Short Reads & Articles
School leadership reflections and essays on AI originally published on LinkedIn, collected here for slower reading. Short Reads are single pieces; Articles combine related reflections into longer essays. Find me on LinkedIn → for new pieces as they're written.
Today’s AI Impact on the Head of School
You're the one who's supposed to have an answer. AI comes up in a board meeting, in a parent conversation, in a hallway question from a faculty member, and each time…
Today’s AI Impact on the Role of Advancement Director
Advancement runs on something no algorithm has ever produced: trust, built one relationship at a time, over years. Which is why capable AI lands differently in your office…
Today’s AI Impact on the Role of Enrollment Director
Recently, I ran an experiment. I asked three of the most capable AI models available the same hard question about four private-school leadership roles. Given where frontier AI is actually…
The Knowledge That Walks Out the Door: An AI Summer Project
How AI finally makes it worth documenting your school's work, and why that matters more than any flashy tool. Every school has a problem it has quietly stopped trying to solve. This summer, I became convinced that AI can finally fix it…
Three Roles, One Scenario — What AI Literacy Actually Looks Like
The previous article in this series laid out a path to AI literacy and AI fluency for private school leaders…
The AI Literacy Path for Private School Leaders
The most common AI question I get from private school administrators isn't about tools, costs, or risks. It's some…
The K-12 AI Conversation in 2026
This article is about where the K-12 AI conversation has actually gotten to — and what's still missing. Three observations I keep coming back to as I watch schools navigate AI…
The AI Divide — Skills, Ambiguity, and the Efficiency Paradox
Why do some leaders take to AI quickly and others stall? The standard explanations — age, technical comfort…