HeyJaredThe CTO Compass
The CTO Compass is a podcast about CTO, CIO, and tech leadership - on strategy, scaling, teams & bringing clarity to technology leadership for real boardroom impact.Hosted by Mark Wormgoor, each episode features candid conversations with experienced CTOs, CIOs, and senior…
- Indexed episodes, last 90 days
- 3
- Latest publication
- Sep 18, 2026
- Audience
- Checking…
- Earliest in this view
- Sep 4, 2026
Latest episodes
AI Replacement: Identifying Decisions You Can Take Back From the Ones You Can't ft. Cameron O'Brien (opens the original)
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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 conve
Why Big Companies Avoid Risk (And How Your Team Can Change) (opens the original)
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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
Break “Can't Culture”: How to Get Your Team to Tell You the Truth ft. JL Heather (opens the original)
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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 sta
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