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.
What Independent Schools Do When Government Money Is Offered
If you're paying attention to the financial sustainability of independent schools, you cannot ignore what is happening with public funds being made available to private schools.
The Redesign Is Coming. Private Schools Should Lead It.
Three days at the largest AI conference there is, one idea from each of the three researchers who built the foundations of modern AI, and the argument they added up to by the time I flew home.
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…