The CTO Compass

Mark Wormgoor
  • 5.0 (1)
  • Technology
  • Updated Weekly

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 interviews, there are solo episodes where Mark shares the leadership lessons from his own career and his executive coaching. This is not a hype show, and it's not theoretical leadership content. Real stories, real mistakes, and lessons you can use. Your host: Mark Wormgoor. He spent 30 years in technology, six of them running global IT teams at JDE, and today he works as an executive coach for IT leaders. If you lead in tech, or you want to, The CTO Compass is built for you.

  1. 5d ago

    Too Good to Be Promoted: Why Being the Best at Your Job Keeps You Stuck and What to Change ft. Kathy Eastwood

    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 a successor, delegate effectively, and make yourself replaceable so you can step into higher leadership without burning bridges. Key Takeaways • Being exceptionally reliable in execution can lock you into your current role because leadership relies on you to keep things running smoothly. • Leaders often hesitate to promote top performers because replacing a proven operator creates operational risk for the business. • Advancing your career requires actively mentoring a replacement by involving them in complex tasks and letting them learn through hands-on experience. • Successors must be introduced to stakeholders and given public credit so leadership clearly sees that your position is covered. • Moving into higher leadership requires balancing your operational strengths with strategic vision, collaboration, and stakeholder management. • Developing a clear succession plan ensures you can transition or exit without leaving the organization vulnerable or burning bridges. Chapters00:00 Intro 02:09 1st Point 04:57 2nd Point 08:37 3rd Point 09:39 Outro My Socials• Website: https://tairi.co • LinkedIn: https://www.linkedin.com/in/mwormgoor • Instagram: https://www.instagram.com/markwormgoor Contact Us• Business Email: team@tairi.co

    Too Good to Be Promoted: Why Being the Best at Your Job Keeps You Stuck and What to Change ft. Kathy Eastwood

  2. Oct 2

    The Strongest Operator Won't Make a Leader: How to Add Vision and Collaboration Without Faking It

    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 the Operator. Kathy shares actionable strategies on how to build influence without formal authority, cascade vision effectively, and break down organizational silos. She also unpacks real-world case studies from her corporate career at HP, demonstrating how taking a people-first approach directly drives high performance and profitability. Key Takeaways • Driving lasting organizational change requires operating as a Visionary, a Collaborator, and an Operator simultaneously. • Successful execution requires learning how to influence and align people when you lack direct authority over them. • Shift from the Golden Rule to the Platinum Rule by adapting your communication style to treat team members the way they want to be treated. • A strategy must be communicated at least seven times across multiple management layers to achieve true organizational alignment. • Focusing on employee engagement and well-being directly boosts productivity and can increase profitability by 23%. • Sharing a personal leadership profile outlining your values and work style drastically accelerates trust across remote and global teams. About KathyKathy Eastwood is a leadership strategist, executive advisor, and CEO of E Equals Why with over thirty years of executive experience across the technology sector. She began her career as a CPA at Ernst & Young and went on to hold diverse roles across startups and global corporations, including Chief People Officer, pre-sales, consulting, and Chief of Staff for R&D at Hewlett Packard Enterprise. Throughout her corporate career, she specialized in driving complex organizational transformations, managing mergers and acquisitions, and scaling cross-functional operations. As the author of The E3 Leadership Code: A Human Approach to High Performance, Kathy helps executives close the gap between strategic intent and everyday execution. Her system equips leaders to balance clear vision, authentic connection, and disciplined operations while leveraging emotional intelligence to sustain results. Today, she advises organizations on building high-trust cultures, breaking down silos, and increasing profitability through people-first leadership. Chapters00:00 From CPA to Consulting 02:14 Managing Operations vs People 06:41 Ad 07:22 Getting to a Vision 15:31 Managing Burnout 18:14 Money Ball Project 23:06 Ad 23:22 Raising Engagement, Cutting Costs 27:52 Communication ≠ Alignment 30:10 Building Trust with Your Teams 33:49 Developing Your Leadership Skills 36:55 Starting with Awareness Where to Find Kathy• LinkedIn: https://www.linkedin.com/in/kathyeastwood/ • Instagram: https://www.instagram.com/kathyeastwoodleadership/ • YouTube: https://www.youtube.com/channel/UC3cYFAUj2Bvf3meKjBZmkGA • Website: https://www.eequalswhy.com • Book: https://www.kathyeastwood.com/book My Socials• Website: https://tairi.co • LinkedIn: https://www.linkedin.com/in/mwormgoor • Instagram: https://www.instagram.com/markwormgoor Contact Us• Business Email: team@tairi.co

    The Strongest Operator Won't Make a Leader: How to Add Vision and Collaboration Without Faking It

  3. Sep 25

    Deep-dive One Hour a Month: How IT Leaders See What Their Reports Never Show

    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. • Effective oversight requires leaders to occasionally step past high-level reports and directly inspect raw data at the source. • Scheduling just one hour per month to observe front-line operations or review line-item data can prevent costly decision-making errors. • Setting aside half a day each quarter completely offline gives leaders the necessary distance to evaluate long-term priorities and habits. • Successful business leadership depends on finding the right balance between deep-dive operational checks and high-level strategic perspective. Chapters00:00 Intro 02:08 Your Numbers 05:24 Own Your Work 07:23 The Habit 08:55 Outro My Socials• Website: https://tairi.co • LinkedIn: https://www.linkedin.com/in/mwormgoor • Instagram: https://www.instagram.com/markwormgoor Contact Us• Business Email: team@tairi.co

  4. Sep 18

    AI Replacement: Identifying Decisions You Can Take Back From the Ones You Can't ft. Cameron O'Brien

    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 conversation uncovers costly AI implementation blunders, including a health insurance firm that prematurely fired its 20-person contact center after a voice AI hallucinated successful sales transfers. Cameron also breaks down another case where a business spent $350,000 to automate a smooth-running $10,000-a-month team, only to end up with a broken system and a costly rehiring process. In contrast, he shares how a top medical spa successfully used behind-the-scenes AI tools to support reception staff and eliminate employee turnover. Listeners will discover actionable strategies for navigating the current AI boom without falling prey to market hype. From establishing simple enterprise policies to prevent data leaks from personal consumer accounts, to building company-wide "AI fluency" and leveraging fractional CTOs to tie tech decisions directly to business ROI, this episode serves as a practical guide for scaling safely. Key Takeaways Carefully assess tech decisions before replacing staff to avoid irreversible operational damage.Deeply audit vendor software to catch errors before relying on reported performance metrics.Apply AI to solve genuine operational friction rather than automating for the sake of hype.Use AI as a copilot to empower employees and boost performance rather than defaulting to staff cuts.Provide official business-tier AI tools to stop staff from leaking sensitive data through personal consumer accounts.Train your team on foundational AI skills before locking into costly enterprise vendor contracts.Hire a fractional CTO to guide tech strategy, ensure ROI, and de-risk major decisions. Cameron O'Brien is the technology leader founders and CEOs trust with the AI and technology decisions they can't afford to get wrong. About CameronHis career didn't start in tech. It started in security at Toronto Pearson, Canada's busiest airport, standing next to objects that might be bombs, protecting the site until the bomb squad arrived. Standing near one, with nothing to do but wait, shaped how he makes high-stakes decisions. Now, as a fractional CTO, he reads the instruments when everyone else just trusts the dashboard, like the time he found AI had cost 20 people their jobs on a success rate that was drastically off. No software to sell, no vendor commissions, just a straight answer. Chapters00:00 AI Implementation Ripple Effects 02:47 Law Enforcement Experience 06:39 Making Tech Decisions 08:55 Tech Decision Consequences 16:44 Ad 17:25 Where Should We Put AI? 22:13 Looking for AI's Value 26:05 Educating Leaders About Tech 30:26 Ad 30:42 Should You Get a Full-Time or a Fractional CTO? 34:40 A Proper AI Policy 39:28 The AI Hype 44:47 Owning The Outcome and AI Implementation Where to find CameronLinkedIn: https://www.linkedin.com/in/obriencameron/Instagram: https://www.instagram.com/DrivenCTO/YouTube: https://www.youtube.com/@DrivenCTOTikTok: https://www.tiktok.com/@DrivenCTOWebsite: brasshelm.com My SocialsWebsite: https://tairi.coLinkedIn: https://www.linkedin.com/in/mwormgoorInstagram: https://www.instagram.com/markwormgoor Contact UsBusiness Email: team@tairi.co

    AI Replacement: Identifying Decisions You Can Take Back From the Ones You Can't ft. Cameron O'Brien

  5. Sep 11

    Why Big Companies Avoid Risk (And How Your Team Can Change)

    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 to drive real innovation. Learn how to run fast, low-cost micro-experiments within your own team without getting bogged down by endless approval chains. Key Takeaways • Taking a risk in a big company can damage your personal reputation, whereas avoiding risk is virtually cost free. • Most innovative corporate ideas die before being proposed due to slow, multi-layered approval chains. • Organizations often hire external consultants to buy an excuse for potential failure rather than to gain actual expertise. • Enterprise AI adoption is stalling because it requires simultaneous personal risk taking across multiple departments. • You can drive real innovation by running small, cheap experiments under 50k and six weeks within your own scope. • Culture change is an ongoing practice rather than a one-time project, so start by promoting dissent and owning your decisions. Chapters00:00 Intro 01:15 The Asymmetry 02:22 The Multiplication 05:13 The Workaround 06:24 The Collision: AI 08:08 The Turn 08:58 Change Your Own Prices 10:12 Outro My Socials• Website: https://tairi.co • LinkedIn: https://www.linkedin.com/in/mwormgoor • Instagram: https://www.instagram.com/markwormgoor Contact Us• Business Email: team@tairi.co

    Why Big Companies Avoid Risk (And How Your Team Can Change)

  6. Sep 4

    Break “Can't Culture”: How to Get Your Team to Tell You the Truth ft. JL Heather

    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 silent than to speak up. Rather than trying to force individuals to be braver or crowding meetings with more oversight, executive leaders and CTOs must focus on making dissent cheaper and actively lowering the personal risk of pointing out critical flaws. The conversation offers practical framework tools for business leaders, ranging from running project pre-mortems and assigning devil's advocates to restructuring decision-making meetings. As technology rapidly evolves alongside AI, fostering managerial openness and psychological safety becomes essential for software engineering teams and enterprise leadership alike. Key Takeaways • Leaders must reward early warning signs to rebalance an environment where staying quiet carries zero career risk. • Focus on lowering the personal cost of speaking up rather than forcing individuals to be braver or adding more oversight. • Real behavioral change requires removing rigid structural approval barriers alongside driving cultural initiatives. • Break consensus bias by assigning devil's advocates, running project premortems, and having senior leaders speak last. • Build psychological safety by soliciting unprompted input, taking visible action on feedback, and protecting messengers. • Treat reported problems as valuable assets so teams feel safe raising red flags before minor issues turn catastrophic. • Define clear overall destinations so teams focus on removing obstacles to deliver business value rather than rigidly following process. About JLJL Heather spent 20 years inside companies like Ford, Pfizer, and HP, first as an engineer, then as an executive coach. He created the Can't Culture framework, co-wrote The Agile Code and Breakthrough Innovation books, and co-hosts the Breakthrough Innovation Podcast with Preston Chandler. Chapters00:00 Can't Culture 04:08 Spotting Real Constraints 09:57 Ad 10:13 Getting People to Speak 15:56 Changing the Culture 21:38 Ad 22:19 The Software/Engineering Side 24:31 Can't Culture Around AI 28:20 You're Own Team's Can't Culture 31:02 What to Actually Do About it Where to find JLWebsite: https://centered.work/LinkedIn: https://www.linkedin.com/in/jlheather/YouTube: https://www.youtube.com/@BreakthroughInnovation My Socials• Website: https://tairi.co • LinkedIn: https://www.linkedin.com/in/mwormgoor • Instagram: https://www.instagram.com/markwormgoor Contact Us• Business Email: team@tairi.co

    Break “Can't Culture”: How to Get Your Team to Tell You the Truth ft. JL Heather

  7. Jun 26

    What to Do When Your Team Is Scared AI Will Replace Them ft. Angela Mulrooney

    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 toward the fundamentals of personal adaptability and sustainable scaling. Angela breaks down her framework for identifying your unique genius. She details how to package that expertise clearly so the market understands your outcome, allowing you to remove yourself as the operational bottleneck to build momentum effectively. The discussion highlights why rapid industry shifts demand that leaders reconsider their current trajectory and step into self-reliance rather than relying on comfortable corporate titles. The episode also explores the human side of steering teams through rapid technological changes, such as the current acceleration of artificial intelligence. Angela challenges conventional thinking about career progression and ageism, offering practical tools to help leaders refine their focus. By prioritizing alignment with your highest potential and leading with empathy, you can move your engineering teams out of fear states and into productive action. Key Takeaways • Use the sticky note exercise to identify your top three capabilities for the next five years, creating absolute clarity on what to accept and what to reject. • Guide your engineering team out of a state of anxiety during rapid artificial intelligence changes by using human kindness and open conversations. • Identify your unique areas of genius and remove yourself as the operational bottleneck so your business can grow. • Reframe external market downturns and personal identity crises as moments to step back, get calm, and locate new business directions. • Recognize why current economic shifts make corporate dependency riskier than stepping into entrepreneurship. • Apply your accumulated insights to new industries, knowing that your strategic frameworks and diagnostic skills are never lost. About AngelaDr. Angela Mulrooney is known globally as The Arsonist. She works with highly accomplished professionals who are questioning their relevance in a rapidly changing world. Not because they lack experience or results. But because the rules that once rewarded expertise have shifted. After a career ending injury forced her out of dentistry, Angela rebuilt by creating and selling four companies across four industries. Each was successful. Each was rooted in a different skill set. Over time, she saw the deeper pattern. Relevance is not about doing more or branding louder. It is about identity. When markets change, the work that survives is not the most polished. It is the most grounded in lived experience, judgment, and trust. Today, Angela helps leaders architect relevance from the inside out. Her work centers on Identity Architecture. The structure that connects who you are, how you think, and why your perspective still matters. From there, visibility and personal branding become natural expressions, not forced performances. Angela is known for burning away what no longer fits and helping people rebuild identities the machine cannot replicate. Chapters00:00 Working Through Crises 09:34 Ad 10:07 You're Skills Matter! 13:07 AI as a Partner, Not a Replacement 15:41 Fear of Change 19:22 Ad 19:34 Helping People Through Change 22:12 Kindness Through Fear 23:51 Falling In Love with Your Idea 26:59 The Sticky Note Exercise 28:43 Unleashing Influence Where to find Angela• Website: http://app.unleashinginfluence.com/v3 • LinkedIn: https://www.linkedin.com/in/angelamulrooney

    What to Do When Your Team Is Scared AI Will Replace Them ft. Angela Mulrooney

  8. Jun 19

    Why The Best Engineering Managers In 2026 Code More, Not Less ft. Alex Ponomarev

    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 deep into the mindset shift required for modern tech executives. Listeners will learn why managers must stop delegating from afar and instead get inside the development process by actively experimenting with new AI tools. Alex breaks down how automating mechanical tasks like meeting summaries can free up limited time for actual strategic leadership and team building. Finally, they tackle the future of the engineering workforce and career progression. Discover why junior engineers are more crucial than ever for bringing fresh perspectives and new experimental energy to your team. The episode also highlights why soft skills and end-to-end "agency" are the most critical traits for developers navigating this rapid technological shift. About AlexAlex Ponomarev is the founder and CEO of Volt, with 20+ years building and scaling global technology companies. He leads teams building AI-native intelligence layers for venture capital firms. His focus is bridging human expertise with AI to improve decision-making and performance. Through his publication Thriving in Engineering, he shares practical frameworks that help engineering leaders navigate complexity and build high-performing teams. Chapters00:00 Coding in 2026 08:56 Utilizing Your Time! 13:32 Ad 14:04 The Truth about AI Agents 16:22 Handling Multiple Teams 17:56 Keeping Up With Modern Technology! 23:01 What Skill Should You Develop? 28:10 Ad 28:21 The Future of Engineering Managers 32:04 Growing in Complexity Where to find Alex• LinkedIn: https://www.linkedin.com/in/alexponomarev/

    Why The Best Engineering Managers In 2026 Code More, Not Less ft. Alex Ponomarev
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About

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 interviews, there are solo episodes where Mark shares the leadership lessons from his own career and his executive coaching. This is not a hype show, and it's not theoretical leadership content. Real stories, real mistakes, and lessons you can use. Your host: Mark Wormgoor. He spent 30 years in technology, six of them running global IT teams at JDE, and today he works as an executive coach for IT leaders. If you lead in tech, or you want to, The CTO Compass is built for you.

Information

  • Creator
    Mark Wormgoor
  • Years Active
    2025 - 2026
  • Episodes
    47
  • Rating
    Clean
  • Copyright
    © Copyright 2026 Tairi
  • Show Website
    The CTO Compass