Show Notes
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.
More from The CTO Playbook
Most leaders treat impostor syndrome as something they need to overcome. But what if the belief that you're not good enough is actually serving a purpose?
AI has made building software dramatically faster. The problem is that the rest of the engineering system hasn’t caught up. AI agents can now produce code, tests, documentation, migrations, and pull requests at a pace most engineering organisations weren’t designed to handle. But when everything around code review accelerates, review becomes the bottleneck. Pull requests pile up, reviewers spend more time reconstructing intent, and experienced engineers can end up reduced to repeatedly saying yes or sending work back for fixes.
AI adoption is getting easier for everyone. The harder question is whether you're using it to optimise the game you're already in, or to build a position that changes the game.
AI isn't just changing how engineers work. It's forcing technology leaders to rethink what makes management valuable.
Quantum computing may not be breaking your security today, but the decisions you make now could determine how exposed your organization is when it does. Conor Deegan explains why CTOs need to start preparing before Q Day arrives.