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 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…
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 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…
Letting the Frame Change
What happens if I have a strong opinion about something and I end up being wrong? Is it easier…
"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…
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…
AI Literacy ≠ AI Fluency
AI literacy and AI fluency are not the same thing. AI literacy is about ORIENTATION…
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…
Vibe Data — How AI Is Redefining Data Literacy
I built a complex enrollment management spreadsheet in three minutes using ChatGPT. The kind of sophisticated…
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…