The CTO Playbook

Shielding your team from context isn't protection, it's a subtle underestimation of the people you hired for their judgment.

Build your own CTO Playbook at www.theCTOplaybook.com - the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.

The thing most technical leaders are proudest of is the same thing slowly cracking them in half. I coach CTOs through this exact pattern, and the reaction is almost always surprise rather than recognition.

You take the hits. You field the awkward questions. You sit in the meeting that would have derailed the sprint, and walk out telling the team not to worry about it. It feels like leadership. It feels like care.

Then I ask one question and the whole frame shifts. What if the way you're protecting your team is what's keeping them small?

This episode is about the structure you've turned yourself into without ever deciding to... The dam versus the firewall. Why one of them is exhausting, rigid, and impossible to sustain, and the other changes your job in a world where AI has collapsed the cost of reaching raw context.

If you've ever felt the strain of holding everything together, the discomfort you feel listening to this isn't a problem. It's the start of doing it differently.

You’ll Learn:

[0:00] Introduction
[3:58] The dam metaphor and why no human was built to hold that much back
[5:58] The instinct nobody trained into us, and why it operates below examination
[8:08] From dam to firewall, a model every technical leader already understands
[10:55] Why filtering for your team robs them of the reps they need to grow
[13:36] The belief hiding under the dam, that they can't handle the truth
[15:46] How AI collapsed the last practical argument for the leader as the filter
[18:14] The four postures for standing in the stream without becoming the wall
[20:39] Choosing which structure you become in relation to the stream

Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

Most CTOs chase value creation. Jaco Vermeulen says the real job is preserving it first.

Build your own CTO Playbook at www.theCTOplaybook.com - the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.

Boards across the mid-market are running AI pilots that return nothing, and revenue is being booked long before it's ever realised. The gap between the story a business tells about itself and what's happening underneath has rarely been wider or more expensive.

My guest is Jaco Vermeulen, an interim CTO, CIO, and M&A specialist who has worked through more than 50 transactions and spent 25 years finding what's hidden in that gap.

Jaco doesn't want to talk about technology. He wants to talk about what the technology is meant to do for the business, and why most leaders get that order wrong. His stories from carve-outs, acquisitions, and portfolio integrations show how much value gets destroyed by assumptions nobody bothered to check.

If you're an engineering or science leader who has never sat close to a transaction, this one will change how you read your own company. And if you have, you'll recognise the patterns immediately. Preserve value first. Create value second. Everything else follows from there.

You'll Learn:

[0:00] Introduction
[4:02] CTO, CIO, CAIO: titles that mean the same thing to most businesses
[9:10] A box of CDs and a $2 billion company still running on paper
[15:00] The real reason AI pilots keep returning nothing
[20:11] The hidden gaps in M&A due diligence that most tech leaders never look for
[23:33] A company that paid £1 million a year to license data it already owned
[26:34] ARR reporting and the disconnect between booked revenue and reality
[29:55] A transaction's success is decided after the deal closes, not at signing
[35:12] A £5 million pricing plan projected to return just £200,000 a year
[38:21] The four steps every technology leader should take to be transaction-ready
[45:44] The incentive hiding behind every KPI you're set

Find more from Jaco Vermeulen on LinkedIn.

Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

Duri's father holds more than 100 patents, filed his latest one at 96, and gave him a one-line philosophy that now drives how his teams approach every problem: most people don't try.

Build your own CTO Playbook at www.theCTOplaybook.com - the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.

Most CTOs think AI failures are technical problems. The data says otherwise, and the gap between a good idea and a great product is almost never where engineers expect it to be.

My guest today is Duri Chitayat, CTO at CINC Systems, leading a 170-person globally distributed product development team across four continents with a background spanning AdTech, MedTech, Banking, and FinTech.

What stood out for me in this conversation was how willing Duri is to question the assumptions other leaders treat as fixed. He grew up around an inventor with over 100 patents, and that shaped a way of thinking that strips problems down to first principles before touching a solution.

The stakes here are real. Innovation tokens are finite. Spend them on the wrong assumption, and you lose the race before you knew it started.

Our conversation moves through a six-part playbook for leading engineering in 2026, the leadership paradox that breaks most CTOs, and why measuring transformation honestly is harder than anyone admits. If you're leading through an AI shift right now, this one is for you.

You'll Learn:

[0:00] Introduction
[3:00] What growing up around a 96-year-old inventor with 100+ patents taught Duri about first principles
[4:54] The difference between writing code and delivering solutions, learned the hard way on an SAP rollout
[7:29] Mount Fuji problems versus dancing landscapes, and how to spend your innovation tokens wisely
[12:59] Why the customer hanging a picture frame isn't really trying to hang a picture frame
[14:55] Finding the borders of the box you didn't know you were in
[24:22] Duri's only juniors are named Claude and Codex, and how he hires senior talent globally
[28:03] How the RFC process creates earned trust and stops Duri from running roughshod over smart engineers
[32:07] Walking through the six-part playbook
[40:33] Why tokens burned is the new lines of code, and what to actually measure instead

Resources Mentioned:

Your Strategy Needs a Strategy by Martin Reeves, Knut Haanaes, Janmejaya Sinha | Book or Audiobook

Find more from Duri on LinkedIn

Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

What if the biggest constraint on your organisation isn't your tech, your funding, or your market, but whether your leaders can think at the level the problem requires?

Build your own CTO Playbook at www.theCTOplaybook.com - the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.

Logan Yonavjak spent nearly two decades in impact investing before co-founding Readiness Engine. Her perspective matters here because she watched the pattern play out across hundreds of well-resourced teams.

The teams weren't short on capital. They were short on cognitive capacity to hold complexity, sit with paradox, and make decisions when the answer wasn't black-and-white. Most leadership assessments snapshot who you are. Logan argues they miss the part that predicts whether you're ready for what's coming next: how you think, not what you've done.

In this episode, we get into developmental psychology, why coachability is the single biggest predictor of growth, and what it looks like to measure a leader's readiness rather than their résumé.

For CTOs who've been told coaching is something other people get, this one reframes the conversation. The cost of staying fixed is higher than you think.

You'll Learn:

[0:00] Introduction
[3:55] What impact investing actually means beyond profit-only capitalism
[5:49] How developmental psychology measures the way adults hold paradox and perspective
[10:40] Why coachability is the single biggest predictor of whether leaders can evolve
[15:37] Myers-Briggs and most leadership assessments miss vertical development entirely
[22:12] How the 45-minute video assessment works and why it's harder to game
[24:40] Building a second brain that channels your highest self into team decisions
[28:11] AI coaching could become the entry point for leaders allergic to therapy
[34:33] What changes when investors start assessing their own leadership capacity before deploying capital

Resources Mentioned:

Myers-Briggs Type Indicator (MBTI) | Website

Find more from Logan on LinkedIn, and see a sample Readiness Engine report here.

Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

The reps that used to turn juniors into seniors are disappearing, and most engineering leaders won't notice until the senior shortage hits in three years.

Build your own CTO Playbook at www.theCTOplaybook.com - the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.

Your dashboards say velocity is up, your seniors are asking careful questions nobody wants to answer, and your juniors are getting confident faster than they're getting capable. I'm a coach for CTOs across startups and enterprises, and this is the pattern I've been hearing in coaching conversations for the last six months.

It usually arrives as unease about velocity or quality. By the time we trace it back, it always lands in the same place. Does our boilerplate still earn its keep in an AI-accelerated world? One camp wants to lock it down further. The other wants to delete half of it. They're both right, and they're both wrong.

The argument is a symptom. The real question is bigger, and almost nobody is pricing it in yet. Our most experienced engineers got their judgment from reps we can no longer reproduce. Our juniors aren't getting those reps. If we don't design a replacement, we'll wake up in a few years with a senior shortage and no good explanation for how it happened.

This episode is about the scaffolding that fixes it.

You'll Learn:

[00:00] Introduction
[00:22] The unease CTOs can't quite name yet
[01:48] Three warning signals hiding inside a healthy-looking engineering team
[03:45] Why both sides of the boilerplate debate are right and wrong at the same time
[05:59] Why boilerplate is no longer just about code, it's doing three jobs now
[08:44] The hidden dial between your code base and your AI that most teams haven't noticed
[11:21] How senior engineering judgment was built and why AI has removed the mechanism
[12:39] The senior shortage nobody sees coming and why your scaffolding is part of the answer
[14:58] A five-step playbook for redesigning your scaffolding as a judgment tool

Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.