, the salesperson asked Ramzi why it took so much preparation to do a demo that was just a few clicks. Nick references David Zweig’s book Invisibles about highly skilled people who, if they are doing their job, you might not know even exist. Likely this is how workers in IT feel when they’ve put forth large amounts of effort to accomplish a task that seems simple. “That’s the big thing. If you’re good at your job, you make things look easy. And one of the things engineers or technical folks in general struggle with is letting people know about the work that they’ve done.” – Ramzi Marjaba Ramzi provides the contrast between former colleagues who would work on the hardest problems that came to the team and someone who would close the most tickets due to finding known issues. The person who closed the most tickets would send out e-mails to let people know how many tickets were closed and would also get all the praise. Ramzi was speaking with an SE manager recently who suggested keeping a brag file in which you document your accomplishments and the impact they’ve made on your company. This can easily be shared with your manager to demonstrate the work you have done and make a business case for a raise or promotion. John likes the emphasis on practice and quantifying the level of effort we put in to make something look simple. We can quantify the level of effort in retrospect for a career advancement file. It’s important to document how the work we’ve done impacted more than just us (our team, a customer, the greater organization, etc.). How did what we did help the team accomplish something? Ramzi says if we have trouble keeping the brag file or sense our manager might not value our work, we can CC our manager on communications about the work we’re doing. The CC is not to escalate to your manager but to keep them informed. “You can do both. You can make sure your manager is in the loop while at the same time figuring out how to say how great you are without coming off as an arrogant person.” – Ramzi Marjaba, on communicating our accomplishments to our leaders in multiple ways John calls this calibrating your self-promotion. You want to be informative enough to let your manager know what you’re doing so they can evaluate your performance without being someone who is looked upon as an arrogant self-promoter. Open communication with your manager and asking for feedback can also help. By keeping your manager informed, Ramzi says you are doing them a favor. A manager of sales engineers may be managing 12 people at the high end. Ramzi has seen support teams with 20-30 people under a single manager. “Support teams…we had 20 people, 30 people on the team. They are not going to know what everyone is doing. They are going to have feelings about what everyone is doing unless you show them exactly what you’re doing. If you make it easier for them to understand what you’re going through, they don’t have to feel about things. They don’t have to worry. They don’t have to wonder.” – Ramzi Marjaba, on keeping your manager informed of the work you do 10:27 – Defining Coaching through What Coaches Do How much of a manager’s work is performance management, and how much is coaching? Ramzi says he’s not really had a manager who has coached him. One manager did try but ended up being more of a mentor than a coach. Nick and John have both had managers who coached them. “I think managers should coach. The problem is there’s a power structure…. How do you differentiate between ‘John is saying this because he cares about me’ versus ‘John is saying this because he’s my manager at this company, and he has to tow the company line?’ So, there is that struggle, and lots of great managers can figure it out.” – Ramzi Marjaba From what Ramzi has seen, most managers don’t coach. A manager might use a 1-1 more to figure out if an SE is doing their job rather and for checking in on key performance indicators (KPIs) than making the 1-1 a time for the individual to own the agenda. “A coaching session the individual should set the agenda, not the manager or the coach. What is it that you want to achieve? What is it that you want to talk about today?” – Ramzi Marjaba, on coaching sessions Some individuals may not feel comfortable being vulnerable with their manager, thinking the manager may use it against them in a performance review. It does not mean managers will do this, but people will have that fear. Ramzi feels SE managers (and any managers) should try to coach employees, but there could be a limit to the effectiveness of a manager’s coaching. Employees may choose to keep certain things to themselves. John suggests we define coaching and shares the definition he was given from new manager training. When someone asks for help with something, coaching means you would talk the person through the process of learning how to do it rather than giving the answer. John gives the example of submitting an expense report and talking through what isn’t clear, what the person tried, etc. “The way I see coaching is…a form of guiding people to come up with their own methodology or their own conclusion or their own way of doing things or their own next steps based on the goals they provided to you.” – Ramzi Marjaba Does coaching have an overlap with mentoring? A mentor has specific experience to share who can provide guidance on going through the same / a similar experience. Coaching is more about helping someone envision the next steps they should take to get closer to a goal. Suppose someone wants to become a salesperson in the next 2 years. Ramzi would want to know why the person wants that in the first place. “Let’s come up with the steps. What are the steps that you need to take? And these are not things that I’m telling that person. They need to come up with the steps. If I think that they’re wrong, I can guide them or nudge them or ask them clarifying questions so that they can see what the right path is versus me telling them.” – Ramzi Marjaba, on the role of a coach compared to that of a mentor Ramzi feels mentors might not be trained to mentor or have an obligation to do it. Senior members of a team might be assigned by the manager to mentor less experienced members of the team. Does a coach need to have the same experience as a mentor and take a slightly different approach, does the coach not need the experience? Ramzi says the coach doesn’t need to have the same experience as the person is trying to get. “A mentor is someone who is right in front of me who can grab me and pull me up, and most of them just reach back and try to grab me. And if they can’t, they just walk away…because there is no obligation. The coach is standing next to you trying to ask you questions so you can pick the right path. And usually, it’s more of a formal relationship. If it’s not a manager, in external coaching there is usually money involved…. My success as a coach is related to your success as an individual. I don’t see mentors thinking that way.” – Ramzi Marjaba Ramzi says coaching is more formal between two individuals, and mentor is a best effort kind of relationship. “A mentor can tell the person exactly what to do to get to where they are. A coach’s job is to help the individual build the plan, their own plan, for success.” – Rami Marjaba Ramzi shares a common scenario of someone coming to him wanting to get a job as a sales engineer. He might let that person know one of the most common ways to get a job is through referrals and that they can connect to people on LinkedIn to build the relationships to ask for the referrals. But Ramzi would guide the person he is coaching through setting a target for how many people to connect with on LinkedIn per day. This allows the person to be more successful than setting the target number for them. According to Ramzi a coach can help someone build a plan of action, while a mentor might only tell someone what they should do. Does a coach also hold someone accountable for the goals they set? Ramzi tells us it’s more than that. If someone doesn’t accomplish a goal they set, a coach will try to figure out the symptom or the reason why. Maybe the goal needs to be adjusted or the way in which the person is trying to achieve their goal needs to be adjusted. If the goal was reaching out to people on LinkedIn, maybe the person was spending too much time typing out the message to send people and needs to use a template they can copy and paste. Ramzi reminds us that if we help someone by providing a valuable service it is ok to accept payment for that help. Ramzi offers paid coaching services and meets with some clients on a monthly basis. He really enjoys coaching and has been doing it for a number of years. Being a successful coach allows Ramzi to coach more people over time. We wouldn’t ask a business like Cisco if they provide routers merely for the love of routers. It is for a business. Ramzi mentions people often have a different perception of someone posting a paid service they offer on LinkedIn versus a business like Cisco. 21:14 – The Skills of a Coach What are some of the skills a coach needs to be successful as a coach? Ramzi says they need a lot of life experience, and they need to be good listeners who can probe deeply into what people really mean when they answer a question (which is not always what they say). Asking good questions is important to help people to get to the bottom of a problem and to help them build a vision. A coach also needs to be able to convince people of something through asking questions. Ramzi says this is the same as what sales engineers do. This is doing a discovery. “You’re doing a discovery, and you’re helping…the individual build a solution in his or her own brain so that they can commit to doing whatever it is they need to do to achieve their goals.” – Ramzi Marjaba Ramzi coaches mainly SEs but also coached some salespeople. If he’s coaching a salesperson, for example, he might be trying to help them figure out what they are missing as a result of losing a number of deals in a row. As a coach, Ramzi would focus on helping his clients become better sales engineers or better salespeople. Ramzi says many times, improving as an SE or a salesperson has nothing to do with working with customers but rather is about internal relationships. Here are some of the patterns Ramzi has noticed: When people tell Ramzi they want to work with him to get better at doing demos for customers, the coaching conversations usually aren’t actually about demos. They are about doing better discovery. Poor discovery leads to poor demos. Have you ever watched someone do a demo for you but not cover anything you cared about as a customer? It probably means no one did any discovery in advance of the demo. Some SEs run into problems interacting with salespeople (an account manager or multiple account managers). In a tough market, an SE might get blamed by an account manager for losing a deal because of a demo or some other reason. Ramzi mentions the SE lifecycle of recruitment, onboarding, and continuous learning. Sometimes an SE can hit a point of stagnation, feeling they are bored with performing the same activities and wondering what to do next. In these cases, Ramzi works with people to find ways to make the job more fun while becoming an even better SE. These clients are usually SEs who have reached the point of boredom and don’t want to go into sales (as a salesperson) or SE management. Nick says this last scenario of fighting against boredom isn’t so different from what Ramzi did with the podcast to keep learning. 24:28 – Managers as Coaches Nick thinks the right manager can be a good or even a great coach because the goals can be aligned to make the manager successful in doing it. Would Ramzi consider a role as a people leader and how that might be the same or different than being a coach? Ramzi would agree an SE leader can be a great coach, but it does not mean they are. He has thought about going into SE management but also mentions being in a small market in Ottawa, Canada. John may be an exception to this rule, but Ramzi feels in general it is easier to get promoted inside an organization into a people management role than applying from outside the company. John highlights the previous reference of crossover skills in SE roles between companies. Ramzi mentions there have been no opportunities to become an SE manager within his organization. His goal going into the role at his current company was to become an SE manager, but it did not happen. The company is not in a hypergrowth mode with new teams popping up, so the opportunities have not been there for Ramzi. As an external coach, Ramzi is beholden to no one except his clients. They are the stakeholders, and this makes life easier. This is different from a people manager at a company who has their employees (members of the team the manager wants to make happy) and their own maangement chain as stakeholders. That situation is more complex. If a people manager gets a decree from leadership that is likely to make members of the team unhappy or frustrated, a lot of the time the people manager has to go through with it because of the mandate from above. John says part of the role of the people manager is filtering and choosing the important battles to fight. A manager may choose to fight something that is a 10% increase in work / effort for the team that has minimal return, for example. “When you are paying a coach, one of the things that you are paying for is their direct honesty and the fact that you are the stakeholder. You can be more honest with a paid coach than maybe with a manager.” – John White As we discussed, people might feel being vulnerable with a manager could be used against them. This is especially true when you do not have a strong relationship with your manager. Ramzi is a pretty blunt person and is honest with his manager 95% of the time. Most people may not be honest with their manager that much of the time. The remaining 5% might be reserved for looking for job opportunities outside the company. If Ramzi was interested in another role inside the same company, he would communicate that to his manager and ask that person to help him get it. Ramzi feels his manager would in fact help him get a different role inside the company, but not every manager is going to be willing to do this. The level of honesty and transparency you decide on with your manager will depend on the manager. “He’s not just serving the engineers. He needs to serve the business. And he’s going to have to balance the benefit to the business versus the benefit to his people…. I’m not balancing anything. My main priority is the people.” – Ramzi Marjaba, on the role of a manager vs. that of a coach 30:27 – Parting Thoughts and the Future of We the SEs Why should Ramzi keep doing with the SEs, and what is his vision for the future? Selling something to a customer helps solve a problem, but it doesn’t change the person’s life. When Ramzi helps an SE learn how to do better discovery or to build a better relationship with their salespeople co-workers, it significantly improves the person’s life. “I have a bigger impact on a person’s life by being their coach than by being a salesperson, which is why I still do We the SEs and why I coach.” – Ramzi Marjaba Ramzi doesn’t want to put himself in a position of needing to sell a coaching service to financially support his family. He can lose clients now due to the fact that he has a full-time job to avoid having to work with clients who aren’t very nice or aren’t a good fit. There are many potential paths forward with We the SEs. Ramzi gives an example of some consulting work on how both salespeople and sales engineers can work together in a more streamlined sales process. Ramzi plans to continue coaching and looking at ways to take on more clients. What is Ramzi’s advice for effectively having a side hustle and making sure you give time to both it and your full-time job? You don’t want to create a conflict of interest, but doing something that is related to the work you do for your job makes it easier to justify the time commitment. Something that makes you better at your job can get you raises at your current job or opportunities to work elsewhere. Having a side hustle / side gig is also for branding purposes so people know who you are. This could lead to more people wanting to connect with you. If your side hustle is completely unrelated to your work, focus it on something you enjoy. If you then try and turn it into a business, your hobby might disappear. Ramzi heard a story about someone who loved skiing but then decided to start a clothing brand, which they started to hate because it kept them from skiing. Pick something you would enjoy doing as your side project. Ramzi does like having multiple income streams but does not want to sacrifice health or mental wellbeing in the process. “I went through a period where I almost burned out and almost quit We the SEs altogether, which was part of the reason I stopped doing the podcast.” – Ramzi Marjaba Since Ramzi almost burned out, what are some of the warning signs that a person might be close to burning out? When Ramzi saw he had podcasts scheduled, he had a negative reaction to it (mentally and physically). Listen to your body’s reactions. To follow up with Ramzi on this discussion… Connect with him on LinkedIn – Ramzi Marjaba. Visit the We the Sales Engineers site Subscribe to the [We the Sales Engineers Podcast].(https://podcasts.apple.com/us/podcast/we-the-sales-engineers-a-resource-for-sales/id1378292171). Check out @WeTheSalesEngineers on YouTube. Mentioned in the Outro Doing discovery is something that applies widely across our personal and professional lives to prevent misunderstandings. Discovery is about giving you more context about a request someone has made. We can do this in 1-1 discussions with our boss to better understand their motivations and the things that are important. Someone working the help desk needs to discover the real problem for which someone submitted a ticket. Asking good questions to get more context about what someone is trying to do may lead you to a totally different solution. This can help in our personal lives as well to get clarity in a conversation and to ensure we understand what someone is saying. Nick enjoyed hearing about the coach being untethered from any company when that person is not the manager. It could be difficult for the manager in the scenario when a manager knows a member of their team is looking for a role outside the company. The good / great managers we’ve spoken to on the show have spoken about their intention to support peoples’ careers even if that means the person leaves the company or the team. For more on this topic, check out: Episode 138 – Apprentice, Amplifier, and People Developer with Don Jones (2/2) Episode 137 – Something to Offer, Something to Share with Don Jones (1/2) We talked about coaching and mentoring to some extent, but if you want a masterclass on mentoring and what it means to be a mentor, check out our episodes with Dale McKay: Episode 288 – Guardrails for Growth: A Mentor’s Experience with Dale McKay (1/2) Episode 289 – Enhance Your Personal Brand: Feedback as a Catalyst for Change with Dale McKay (2/2) Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.