The CTO Playbook

Afleveringen

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  106: Trust, temper, override: managing the AI you don't control 28.07.2026 22min

  One CTO spent two weeks tearing frontier models out and ended up back where they started. Another spent a few days building a tested escape route for what actually mattered.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.The safe CTOs aren't the ones who trust their AI provider, and they aren't the ones tearing frontier models out of every workflow; they're the ones who've triaged their dependencies and tested a real escape route for the handful that matter. I'm walking through this one solo because it's a structural risk most engineering leaders felt this year but haven't priced.Frontier AI is a supplier you can't audit, and it can be switched off by forces sitting outside your contract. Your invoices can be paid in full, and the capability can still vanish.Most of us onboarded this dependency without ever writing it down. It spread the way water finds its level, and it became load-bearing before anyone noticed. Where in your stack would a frontier model going dark tomorrow actually hurt, not annoy you, but hurt?The third option is triage: trust the dependency where stakes are low, temper it where you're more reliant than is wise, and override it with a tested alternative for the workflows that would cost you the business.Two CTOs I work with responded to the same news in almost opposite ways, and only one of them still has a working escape route.You'll Learn:[0:00] Introduction[2:06] What actually happened when two frontier AI models went dark for eighteen days[4:26] Why a frontier AI model is a supplier you can't audit or control[6:37] The dependency most teams priced at zero and never wrote down[8:41] The fire drill that went off for someone else's building[11:39] Two CTOs face the same news and respond in almost opposite ways[15:02] Where in your stack would a model going dark tomorrow actually hurt?[19:27] Why an untested escape route is just a hope, not a fallbackFind more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.
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  105: The CTO's real job when agents write the code (belief reversal) 21.07.2026 45min

  A founder went from zero to $10 million ARR in six months with six engineers and fifty agents, and the gap between idea and shipped feature was nine hours.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.Most CTOs think going deeper on the tech is how they win this AI wave. My guest this week thinks that instinct is working against them.Nat (Rajesh) Natarajan is COO at G-P and has had a front row seat to every major platform shift since he helped found Travelocity in 1995, which is why his read on this moment carries weight.He's convinced this shift is bigger than the internet, mobile, and cloud combined. But the CTOs who pull ahead won't be the ones with the deepest technical mastery. They'll be the ones who understand the business well enough to know which problems are actually worth solving.Nat shared a story about a founder who went from zero to $10 million ARR in six months, with six engineers and roughly fifty agents doing the work. The gap between a customer idea and shipped capability was nine hours.That's the world CTOs are now leading in. Technical skills are becoming a commodity. Critical thinking, business judgment, and knowing what the CEO actually needs from you are not.If you're a CTO trying to figure out where to stand in this shift, start here.You'll Learn:[0:00] Introduction[3:06] How early machine learning at PayPal and Ancestry taught Nat what AI is really for[9:43] Why this AI shift is bigger than internet, mobile, and cloud combined[11:06] The 5% who see the future, and why they're rarely your best engineers[15:34] Why a 1976 prediction about paper currency should humble every AI evangelist[17:50] Six engineers, 50 agents, $10 million ARR in six months[23:32] Why only the CEO can actually make a company AI-first[32:12] Unreasonably reasonable: how Nat pushes teams toward goals they won't fully hit[35:54] The guardrails problem most agentic solutions are ignoring[42:32] Why technical skills are now a commodity and critical thinking is the North StarTo learn more about G-P and its agentic AI innovation, please visit g-p.com.If you’re on LinkedIn, be sure to follow G-P there too.Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.
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  104: Why the Best CTOs Filter the Firehose Instead of Blocking It 14.07.2026 22min

  Shielding your team from context isn't protection, it's a subtle underestimation of the people you hired for their judgment.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.The thing most technical leaders are proudest of is the same thing slowly cracking them in half. I coach CTOs through this exact pattern, and the reaction is almost always surprise rather than recognition.You take the hits. You field the awkward questions. You sit in the meeting that would have derailed the sprint, and walk out telling the team not to worry about it. It feels like leadership. It feels like care.Then I ask one question and the whole frame shifts. What if the way you're protecting your team is what's keeping them small?This episode is about the structure you've turned yourself into without ever deciding to... The dam versus the firewall. Why one of them is exhausting, rigid, and impossible to sustain, and the other changes your job in a world where AI has collapsed the cost of reaching raw context.If you've ever felt the strain of holding everything together, the discomfort you feel listening to this isn't a problem. It's the start of doing it differently.You’ll Learn:[0:00] Introduction[3:58] The dam metaphor and why no human was built to hold that much back[5:58] The instinct nobody trained into us, and why it operates below examination[8:08] From dam to firewall, a model every technical leader already understands[10:55] Why filtering for your team robs them of the reps they need to grow[13:36] The belief hiding under the dam, that they can't handle the truth[15:46] How AI collapsed the last practical argument for the leader as the filter[18:14] The four postures for standing in the stream without becoming the wall[20:39] Choosing which structure you become in relation to the streamFind more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.
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  103: What CTOs Miss Before an M&A Deal Hits 07.07.2026 49min

  Most CTOs chase value creation. Jaco Vermeulen says the real job is preserving it first. 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.Boards across the mid-market are running AI pilots that return nothing, and revenue is being booked long before it's ever realised. The gap between the story a business tells about itself and what's happening underneath has rarely been wider or more expensive.My guest is Jaco Vermeulen, an interim CTO, CIO, and M&A specialist who has worked through more than 50 transactions and spent 25 years finding what's hidden in that gap.Jaco doesn't want to talk about technology. He wants to talk about what the technology is meant to do for the business, and why most leaders get that order wrong. His stories from carve-outs, acquisitions, and portfolio integrations show how much value gets destroyed by assumptions nobody bothered to check.If you're an engineering or science leader who has never sat close to a transaction, this one will change how you read your own company. And if you have, you'll recognise the patterns immediately. Preserve value first. Create value second. Everything else follows from there.You'll Learn:[0:00] Introduction[4:02] CTO, CIO, CAIO: titles that mean the same thing to most businesses[9:10] A box of CDs and a $2 billion company still running on paper[15:00] The real reason AI pilots keep returning nothing[20:11] The hidden gaps in M&A due diligence that most tech leaders never look for[23:33] A company that paid £1 million a year to license data it already owned[26:34] ARR reporting and the disconnect between booked revenue and reality[29:55] A transaction's success is decided after the deal closes, not at signing[35:12] A £5 million pricing plan projected to return just £200,000 a year[38:21] The four steps every technology leader should take to be transaction-ready[45:44] The incentive hiding behind every KPI you're setFind more from Jaco Vermeulen on LinkedIn.Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.
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  102: AI Transformation Starts With What You Don't Know You're Assuming — with Duri Chitayat 30.06.2026 46min

  Duri's father holds more than 100 patents, filed his latest one at 96, and gave him a one-line philosophy that now drives how his teams approach every problem: most people don't try.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.Most CTOs think AI failures are technical problems. The data says otherwise, and the gap between a good idea and a great product is almost never where engineers expect it to be.My guest today is Duri Chitayat, CTO at CINC Systems, leading a 170-person globally distributed product development team across four continents with a background spanning AdTech, MedTech, Banking, and FinTech.What stood out for me in this conversation was how willing Duri is to question the assumptions other leaders treat as fixed. He grew up around an inventor with over 100 patents, and that shaped a way of thinking that strips problems down to first principles before touching a solution.The stakes here are real. Innovation tokens are finite. Spend them on the wrong assumption, and you lose the race before you knew it started.Our conversation moves through a six-part playbook for leading engineering in 2026, the leadership paradox that breaks most CTOs, and why measuring transformation honestly is harder than anyone admits. If you're leading through an AI shift right now, this one is for you.You'll Learn:[0:00] Introduction[3:00] What growing up around a 96-year-old inventor with 100+ patents taught Duri about first principles[4:54] The difference between writing code and delivering solutions, learned the hard way on an SAP rollout[7:29] Mount Fuji problems versus dancing landscapes, and how to spend your innovation tokens wisely[12:59] Why the customer hanging a picture frame isn't really trying to hang a picture frame[14:55] Finding the borders of the box you didn't know you were in[24:22] Duri's only juniors are named Claude and Codex, and how he hires senior talent globally[28:03] How the RFC process creates earned trust and stops Duri from running roughshod over smart engineers[32:07] Walking through the six-part playbook[40:33] Why tokens burned is the new lines of code, and what to actually measure insteadResources Mentioned:Your Strategy Needs a Strategy by Martin Reeves, Knut Haanaes, Janmejaya Sinha | Book or AudiobookFind more from Duri on LinkedInFind more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.
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  101: Why Most Leadership Assessments Are Measuring the Wrong Thing 23.06.2026 36min

  What if the biggest constraint on your organisation isn't your tech, your funding, or your market, but whether your leaders can think at the level the problem requires?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.Logan Yonavjak spent nearly two decades in impact investing before co-founding Readiness Engine. Her perspective matters here because she watched the pattern play out across hundreds of well-resourced teams.The teams weren't short on capital. They were short on cognitive capacity to hold complexity, sit with paradox, and make decisions when the answer wasn't black-and-white. Most leadership assessments snapshot who you are. Logan argues they miss the part that predicts whether you're ready for what's coming next: how you think, not what you've done.In this episode, we get into developmental psychology, why coachability is the single biggest predictor of growth, and what it looks like to measure a leader's readiness rather than their résumé.For CTOs who've been told coaching is something other people get, this one reframes the conversation. The cost of staying fixed is higher than you think.You'll Learn:[0:00] Introduction[3:55] What impact investing actually means beyond profit-only capitalism[5:49] How developmental psychology measures the way adults hold paradox and perspective[10:40] Why coachability is the single biggest predictor of whether leaders can evolve[15:37] Myers-Briggs and most leadership assessments miss vertical development entirely[22:12] How the 45-minute video assessment works and why it's harder to game[24:40] Building a second brain that channels your highest self into team decisions[28:11] AI coaching could become the entry point for leaders allergic to therapy[34:33] What changes when investors start assessing their own leadership capacity before deploying capitalResources Mentioned:Myers-Briggs Type Indicator (MBTI) | WebsiteFind more from Logan on LinkedIn, and see a sample Readiness Engine report here.Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.
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  100: Why AI Is Quietly Draining Your Senior Engineer Pipeline 16.06.2026 22min

  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 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.Your dashboards say velocity is up, your seniors are asking careful questions nobody wants to answer, and your juniors are getting confident faster than they're getting capable. I'm a coach for CTOs across startups and enterprises, and this is the pattern I've been hearing in coaching conversations for the last six months.It usually arrives as unease about velocity or quality. By the time we trace it back, it always lands in the same place. Does our boilerplate still earn its keep in an AI-accelerated world? One camp wants to lock it down further. The other wants to delete half of it. They're both right, and they're both wrong.The argument is a symptom. The real question is bigger, and almost nobody is pricing it in yet. Our most experienced engineers got their judgment from reps we can no longer reproduce. Our juniors aren't getting those reps. If we don't design a replacement, we'll wake up in a few years with a senior shortage and no good explanation for how it happened.This episode is about the scaffolding that fixes it.You'll Learn:[00:00] Introduction[00:22] The unease CTOs can't quite name yet[01:48] Three warning signals hiding inside a healthy-looking engineering team[03:45] Why both sides of the boilerplate debate are right and wrong at the same time[05:59] Why boilerplate is no longer just about code, it's doing three jobs now[08:44] The hidden dial between your code base and your AI that most teams haven't noticed[11:21] How senior engineering judgment was built and why AI has removed the mechanism[12:39] The senior shortage nobody sees coming and why your scaffolding is part of the answer[14:58] A five-step playbook for redesigning your scaffolding as a judgment toolFind more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.
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  99: Why Transformations Die Just Before They Succeed 09.06.2026 58min

  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 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.My guest is Anders Wengelin, partner at Friktion in Malmö, who spends his weeks inside large Swedish healthcare organizations trying to help them build new core capabilities without reaching for a neat plan.Leaders kill change at the exact moment it's about to take hold. Not because the work is failing, but because nothing visible has shipped yet.Anders walks through how his team thinks about behaviours as the only concrete thing in an organization, and why operating models, maps and rollout plans are abstractions people hide behind. If you've ever felt the pull to add structure the moment ambiguity shows up, this one will sit with you.Three questions, nine parts, and one uncomfortable truth about what real change looks like inside large, regulated organizations.You'll Learn:[0:00] Introduction[2:40] Why large, compliance-heavy organizations struggle most with acquiring adaptivity[6:00] The detour every tech-heavy org takes before talking about what actually matters[14:06] Why leadership teams grasp for maps and plans the moment complexity shows up[21:13] The three questions behind Friktion’s transformation strategy playbook[30:00] The camera test for behaviours, and why curiosity isn't a behaviour[33:45] How behaviour spreads like a virus, and why rollouts never work[38:26] The three nested loops that keep continuous change moving[41:11] Success looks like nothing is happening right before momentum kicks in[45:41] Why you don't need a majority before behaviour change tips[52:34] The trap of sneezing at a crowd instead of infecting one context properlyWant to go deeper on everything Anders covered? Friktion's sandpapers are free to download at friktion.se/sandpapers.Find more from Anders on LinkedIn.Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.
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  98: The Office of the CTO at RevenueCat, with Miguel Carranza 02.06.2026 47min

  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 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.Miguel Carranza built RevenueCat into critical infrastructure for thousands of mobile apps, and he'll tell you straight that he never wanted to be a manager.He got his first computer at age eight and moved from Sevilla to Silicon Valley to build things. Somewhere along the way, he had to stop being the best engineer in the room and start hiring people better than him.His worst hire is already on the team. That's not a red flag, it's the whole point of how he builds. The Office of the CTO, which he set up, exists precisely to keep that bar moving.The engineering managers who never wanted the job are the ones who work out. The smallest pull requests have caused the biggest outages. And AI is making his teams smaller, not larger.If you're a founder CTO trying to figure out when to delegate and when to dig in, this one will sit with you.You'll Learn:[00:00] Introduction[01:12] From Sevilla to Silicon Valley: what drove Miguel to chase computers over everything else[08:15] Building Elevate revealed a mobile subscription problem nobody had solved yet[10:48] What changed Miguel’s mind when he doubted himself as a CTO[17:16] Why engineering managers at RevenueCat must be ex-engineers first[20:31] The mental model Miguel uses to hire people better than himself[22:23] How AI is shrinking team sizes and who it benefits most[29:45] The small internal team Miguel deploys to new bets and stuck projects[35:49] The five rules Miguel refuses to bend on as an engineering leader[42:01] Why RevenueCat's biggest outages came from one-line pull requests[43:39] What actually makes RevenueCat's engineering culture distinctConnect more with Miguel on X and the RevenueCat website.Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.
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  97: Stop Hiring More of the Same — Michelle McDaid, The Leading Place 26.05.2026 46min

  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 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.Most engineering leaders think their hiring process is neutral. Changing the job spec brought my guest three women applicants the following week, and her team hired two of them. Michelle McDaid spent two decades leading globally distributed engineering teams, became the first female director of engineering at her last company, and left it with 50% women in that role.She then went back to university to put the evidence behind what she'd already seen on the ground. We sat with some of these ideas together at CTO Craft Con in London a couple of weeks ago, and the conversation was good enough that I wanted to bring it here. She's unusually calm about uncomfortable truths, and that's exactly why this matters. If you believe in diverse teams but keep ending up with more of the same, the gap isn't your intent. It's what you don't even know to look for. This one challenges the default assumptions most technical leaders never examine, and gives you something practical to do about it.You'll Learn:[00:00] Introduction[02:29] What trust actually has to do with uncovering the real problem in any organization [06:50] What Michelle's career across banking and tech revealed about leadership and self-worth [15:56] Why the gender gap in tech is neither natural nor inevitable [24:36] How the language in your job spec is quietly filtering out the people you want to hire [28:36] The smallest changes that move teams from fearful to collaborative and how AI fits in [33:47] A 10-point framework for intentionally broadening your talent pool [44:20] What women lose in meetings every day and how anyone can change it Resources Mentioned:The Authority Gap by Mary Ann Sieghart | BookWhere Did the Women Go? by Michelle McDaid | ArticleTextio | WebsiteGender Decoder by Kat Matfield | WebsiteLearn more from Michelle on her LinkedIn and The Leading Place website.Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.
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  96: Why the Best CTOs Don't Have a Playbook — Ric Hill, Ghyston 19.05.2026 41min

  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 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.Ric Hill has spent 14 years running Ghyston with his wife, CTO'd for startups and mid-corporates, and earned a spot on the CTO Craft 100. His central conviction is that there is no playbook worth following blindly.Most CTOs are promoted on technical skill and then judged on leadership. The reflex is to import what worked last time. Ric argues that reflex is the problem.What replaces the playbook is a sharper version of listening, knowing how long your "fresh eyes" window actually lasts, reading the difference between an unhealthy political culture and an unhealthy apathetic one, and noticing which person on your team has gone quiet.This is a conversation about staying flexible without being indecisive, and delivering results without forcing a template onto a situation that doesn't fit it.You’ll Learn:[00:00] Introduction[11:29] Why bespoke beats cookie-cutter software[13:50] The first few weeks decide everything[16:23] How long until you're part of the furniture[18:19] Health versus outcomes in tech leadership[20:21] The sticky note roadmap that changes everything[25:38] Disagree and commit without losing trust[28:40] When stubbornness becomes a liability[30:35] Listen for the silences in your team[32:59] Why engineering culture can stand apart[40:20] The one tip every new CTO needsCheck out Ghyston for your software development needs.Find more from Ric on LinkedIn.Listen to Ric’s podcast, Giant Minds: From The Bristol Tech Community, on Spotify or Apple.Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.
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  95: The Leadership Signals CTOs Send Without Realising It with Paul Kinkaid 12.05.2026 1u 9min

  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 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, Paul Kinkaid, a former British Army officer, founder of Forensic Outcomes, and executive leadership coach, introduces a principle from forensic science: every contact leaves a trace. Those small moments, the way you listen, the way you respond, the way you make decisions, shape how your leadership is experienced across an organization.The focus is on the smallest behaviours that most leaders overlook, and how those behaviours shape trust, culture, and performance.Leadership isn’t just about decisions or strategy. It’s about the signals you send every day.You’ll Learn:[00:00] Introduction[00:06:02] What leadership presence is and why people listen before you speak[00:09:10] Why pressure exposes the difference between real and performative leadership[00:12:04] How small behaviours shape trust, clarity, and psychological safety[00:21:36] What happens when leaders send the wrong signals without realizing[00:34:12] Why the gap between intention and impact grows over time[00:48:27] How communication patterns shape culture more than strategy[01:02:14] What it takes to notice and shift the signals you sendResources Mentioned:Locard Exchange Principle by Saferstein, R., et al. | ArticleGet Paul’s book, Forensic Leadership, in print or audiobook and start noticing the signals you’re sending every day. Find more from Paul on LinkedIn, and visit his DactoApp landing page at Forensic Outcomes.Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.
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  94: Execution Beats Strategy? Rethinking the CTO Role in the Age of AI 05.05.2026 44min

  What happens when execution matters more than strategy?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.Adam Spector is a four-time founder and investor in over 200 startups. He has seen firsthand how quickly expectations have shifted, and why what worked even a few years ago no longer holds up. The bar for startups has moved. Companies that once raised capital on early traction are now expected to show real revenue, working products, and meaningful growth almost immediately.AI is beginning to change what teams can produce, even if it has not fully transformed day-to-day work yet. The pace is increasing, and the gap between what is possible and what most teams deliver is widening. Rigid strategy is becoming a liability. Founders who cannot adapt in real time are more likely to fail as conditions shift underneath them.Efficiency is under a new lens. Metrics like revenue per employee are becoming signals of how well a company actually operates. The underlying question is harder to ignore: what is your role when code is no longer the constraint?You’ll Learn:[00:00] Introduction[06:12] Why the bar for startups has changed faster than most founders realize[10:47] What investors expect now and why early traction is no longer enough[14:33] How AI is starting to affect workflows without fully replacing them[18:05] Why time is becoming the only truly scarce resource[22:41] What happens when startups grow fast but lack a real moat[27:18] Why rigid strategy increases your risk of failure[31:56] How revenue per employee is becoming a key efficiency signal[36:22] What breaks when competitors move faster than you[40:08] How to think about your role when code is no longer the constraintFind more from Adam Spector on LinkedIn and the Chore Website.Find more from Adam Horner on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.
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  93: From SDLC to ADLC: How Engineering Teams are Actually Adopting AI 28.04.2026 24min

  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 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.Almost every CTO Adam speaks to right now is carrying the same thing: exhaustion beneath loud pressure. The board wants speed. Investors want an AI strategy. The voice in their own head says everyone else has worked something out that they haven't.The pressure to go faster with AI is usually the signal that the real work is somewhere else. Adam has watched organizations try to leap from pure experimentation to mature AI practice through a single hire, and watched what breaks when they do.The fastest engineering teams aren't tuning the engine first. They're upgrading the brakes and tires, the testing automation, the review systems, and the people around the work, before they touch raw speed.Tune in to learn about the three-stage pattern of AI adoption, two contrasting examples that show what acceleration actually costs, and the three postures that separate the CTOs making real progress from the ones spending money to look busy.You’ll Learn:[00:00] Introduction[01:08] Why CTOs feel behind even when they’re moving fast[02:48] The three stages of AI adoption and where most teams get stuck[05:12] Why skipping stages creates friction that slows the whole team[08:34] How lack of standards turns fast progress into team-wide frustration[15:06] Why slowing down in the right way is what actually moves teams forward[23:11] How to spot your team’s real stage and decide what to do nextFind more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.
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  92: The CTO Playbook: How to Build Trust, Consistency, and Psychological Safety in Engineering Teams 21.04.2026 43min

  The difference between a good CTO and a trusted one often comes down to a personal 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.Sam Boswell is the CTO of Terralayr, an energy tech company focused on solving global energy storage challenges. With a background in high-risk infrastructure and scaling engineering teams, he brings a practical lens to how leadership actually works.At the center of that philosophy is a simple idea. Engineers don’t follow leaders because they’re the most technically brilliant person in the room. They follow leaders who are consistent.That consistency doesn’t happen by accident. It comes from a personal playbook. A set of lived principles that shape how decisions are made, how problems are approached, and how people are treated.We get into how that playbook forms over time, why documenting how you think matters more than most leaders realize, and what happens inside teams when that consistency is missing.The result is a grounded look at leadership that moves beyond theory. It shows what it takes to build trust, create safety, and lead in a way people actually want to follow.You’ll Learn:[00:00] Introduction[05:12] The shift from coding to leading people[07:45] Turning ideas into outcomes without touching the code[12:18] Why consistency earns trust faster than brilliance[15:42] Writing as a tool for clearer thinking and better leadership[18:36] What breaks inside teams when leadership is inconsistent[22:04] The power of a personal user manual for faster trust[26:31] There’s always a move, even when you feel stuck[30:12] Small principles that compound into better decisions[36:48] Psychological safety as the foundation of real performanceResources Mentioned:OODA Loop | WikipediaThe Joel Test: 12 Steps to Better Code | WebsiteNotion | WebsiteKnolling | WebsiteTom Sachs’ 10 Bullets | WebsiteTime Enough for Love by Robert Heinlein | Book or AudiobookJoyful Militancy: Building Thriving Resistance in Toxic Times by Carla Bergman and Nick Montgomery | Book or AudiobookEve Online | Video GameKanban Tool | WebsiteFind more from Sam on LinkedIn.Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.
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  91: The Hardest Upgrade for Technical Leaders: Leading Without Losing Your Edge 14.04.2026 38min

  What if leadership isn’t about managing people, but about owning decisions?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 Michael Di Prisco, who describes himself as “a software engineer struggling to realize that he became a tech leader”.Michael was pretty reluctant to become an engineering manager and leave the keyboard, but he started moving outside his comfort zone one step at a time. He gradually found a balance where he still writes code, but it is not expected of him.We explore how authority and responsibility actually work inside a team. He explains why every engineer should understand the business, and what changed when he started delegating code instead of doing everything himself. That shift did not slow the team down. The quality of their coding was becoming better, and people could focus on what they wanted to do more.We also get into documenting technical debt and how his team reached a point where they solved more debt than they created.If you are thinking about the move into leadership, this is a grounded look at what that shift might actually involve.You’ll Learn:[00:00] Introduction[02:05] Stepping into leadership felt like losing his edge as an engineer[06:45] A small move outside your comfort zone can shift your entire career path[08:30] Coding stopped being expected and started becoming a deliberate choice[12:10] Teams can improve when a tech lead stops doing all the coding and starts delegating[16:20] The hidden gap between responsibility and authority most teams never fix[20:15] Engineers make weaker decisions when they don’t understand the business[24:40] Letting go of best practices can reveal what actually works in your context[27:10] Documenting technical debt can lead to actually reducing it over time[31:25] Small steps and honest feedback often outperform big career movesResources Mentioned:The Software Architect Elevator: Redefining the Architect's Role in the Digital Enterprise by Gregor Hohpe | BookArchitectural Decision Records (ADR) | WebsiteGitHub | WebsiteAstro | WebsiteCodeMotion Conference | Websitejsday - The Italian JavaScript Conference | WebsiteItalian Agile Days Conference | WebsiteDive deeper into Michael’s ideas on software engineering and leadership on his blog.Find more from Michael on LinkedIn.Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.
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  90: Data Is a Leadership Problem, Not a Technical One — A Playbook for CTOs 07.04.2026 38min

  Most teams don’t have a data problem; they have a decision 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.Nic Granger, Chief Information and Financial Officer at the North Sea Transition Authority, joins me to share her perspective from the intersection of data, finance, and transformation in a highly complex, regulated industry.Nic leads a multidisciplinary portfolio spanning digital, data, and core services, with a focus on enabling better decisions across the energy transition.We get into why data strategy is fundamentally a human challenge, not just a technical one, and how data-driven decision making only works when people can actually access and trust the data. You’ll hear how data leadership shifts when the goal isn’t dashboards, but real-world outcomes like energy security and decarbonization.We also unpack why jumping straight to AI in business often misses the point, and what it really takes to build strong data foundations that support scale. If you’re responsible for digital transformation or shaping CTO strategy, this will likely reframe how you think about value, not just volume.You’ll Learn:[00:00] Introduction[03:15] The value of data has nothing to do with the data itself, and what it actually comes down to[07:30] Nic's realization that turning petabytes into value is a people problem, not a technology problem[10:05] The mistake most organizations make with data is jumping to AI before they've solved anything[13:00] What decades of vital data trapped in unreadable PDFs look like, and what AI is doing about it[16:45] Making industry data freely available unlocked competition from smaller players and academia in ways nobody expected[21:20] Your team is probably already asking the right data questions; you just have to listen for them[27:45] The reason Nic's team swapped the word "process" for "workflow" and what the language shift actually changed[31:20] Digitizing a paper trolley process revealed hidden data that now predicts industry trends[37:00] The one thing Nic says every CTO should prioritize in the next 90 days to unlock data valueIf you want to support the work Nic mentioned, become a member of the Bat Conservation Trust. Resources Mentioned:CTO Craft | WebsiteUK National Data Repository (NDR) | WebsiteBat Conservation Trust | WebsiteFalklands Conservation | WebsiteLovable AI | WebsiteBase44 | WebsiteIf you want to support the work Nic mentioned, become a member of the Bat Conservation Trust. Find more from Nic Granger on LinkedIn.Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.
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  89: Engineering Velocity for CTOs: How Superhuman Moves Fast Without Sacrificing Quality 31.03.2026 48min

  If your team feels busy but nothing meaningful gets delivered, this might explain why.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.Loïc Houssier, an engineering leader with two decades of experience across startups, scale-ups, and global companies, joins me today to explore how engineering velocity really works beyond output metrics.We get into why decision-making speed is often a better indicator of performance than output, and how long feedback loops kill momentum, even in teams that look productive on the surface. You’ll hear how product-led SaaS organizations sustain speed without sacrificing quality, and why reducing the cycle from idea to impact matters more than optimizing coding time.Loïc shares how career ladders and incentives shape behavior in ways most leaders overlook, along with a practical way to spot whether your team is truly fast or just performing speed. We also unpack how user empathy becomes a strategic advantage, not just a design principle.If you’re trying to scale without losing control, this will change how you think about speed, decisions, and what actually drives results.You’ll Learn:[00:00] Introduction[8:52] Why velocity isn't really about writing code faster, and where the time is actually going[17:00] The costly mistake Loïc made at DocuSign that he'd still fix if he could go back[21:55] The career ladder is slowly shaping engineer behaviour, and most CTOs aren't using that deliberately enough[31:55] Moving fast without losing quality; what aligned autonomy looks like in practice, and the hiring filter that makes it possible[38:57] How Superhuman's founder uses game design thinking, a 100ms rule, and an 11-star standard to build experiences people actually feelSave 4 hours every week with Superhuman Mail.Find more from Loïc Houssier on LinkedIn.Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.
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  88: The CTO Role Has Changed — Why Doing More Isn’t the Answer 24.03.2026 17min

  Why does the CTO role feel heavier after you start winning?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.Many leaders in CTO leadership roles are shipping products, raising funding, and hiring well, yet describing a new weight in the role. Decisions feel more loaded. Progress becomes harder to define. The work carries more consequence even when the calendar looks the same.The modern Chief Technology Officer now sits at the intersection of strategy, narrative, and emerging AI strategy expectations. Boards want direction. Executive teams want clarity. The scope expands faster than it is redefined. Pressure no longer replaces pressure. It stacks. That stacking changes the nature of technology leadership.This episode focuses on leadership orientation as the skill that restores executive clarity. Orientation answers two questions before speed: where you are, and which way you are facing. Without it, motion creates confusion at scale.For startup and scale-up leaders navigating CTO career growth, this reframes heaviness as a threshold moment that requires recalibration before acceleration.You’ll Learn:[00:00] Introduction[00:46] Why feeling heavier after success can mean the role itself has shifted into a new level of leadership[02:12] What it means when momentum is strong but you are no longer sure where the role is taking you[03:18] How the CTO role crosses a threshold from execution into something more abstract and executive[05:32] Why stacked pressures are changing the nature of the work rather than simply increasing it[06:34] How expanded scope and collapsing time to credibility create hidden cognitive load[09:42] What the treadmill metaphor reveals about working harder without changing your position[11:02] Why reorienting before accelerating is the maturity move most CTOs resist[14:32] The four diagnostic questions that expose where you are still leading from old metrics[15:47] Three practical orientation shifts that reduce friction and restore clarity in real timeFind more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path
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  87: AI Governance for CTOs: Turning AI Risk Into Competitive Advantage 17.03.2026 45min

  What if the biggest risk in your AI strategy isn’t the technology, but the assumptions you never question?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.Today I’m joined by Jill Heinze, an AI Foresight and Strategy Architect who helps mid-size organizations turn AI risk management into sustainable competitive advantage. With a background spanning academic librarianship, market research, digital product strategy, and executive AI governance, Jill has built responsible AI frameworks for Fortune 500 clients and led the creation of a formal governance committee inside a major consultancy.Many executive teams default to speed and competitive pressure when shaping AI strategy, often without structured reflection on downstream impact. Jill explains how anticipatory thinking and structured empathy exercises surface risks that technical teams rarely identify in isolation. She introduces her anticipatory AI horizons and outlines how reframing responsible AI from compliance overhead to strategic discipline strengthens long-term positioning.If you are a CTO balancing board expectations, generative experimentation, and operational deployment, this episode sharpens your thinking around AI leadership, foresight, and building technology that accounts for the human systems it touches.You’ll Learn:[00:00] Introduction[03:18] Why generative AI felt like a whole new animal and the moment that forced a rethink of responsible deployment[05:12] The pattern of we need to be first we need to be fast and what that urgency costs organizations[06:47] How direct user research exposes risks teams never see when they focus only on the technical problem[09:08] What shifts when you treat risk evaluation as part of every AI proof of concept instead of a brake on progress[12:14] The reason some risks are endemic to generative AI itself and how that reframes acceptable use cases[17:36] Why checklists create false confidence and how thinking in horizons changes the way you design and deploy[33:02] The question how do you know that’s true and why challenging embedded assumptions can alter the trajectory of a project[40:18] Where to start if you already have a live AI system and a concern you can’t quite articulate[44:07] The grounding question every CTO should ask before the next AI initiative what are we hurrying up forResources Mentioned:NIST AI Risk Management Framework | WebsiteDownload The Four AI Horizons Guide or schedule a free consultation with Jill Heinze.Find more from Jill on her LinkedIn, YouTube, and Website. Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.