The End-of-Year Debrief Every School Leader Needs

What happened in September?

What was your favorite moment from March?

You probably can’t quite remember—and honestly, who could blame you?

This year was full. Of pivots. Progress. Challenges. Quiet wins. And you’re likely already thinking about what’s next before the dust from what just happened even settles.

Before retreat season kicks in or fall planning takes over, we want to offer this: Take one hour with your leadership team. Not to plan. Not to solve. Just to remember. Debrief your team before summer, before the insights from this year fade away.

Why a Debrief Matters

Superintendents and cabinet teams often go from celebrating the last day of school to planning the first day of the next one without a breath in between. If you don’t create a moment to capture the wisdom from this year, it often gets lost. Forgotten. And that wisdom? That’s where your culture lives. Where trust builds. Where your strategy starts. 

This doesn’t have to be a full report or a half-day event. It can be one hour, one conversation, or even one shared doc. 

Don’t skip the opportunity to debrief your team and gather that hard-earned wisdom. A debrief isn’t about patting ourselves on the back. It’s about gathering data and stories that will help us continually improve.

A Light Debrief: 5 Questions to Ask

Here’s one way to structure a short team conversation before everyone heads into summer.

Five questions. One hour. No slide deck is necessary.

1. What are we proud of from this year?

2. Where did something go better than expected—and why?

3. What changed for our staff, students, or families? How did we respond?

4. What did we stop doing this year—and was it the right call? Or, what should we stop doing next year and why?

5. What’s one thing we want to carry forward into next year?

That’s it. No binders. No Post-it notes (unless you like Post-its). Just space to say the real things out loud. 

Now What?
What To Do With Your Debrief

Schools run on data, but the insights that matter most? They often come from what we notice and feel:

• • Families not engaging like they used to
  • School tours feeling flat
  • Staff showing signs of burnout earlier and harder

These are signals. And your debrief probably surfaced a few.

You don’t have to solve everything right away. But categorizing what you heard helps make space for clarity—and the next steps.

Here’s one way to move forward: sort the insights.

• • Things we can fix quickly
    Low-lift wins that show responsiveness and build momentum
  • Things we’ll need time and resources to address
    These go into planning conversations or strategic goal-setting
  • Things that are outside of our current scope or strategic plan
    Good to know, even if they’re not on your plate yet
  • Things that are outside of our control
    Helpful for team morale to name what’s real—but not ours to carry
    

It doesn’t need to be formal. Even a Google Doc or sticky note board helps keep your team’s insight from getting lost.

The goal isn’t a solution for everything. The goal is intentional progress.

Turn Your Debrief Insights Into Impact

Reflection is valuable. But impact comes when you act on what you learn.

“During the school year, time’s not on your side. I know leaders who decide what to say as each month rolls in, but it’s stronger when you’ve got a clear focus. What’s your mantra for next year? It might be your mission, a strategic goal, your school values—or something deeply personal to your leadership.

Plan your messaging themes now, while the year is still fresh in your mind. What’s the one message you really want to land next year? Saying it once isn’t enough. Think: every message, every month.”
—Ashley Winter, Content Marketing Coordinator at CEL

Now is the perfect time to set up a monthly messaging calendar for next school year. Pick one key focus for each month that aligns with your strategic priorities, your values, and your community’s needs.

Even better? Pair that calendar with a way to track what actually connects.

• • Which emails got opened?
  • Which social posts got shared?
  • Which messages sparked feedback, trust, or action?

It doesn’t have to be complex. It just has to be consistent. Plan now. Lead with clarity later. Make this year’s learning the foundation of what comes next. Start your one-page leadership communications now, not in August.