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One Foot in May, One Foot in August

May 23, 2026

One Foot in May, One Foot in August

You're sitting across from a teaching candidate, asking about their classroom management philosophy, and somewhere in the back of your mind, you're thinking about the parent email you haven't returned and the staff meeting that starts in 45 minutes.

Welcome to May as a principal.

While everyone else is counting down to summer, we're already living in two school years at once. Hiring for next year. Building a master schedule for students who haven't even registered yet. Visioning for August while May is still full of testing schedules, staff evaluations, and the kind of parent emails that require a deep breath before you open them.

We are making high-stakes decisions about people while also being fully responsible for the building in front of us. The hiring, the scheduling, the budgeting for a year that has not started yet, all of it is happening while this year still needs our full attention every single day.

So how do we actually do this without losing our minds?

One thing that helps is thinking about it this way: May is for closure, summer is for construction, and August is for launch. When you have that framing in your head, the work stops feeling like one giant pile you have to climb all at once. You know what closes out the year and what builds the next one.

May belongs to your people. Your staff is managing field trips, finalizing grades, running spring events, and answering the same five questions from parents every single day. They are finishing strong for kids while running on fumes. When principals go quiet in May, staff feel abandoned right when they need leadership most. A genuine check-in in the hallway, a short note that says you notice, showing up to cover a duty without being asked. That is what keeps your culture intact all the way through the last day.

Every principal has a to-do list that never gets shorter this time of year. The goal is not to finish everything. The goal is to finish the right things. That means looking at your list and asking what only you can do, what you can hand off, and what honestly does not need to happen before August. Those three questions will cut your list in half faster than any productivity system ever could.

The work will always overlap, but strong principals decide what closes today, what builds tomorrow, and what deserves their people first.

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