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.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.