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.
Your Second Brain, for Running a School
f 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…
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 K-12 AI Conversation Has Bifurcated
The most striking thing I've come to see about the K-12 AI conversation is that it has split into two. AI was once…
Private Schools Have a Real Advantage in AI Integration
Private schools have a real opportunity to successfully implement AI. I've been paying close attention to…
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…
Letting the Frame Change
What happens if I have a strong opinion about something and I end up being wrong? Is it easier…
Should AI Agents Be Banned From Board Governance?
My colleague Myra McGovern recently shared a question that a school board debated while updating its bylaws…
"It's Faster to Just Do It Myself" — The Efficiency Paradox
"It's faster to just do it myself." If you've tried using AI for complex work, you've probably said this. And here's the thing. You're not wrong…
The AI Divide Is About Comfort with Ambiguity
The AI divide isn't about intelligence. It's about comfort with ambiguity…
AI Skills Compound. Waiting Isn't as Neutral as It Feels.
I'm not writing this to scare anyone or to persuade anyone. I'm writing it because I'm starting to feel a growing disconnect…
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…
ChatGPT Is Now Better at Strategic Problem-Solving Than I Am
It just hit me: ChatGPT is now better at strategic problem-solving than I am. I don't know when this tipping point happened…
Journey Mapping With Emotions — A Team Activity for Enrollment Directors
I've been thinking about example activities an enrollment director could run to help their team practice AI skills and…
I Think in Voice
I think in voice and AI is helping me get my thoughts into a computer. I've always been that person who talks…
Good Prompting Is Messy
A friend recently told me he was intimidated by the polished prompt examples I share in my posts…