The CTO Playbook

The real reason invoices don’t get paid has nothing to do with accounting. Build your own CTO Playbook at  www.theCTOplaybook.com  — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact. Late payments aren’t just annoying, they quietly drain focus, energy, and leadership bandwidth. In this...

What if the biggest challenge in scaling your organization isn’t execution, but knowing where you actually are? Build your own CTO Playbook at  www.theCTOplaybook.com  — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact. In this episode, I sit down with James Webster, former Amazon engi...

What if the real blocker in your certification isn’t the rules at all, but how you’re playing the game? Build your own CTO Playbook at  www.theCTOplaybook.com  — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact. What really happens when you treat compliance like a fixed checklist and t...

What if your team's biggest problem isn't talent, it's the rules you've never written down?  Build your own CTO Playbook at  www.theCTOplaybook.com  — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact. In this episode, I'm talking with Gerald Chablowski, a lead developer based in Thai...

What if your biggest advantage as a CTO has almost nothing to do with technology at all? Build your own CTO Playbook at  www.theCTOplaybook.com  — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.  In this episode, I sit down with Rory Herriman, US CTO at Zip Co, whose thirty year c...

What if your calmest moment showed up in the middle of a crisis? Build your own CTO Playbook at  www.theCTOplaybook.com  — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact. I'm joined by Caroline Elliott, who has made life and death calls in avalanche rescue and now brings that same re...

What if goals are the real problem? Build your own CTO Playbook at  www.theCTOplaybook.com  — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact. In this episode, I’m joined by Radhika Dutt, an engineer who studied electrical engineering at MIT. She wrote Radical Product Thinking and is...

What if the real bottleneck isn’t people or tech but the thing between them? Build your own CTO Playbook at  www.theCTOplaybook.com  — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.  In this episode, I’m joined by Michael Louis Schank, author of Digital Transformation Success. He’...

Ever tried to explain a technical decision and felt the room silently check out? Build your own CTO Playbook at  www.theCTOplaybook.com  — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact. Why do brilliant ideas so often get lost in translation? There is one simple metaphor that change...

When your CTO dies and no one can read the code, you realize the real problem was never the software. Build your own CTO Playbook at  www.theCTOplaybook.com  — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact. In this episode, I sit down with Matteo Di Battista and Marcello Modica, two...

What if the future of startups isn’t decided by who builds the flashiest AI, but by who solves the right problems? Build your own CTO Playbook at  www.theCTOplaybook.com  — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.  In this episode, I’m joined again by my friend Thorgeir Eina...

What if the real lever isn’t the tech at all? Build your own CTO Playbook at  www.theCTOplaybook.com  — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.  In this episode, I sit down with Matthew Carr, who does interim work and often comes in as the firefighter when a company has tak...

Logic alone won’t land; people react to change emotionally. Build your own CTO Playbook at  www.theCTOplaybook.com  — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.  In this episode, I sit down with Giorgia Prestento, a behavioral scientist and author of The Change Maze. She’s her...

Are you optimizing for starting work instead of finishing? Build your own CTO Playbook at  www.theCTOplaybook.com  — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.  In this episode, I’m joined by Joakim von Prónay , an engineer and psychologist by education and a coach by passion....

What if the playbook that built your career suddenly stopped working and nobody told you? Build your own CTO Playbook at  www.theCTOplaybook.com  — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.  In this episode, I sit down with Catherine Stagg-Macey, an executive coach who works...

Would you say yes to leading through chaos with no plan, little information, and no guarantee of success? Build your own CTO Playbook at  www.theCTOplaybook.com  — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.  In this episode, I sit down with Corey Hart, a crisis operator who’s...

What if the biggest reason your team feels stuck isn’t money, but the weight of your own code? Build your own CTO Playbook at  www.theCTOplaybook.com  — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.  In this episode, I sit down with Lou Franco, author of Swimming in Tech Debt and...

What if the only difference between freezing in chaos and staying calm is how much practice you’ve done before the storm hits? Build your own CTO Playbook at  www.theCTOplaybook.com  — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.  In this episode, I trace the moments that shape...

Proactivity isn’t an all-or-nothing game. Build your own CTO Playbook at  www.theCTOplaybook.com  — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.  In this episode, I break down the myth that leaders are either “proactive” or “reactive” and share why even small, flickering moment...

What if the hardest part of being a CTO isn’t about the technology at all, but learning to lead without a map? Build your own CTO Playbook at  www.theCTOplaybook.com  — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.  In this episode, I’m joined by Etienne de Bruin, founder of Sev...

What if your most important leadership skill had nothing to do with technology, and everything to do with how people feel? Build your own CTO Playbook at  www.theCTOplaybook.com  — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact. In this episode, I’m joined by Wesley Eugene, SVP at HI...

What if the very habits that once made you successful are now holding you back? Build your own CTO Playbook at  www.theCTOplaybook.com  — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact. In this episode, I talk with Dr. Ravi Iyer, a physician, scientist, and leader with over four deca...

Stop Doing These 14 Things If You Want to Be a Great CTO  Build your own CTO Playbook at  www.theCTOplaybook.com  — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact. I’m not adding to your to-do list—I’m flipping it. These are the habits that keep you reactive, overwhelmed, or st...

Are you managing your individual contributors in a way that fuels growth, performance, and alignment? Build your own CTO Playbook at  www.theCTOplaybook.com  — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact. In this episode, I’m talking with Faris Aranki, founder of Shiageto Consulti...

Are you managing individual contributors the best way possible? Build your own CTO Playbook at  www.theCTOplaybook.com  — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.  In this episode, I sit down with Peter Wong, a seasoned CTO, to discuss how to lead individual contributors ef...