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 pressure

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.

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 hindsight

Resources Mentioned:

The CTO Playbook episode on The Key Relationship That Drives Startup Growth with Steven Renwick | Spotify or Apple

Steve Jobs Stanford Commencement Speech | YouTube

You 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 hired

You 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 everything

You 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 progress

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 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 yourself

You 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 balance

You 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 seasons

Resources Mentioned:

Fjord’s Mountain Mission: Avalanche Safety Children’s Book by Caroline Elliott | Book

You 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 loops

Resources Mentioned:

Radical Product Thinking by Radhika Dutt | Book or Audiobook

It’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 last

Resources Mentioned:

Digital Transformation Success by Michael Schank | Book

You can connect with Michael on his LinkedIn.

Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.