The CTO Playbook

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.

Women weren't pushed out of tech once. There were multiple waves, and the patterns are still showing up in how teams get built today.

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 engineering leaders think their hiring process is neutral. Changing the job spec brought my guest three women applicants the following week, and her team hired two of them. Michelle McDaid spent two decades leading globally distributed engineering teams, became the first female director of engineering at her last company, and left it with 50% women in that role.

She then went back to university to put the evidence behind what she'd already seen on the ground. We sat with some of these ideas together at CTO Craft Con in London a couple of weeks ago, and the conversation was good enough that I wanted to bring it here. She's unusually calm about uncomfortable truths, and that's exactly why this matters. If you believe in diverse teams but keep ending up with more of the same, the gap isn't your intent. It's what you don't even know to look for. This one challenges the default assumptions most technical leaders never examine, and gives you something practical to do about it.

You'll Learn:

[00:00] Introduction
[02:29] What trust actually has to do with uncovering the real problem in any organization
[06:50] What Michelle's career across banking and tech revealed about leadership and self-worth
[15:56] Why the gender gap in tech is neither natural nor inevitable
[24:36] How the language in your job spec is quietly filtering out the people you want to hire
[28:36] The smallest changes that move teams from fearful to collaborative and how AI fits in
[33:47] A 10-point framework for intentionally broadening your talent pool
[44:20] What women lose in meetings every day and how anyone can change it

Resources Mentioned:

The Authority Gap by Mary Ann Sieghart | Book
Where Did the Women Go? by Michelle McDaid | Article
Textio | Website
Gender Decoder by Kat Matfield | Website

Learn more from Michelle on her LinkedIn and The Leading Place 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.

Most CTOs are promoted for technical judgment, then get stuck trying to lead people with the same playbook that got them there.

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.

Ric Hill has spent 14 years running Ghyston with his wife, CTO'd for startups and mid-corporates, and earned a spot on the CTO Craft 100. His central conviction is that there is no playbook worth following blindly.

Most CTOs are promoted on technical skill and then judged on leadership. The reflex is to import what worked last time. Ric argues that reflex is the problem.

What replaces the playbook is a sharper version of listening, knowing how long your "fresh eyes" window actually lasts, reading the difference between an unhealthy political culture and an unhealthy apathetic one, and noticing which person on your team has gone quiet.

This is a conversation about staying flexible without being indecisive, and delivering results without forcing a template onto a situation that doesn't fit it.

You’ll Learn:

[00:00] Introduction
[11:29] Why bespoke beats cookie-cutter software
[13:50] The first few weeks decide everything
[16:23] How long until you're part of the furniture
[18:19] Health versus outcomes in tech leadership
[20:21] The sticky note roadmap that changes everything
[25:38] Disagree and commit without losing trust
[28:40] When stubbornness becomes a liability
[30:35] Listen for the silences in your team
[32:59] Why engineering culture can stand apart
[40:20] The one tip every new CTO needs

Check out Ghyston for your software development needs.

Find more from Ric on LinkedIn.

Listen to Ric’s podcast, Giant Minds: From The Bristol Tech Community, on Spotify or Apple.

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 impact you have as a leader isn’t the strategy you set, but the signals you leave behind in every interaction?

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.

In this episode, Paul Kinkaid, a former British Army officer, founder of Forensic Outcomes, and executive leadership coach, introduces a principle from forensic science: every contact leaves a trace.

Those small moments, the way you listen, the way you respond, the way you make decisions, shape how your leadership is experienced across an organization.

The focus is on the smallest behaviours that most leaders overlook, and how those behaviours shape trust, culture, and performance.

Leadership isn’t just about decisions or strategy. It’s about the signals you send every day.

You’ll Learn:

[00:00] Introduction
[00:06:02] What leadership presence is and why people listen before you speak
[00:09:10] Why pressure exposes the difference between real and performative leadership
[00:12:04] How small behaviours shape trust, clarity, and psychological safety
[00:21:36] What happens when leaders send the wrong signals without realizing
[00:34:12] Why the gap between intention and impact grows over time
[00:48:27] How communication patterns shape culture more than strategy
[01:02:14] What it takes to notice and shift the signals you send

Resources Mentioned:

Locard Exchange Principle by Saferstein, R., et al. | Article

Get Paul’s book, Forensic Leadership, in print or audiobook and start noticing the signals you’re sending every day.

Find more from Paul on LinkedIn, and visit his DactoApp landing page at Forensic Outcomes.

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.