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 strongest part of your engineering organization isn’t your tech stack, but the culture you protect every day?In this episode, I’m joined by CTO Pasha Jam, who has grown an engineering team from three people to 110, expanded internationally, and navigated company acquisitions while keeping culture a central focus. We define what a healthy engineering culture looks like, and why it consistently outperforms strategy and process.Culture became a priority after working in environments that were difficult to enjoy, even when the products and compensation were strong. Psychological safety is explored through the lens of engineering teams, including the ability to ask questions, raise risks, challenge decisions, and fail without fear.Culture’s impact on hiring, onboarding, and communication across teams in multiple countries is explored, along with why people who leave often say they miss the culture and sometimes choose to return.If you’re responsible for engineering teams and want to think more intentionally about culture, leadership, and long-term team health, this episode offers practical perspective grounded in lived experience.You’ll Learn:[00:00] Introduction [05:18] Why job dissatisfaction often traces back to culture instead of pay or products[06:42] What psychological safety looks like when engineers challenge decisions without fear[11:07] How empowerment leads teams to take ownership without being pushed[24:21] Why fixing incidents together matters more than assigning blame[28:36] How putting people before process changes commitment and delivery[30:14] Why micromanagement quietly erodes trust and culture[33:09] What it looks like when leaders carry culture forward without seeking credit[35:27] Why culture must evolve as teams scale and contexts changeResources Mentioned:Agile Manifesto | WebsiteNeed car repairs but not the upfront cash? If you're in the UK, get approved in seconds and pay interest‑free over time, apply with Bumper today and stay on the road.You can connect with Pasha Jam on his LinkedinFind 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.Your most powerful decision engine isn’t your data, your dashboards, or your AI, it’s your gut.There is a topic that most technical leaders quietly wrestle with: gut instinct. Not as mysticism. Not as guesswork. But as a real decision-making tool for modern CTO leadership.This episode is all about why your instincts are often your experience compressed into a feeling, when you should trust that signal, and when you absolutely shouldn’t. You’ll hear real coaching stories from seasoned CTOs navigating technical leadership, roadmap trade-offs, scaling engineering teams, and high-stakes calls where the data wasn’t enough.We’ll talk about how engineering leadership changes when you treat instinct like a cached function, fast, powerful, but sometimes stale, and how to validate it without killing its speed. This episode is for startup and enterprise technology leaders who want sharper judgment, fewer regret-filled postmortems, and more confidence saying, “Something about this feels off, and here’s why.”If you’ve ever ignored your gut and paid for it later, or trusted it blindly and been burned, this conversation will give you a practical way forward. It’s about building better instincts, not just better systems.You’ll Learn:[00:00] Introduction[01:02] Why seasoned CTOs sense problems before they can explain them[03:18] How ignoring gut signals leads to overcommitment and roadmap failure[05:07] What gut instinct really is — experience compressed into a signal[07:26] When instinct fails in new or emotionally charged situations[09:41] How to spot where your instincts are strong, weak, or distorted[12:12] Treating instinct like a cached function — fast but fallible[16:34] Using gut instinct as a warning without turning it into dogma[20:18] How data can validate instinct without slowing decisions[24:47] A playbook for sharpening instinct under pressureFind 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.Most CTOs fail not because of bad decisions, but because they stop asking why.In this episode, I sit down with Massimo Belloni, Head of Machine Learning and Data Science at Docplanner, to discuss what real technical leadership looks like when the answers aren’t obvious.We dig into bold CTO leadership, why engineering leadership is mostly about people, and how curiosity in leadership builds trust faster than authority ever will. Massimo shares hard-earned lessons from leading ML teams across industries, and why the job isn’t about being the smartest person in the room, but creating conditions where teams thrive.If you’re navigating CTO mindset shifts, managing high-performing engineering teams, or feeling the quiet weight of imposter syndrome in tech leadership, this conversation will land. We talk about invisible leadership work, asking better questions, and why progress only makes sense in hindsight.Iif you’re leading through complexity and change, this episode is your reminder: certainty isn’t the goal, clarity is.You’ll Learn:[00:00] Introduction[02:14] How Massimo realized leadership is about people, not technical mastery[05:48] Why trying to be the smartest person in the room backfires[09:37] What changes when you lead systems you don’t fully understand[13:22] Why most leadership problems aren’t actually technical[17:54] How asking why builds trust faster than giving answers[22:41] Why strong teams come from safety, not fearlessness[27:36] How invisible leadership work compounds over time[33:18] The question Massimo uses to measure leadership progress[38:47] Why leadership only makes sense in hindsightResources Mentioned:The CTO Playbook episode on The Key Relationship That Drives Startup Growth with Steven Renwick | Spotify or AppleSteve Jobs Stanford Commencement Speech | YouTubeYou can connect with Massimo on LinkedIn and learn more about his work on his substack 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.The real reason invoices don’t get paid has nothing to do with accounting.Late payments aren’t just annoying, they quietly drain focus, energy, and leadership bandwidth. In this episode I sit down with entrepreneur Maximiliaan van Kuyk to discuss why trust in business payments is breaking down, and what CTOs can do about it.Drawing on years of experience across startups, agencies, and global markets, Maximiliaan explains why accounts receivable is no longer just a finance function, but a leadership and systems problem. They explore how late invoice payments persist not because people are malicious, but because incentives are misaligned, and accountability is invisible.You’ll hear why consistency beats confrontation, how social accountability in business can outperform legal threats, and why CTOs should care deeply about cash flow management even if they never touch invoicing.If you’ve ever felt the quiet frustration of waiting to get paid, or watched payment delays impact runway, morale, or growth, this conversation will reshape how you think about trust systems, AI in accounts receivable, and the future of getting paid on time.You’ll Learn:[00:00] Introduction[02:18] Why getting paid is really a trust problem, not a money problem[06:41] How chasing payments drains founders emotionally and why it usually lands leadership[10:52] What happens when small businesses become accidental lenders, and why the system works against them[15:37] Why consistent follow-ups beat confrontation and legal threats when recovering unpaid invoices[21:04] Why late payments persist even with contracts and how incentives shape behavior[27:56] How social accountability changes payment behavior faster than reminders or credit scores[34:48] Why reputation only works when it’s visible, and what hidden payment history enables[41:22] Why CTOs need to understand cash flow risk even if they never touch invoicing[48:09] How tracking payment behavior could reshape trust, partnerships, and who gets hiredYou can connect with Maximiliaan on Instagram or find 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 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.

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.

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.

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.

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.When your CTO dies and no one can read the code, you realize the real problem was never the software.In this episode, I sit down with Matteo Di Battista and Marcello Modica, two Italian innovators who’ve spent decades helping companies escape the grip of outdated ERP systems. From IBM mainframes to cloud-native development, they’ve seen how technical debt and siloed knowledge can quietly strangle growth.We get into what happens when your tech stack outlives your people, why monoliths breed fragility, and how breaking systems into small, pluggable services changes everything. It’s not just about new tools—it’s about a new kind of teamwork that keeps knowledge alive even when key players leave.Because modernization isn’t just a tech upgrade—it’s a survival strategy.You’ll Learn:[00:00] Introduction[05:32] Why monolithic ERP systems quietly trap companies in technical debt[09:47] What happens when a CTO’s death exposes a company’s hidden knowledge silos[12:18] The moment you know it’s time to modernize your software before it collapses[15:44] How low-code and visual tools can close the gap between design and delivery[18:56] Why developers are becoming replaceable, and what that means for software teams[23:51] How building a shared development community protects both companies and clients[26:28] The real reason developers resist change even when innovation would make life easier[33:42] What the new network API standard means for identity, payments, and fraud prevention[45:37] How converting old databases into REST APIs transforms legacy systems into living platformsYou can connect on LinkedIn with both Matteo and Marcello, and their work though wavemaker.com and oneclickapp.it.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 future of startups isn’t decided by who builds the flashiest AI, but by who solves the right problems?In this episode, I’m joined again by my friend Thorgeir Einarsson, almost a year since we last spoke, to unpack how AI funding and investor expectations have shifted from hype cycles to hard realities. Thor runs PGO, a service that helps founders get truly investment-ready with real pre-diligence instead of lipstick on a pig.Pre-seed and seed are brutal right now, and traction beats vibes. Investors are placing smaller, option-like bets at the AI application layer while steering clear of generic models. Hardware is back where it matters, from defense tech to medical devices, when firmware and software meet close to the metal. We trace the PE-ification of VC: rolling up vertical SaaS, “AI-firing” them, and rebuilding moats from customer bases and domain data. Thor flags a blind spot worth building for: AI safety and guardrails for agentic workflows. Then we get practical: preparation beats performative decks, checklist-driven pre-diligence forces the hard questions, and the playbook is simple… know yourself, know your co-founders, keep investors updated, and track the numbers.You’ll Learn:The reason many VCs focus on the AI application layerWhat happens when nobody knows what a great AI company looks like yetThe link between defense and medical devices and hardware-plus-software productsThe damage of skipping investor updates and simple monthly KPIsWhat it feels like to raise when only one to three percent get a checkThe reason pre-diligence and checklists come before the pitchWhat happens when agentic workflows scale without safety guardrailsTimestamps:[00:00] Introduction[05:42] Why AI investment has shifted from hype to hard reality[12:18] The brutal truth about pre-seed and seed fundraising in 2025[18:33] Why investors are betting smaller at the AI application layer[25:47] How defense tech and medical devices are bringing hardware back[32:11] The rise of “AI-firing” old SaaS companies and the PE-ification of VC[40:26] The missed opportunity in AI safety and agentic workflow guardrails[48:59] How founders can prepare for due diligence the right way[56:22] Why investor updates and clear KPIs determine long-term trustConnect more with Thorgeir on 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 the real lever isn’t the tech at all?In this episode, I sit down with Matthew Carr, who does interim work and often comes in as the firefighter when a company has taken a wrong turn. He lays out why people come first, processes second, and technology follows.He started in classic ASP and built a loyalty program for the heating and engineering sector. Real-time results beat long compile cycles and changed how he delivered. A private-equity buyout couldn’t get the startup’s tech delivered, so he sat one-to-one with everyone to map the problems. Turns out, fixing broken delivery isn’t about new tools. It’s about people, trust, and having the guts to act fast.You’ll Learn:The reason putting people first makes process work and technology followWhat happens when you plan three sprints ahead and tie outcomes to business valueThe link between quick wins and winning trust in the first 30 daysThe damage of being six to twelve months off on deliverables after a PE acquisitionWhat it feels like to inherit a program that hasn’t shipped in 18 monthsThe link between weekly iterations, monthly demos, and a product becoming a bedrock of the businessThe reason trust, leadership, and alignment are the core enablers of the people pillarWhat happens when you play their game first by showing a six-week plan the board can approveThe reason “believe in yourself” is the sharpest one-line tip for new CTOsTimestamps:[00:00] Introduction[05:12] Why people come first before process and technology[10:46] Lessons from early development work in classic ASP and loyalty programs[15:58] How a private equity acquisition exposed major delivery delays[21:37] Running a massive retrospective and uncovering 110 problems[28:04] The importance of quick wins and building trust in the first 30 days[33:41] Planning three sprints ahead and reporting outcomes instead of outputs[38:22] Turning around a project that hadn’t shipped in 18 months[45:09] How weekly iterations and monthly demos rebuilt momentum[51:28] The one-line advice Matthew gives every new CTOLearn more from Matthew on 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.Logic alone won’t land; people react to change emotionally.In this episode, I sit down with Giorgia Prestento, a behavioral scientist and author of The Change Maze. She’s here to show why change so often derails and how CTOs can lead through it with clarity and confidence.We break down why rational explanations fall flat, the different speeds leaders and teams move at, and how losing control sparks uncertainty and anxiety. A call center story shows how rewarding quick answers without customer outcomes skews behavior. A Hong Kong example proves that “ask your line manager” messaging failed culturally, so we rewrote it to a nominated peer contact. A pre-mortem setup surfaces blind spots by declaring the project failed and collecting reasons before execution. We run through an eight-step playbook from purpose and alignment to blind spots, impacts, resistance, indicators, validation, and finally execution.You’ll Learn:The reason logic-only change pitches backfireWhat happens when leaders move faster than teamsThe link between the metric you reward and the behavior you getWhat it feels like to run layoffs twiceThe reason pre-mortems workWhat happens when you don’t set indicators earlyThe link between purpose, alignment, and smoother executionWhat happens when a key trainer is missingThe damage of losing clarity at the topTimestamps:[00:00] Introduction[05:18] Why logic fails when leading change[10:42] The emotional side of resistance and uncertainty[15:56] How leaders move faster than their teams[20:11] The blind spot that halted a global SAP rollout[26:27] Why bad metrics destroy good behavior[31:03] Cultural barriers that derail transformation[36:49] The pre-mortem method for spotting hidden risks[42:08] The eight-step change playbookResources Mentioned:Master the Change Maze by Giorgia Prestento | BookGiorgia offers a short assessment 'Leaders: Are You Change Ready?' You will gain valuable insights across the categories of Leadership Style, Change Expertise and the Readiness of your organisation. It takes less than 3 minutes. You get readiness scores in a personalised report. Plus a digital copy of her book, Master the Change Maze. Click here to get started.You can connect more with Giorgia on 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.Are you optimizing for starting work instead of finishing?In this episode, I’m joined by Joakim von Prónay, an engineer and psychologist by education and a coach by passion.We break down how fake roadmaps and a “Global Roadmap Owner” role turn planning into a Gantt chart exercise. We make planning useful with a simple rule: it’s better to be roughly right than precisely wrong. Predictability becomes the lever for real accountability, measured by “did we do the things we said we were gonna do.” Escalation culture gives way to real collaboration, not the default “ask the boss” reflex.You’ll Learn:The reason long-term planning works when it’s roughly right instead of precisely wrongWhat happens when teams are incentivized to start work instead of finish itThe link between delivery predictability and real prioritization and accountabilityThe damage of treating roadmaps like a Gantt chart exerciseWhat it feels like when every question defaults to “ask the boss” instead of talking directlyThe reason fragmented steering creates conflicting directionsThe link between a single “central rule” and measurable goalsTimestamps:[00:00] Introduction[06:14] Why high-performing teams are so rare[09:27] The danger of planning for perfection[15:46] Why teams start work instead of finishing it[19:32] The power of predictability and real accountability[25:40] When collaboration breaks down into escalation[31:58] What fragmented steering really looks like[38:45] The rule that defines true strategy[46:23] A Spotify story and the engineer’s warning[51:17] How alignment turns insight into actionConnect more with Joakim on LinkedIn.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

Build your own CTO Playbook here, 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 playbook that built your career suddenly stopped working and nobody told you?In this episode, I sit down with Catherine Stagg-Macey, an executive coach who works with technical experts turned leaders. She knows firsthand what it’s like to move from coding and spreadsheets into managing people, and the struggle that comes with it.We get into what happens when being the smartest person in the room is no longer enough, the patterns that keep leaders trapped in the systems they built, and the hard pivot it takes to step into a new kind of leadership.You’ll Learn:The reason smart technical leaders hit a wall when old habits stop workingWhat happens when you try to manage people with the same mindset you used to write codeThe link between control, trust issues, and being stuck in endless meetingsThe damage of wearing the “superhero cape” and building a culture of firefightingWhy skepticism is common when leaders are first asked to work with a coachThe pivotal moment that led Catherine from consulting success to a coaching careerHow childhood patterns and early work experiences quietly shape leadership behaviorsThe role of feedback, or the lack of it, in pushing leaders toward breaking pointsWhy creating distance from your triggers opens space for better choicesTimestamps:[00:00] Introduction[06:15] Breaking patterns of overwork and constant meetings[08:55] The lure and cost of playing the workplace superhero[10:20] Catherine’s pivot from consulting success to coaching[16:05] When rock bottom moments force change[20:15] Early warning signs leaders ignore before burnout[26:45] Identity shifts required to let go of old leadership habits[30:10] Recognizing triggers and unconscious behavior patterns[41:20] How upbringing and culture shape leadership reactions[53:00] Building range as a leader in times of uncertaintyResources Mentioned:Conversations at the Edge | WebsiteYou Didn’t Chase Leadership. Leadership CHASED You. Join Catherine’s Inner Circle.Unlock your leadership superpower, discover what your leadership style is with Catherine’s Leadership Style Quiz.You can connect with Catherine on LinkedIn and listen to her podcast here. Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

Build your own CTO Playbook here, the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact!Would you say yes to leading through chaos with no plan, little information, and no guarantee of success?In this episode, I sit down with Corey Hart, a crisis operator who’s built a career on scaling massive humanitarian and operations projects under extreme pressure. He’s said yes to projects most people would run from, from helping New York City respond to a sudden influx of asylum seekers to standing up global call centers and navigating cruise ship operations post-lockdown.We get into how he prepares for the unknown, what it takes to build trust in the middle of a storm, and why surrounding yourself with the right people makes the difference between collapse and momentum.You’ll Learn:The reason Corey says yes to high-stakes projects others avoidWhat happens when you’re asked to launch a humanitarian response overnightThe link between early onboarding and a culture of openness and candorThe damage of overcomplicating operations when speed is criticalWhat it feels like to land in a crisis with little info and no certaintyWhy bringing compliance and tech in early turns them into strategistsThe role of trust in holding teams together under extreme pressureHow living autopsies fix problems in real time, not after the factThe mindset shift that turns specialists into early-stage leadersWhy tracking from day one helps you see around corners in chaosTimestamps:[00:00] Introduction[05:58] Saying yes to unpredictable challenges[07:02] Scaling New York’s asylum seeker response[11:58] Handling moments when operations nearly collapse[14:02] Filtering signal from noise in crisis decision-making[17:56] Building openness and candor into team culture[20:06] Creating trust and making failure safe[22:01] Why saying yes builds momentum and possibility[27:00] Unlikely outcomes from saying yes[31:00] Keeping operations simple and avoiding scope creep[33:02] Tracking data early to guide decisions under pressure[35:00] Bringing compliance and tech in early to shape solutions[37:56] Knowing when and how to step out of a crisis projectResources Mentioned:Podcast Episode The CEO’s Playbook for Hiring the Right CTO with Warren Beasley | YouTubeYou can connect with Corey on 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 here, 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 reason your team feels stuck isn’t money, but the weight of your own code?In this episode, I sit down with Lou Franco, author of Swimming in Tech Debt and a veteran software engineer who’s been a founding engineer at three successful startups, a principal engineer at Trello through its Atlassian acquisition, and now an advisor to software teams.We trace his journey from early lessons in fintech and startup acquisitions to the moments that exposed just how costly ignored tech debt can be. Lou shares what he learned from engineers on the ground, how small fixes can deliver outsized productivity gains, and why culture and process matter just as much as code when tackling debt.You’ll Learn:The reason most engineering teams carry hidden tech debt without clear solutionsWhat happens when day-to-day friction drags down delivery speed and moraleThe ROI of small, focused fixes that start paying back almost immediatelyThe damage that builds when debt is ignored until it hits a breaking pointThe link between a product’s lifecycle stage and the right level of debt reductionWhy dedicated engineering-led time creates accountability and better outcomesHow visible progress metrics help leadership see the value of paying down debtThe risk of jumping too fast into shiny new tech that stalls out in productionThe role of culture, style guides, and clear values in preventing runaway debtTimestamps:[00:00] Introduction[05:01] Early lessons on tech debt in fintech and startups[07:02] The exit interview that exposed ignored debt[08:59] Small fixes that delivered immediate productivity gains[11:00] When debt grows into brick walls and forced rewrites[14:01] Building team culture and values to tackle debt[16:59] Splitting engineering-led time from product-led work[23:00] Measuring debt payoff with metrics and visibility[29:01] Leading indicators of productivity and developer experience[36:59] High-risk systems, regressions, and measured approachesResources Mentioned:Swimming in Tech Debt by Lou Franco | BookCrossing the Chasm by Geoffrey Moore | Book or AudiobookYou can connect with Lou on LinkedIn and find his book here.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.