Show Notes
What if your team's biggest problem isn't talent, it's the rules you've never written down?
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, I'm talking with Gerald Chablowski, a lead developer based in Thailand whose journey from archaeology and history into tech leadership gives him a very human lens on engineering. I’m drawn to the way he thinks less about shiny tools and more about how people organize themselves, how rules get explained, and how work actually feels. His experience leading teams across different countries and cultures makes him obsessed with one question: what happens when we use structure to protect humans instead of control them.
Too many engineering teams are playing a game where nobody can see the rulebook, then wondering why everything feels chaotic. Here we get brutally honest about what happens when goals change every week, when leaders “delegate” but still pull every string, and when trust gets treated like a slogan instead of something you earn in tiny daily moments. You’ll hear how simple constraints like clear rules, small pull requests, and real documentation can unlock creativity instead of killing it, especially in environments where people are scared to challenge the plan.
You’ll Learn:
[00:00] Introduction [03:48] Why tech only matters when it serves people, not the other way around [06:19] What happens when a team works without clear rules or shared understanding [09:14] The reason trust is built through tiny daily behavior, not speeches or titles [11:47] How unclear systems force developers into chaos even when rules technically exist [14:52] Why documentation becomes leverage when knowledge needs to outlive individuals [17:01] The leadership mistake that made a senior dev refuse to work with him [23:08] What learning hard physical skills teaches about leadership discomfort [28:19] How asking people to rewrite a task in their own words exposes hidden gaps fast [34:22] Why tiny pull requests transform code quality when systems enforce them [42:08] How relying on juniors teaches humility and system thinking faster than doing it all yourself
You can connect with Gerald and his work on his 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.