Org Design

Decision Boundaries: Where Judgment Actually Lives In the previous posts, I argued that execution is no longer scarce and that judgment, not effort, has become the limiting factor. I also argued that judgment without memory slowly degrades into improvisation. But even if you solve memory, even if context is accessible and history is visible, something can still go wrong. You can have full information, experienced people, and AI assisting at every step, and still end up making decisions that gradually weaken the system. ...

Memory Is the Missing Layer in AI-Assisted Development In the previous posts, I argued that execution is no longer the bottleneck and that judgment isn’t intuition, it’s accountability. Those two shifts already change how we should think about building software. But there is a third layer that matters just as much and is far less visible. Memory. Not model memory. Not guardrails. Not rule engines. Institutional memory. The living history of why things exist. ...

The Stages of Judgment-Driven Development Most of the pain I’ve seen in software wasn’t caused by bad code. It was caused by bad decisions that were never treated explicitly as such. In the last two posts, I argued that execution is no longer the bottleneck. AI made building cheap. Judgment is now the scarce resource. If that’s true, the way we develop software must change, not in terminology or ceremonies, but in where and how we place judgment. ...

What “Human Judgment” Actually Means in the Age of AI We often talk about judgment as if it were intuition, taste, or seniority, something vague that people either have or don’t. That framing is wrong. Judgment is not intuition. It’s accountability. In real systems, judgment isn’t about gut feeling or instinct. It’s about being accountable for decisions made under uncertainty. Judgment shows up in moments like deciding something is good enough to ship, deciding not to ship even though it technically works, deciding to stop a direction after weeks of investment, or deciding that a shortcut today will become an unacceptable liability six months from now. ...

When Vibe Coding Meets Reality I didn’t start thinking about this because I’m excited about AI writing code. I started thinking about it because I kept seeing the same patterns repeat over the years. This time, they come under a new name: vibe coding, the habit of describing what you want in natural language and letting an AI scaffold the system for you, often without deeply understanding the code it produces. ...

I heard Satya Nadella describe this week on the All-In podcast how LinkedIn has been collapsing product management, UX, and engineering roles into a single “full-stack builder” role. The framing was optimistic: AI reduces construction costs and speeds up delivery. At a surface level, this makes sense. AI dramatically accelerates prototyping, implementation, and iteration. In many environments, the traditional separation between PM, design, and engineering really does introduce friction that slows learning and execution. ...