PODCAST · technology
Coffee With Digital Trailblazers
by StarCIO Digital Trailblazer Community
Recordings from the weekly Coffee with Digital Trailblazers that airs on LinkedIn Audio 11am ET every week. Join us at https://starcio.com/coffeeDigital Trailblazers are product managers, DevOps engineers, agile leaders, data experts (scientists, governance, dataops), and other innovators driving transformations in their organizations and life.About the Coffee with Digital TrailblazersEvery week we explore a topic and share lessons learned. All are welcome to attend, and please raise your hand to participate.Topics that we cover: digital transformation, AI. genAI, AI agents, agile, DevOps, data science, data governance, IT leadership, CIO, CDO, CMO, CHRO
Episodes
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AI Infrastructure Debt: Strategies for Capacity, Resiliency, and Modernization
The episode on AI infrastructure debt highlights that weak data foundations limit AI potential, with organizations misidentifying performance challenges as only GPU issues. Experts stress the necessity of a hybrid cloud approach, emphasizing the importance of resiliency, human accountability, and...
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Change Management: Why AI Adoption Stalls and How to Measure Progress
The episode highlights challenges in AI adoption among employees, with few reporting significant changes in work processes. Key issues include lack of workflow redesign, unclear business strategy alignment, and the rapid evolution of AI complicating stable strategies. Emphasis is placed on...
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Vibe, Buy, or Automate? Deciding How to Build AI Agents
We discuss a framework for organizations deciding to buy, build, or vibe AI agents. Key factors included data availability, risk levels, and governance to prevent unregulated AI use. The panel emphasized the distinction between automations and true AI agents, suggesting clear guidelines for...
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Getting Hired in the AI Era: Stand Out, Signal Judgment, Land the Role
Isaac led a discussion focusing on strategies for job seekers in the AI era, highlighting the importance of standing out, signaling judgment, and landing roles. Panelists emphasized showcasing AI expertise, adaptability for C-level positions, and the significance of cultural fit. Insights…
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Tech Budget 2027: What AI Bets to Fund + IT/Security to Protect
We focused on technology budget planning for 2027, particularly AI funding strategies. Host Isaac Sacolick led a discussion with panelists on prioritizing AI initiatives, emphasizing strategic clarity and measurable outcomes, while addressing budget protection and identifying areas for potential...
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The Hidden Cost of Confident AI: Semantics, Guardrails, and the Context Layer
The discussion led by Isaac Sacolick focused on AI challenges, particularly the "hallucination tax," emphasized by Felix Van de Maele, CEO of Collibra. Contributors highlighted the importance of governance, context engineering, and policy to mitigate AI failures and improve trust. Future topics...
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SaaS, Cloud, and AI Contracts: Where Technology Leaders Lose Leverage
The 186th episode of Coffee with Digital Trailblazers focused on negotiation tactics for SaaS contracts. Key topics included competitive bidding, avoiding auto-renewals, and ensuring data ownership. Martin Davis presented a checklist of 88 clauses, while participants emphasized the importance of...
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Shadow AI at Work: Real Risks, Practical Guardrails, Hidden Innovation
The real risks and practical guardrails around shadow AI, which goes beyond traditional shadow IT with new risks including data leakage, agentic AI poor decisions, and potential legal compliance issues. Chapters (00:00:02) - Coffee With Digital Trailblazers (00:01:09) - CIO Chat (00:01:51)…
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Beyond Legacy Processes: Engineering the High-Velocity Enterprise
The session sponsored by Camunda, featuring CTO Daniel Meyer, focused on transforming legacy business processes for high-velocity enterprises in the AI era. Meyer highlighted the advantages of orchestrating workflows and selectively integrating AI, with examples of significant efficiency gains. A...
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Networking in the AI Era: A Guide for Digital Transformation Leaders
An expert advisory panel discussed networking in the AI era, emphasized the importance of authenticity, curiosity, and relationship-building. Panelists explored strategies for meaningful connections at events and highlighted how AI has transformed networking, necessitating thoughtful preparation....
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Evaluating Technologies in the AI Era: Value, Risk, Ecosystem Evaluation
This week's "Coffee with Digital Trailblazers" episode featured industry analyst Maribel Lopez discussing the evaluation of AI technologies. Key topics included the significance of aligning AI selection with business goals, assessing vendor trustworthiness, and managing risks. The panel stressed...
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Does IT Leadership in the AI Era Require an IT Background Anymore?
The 180th episode of Coffee with Digital Trailblazers explored whether IT leadership in the AI era necessitates an IT background. Host Isaac Sacolick and guests discussed the importance of IT knowledge for managing AI systems and emphasized clear communication for non-technical leaders to foster...
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Reskilling Mid-Career Leaders: What Senior Talent Needs to Stay Relevant
Our discussion focused on reskilling mid-career leaders in the AI era, featuring Dean Cantave. Participants shared experiences on adapting to AI’s impact on careers, emphasizing critical thinking, collaborative leadership, and data governance. Strategies for showcasing leadership skills, moving...
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AI Agents for Skeptical Boards: What's Actually Working in Production
In the 178th episode of Coffee with Digital Trailblazers, hosted by Isaac Sacolick, a panel discussed board perspectives on AI investments. They highlighted challenges like FOMO versus cost concerns, the shift from replacement to augmentation of human roles, and emphasized governance and…
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From Idea to Impact: Shrinking Innovation Cycles With AI
Isaac Sacolick hosted a discussion on innovation in the AI era. Key insights highlighted the convergence of roles, efficiency of smaller DevOps teams, and the transformative impact of AI coding tools. Despite advancements, challenges in governance and quality assurance in production remain...
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Mental Health in the AI Era: Easing Fears About the Future of Work
The episode of Coffee with Digital Trailblazers, hosted by Isaac Sacolick, addressed mental health in the context of AI's impact on employment. The panel emphasized the importance of transparency, psychological safety, and ongoing learning. Key insights included the need for ethical leadership…
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AI Coding Competencies: Hype, Realities, and the Future
In a recent episode of Coffee with Digital Trailblazers, Isaac Sacolick led a discussion on AI coding competencies with experts Dave Bachman and David Cassel. They examined AI development tools, emphasizing effective requirement engineering, security considerations, and the challenges of…
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Developing Your Personal Brand: Best Practices From Thought Leaders
This episode of Coffee with Digital Trailblazers, hosted by Isaac Sacolick, features a discussion on personal branding and thought leadership in technology. Key speakers shared their experiences and best practices, emphasizing authenticity, consistency, and gradual progress in building a personal...
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Managing AI Agents: New Skills, Operating Models, and Tools
In a recent episode of "Coffee with Digital Trailblazers," participants discussed the management of AI agents. Host Isaac Sacolick and guests debated whether organizations should treat AI agents like employees. Insights highlighted concerns over performance management approaches, emphasizing the...
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National Entrepreneurship Week: Opportunities for Digital Trailblazers
Participants Hosted by Isaac Sacolick, CEO of StarCIO Special Guests Tyler James Johnson Digital Trailblazers Joanne Friedman Liz Martinez Joseph Puglisi Martin Davis John Patrick Luethe Heather May Derrick Butts Summary The episode focused on discussing entrepreneurship and the challenges of...
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AI-First UX: Planning for the Evolution of GenAI-Enabled Customer Journeys
Participants Hosted by Isaac Sacolick, CEO of StarCIO Special Guests Roman Dumiak Digital Trailblazers Joanne Friedman Liz Martinez Joseph Puglisi Martin Davis John Patrick Luethe Heather May Derrick Butts Summary The episode focused on AI-first user experiences and the challenges organizations...
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Talent Crunch: Developing Level-1 Expertise in the GenAI Era
Participants Hosted by Isaac Sacolick, CEO of StarCIO Special Guests Kevin Wallis-Eade Digital Trailblazers Joanne Friedman Liz Martinez Joseph Puglisi Martin Davis John Patrick Luethe Heather May Derrick Butts Summary The episode focused on the impact of AI on Level 1 expertise and entry-level...
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CIO and CMO: Partnering on AI to Drive Growth
Participants Hosted by Isaac Sacolick, CEO of StarCIO Special Guests Adrianna Hosford Elena Putilina Digital Trailblazers Joanne Friedman Liz Martinez Joseph Puglisi Martin Davis John Patrick Luethe Derrick Butts Heather May Summary Today’s panel explored AI’s role in driving revenue and growth...
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AI for Social Good: Insights From Nonprofit Leaders
Isaac hosted a special episode of “Coffee with Digital Trailblazers” focused on AI in nonprofits ahead of Giving Tuesday. Participants Hosted by Isaac Sacolick, CEO of StarCIO Special Guests – Non-profit executives Larry Lieberman, CEO of Mouse.org Stephen Rockwell, Chief Innovation Officer of...
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AI Agents at Work: The IT and HR Alliance to Drive Adoption and Value
In this episode of Coffee With Digital Trailblazers, the group takes a candid look at how AI adoption is reshaping the workplace—and what it means for people caught in the middle of change. Participants Isaac Sacolick Joanne Friedman Liz Martinez Derrick Butts Joseph Puglisi Martin Davis John...
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The Co-Creation Mandate: How Partnerships Accelerate Innovation & Talent
In this episode of Coffee With Digital Trailblazers, we dive into the art of co-creation and what it really takes to build strong innovation partnerships. Participants Isaac Sacolick Juanita Olguin Jay Cohen Joanne Friedman Heather May Joseph Puglisi Martin Davis John Patrick Luethe Summary Our...
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The Cost of Tribal Knowledge: Losing People Can Bring Ops to a Standstill
The discussion revolves around the challenges of knowledge management, particularly in construction and manufacturing settings. Emphasis is placed on tribal knowledge, which risks losing operations continuity when key personnel depart. Participants dialogue on barriers like culture and...
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AI as a Teammate: Crafting Purposeful Digital Workplaces
Participants Isaac Sacolick Stephanie Sylvestre Joanne Friedman Heather May Joseph Puglisi Martin Davis Derrick Butts John Patrick Luethe Liz Martinez Summary The 139th episode of “Coffee with Digital Trailblazers” focused on the AI teammate role in digital workplaces, featuring Stephanie…
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From Digital Leader to Frontier Firm: AI and Governance Strategies
Participants Isaac Sacolick Joanne Friedman Heather May Joseph Puglisi Martin Davis Derrick Butts John Patrick Luethe Liz Martinez Niraj Tenary Episode Summary This week’s episode of “Coffee with Digital Trailblazers” focused on the concept of “frontier firms” – organizations that are embracing…
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AI Era Transformation: Is AI the End of IT (as we know it)
Participants Isaac Sacolick Joanne Friedman Heather May Joseph Puglisi Martin Davis John Patrick Luethe Episode Summary AI is increasingly automating and transforming traditional IT functions like software development, testing, operations, and infrastructure management. This raises questions…
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The Silent Drag on Productivity: Navigating Digital Sprawl
Participants Isaac Sacolick Christian Potts Joanne Friedman Heather May Joseph Puglisi Martin Davis Derrick Butts John Patrick Luethe Liz Martinez Episode Summary This session discusses the “silent drag on productivity” caused by digital sprawl and the proliferation of SaaS applications in...
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Unplugging Experiments, Products, and Businesses That Aren’t Working
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Building Smarter Organizations: Transforming to Intelligent Operations
10 Memorable Insights Matthew Frye: “Intelligent operations today is really speaking to visibility and control across the field and back to the office… automating frontline data collection, connecting data and workflows and dashboards to decision makers, and really reducing those manual handoffs...
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SMB Transformation: How Smaller, Faster, Safer Wins Against Big and Slow
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Demystifying Quantum Computing: What Digital Leaders Need to Know
Summary The team discussed the potential and challenges of quantum computing, with a focus on its applications in various industries and its potential to revolutionize fields like cryptography, optimization, and drug discovery. They also explored the process of adopting new technology, the...
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AI Era Transformation: Gen AI + Design Thinking + Creative Problem Solving
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Accelerate Transformation: Why AI is Boring in 2025
About this episode This episode of the Coffee With Digital Trailblazers was sponsored by Appian. Speakers Isaac Sacolick – President of StarCIO. Bestselling author. 1,000+ articles on StarCIO, CIO.com, and InfoWorld. Keynote speaker. CIO and Digital Transformation influencer. Thinkers360 top IT,...
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AI Era Transformation: The Future of Work with AI Agents
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Culture Transformation: Communicating Bad News to Executives
Summary on Culture Transformation This episode of Coffee with Digital Trailblazers focuses on how to communicate bad news to executives in ways that are calm, constructive, and aligned with organizational culture. Host Isaac Sacolick frames the discussion around recent outages and crises, asking...
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Accelerating Transformation: Top Digital Trailblazer Competencies
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Culture Transformation: Turning Around a Jaded, Demoralized Department
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Lifelong Learning: Digital Trailblazer Fun & Growth Activities
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Agile Innovation: Leading Innovation Labs from POC to Production
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ABOUT THIS SHOW
Recordings from the weekly Coffee with Digital Trailblazers that airs on LinkedIn Audio 11am ET every week. Join us at https://starcio.com/coffeeDigital Trailblazers are product managers, DevOps engineers, agile leaders, data experts (scientists, governance, dataops), and other innovators driving transformations in their organizations and life.About the Coffee with Digital TrailblazersEvery week we explore a topic and share lessons learned. All are welcome to attend, and please raise your hand to participate.Topics that we cover: digital transformation, AI. genAI, AI agents, agile, DevOps, data science, data governance, IT leadership, CIO, CDO, CMO, CHRO
HOSTED BY
StarCIO Digital Trailblazer Community
CATEGORIES
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Frequently Asked Questions
How many episodes does Coffee With Digital Trailblazers have?
Coffee With Digital Trailblazers currently has 45 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Coffee With Digital Trailblazers about?
Recordings from the weekly Coffee with Digital Trailblazers that airs on LinkedIn Audio 11am ET every week. Join us at https://starcio.com/coffeeDigital Trailblazers are product managers, DevOps engineers, agile leaders, data experts (scientists, governance, dataops), and other innovators driving...
How often does Coffee With Digital Trailblazers release new episodes?
Coffee With Digital Trailblazers has 45 episodes. Check the episode list to see recent publication dates and frequency.
Where can I listen to Coffee With Digital Trailblazers?
You can listen to Coffee With Digital Trailblazers on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Coffee With Digital Trailblazers?
Coffee With Digital Trailblazers is created and hosted by StarCIO Digital Trailblazer Community.
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