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PODCAST

The CTO Compass

The CTO Compass is a podcast for CTOs, CIOs, IT directors, and everyone leading technology teams. The hardest part of leading in tech was never the technology. It"s leading people, growing into the job while everyone assumes you already know how to do it. That"s what this show is about. Every guest brings one lesson: the one thing they"d teach every tech leader, backed by their real stories. The growth, the setbacks, and the decisions that made them the leader they are today. Alongside the

technology management

All Episodes

11:02

Too Good to Be Promoted: Why Being the Best at Your...

The CTO Compass ·

2026/10/09

Are you so good at your job that you cannot get promoted? In this solo episode of the CTO Compass Podcast, we explore the paradox of being "too good to move up" and why high praise can sometimes keep your career locked in place. Drawing from a personal experience managing identity systems at a major bank to key insights from a conversation with Kathy Eastwood, this episode breaks down why execution-focused tech leaders get trapped in operational roles. You will learn actionable strategies to build

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39:17

The Strongest Operator Won't Make a Leader: How to...

The CTO Compass ·

2026/10/02

How do you lead successful organizational change when technical execution alone is not enough? Host Mark Wormgoor sits down with Kathy Eastwood, former Chief People Officer and author of The E3 Leadership Code. Kathy breaks down why tech and operational leaders often struggle with change management, and reveals the framework needed to bridge the gap between execution and long-term vision.Discover why true leadership requires balancing three roles simultaneously: the Visionary, the Collaborator, and

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10:24

Deep-dive One Hour a Month: How IT Leaders See What...

The CTO Compass ·

2026/09/25

High-level dashboard reports look clean and simple, but aggregated data frequently hides critical operational mistakes and distorts reality. In this episode, 30-year IT veteran Mark Wormgoor shares why effective leadership requires mastering the distance from your work by balancing granular deep-dives into raw data with periodic offline strategic reflection.Key Takeaways• Aggregated dashboard summaries often round or omit critical details, masking - operational problems behind clean metrics.•

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47:37

AI Replacement: Identifying Decisions You Can Take...

The CTO Compass ·

2026/09/18

Cameron O'Brien shares how standing over potential explosive devices during his time in airport security taught him a vital lesson about tech leadership: some choices carry unintended ripple effects that cannot be undone. Cameron details why business leaders must exercise caution when deploying artificial intelligence, drawing from his background in geographic data analysis to illustrate how rushing to replace staff or patch broken systems can trigger unforeseen long-term consequences.The

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11:47

Why Big Companies Avoid Risk (And How Your Team Can...

The CTO Compass ·

2026/09/11

In large organizations, saying "yes" to a risky idea can cost you your career, while saying "no" carries almost no personal penalty. This asymmetry creates a pervasive "Can't Culture" where good ideas die before they are ever proposed, and leaders hide behind external consultants to avoid personal accountability.This episode breaks down the three hidden forms of corporate risk aversion, explores why this dynamic is stalling enterprise AI adoption, and offers a practical playbook for leaders who want

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36:21

Break “Can't Culture”: How to Get Your Team to Tell...

The CTO Compass ·

2026/09/04

Mark Wormgoor speaks with organizational design expert JL Heather about the hidden forces halting innovation and progress in modern tech companies. They dive deep into the concept of "can't culture," an invisible web of structural and cultural barriers that prevents teams from voicing problems, challenging the status quo, and driving meaningful organizational change.Heather explains how omission bias and asymmetrical accountability create environments where employees feel it is far safer to stay

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31:10

What to Do When Your Team Is Scared AI Will Replace...

The CTO Compass ·

2026/06/26

In this season finale of The CTO Compass, host Mark Wormgoor sits down with Dr. Angela Mulrooney, an entrepreneur who has successfully built five companies and sold four. Angela shares her remarkable journey of navigating sudden career shifts and personal identity crises, proving that major industry turns and external downturns are often the best moments for finding unexpected opportunities.For technology leaders and business owners, this conversation shifts focus away from standard growth tactics

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36:43

Why The Best Engineering Managers In 2026 Code More,...

The CTO Compass ·

2026/06/19

Alex Ponomarev, founder of Volt and author of the Thriving in Engineering Substack, joins host Mark Wormgoor to decode the reality of the AI talent gap. They explore what it takes to build AI-native engineering teams and how the role of the tech leader is fundamentally changing. Alex shares his personal transition from an overwhelmed engineering manager back to a hands-on contributor, highlighting how modern coding assistants allow leaders to analyze massive codebases quickly.The conversation dives

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48:14

People Over Clients Over Projects (Why Most Agencies...

The CTO Compass ·

2026/06/12

Most digital agencies do not survive past year five. Dominic Tancredi has been running Dom & Tom for 17 years, navigating every technology wave from the birth of mobile to the current AI agent explosion. Surviving that long requires more than just technical capability. It requires making painful leadership decisions when the pressure is highest.Mark Wormgoor pressure-tests Dominic's contrarian approach to technology and team building. They discuss the realities of the current tech market,

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34:08

The Model Doesn't Matter: What Actually Creates 10x...

The CTO Compass ·

2026/06/05

Technology decisions feel heavy when AI and data privacy collide. In this episode of The CTO Compass, I sit down with Clive Moore, a UI/UX designer with 25 years of experience who became the founder of GPT Studio and Workilo. After experiencing a severe ransomware attack on his agency's self-hosted GitLab instance, Clive shifted his focus to building safer infrastructure for agencies and businesses.We discuss why the underlying AI model does not actually matter as much as the foundation you build it

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43:56

Stop Panic-Buying AI: The Silver Bullet Myth That's...

The CTO Compass ·

2026/05/29

Mark Wormgoor sits down with network architecture veteran Asim to unpack what 32 years in the technology trenches teaches you about surviving massive industry shifts. Asim earned his CCIE certification in the year 2000, right before the dot-com bubble burst, and later pursued an MBA and CFA prep right into the teeth of the 2008 financial crash. Now, as the industry faces the wave of generative AI and agentic automation, Asim shares how those historical failures forced him to stop buying the industry

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41:05

Why Dropping AI Into a Broken Process Makes...

The CTO Compass ·

2026/05/22

Most technology leaders start by looking at the tool. Mike Toguchi, Chief Strategy Officer at Tectonic, argues that is the wrong beginning. If you drop AI into a broken process, you don't fix the problem, you only accelerate the failure. Mike joins the conversation to discuss why the most critical technology decisions often happen outside the engineering team and how to build systems that scale without drowning in technical debt.Mike brings a unique perspective as a strategist who studied government

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42:43

3 Critical Career Mistakes Engineering Leaders Make...

The CTO Compass ·

2026/05/15

This episode focuses on the transition from technical execution to organizational impact. Limor Bergman Gross shares how many engineering managers get stuck because they focus solely on being good at their jobs. She explains that promotion to director or VP levels requires a shift in focus. It is no longer about how well you code or manage a sprint, but about how well the organization knows your impact.The conversation explores the "trust gap," where leaders mistakenly believe their direct manager

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36:06

Your AI Strategy Will Fail for the Same Reason Your...

The CTO Compass ·

2026/05/08

Most large-scale technology projects don't fail because the software is broken; they fail because the incentives are misaligned long before the first line of code is written. AV, founder of Avira Advisors and author of Start at Zero, joins Mark Wormgoor to discuss why massive ERP implementations, like the Birmingham City Council’s £200 million disaster spiral out of control and how tech leaders can prevent the same history from repeating itself with AI.AV argues that the "abusive" nature of

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51:11

Why Organizational Change Fails: The Hidden Politics...

The CTO Compass ·

2026/05/01

Mark Wormgoor sits down with Bud Caddell, founder of NOBL, to explore the human friction that often stalls massive technology initiatives. Bud shares his transition from a software developer to a change management expert, triggered by witnessing "shiny" innovation projects collapse under the weight of organizational politics and conflicting incentives. The conversation dives deep into why many digital transformations are dead on arrival, often due to manufactured urgency and a lack of focus that

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47:31

We Sacrifice People for Performance. AI Is About to...

The CTO Compass ·

2026/04/24

This episode challenges a core assumption most tech leaders still operate under: that intelligence is our primary advantage. As AI systems begin to outperform humans in reasoning and decision-making, this conversation reframes AI not as another step in the industrial revolution, but as the start of an intelligence revolution. For CTOs and business leaders, this shift forces a deeper question. If machines can think, what is left for humans to lead?You’ll learn why performance-driven organizations are

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36:40

How User Psychology Grew a Dating App to 17 Million...

The CTO Compass ·

2026/04/17

Colin shares the raw, behind-the-scenes reality of moving from a cushy engineering role at Microsoft to the high-stakes environment of a Silicon Valley accelerator. He discusses the pivotal "moment of liberation" when he admitted his initial startup idea was failing, a realization that cleared the path for him to co-found a viral sensation overnight.The conversation dives deep into the intersection of technology and user psychology. Colin explains how understanding human behavior allowed him to

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53:29

Why 95% of AI Pilots Deliver Zero Business Impact and...

The CTO Compass ·

2026/04/10

Most AI projects don’t fail because of bad models. They fail because the data underneath is broken.Matt Soltau breaks down why “AI readiness” is really a data problem and why most organizations are building on fragile, disconnected systems that can’t survive outside a demo. From hidden data silos to untraceable pipelines and compliance risks, this conversation exposes the real reason AI initiatives stall and what CTOs must fix before scaling anything to production.You’ll learn how to move from

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33:25

The Software That Can’t Be Wrong: Building Fintech...

The CTO Compass ·

2026/04/03

What happens when you take a trust-based, offline financial system and turn it into software that people depend on with their money? In this episode, Erioluwa shares the real pressure behind building a fintech startup in Nigeria, where every product decision, line of code, and feature trade-off directly impacts user trust and financial safety.For startup founders, this conversation goes beyond fintech. It reveals what it actually takes to move users from familiar, manual systems into digital

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42:43

3 Ways to Build AI Systems That Survive the Real...

The CTO Compass ·

2026/03/27

Most AI initiatives don’t fail because of weak models. They fail because they collapse under real-world complexity. This episode breaks down how CTOs and business leaders can design AI systems that survive messy data, unpredictable users, and production reality.You’ll learn how to shift from “build a model” thinking to system-level strategy, manage AI as a high-risk investment, and align business expectations with technical uncertainty.Key Takeaways• Why AI success depends more on system design than

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47 results

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