The CTO Playbook

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 biggest challenge in scaling your organization isn’t execution, but knowing where you actually are?In this episode, I sit down with James Webster, former Amazon engineer and founder of Sheep CRM, to unpack a deceptively simple idea that cuts through years of confusion around operational maturity. James introduces his Three Mountains model, a practical way for CTOs to assess reality without ego, optimism, or wishful thinking.We talk about what CTO leadership really looks like during hypergrowth, why engineering leadership breaks when teams skip stages, and how misaligned expectations quietly derail even strong organizations. Drawing from James’s experience inside Amazon and years working with scaling teams, we explore why clarity beats speed, and why naming constraints honestly is a leadership advantage, not a liability.If you’re navigating startup scaling, leading teams through change, or trying to align technology with business reality, this conversation will help you reset your internal compass.This episode is about perspective, precision, and building from where you are, not where you wish you were.You’ll Learn:[00:00] Introduction[01:08] Why scaling fails when leaders misread where they actually are[02:21] How Amazon hypergrowth reshaped James Webster’s view of pace and pressure[03:37] Why constant role change breaks traditional playbooks[14:26] Why thinking too far ahead undermines real transformation[41:12] How repeated problems signal when process really matters[42:18] Why “sloppy” processes beat perfection early on[43:34] How optimism bias keeps leaders from seeing reality[47:09] Why losing your position on the map becomes dangerous at speed[48:22] How choosing the right problem changes everythingYou can connect with James on LinkedIn and learn more about his work on his website here.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

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 blocker in your certification isn’t the rules at all, but how you’re playing the game?What really happens when you treat compliance like a fixed checklist and then get hit with yet another vague delay? I take you into the moment a CTO realized that being technically right still left him carrying months of uncertainty on his shoulders. That crack in his old mental model opened the door to seeing regulation as a human system shaped by people instead of boxes to tick.The same compliance posture can lead to totally different timelines depending on relationships, incentives, and how you show up in the room. Instead of obsessing over perfection, the focus shifts to mapping the people in the process and asking sharper questions that actually move things forward. By the end of this episode, you’ll see how small moves of influence can change a certification journey that once felt completely out of your hands.You’ll Learn:[00:00] Introduction[01:12] Why the real certification roadblock is rarely the checklist[03:56] What changes when you treat compliance as a human system instead of binary rules[05:22] The question that flips frustration into influence and momentum[07:18] How a single shift in communication makes leadership lean in[08:42] The reason two identical compliance postures get wildly different timelines[09:31] How mapping people instead of tasks reveals hidden bottlenecks and unstuck paths[11:54] What a high-stakes UK implementation showed about friction-free compliance[14:38] Why aligned incentives accelerate timelines faster than documentation ever will[17:42] Where influence replaces waiting and CTOs move from reactive to strategic[18:22] Five steps that turn regulatory uncertainty into predictable progressFind more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

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 team's biggest problem isn't talent, it's the rules you've never written down?In this episode, I'm talking with Gerald Chablowski, a lead developer based in Thailand whose journey from archaeology and history into tech leadership gives him a very human lens on engineering. I’m drawn to the way he thinks less about shiny tools and more about how people organize themselves, how rules get explained, and how work actually feels. His experience leading teams across different countries and cultures makes him obsessed with one question: what happens when we use structure to protect humans instead of control them.Too many engineering teams are playing a game where nobody can see the rulebook, then wondering why everything feels chaotic. Here we get brutally honest about what happens when goals change every week, when leaders “delegate” but still pull every string, and when trust gets treated like a slogan instead of something you earn in tiny daily moments. You’ll hear how simple constraints like clear rules, small pull requests, and real documentation can unlock creativity instead of killing it, especially in environments where people are scared to challenge the plan. You’ll Learn:[00:00] Introduction[03:48] Why tech only matters when it serves people, not the other way around[06:19] What happens when a team works without clear rules or shared understanding[09:14] The reason trust is built through tiny daily behavior, not speeches or titles[11:47] How unclear systems force developers into chaos even when rules technically exist[14:52] Why documentation becomes leverage when knowledge needs to outlive individuals[17:01] The leadership mistake that made a senior dev refuse to work with him[23:08] What learning hard physical skills teaches about leadership discomfort[28:19] How asking people to rewrite a task in their own words exposes hidden gaps fast[34:22] Why tiny pull requests transform code quality when systems enforce them[42:08] How relying on juniors teaches humility and system thinking faster than doing it all yourselfYou can connect with Gerald and his work on his LinkedIn.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

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.

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.