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.
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…
Letting the Frame Change
What happens if I have a strong opinion about something and I end up being wrong? Is it easier…
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…
"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…
AI Literacy ≠ AI Fluency
AI literacy and AI fluency are not the same thing. AI literacy is about ORIENTATION…
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 …
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…
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...