Episodes
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100: Why AI Is Quietly Draining Your Senior Engineer Pipeline
JUNE 16, 2026
The reps that used to turn juniors into seniors are disappearing, and most engineering leaders won't notice until the senior shortage hits in three years.Build your own CTO Pl...
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99: Why Transformations Die Just Before They Succeed
JUNE 09, 2026
The most dangerous moment in a transformation isn't the start, it's the stretch right before behaviours actually start sticking.Build your own CTO Playbook at
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98: The Office of the CTO at RevenueCat, with Miguel Carranza
JUNE 02, 2026
When do you stop being the CTO with all the answers and start being the one who asks better questions?Build your own CTO Playbook at
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97: Stop Hiring More of the Same — Michelle McDaid, The Leading Place
MAY 26, 2026
Women weren't pushed out of tech once. There were multiple waves, and the patterns are still showing up in how teams get built today.Build your own CTO Playbook at
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96: Why the Best CTOs Don't Have a Playbook — Ric Hill, Ghyston
MAY 19, 2026
Most CTOs are promoted for technical judgment, then get stuck trying to lead people with the same playbook that got them there.Build your own CTO Playbook at
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95: The Leadership Signals CTOs Send Without Realising It with Paul Kinkaid
MAY 12, 2026
What if the biggest impact you have as a leader isn’t the strategy you set, but the signals you leave behind in every interaction?Build your own CTO Playbook at
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94: Execution Beats Strategy? Rethinking the CTO Role in the Age of AI
MAY 05, 2026
What happens when execution matters more than strategy?Build your own CTO Playbook at
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93: From SDLC to ADLC: How Engineering Teams are Actually Adopting AI
APRIL 28, 2026
A CTO hired a star engineer to push AI adoption forward, and within months, the team had lost its momentum, the new hire, and any sense of where they actually were.Build your ow...
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92: The CTO Playbook: How to Build Trust, Consistency, and Psychological Safety in Engineering Teams
APRIL 21, 2026
The difference between a good CTO and a trusted one often comes down to a personal playbook.Build your own CTO Playbook at
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91: The Hardest Upgrade for Technical Leaders: Leading Without Losing Your Edge
APRIL 14, 2026
What if leadership isn’t about managing people, but about owning decisions?Build your own CTO Playbook at
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