The CTO Playbook

Twenty years at one company should have made my guest predictable, and that is exactly the trap he built a method to escape.

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.

Krystian Kolondra runs the browser portfolio at Opera, a set of products used by more than 300 million people, and he has spent two decades watching what happens to technical judgment when the work that built it starts to disappear.

His argument is uncomfortable. Your judgment was earned through execution, and AI compresses execution. So what is training your judgment now?

His answer starts somewhere I did not expect: an audit of the questions you stop asking. He calls it the shape of your curiosity, and he thinks most leaders have never looked at theirs.

We get into why he refuses to check AI's output and flips the task back on the model instead. There is a sniper analogy that reframes what "learning from failure" actually requires. There is a story about Opera GX where the first questions his team asked turned out to be the wrong ones, and the right ones only appeared once they went somewhere uncomfortable.

If you lead engineers, and you have felt the ground shift under what "senior judgment" means, this conversation gives you something concrete to practice tomorrow morning, before your first coffee.

You'll Learn:

[0:00] Introduction
[5:46] Twenty years at Opera and the business behind free browsers
[7:18] Why leading five hundred people is a different job entirely
[9:39] The temptation to stick with what already worked
[12:39] Curiosity as a counterweight to accumulated experience
[17:44] How the gamer browser came from asking the wrong questions
[23:26] Learning from failure means planning the shot before firing
[29:06] How AI compresses execution but never the judgment
[36:14] Auditing the questions you never ask to find blind spots

Resources Mentioned:

A Beautiful Constraint by Adam Morgan and Mark Barden | Book
Theory of Constraints by Eliyahu M. Goldratt | Book
Really Achieving Your Childhood Dreams (aka The Last Lecture) with Randy Pausch | TED Talk
Eric Ries, Validated Learning | Wikipedia
Igor Grossmann | Website
A route to well-being: intelligence versus wise reasoning by Grossmann, I. et al. | Article

Unlock more ways to make your browser yours with deeper personalization and an expanded modding universe with the Opera GX Gaming Browser here.

Find more from Krystian Kolondra 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.

Most CTOs think adopting AI means picking the right tools, but Sumeet argues the real work is closing the accountability gap between agents and engineers.

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 this week is Sumeet Vaidya, co-founder and CEO of Crafting, who spent years at Facebook, Uber, and Discord before building the infrastructure enterprise engineering teams now use to put agents to work safely.

His perspective matters because he sees what CTOs say publicly, and what their teams are actually doing internally, and the gap is bigger than most leaders want to admit.

Roughly 80% of enterprise engineering orgs, he estimates, are doing close to nothing meaningful with AI. The rest are either reacting to hype or trying to build something durable, and the difference is not the tools they pick.

One partner running 3,000 agents against 250 engineers changed how he thinks about capacity entirely. That number is where his six diagnostic questions come from and where the cracks appear first: brittle CI/CD, accountability gaps for agents, and a hiring pattern that's storing up debt for the next downturn.

If you're under pressure to show AI gains while cutting token spend, this one is aimed at you.

You'll Learn:

[0:00] Introduction
[2:25] The disconnect between what companies say and what teams do
[4:38] Why 80% of enterprises watch and wait on agents
[9:31] Chasing the latest model as a vanity metric
[14:14] Resilient cultures survive shocks that short-term thinking cannot
[15:46] The engineering cultures that shaped Sumeet's career
[28:51] Silicon Valley is not the whole world
[33:02] What breaks if you 10X the team today
[42:31] Hiring only senior engineers stores up hidden debt
[47:11] Turning engineers from code writers into builders

Find more from Sumeet Vaidya on LinkedIn, X, or explore the Crafting 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.

Ask a CTO which executive relationship matters most, and they'll name the CEO, but my guest today would send you to the CFO instead.

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.

Anoop Tripathi is 32 years into a career that spans from writing firmware for telephone exchanges to sitting as CTO at Sauce Labs, and he's unusually direct about what decides whether your technical work gets funded.

Most of us step into this role believing the job is to be the strongest technologist in the building. Anoop thinks that's the fastest way to build an organisation of people waiting for commandments from the top.

The conversation gets sharper when he talks about scaling an engineering team from zero to over 100, then having to bring it back down to 70 in a tough market. His lessons from that period are not the ones I expected.

There's also a serious defence of laziness as an engineering virtue, a story about resellers walking out of a Citrix demo because the product was too good, and a framework he calls SHAPE that he uses to run his own career.

Fear is the dominant feeling across my coaching practice right now. Anoop's take on what that fear is costing tech leaders is worth contemplating.

You'll Learn:

[0:00] Introduction
[2:51] The double-edged sword of laziness as an engineering trait
[7:18] Reframing tech debt as a business outcome your CEO hears
[10:24] How investor pressure and a faster POC upended the Citrix integration story
[18:01] What he learned cutting a team from 100 to 70
[26:19] Spotting an inflection point before hindsight makes it obvious
[29:50] Fear you plant in your head tends to come true
[32:52] The SHAPE framework for tech leadership
[47:44] One piece of advice for a first-time CTO

Resources Mentioned:

Sauce Labs | Website

Find more from Anoop Tripathi 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.

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.