The CTO Playbook

I nearly turned my own summer into the cautionary tale. The thing that saved me was a last-minute week in the Swedish mountains.

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.

I came home with a small number of clear thoughts about my business that I couldn't have produced at my desk, and they fade fast once you're back. This episode is for anyone heading back into work in the next fortnight, because how we come back in late August shapes the rest of the year more than almost anything else in September.

Real intent goes in on day one. The stack gets attacked head on. Two or three weeks later, we're extremely busy and have moved nothing forward.

There's a spaceflight analogy in here about why the most dangerous part of any return is the descent, and the one small decision that sets the angle for everything after it. Most of us come in too steep, and the queue gets to decide what matters so we don't have to. The cost is specific: the decisions only you could have made never surface, because they're never the loudest thing in the queue. There's a practical exercise at the end.

You'll Learn:

[0:00] Introduction
[2:05] The summer move that nearly made me the cautionary tale
[4:16] How spacecraft reentry explains a bad return to work
[6:52] Why late August beats January for real resolutions
[9:36] Career trains every leader to choose the steep angle
[10:52] Heavy first week is the friction doing its job
[12:37] Naming your own re-entry angle before the queue decides
[17:14] A controlled re-entry playbook in four steps

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.

One CTO spent two weeks tearing frontier models out and ended up back where they started. Another spent a few days building a tested escape route for what actually mattered.

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 safe CTOs aren't the ones who trust their AI provider, and they aren't the ones tearing frontier models out of every workflow; they're the ones who've triaged their dependencies and tested a real escape route for the handful that matter. I'm walking through this one solo because it's a structural risk most engineering leaders felt this year but haven't priced.

Frontier AI is a supplier you can't audit, and it can be switched off by forces sitting outside your contract. Your invoices can be paid in full, and the capability can still vanish.

Most of us onboarded this dependency without ever writing it down. It spread the way water finds its level, and it became load-bearing before anyone noticed. Where in your stack would a frontier model going dark tomorrow actually hurt, not annoy you, but hurt?

The third option is triage: trust the dependency where stakes are low, temper it where you're more reliant than is wise, and override it with a tested alternative for the workflows that would cost you the business.

Two CTOs I work with responded to the same news in almost opposite ways, and only one of them still has a working escape route.

You'll Learn:

[0:00] Introduction
[2:06] What actually happened when two frontier AI models went dark for eighteen days
[4:26] Why a frontier AI model is a supplier you can't audit or control
[6:37] The dependency most teams priced at zero and never wrote down
[8:41] The fire drill that went off for someone else's building
[11:39] Two CTOs face the same news and respond in almost opposite ways
[15:02] Where in your stack would a model going dark tomorrow actually hurt?
[19:27] Why an untested escape route is just a hope, not a fallback

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.

A founder went from zero to $10 million ARR in six months with six engineers and fifty agents, and the gap between idea and shipped feature was nine hours.

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 going deeper on the tech is how they win this AI wave. My guest this week thinks that instinct is working against them.

Nat (Rajesh) Natarajan is COO at G-P and has had a front row seat to every major platform shift since he helped found Travelocity in 1995, which is why his read on this moment carries weight.

He's convinced this shift is bigger than the internet, mobile, and cloud combined. But the CTOs who pull ahead won't be the ones with the deepest technical mastery. They'll be the ones who understand the business well enough to know which problems are actually worth solving.

Nat shared a story about a founder who went from zero to $10 million ARR in six months, with six engineers and roughly fifty agents doing the work. The gap between a customer idea and shipped capability was nine hours.

That's the world CTOs are now leading in. Technical skills are becoming a commodity. Critical thinking, business judgment, and knowing what the CEO actually needs from you are not.

If you're a CTO trying to figure out where to stand in this shift, start here.

You'll Learn:

[0:00] Introduction
[3:06] How early machine learning at PayPal and Ancestry taught Nat what AI is really for
[9:43] Why this AI shift is bigger than internet, mobile, and cloud combined
[11:06] The 5% who see the future, and why they're rarely your best engineers
[15:34] Why a 1976 prediction about paper currency should humble every AI evangelist
[17:50] Six engineers, 50 agents, $10 million ARR in six months
[23:32] Why only the CEO can actually make a company AI-first
[32:12] Unreasonably reasonable: how Nat pushes teams toward goals they won't fully hit
[35:54] The guardrails problem most agentic solutions are ignoring
[42:32] Why technical skills are now a commodity and critical thinking is the North Star

To learn more about G-P and its agentic AI innovation, please visit g-p.com.

If you’re on LinkedIn, be sure to follow G-P there too.

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.

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.