The CTO Playbook

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.

The most dangerous moment in a transformation isn't the start, it's the stretch right before behaviours actually start sticking.

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.

My guest is Anders Wengelin, partner at Friktion in Malmö, who spends his weeks inside large Swedish healthcare organizations trying to help them build new core capabilities without reaching for a neat plan.

Leaders kill change at the exact moment it's about to take hold. Not because the work is failing, but because nothing visible has shipped yet.

Anders walks through how his team thinks about behaviours as the only concrete thing in an organization, and why operating models, maps and rollout plans are abstractions people hide behind. If you've ever felt the pull to add structure the moment ambiguity shows up, this one will sit with you.

Three questions, nine parts, and one uncomfortable truth about what real change looks like inside large, regulated organizations.

You'll Learn:

[0:00] Introduction
[2:40] Why large, compliance-heavy organizations struggle most with acquiring adaptivity
[6:00] The detour every tech-heavy org takes before talking about what actually matters
[14:06] Why leadership teams grasp for maps and plans the moment complexity shows up
[21:13] The three questions behind Friktion’s transformation strategy playbook
[30:00] The camera test for behaviours, and why curiosity isn't a behaviour
[33:45] How behaviour spreads like a virus, and why rollouts never work
[38:26] The three nested loops that keep continuous change moving
[41:11] Success looks like nothing is happening right before momentum kicks in
[45:41] Why you don't need a majority before behaviour change tips
[52:34] The trap of sneezing at a crowd instead of infecting one context properly

Want to go deeper on everything Anders covered? Friktion's sandpapers are free to download at friktion.se/sandpapers.

Find more from Anders 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.

When do you stop being the CTO with all the answers and start being the one who asks better questions?

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.

Miguel Carranza built RevenueCat into critical infrastructure for thousands of mobile apps, and he'll tell you straight that he never wanted to be a manager.

He got his first computer at age eight and moved from Sevilla to Silicon Valley to build things. Somewhere along the way, he had to stop being the best engineer in the room and start hiring people better than him.

His worst hire is already on the team. That's not a red flag, it's the whole point of how he builds. The Office of the CTO, which he set up, exists precisely to keep that bar moving.

The engineering managers who never wanted the job are the ones who work out. The smallest pull requests have caused the biggest outages. And AI is making his teams smaller, not larger.

If you're a founder CTO trying to figure out when to delegate and when to dig in, this one will sit with you.

You'll Learn:

[00:00] Introduction
[01:12] From Sevilla to Silicon Valley: what drove Miguel to chase computers over everything else
[08:15] Building Elevate revealed a mobile subscription problem nobody had solved yet
[10:48] What changed Miguel’s mind when he doubted himself as a CTO
[17:16] Why engineering managers at RevenueCat must be ex-engineers first
[20:31] The mental model Miguel uses to hire people better than himself
[22:23] How AI is shrinking team sizes and who it benefits most
[29:45] The small internal team Miguel deploys to new bets and stuck projects
[35:49] The five rules Miguel refuses to bend on as an engineering leader
[42:01] Why RevenueCat's biggest outages came from one-line pull requests
[43:39] What actually makes RevenueCat's engineering culture distinct

Connect more with Miguel on X and the RevenueCat website.

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.