The CTO Playbook

• 74: How Great CTOs Lead: Rory Herriman’s Five-Part Framework for High-Performance Technology Teams

  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 if your biggest advantage as a CTO has almost nothing to do with technology at all?In this episode, I sit down with Rory Herriman, US CTO at Zip Co, whose thirty year career runs from the military through large enterprises to high growth fintech. Rory brings a playbook forged in real world pressure, from learning to stay calm under fire to realizing that the job is as much about business impact as it is about systems and code. That journey taught him to care less about flashy problems and more about culture, fundamentals and the people he is working with every day.We get honest about what it feels like when you're the one carrying the unspoken weight of every decision while everyone else assumes you've got it handled. It is very easy to slip into chasing hype or focusing on the wrong signals when the real leverage is in resilient fundamentals and a clear link between decisions and business impact. We explore what it actually looks like to stand on that bedrock, keep things fluid around your people, and lean into a near-term future where humans and AI are working side by side. And you'll see why leading this way makes the CTO journey feel a lot less lonely and a lot more sustainable.You’ll Learn:[00:00] Introduction[04:14] How military calm under pressure becomes one of a CTO’s most transferable advantages[08:02] Why the real job isn’t technology but understanding business impact at a deep level[13:03] What shifts when you stop being the smartest technologist and start leading through people[17:06] The humbling moment that proved one org chart can’t fix cultural differences[19:48] Why a strong bedrock of fundamentals makes everything else faster and easier[24:58] How treating people and systems as symbiotic unlocks execution instead of friction[28:54] The power of fluid teams that move to the work rather than waiting for work to come to them[33:04] What changes when a CTO stops chasing the future and starts shaping it[46:12] The reason AI isn’t cost-cutting, but a resource multiplier that expands what humans can do[50:28] What hybrid human + AI teams look like inside an organization right now[55:02] Why excellence, velocity and integrity aren’t trade-offs but a three-part operating balanceYou can connect with Rory and his work on his LinkedIn and his website.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

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• 73: How Avalanche Rescue Taught Me to Lead Calmly in Crisis | Leadership Lessons for CTOs

  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 if your calmest moment showed up in the middle of a crisis?I'm joined by Caroline Elliott, who has made life and death calls in avalanche rescue and now brings that same rescue mindset into high pressure corporate teams. She trained in mountain rescue as a ski patroller, then joined an elite unit in France as a dog handler working avalanches, rubble, gas explosions, and large area searches. In this episode, I pull her mountain stories into the world of tech leadership so you can see what avalanche work can teach us about leading under pressure.We get into what happens to your body when a crisis hits and your team reads every signal you send. I want you to notice how a brief reset and calm language can turn spikes of stress into something you can grow from. And you'll see why staying just a little calmer than the room can change everything when the pressure hits.You’ll Learn:[00:00] Introduction[04:12] Why the body’s first response to crisis can shut down your ability to think clearly[09:47] How a three-second reset changes the entire tone of a high-pressure moment[14:58] The reason stress spreads through a team faster than any words you say[21:36] What happens when leaders use calm language to anchor people who are already overwhelmed[27:44] How a simple breathing sound becomes a reliable reset for staying functional under pressure[33:51] A dog’s reaction in avalanche rescue reveals how humans read stress signals from leaders[39:22] The surprising link between positive reinforcement and team performance when stakes are high[46:05] What shifts inside a team when leaders stay just slightly calmer than the room[51:10] Why caring for your people becomes the deciding factor in whether they’ll stay through hard seasonsResources Mentioned:Fjord’s Mountain Mission: Avalanche Safety Children’s Book by Caroline Elliott | BookYou can connect with Caroline on Instagram or through her website here, where she is happy to do an intro call to discuss how she can help your team.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

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• 72: Why OKRs Fail — and What to Use Instead (with Radhika Dutt)

  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 if goals are the real problem?In this episode, I’m joined by Radhika Dutt, an engineer who studied electrical engineering at MIT. She wrote Radical Product Thinking and is now working on a new book exploring why goals and OKRs backfire, and what to do instead.Targets can look great on paper while the foundation quietly erodes beneath them, leaving leaders focused on green dashboards instead of genuine learning. Together we unpack how shifting from goal setting to puzzle setting can unlock motivation, creativity, and alignment, using a simple framework that turns experiments into smarter decisions. By the end, you’ll see why puzzle setting beats targets when progress actually matters.You’ll Learn:[00:00] Introduction[04:12] The story of how chasing perfect targets blinded a company to a crumbling foundation[05:47] Why leaders often get good news first and the truth too late[06:32] The hidden reason goal-setting traps teams in the wrong solutions[07:15] How puzzle thinking rewires teams to stay in the problem space longer[33:04] What happens when you replace optimization with exploration[35:41] Why surfacing bad news early helps leaders make smarter choices[37:18] How one company built real trust by modeling puzzle-solving from the top[38:21] The three questions that turn metrics into learning loopsResources Mentioned:Radical Product Thinking by Radhika Dutt | Book or AudiobookIt’s soul-sucking to chase arbitrary targets. OHLs—Objectives, Hypotheses, and Learnings—shift the focus to learning, experimentation, and real progress. These templates help you break up with OKRs (without a career limiting move) and reclaim meaning at work.If you want to connect more with Radhika, follow her on Linkedin.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

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• 71: The Real Reason Digital Transformations Fail — It’s Not Technology or People

  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 if the real bottleneck isn’t people or tech but the thing between them?In this episode, I’m joined by Michael Louis Schank, author of Digital Transformation Success. He’s spent years in the trenches at Accenture, Bank of America, EY, and Citi, then struck out on his own to codify what actually works. We dig into his process inventory framework and how it transforms complexity into clarity without wishful thinking.Most transformations stumble not because teams are bad, but because complexity breeds chaos. The fix starts with mapping what the business actually does, naming owners, and tying change to those specific processes. No buzzwords, just the hard work that kills the telephone game and keeps scope, design, and testing honest. And you’ll see why getting the map right beats chasing shiny tools.You’ll Learn:[00:00] Introduction[10:52] Why alignment and systems thinking are the two foundations every transformation depends on[13:17] What happens when business and tech speak different languages and how to finally bridge that gap[19:40] The real reason “easy buttons” and buzzwords keep derailing enterprise change[27:05] How a simple process inventory turns chaos into clarity across teams[31:14] What mapping COBOL systems taught one bank about risk and modernization[33:42] Why ignoring side effects in process change can quietly destroy entire workflows[43:05] How visualizing current state exposes waste and redundancy no one noticed before[45:11] The hidden danger of optimizing what should’ve been deleted in the first place[56:09] What transformation leaders get wrong about ownership, and the one fix that makes it lastResources Mentioned:Digital Transformation Success by Michael Schank | BookYou can connect with Michael on his LinkedIn.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

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• 70: A Better Way to Explain Your Platform to Non-Technical Executives

  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.Ever tried to explain a technical decision and felt the room silently check out?Why do brilliant ideas so often get lost in translation? There is one simple metaphor that changes everything. In this episode, I share the story of a growth-stage CTO who could see a scale crisis coming, but couldn’t get his co-founders to see it too. It took one unexpected image, a floating city at sea, to finally bridge the gap.Why does the old “building” analogy fail? How does reframing your stack as something alive, modular, and adaptable change the whole conversation? The right metaphor doesn’t just explain your system, it earns you buy-in. Because oftentimes, leading isn’t about simplifying the truth, it’s about telling the right story.You’ll Learn:[00:00] Introduction[01:47] Why technical insight isn’t enough when your team can’t see the urgency you do[03:18] How one metaphor turned a frustrating explanation into an instant lightbulb moment[04:41] What happens when you frame your platform as a living, floating system instead of a fixed foundation[06:52] The reason most architectural metaphors fail modern software and what replaces them[08:36] How a single story helped a CTO win over skeptical co-founders and a cautious CFO[09:24] Why the right analogy frees you to teach complexity without losing the room[10:48] How to build metaphors that empower non-technical leaders to see real platform value[11:51] The mindset shift that turns architecture into leadership and communication into strategyFind more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

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