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.

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 strategy

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.

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 platforms

You 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 layer
• What happens when nobody knows what a great AI company looks like yet
• The link between defense and medical devices and hardware-plus-software products
• The damage of skipping investor updates and simple monthly KPIs
• What it feels like to raise when only one to three percent get a check
• The reason pre-diligence and checklists come before the pitch
• What happens when agentic workflows scale without safety guardrails

Timestamps:

[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 trust

Connect 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 follow
• What happens when you plan three sprints ahead and tie outcomes to business value
• The link between quick wins and winning trust in the first 30 days
• The damage of being six to twelve months off on deliverables after a PE acquisition
• What it feels like to inherit a program that hasn’t shipped in 18 months
• The link between weekly iterations, monthly demos, and a product becoming a bedrock of the business
• The reason trust, leadership, and alignment are the core enablers of the people pillar
• What happens when you play their game first by showing a six-week plan the board can approve
• The reason “believe in yourself” is the sharpest one-line tip for new CTOs

Timestamps:

[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 CTO

Learn more from Matthew on LinkedIn.

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