Lead with Learning

Observation stops feeling like a threat when we treat it as a tool for learning instead of a surprise evaluation. We share how leaders can use quick, low-stakes moments of watching the work to coach with precision, build psychological safety, and help people improve faster. • why “observation” triggers anxiety at work and how organizations create that reaction • a simple story that shows why staying to watch matters • how educators use observation to spot thinking, not just mistakes • why “do you understand?” fails and performance becomes visible in action • how to “watch the work” in real workflows and software struggles • modeling as leadership development through seeing an experienced leader think • psychological safety as the condition that makes observation useful • language shifts that change observation from judging to learning • making observation ordinary through small, frequent, low-stakes check-ins Look at your calendar. Find the next formal observation or performance review that you have scheduled. Keep it. You might need it. But then ask yourself, why am I waiting until then to see the work? What if before the formal observation you had three or four much smaller moments of observation? Not evaluation or scores or documentation, but just curiosity, just learning.

What if your next performance problem isn't really a performance problem?What if it's a learning problem?In this episode of Steal This Strategy, I'm taking one of education's most powerful learning strategies—formative assessment—and showing you how leaders can use it to develop people, improve performance, and catch learning gaps before they become bigger problems.Teachers don't wait until the final exam to discover that a student doesn't understand. They check for understanding along the way, use what they learn to adjust instruction, provide feedback, create opportunities for practice, and gradually release responsibility as the learner becomes more capable.So why do we often do the opposite at work?We train someone once, assume they understand, and then wait for a performance review—or worse, a customer complaint or failed project—to discover that something went wrong.In this episode, you'll learn how to:• Use formative assessment to check learning while it's happening• Move beyond “Do you understand?” and ask questions that reveal what people can actually do• Use simple classroom strategies like the exit ticket in your next team meeting• Distinguish formative assessment from summative assessment• Give feedback that actually changes future performance• Avoid confusing formative assessment with micromanagement• Use a simple five-step Formative Leadership Loop: Teach → Check → Respond → Apply → ReleaseThe goal isn't to watch your employees forever. It's to give them the right support while they're learning—and then get out of the way as their confidence and independence grow.Because if your assessment doesn't change what happens next, it's probably not formative.Don't wait for the final exam. Check the learning while there's still time to change the outcome.This is Lead with Learning—where we steal what works in education and put it to work in leadership.

Your team walks in with a problem and your brain lights up with solutions. You can feel the “here’s what I’d do” forming before they even finish the sentence and it works… until it doesn’t. Because when you become the place where every hard decision goes to get solved, your team’s confidence shrinks while your workload explodes. I’m Tess, and I’m unpacking a simple leadership shift: moving from being the answer machine to being more coach-like in the conversations you’re already having. Drawing on Michael Bungay Stanier’s The Coaching Habit, we name the advice monster, talk about why default advice creates dependence, and show how coaching can happen in 10 minutes or less. This is leadership coaching for real life: no extra meetings, no awkward scripts, just better questions at the right moment. We get practical with tools you can use immediately, including the 2-second pause, the deceptively powerful “And what else?”, listening for the person behind the problem, and using silence so people can actually think. We also cover a critical boundary for managers: helping without taking ownership, staying accountable, and leading the thinking rather than doing all the thinking. You’ll leave with a simple five-step coaching flow that builds autonomy, problem-solving, and a stronger learning culture over time. If you’re ready to coach without losing authority, press play. Subscribe, share this with a fellow “fixer,” and leave a quick review, then tell me: which coaching question will you try first?

We spend a lot of time at work showing people what to do. We explain the process, provide the resources, hold the training, answer questions—and then expect people to perform.But what if we’re skipping one of the most important parts of learning?Practice.In this episode of Lead with Learning, we’re talking about the gap between knowing something and actually being able to do it. Because understanding a new process, skill, or responsibility doesn’t automatically mean someone is ready to perform it when the stakes are high.And practice doesn’t have to mean another training session, hours of role-playing, or pulling your team away from their work.Instead, it can be built into the work you’re already doing.We’ll explore how leaders can create small, intentional opportunities for people to try new skills before they have to use them for real—whether that happens in a team meeting, a one-on-one, a new role, or before a major rollout.You’ll also learn a simple practice cycle:Try → Reflect → Adjust → Try AgainBecause if we want capable, confident teams, we can’t just give people more responsibility and hope capability follows. We have to create opportunities for people to build the skills they need to carry that responsibility.In this episode, we’ll explore:Why learning doesn’t automatically transfer into workplace performanceThe hidden cost of skipping practiceHow to build practice into meetings and one-on-onesWhy people should have opportunities to practice before they officially need a skillWhy practice doesn’t have to mean traditional role-playingHow to make mistakes cheaper and learning saferWhy leaders shouldn’t always jump in with feedbackHow increasing complexity can prepare people for the messy reality of workA simple way to start incorporating practice into your team’s everyday workYour challengeThink about one thing your team is currently learning—a process, skill, behavior, responsibility, or leadership competency.Then ask yourself:“Where can I give them a chance to practice before the stakes are high?”It might take five minutes in your next team meeting or three minutes in your next one-on-one.Because sometimes people don’t need more information.They need another opportunity to use the information they already have.And that’s where learning starts to become capability.

You’ve explained the new process. You sent the email. You held the meeting. Everyone nodded their heads.So why isn’t anyone actually doing it?One of the biggest mistakes leaders make when introducing a new process, initiative, or way of working is assuming that telling people what to do is the same as teaching them how to do it.In this episode of Lead with Learning, we’re borrowing a powerful practice from education: gradual release of responsibility.In the classroom, teachers don’t typically introduce a brand-new skill and immediately expect students to master it independently. They model it. They practice it together. They provide support. They watch for understanding. And then, as the learner becomes more capable, they gradually hand over responsibility.So what if businesses approached change the same way?When you’re asking a team to do something new or different, you need more than an announcement and a set of instructions. You need a process that helps people move from understanding → practice → confidence → independence.In this episode, we’ll explore how leaders can use the principles of gradual release to make new processes and initiatives more likely to actually stick.We’ll look at how to:Model what the new expectation looks likePractice together before expecting independent implementationProvide support and feedback while people are learningGradually transfer ownership to individuals and teamsRecognize when people need more support instead of assuming they’re resistant to changeMove from simply launching an initiative to actually building the capability to sustain itBecause lasting change doesn't happen because you told people what to do.It happens when you give people the opportunity to learn how to do it, practice doing it, get feedback, and eventually own it themselves.Sometimes the best ideas for building stronger businesses are hiding in places leaders aren't usually looking.This one happens to be hiding in the classroom.

What would your employees tell you if they knew you couldn’t see their name?Sometimes, the most valuable feedback is the feedback people don’t feel comfortable giving you directly.In this episode of Lead with Learning, we’re exploring the power of anonymous feedback—and why creating a simple, safe way for employees to share what they really think can give leaders insight they might otherwise never see.Anonymous feedback can surface the things that are easy to miss: frustrations, ideas, barriers, communication breakdowns, leadership blind spots, and opportunities for improvement. But collecting feedback is only the beginning.The real leadership skill is knowing what to do with it.We’ll talk about how to move beyond reading individual comments and reacting to the loudest response. Instead, look for patterns and themes. What are multiple people experiencing? What keeps coming up? Where might the feedback point to a larger issue worth addressing?And most importantly: What decisions should you make because of what you’re hearing?You’ll also get simple, practical ideas for gathering anonymous feedback without creating a complicated survey process or adding another massive initiative to your to-do list.Because sometimes a five-minute anonymous check-in can tell you more than an hour-long team meeting.In this episode, we’ll explore:Why employees may share more honestly when their identity isn’t attached to their feedbackWhat anonymous feedback can reveal that traditional conversations may notHow to look for patterns instead of getting stuck on individual commentsHow leaders can turn feedback into meaningful decisions and actionSimple ways to gather anonymous feedback from your teamWhy asking for feedback is only half the job—the response is what builds trustAnonymous feedback isn't about giving employees a place to complain.It’s about creating another pathway for learning.And when leaders are willing to listen, look for patterns, and act on what they learn, feedback can become one of the most powerful tools they have for improving their teams.

“Good job!”It’s positive. It’s encouraging. But is it actually useful?In this episode of Lead with Learning, we’re talking about one of the simplest—and most overlooked—leadership skills: giving specific, targeted feedback.When feedback is too broad, employees are left guessing. What exactly did I do well? What should I do differently? What should I make sure I repeat next time?Effective feedback gives people something they can actually use. Instead of simply saying, “Great presentation,” we can identify what made it great. Instead of saying, “You need to communicate better,” we can pinpoint the specific behavior that needs to change.And there’s another important piece of the conversation: positive feedback.As leaders, we often make time for negative feedback. We’ll sit down, address the problem, explain what needs to change, and make sure the message is clear.But when someone does something really well? We may be quick to say, “Nice job!” and move on.That’s a missed learning opportunity.Specific positive feedback helps people understand what success looks like—and gives them something they can intentionally repeat. When we tell people exactly what’s working, we aren’t just making them feel good. We’re helping them learn.In this episode, we’ll look at how to make feedback more targeted, actionable, and meaningful—and how shifting the way we give feedback can help employees learn faster, build confidence, and improve performance.Because feedback shouldn’t just tell someone how they did.It should help them know what to do next.

You were great at the work. So they promoted you to lead the people doing it.But here's the catch: knowing how to do the job and knowing how to lead someone else to do the job are two very different skills.In this episode of Lead with Learning, we explore one of the biggest—and often overlooked—transitions in leadership: moving from individual contributor to manager.And this isn't about assuming you don't know how to lead. Chances are, you're already learning, adapting, reading the books, having the conversations, and trying to become the kind of leader your team needs.But what if part of the challenge is that you're still approaching leadership like an expert at the work?We'll look at what happens when you shift from:→ Being the expert → Developing experts→ Solving problems → Building problem-solvers→ Giving answers → Asking better questions→ Measuring your performance → Building your team's capabilityUsing principles from adult learning theory, we'll explore why effective leadership isn't simply about transferring what you know. It's about understanding what your people already know, identifying what they need to learn, creating opportunities to practice, providing meaningful feedback, and gradually giving them the independence to succeed without you.Because your new job isn't to be the person with all the answers.It's to create the conditions for other people to become capable, confident, independent contributors.If you've ever thought, "I was really good at my old job. Why is managing people so much harder?"—this episode is for you.🎧 Listen in and rethink what it really means to make the leap from doing the work to leading the work.Lead with Learning with TessWhere the science of learning meets the art of leadership.

What if the training isn’t actually where learning happens?We spend a lot of time and money getting employees into training. Workshops. Courses. Presentations. Onboarding sessions. And when the training is over, we often assume the learning is over, too.But it’s not.In this episode of Lead With Learning, Tess Colucci explores a simple idea borrowed from education: learning doesn’t happen just because someone was taught something.The real learning begins when employees leave the training and have to use what they learned.That’s when they try it. Make mistakes. Ask questions. Get feedback. Figure out what works. Adjust. Try again.The workplace becomes the classroom.So what happens if we stop thinking about training as the finish line—and start designing what happens after the training as part of the learning itself?In this episode, we’ll explore how leaders can create more opportunities for employees to:Apply what they’ve learnedReflect on what worked—and what didn’tGet feedback while they’re actually doing the workAdjust their approachTry againBecause a great training session might give someone new knowledge.But practice, application, reflection, and feedback are what help turn that knowledge into something they can actually use.The training may end when the employee walks out the door.The learning doesn’t.And that might change the way you think about onboarding, professional development, coaching—and what it really means to develop people.

What Is a Learning Architect?What if some of the best ideas for leading people have been hiding in education all along?After 20+ years in education—as a teacher, reading specialist, curriculum designer, instructional coach, and staff developer—I’ve realized I’ve been doing something bigger than teaching.I’ve been designing the conditions that help people learn, apply, grow, and succeed.And now I’m asking: What if we brought that same thinking into leadership?In this episode of Lead With Learning, I’m introducing the idea of the Learning Architect—a leader who looks beyond simply getting people to do their jobs and focuses on creating the conditions where people can actually learn, grow, and perform at their best.We’ll explore the difference between managing, training, coaching, and architecting learning—and I’ll introduce the framework at the heart of my work:Understand → Diagnose → Design → Apply → Refine → AccountI’ll share where this idea came from, why I believe educators have been sitting on some powerful leadership knowledge for decades, and how we can use what we know about learning to rethink everything from onboarding and professional development to coaching, feedback, and team performance.Because leadership isn't about making everyone do things your way.It’s about helping people become capable of doing great work their way.And I think that changes everything.Welcome to the Learning Architect.

What if your biggest performance problem isn’t a people problem?When an employee isn't performing the way you expect, it's easy to assume the problem is them.They're unmotivated.They don't understand.They're resistant.They just don't care.But what if you're asking the wrong question?In this episode of Lead With Learning, Tess Colucci challenges leaders to pause before jumping to judgment and ask a better question:What's getting in the way?Using her background in education and instructional coaching, Tess explores how leaders can diagnose performance problems before prescribing solutions. Is it a knowledge gap? A skill gap? A broken process? A lack of clarity? The wrong support? Or is accountability actually the issue?Because sometimes the employee needs to change.And sometimes the system needs to change."What's getting in the way?"Sometimes the answer is a skill gap.Sometimes it's the system.Sometimes it's the strategy.Sometimes it's the environment.And sometimes...it's us.No matter what you're leading—a team, a business, or yourself—this podcast will help you get curious, think differently, and turn what we know about how people learn into a better way to lead.More curiosity. Better learning. Stronger teams.Lead with Learning

Everyone said they understood. So why did nobody know what to do?In this episode of Lead with Learning, you'll hear an unexpected lesson from a circuit class at the gym—and the surprisingly powerful leadership lesson hiding inside it.We'll explore the difference between receiving information and actually learning, and why this distinction matters so much for leaders. When employees don't implement something we've explained, our first instinct may be to assume they weren't listening, don't care, or aren't willing to change. But what if they simply haven't learned how to apply what we've told them?Drawing on more than 20 years of experience in education, instructional coaching, and learning design, Tess explores what leaders can do differently—from modeling and practice to feedback and checking for understanding—in order to move people from “I know” to “I can.”Because hearing something isn't the same as learning it.And saying “yes, I understand” doesn't necessarily mean you do.

What if better leadership starts with understanding how people learn?Lead with Learning, hosted by educator and Learning Architect Tessa Colucci, explores the intersection of learning, leadership, and human performance. Drawing on more than 20 years of experience in education, instructional coaching, curriculum design, adult learning, and professional development, Tessa examines the everyday leadership challenges organizations face through a learning-centered lens.Why doesn't training always translate into behavior change? Is an employee struggling because of a performance problem—or a learning, process, or support problem? How can leaders build capacity instead of dependence?Because telling isn't teaching. Training isn't always learning. And understanding enables accountability.If you believe people are capable of more when we understand what they need to learn, Lead with Learning is for you.