Your Second Brain, for Running a School

If you're a head of school trying to figure out where AI can genuinely change your day-to-day work — the real work of insight, problem-solving, communication, writing, ideation — this is where I'd point you first.

The newest models have become remarkably good at synthesizing enormous amounts of context and turning it into exactly those things. Testing that was one of the things I most wanted to do when the latest frontier models landed over the past couple of weeks.

Over those same two weeks, I published four in-depth articles on how AI is reshaping the four roles that run a school: the head of school, the business officer, the advancement director, and the enrollment director.

My ability to write them didn't come from a clever prompt. It came from the fact that, for the past year, I've saved everything — my content, my thinking, my research, my writing, the products of my work — into a folder structure that lives on my computer (safe and private). The structure is the intelligence. It's what lets AI pull exactly what it needs from across my vault, which now runs to 1.06 million words, according to Claude.

If you've worked with AI for a while, you'll recognize this. It's usually called a "second brain." Mine is built in Obsidian, connected to both Claude and ChatGPT so I can toggle between the two.

I've also written about a simplified version made for heads of school — a place to store and manage all your thinking and tasks around executing your school's five-year strategic plan. I call that the Leadership Layer, and there's a video in my library that walks through how to build one. It's more approachable than it sounds.

As a school leader, you carry an enormous amount of institutional knowledge in your head — the history, the people, the plan, the tensions no one else fully holds. AI now lets you put that context somewhere it compounds, instead of leaving it locked in one person's memory. It removes the barrier that has always stood between everything you know and your ability to synthesize it.

And if you're intrigued by AI but not sure where to start, that's the whole idea behind the Head of School Field Guide. It's my synthesis of a full year of real work. If any of this resonates, you can see what's inside.