Episodes
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86: Why Communication Is Now a Core Skill for CTOs and Senior Engineering Leaders
MARCH 10, 2026
What if the most underused asset in your tech organization is your voice?Build your own CTO Playbook at
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85: From Firefighting to Flow: How CTOs Build Teams That Learn Fast
MARCH 03, 2026
What if speed as a CTO has less to do with urgency and more to do with discipline?Build your own CTO Playbook at 
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84: Why Your Definition of Done Is Limiting Engineering’s Business Impact
FEBRUARY 24, 2026
What if redefining one simple phrase could change how your entire organization delivers value?Build your own CTO Playbook at
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83: Are We Building the Right Things? A CTO’s Guide to Influence, Ethics, and Responsible Innovation
FEBRUARY 17, 2026
What if the most dangerous thing we build as leaders is certainty?Build your own CTO Playbook at 
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82: Are You Running Fast in the Wrong Direction? A CTO’s Guide to Clarity with Jason McGhee
FEBRUARY 10, 2026
Are you running faster with AI, or just running blind?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 ...
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81: The Culture Playbook for High-Performing Engineering Teams — with CTO Pasha Jam
FEBRUARY 03, 2026
What if the strongest part of your engineering organization isn’t your tech stack, but the culture you protect every day?Build your own CTO Playbook at www.theCTOplaybook.com — the l...
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80: Gut Instinct in Tech Leadership: When to Trust It, When to Challenge It
JANUARY 27, 2026
Your most powerful decision engine isn’t your data, your dashboards, or your AI, it’s your gut.Build your own CTO Playbook at 
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79: What Engineers Really Need from Their Leaders: A Conversation with Massimo Belloni
JANUARY 20, 2026
Most CTOs fail not because of bad decisions, but because they stop asking why.Build your own CTO Playbook at 
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78: The Hidden Cost of Getting Paid: Why Trust Is a CTO’s Blind Spot
JANUARY 13, 2026
The real reason invoices don’t get paid has nothing to do with accounting.Build your own CTO Playbook at 
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77: The CTO Guide to Scaling Operational Maturity — Lessons from Amazon to Startups
JANUARY 06, 2026
What if the biggest challenge in scaling your organization isn’t execution, but knowing where you actually are?Build your own CTO Playbook at 
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