Time required: 30 minutes | Who leads it: Head of School or Division Head
There are some moments of clarity that can come at the end of a school year. Students leave. The noise quiets. The urgency that drove decisions all year lifts, and for a brief window senior leaders can see the year they just lived through.
That visibility is a gift.
And there is something worth doing before the faculty disperses. I’m not referring to the year end retrospective or post-mortem – that’s examining what happened and it’s incredibly important. What I’m thinking about is what questions were you actually asking all year? Because the quality of a team's decisions is only as good as the quality of the questions driving them.
The Exercise
The head of school (or whoever is leading the session) surfaces one question that came up repeatedly during the year. Something the team spent real time on. Not a crisis that has passed, but a recurring question, the kind that kept reappearing in different forms across different conversations.
Then the team spends half an hour not answering it. Instead, they interrogate it.
For each version of the question, ask:
- What does this question assume?
- What question is actually underneath it?
- If we answered this perfectly, what would we still not have addressed?
Framing Matters
The way a question is framed almost always bakes in assumptions about what the right answer looks like. A leadership team that spends significant energy on "How do we improve communication between divisions?" has already decided the problem is communication. But the problem might be unclear decision-making authority. Or it might be that the divisions don't actually share enough common purpose to have productive conversations in the first place.
Reframing the question changes what solutions become visible.
And June is actually one of the best times to do this. Leaders are close enough to the year to remember the texture of it, but far enough from the urgency to see the patterns. You're not trying to solve anything. You're just trying to see more clearly before you begin again.
An Example: A question that recurs in senior leadership teams
Surface question: "How do we improve our communication with parents?"
- What does this assume? That the problem is volume, frequency, or clarity. That if we send more, send better, or send more consistently, parents will feel more informed and more confident. It assumes that what parents are experiencing is primarily an information deficit.
- What question is underneath it? "What are parents actually anxious about — and is more communication the answer to that, or just a response to it?" Anxiety isn't primarily an information deficit. A parent who doesn't trust the school won't be reassured by a better newsletter. (Early in my deaning days at Northfield Mount Hermon School, my colleague, David Torcoletti, wisely summed up where a pair of anxious parents stood. “More information isn’t going to help them. They are sitting at the bottom of a hole that no one will ever be able to fill.”)
- If we answered this perfectly, what would we still not have addressed? Whether the school is delivering enough genuine value that parents feel good about what they're paying — emotionally and financially — and whether communication is doing work that program should be doing.
Better questions that might emerge:
- "Where do parents feel most in the dark and is that because we're not communicating, or because we're doing something we're not confident they'd agree with?"
- "Which parent concerns did we hear repeatedly this year that we treated as communication problems rather than program questions?"
- "What would it look like to communicate less but more meaningfully?"
How to run it
- The head names the recurring question and gives it one sentence of context
- Two minutes of independent writing: What does this question assume? What's underneath it?
- Go around the table — one observation each, no commentary or debate yet
- The facilitator captures the reframings on a whiteboard or shared document
- Five minutes of open reflection: Given what we've surfaced, is this still the right question? Or did we spend the year working on the wrong thing?
- Close with: What's one question we want to make sure we're asking better next year?
A Note on Tone
This exercise is not a verdict on the year. It's not an invitation to relitigate decisions or surface blame. The goal is simply to arrive at the new school year with sharper questions than the ones you carried into this past year because sharper questions lead to better conversations, better decisions, and a leadership team that feels like it's actually thinking together rather than just managing together.
Most years are good years with some things that could have been better. This exercise is about upping the chances that next year can be a little better.