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 Business Officer
If you run a school's finances, I want to offer you a picture of where your role is heading in this new era of AI…
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…
That inspiring conference is fading: Capture it in one hour
If you're attending any professional development conferences this summer, here's a simple way to get far more value out of them using AI…
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 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…
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…
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…
AI Is Starting to Understand Intent
Something happened recently that stopped me mid-task. I gave Claude the wrong instruction and it did the right thing anyway…
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…
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…
Where Do I Even Start with AI?
"I want to learn more about AI, but I don't know what I should know — and I don't know what to do next." In my conversations …
AI Policy Is Necessary But Not Sufficient
This isn't another post telling you you need an AI policy; you already know that. In many of my AI posts...