Ten Questions Every School Leader Should Ask Themselves Before Fall

As summer winds down and the new school year starts taking shape, there’s a set of questions I think every building and district leader deserves to sit with honestly before the pace picks up again.

Not for a formal self-assessment. Just for a real conversation with yourself about where you are and where you want to be.

How do your meetings make people feel when they’re over? Are they energized? Informed? Heard? Or just relieved it’s done?

When did you last have an unscheduled conversation with a teacher, not about anything specific, just to connect?

Does every person on your staff know their work is seen? Not in general. Specifically, by you.

Do you have a communication system your team actually trusts? Or are people checking three different places and still missing things?

When a major decision is made, do teachers understand why, even when they weren’t part of making it?

What’s the most recent thing you did specifically for one person’s professional growth, not the whole staff’s?

Are you in the hallways and classrooms enough that teachers see you as present rather than administrative?

When’s the last time you asked someone on your staff about their wellbeing and actually created space for an honest answer?

Do your teachers know how they’re doing? Not from an evaluation. From you, in an actual conversation?

When conflict surfaces in your building, does your team know how to work through it? Or does it just get buried?

These aren’t trick questions. They’re a map. The areas where you answered confidently point to the practices you’ve made structural. The areas where you hesitated point to where this year’s most important leadership work lives.

Pick one. Start there.