4 Questions Worth Asking Your Principals This Summer

In most districts, the school year is over or nearly there. Schedules are winding down, students have cleared out, and principals may finally have access to something that’s been in short supply for months: space to reflect.

For principal supervisors, it’s also a valuable coaching opportunity. The end of the school year is a prime opportunity for principals to step back from the daily demands of school leadership and make sense of where they’ve grown and what they’ll do differently next year.

Before principals fully shift into summer mode, principal supervisors should consider asking these four questions to help them capture lessons from the year and prepare for the one ahead

1. What’s one leadership decision you’d make differently this year?

Every principal has a moment they’d handle differently if given another chance, but leaders who reflect on these moments as learning opportunities grow faster over time.  As principal supervisors, listen for how principals make sense of difficult decisions, what they’ve learned from the experience, and whether they can translate reflection into future action.

2. What do your teachers need next year that they’re not getting today?

This question shifts the conversation from managing a school to leading one. Strong principals think beyond individual personnel issues and consider how to strengthen teaching across the building. Their answers can reveal how they view teacher development, instructional leadership, and the conditions needed for staff to succeed.

3. What do you want your leadership to be known for next year?

The most effective principals have a clear sense of what they’re trying to build. Whether the answer is stronger instruction, a more positive culture, greater accountability, or something else entirely, this question helps principals articulate a vision for their leadership and identify the priorities that will guide their decisions throughout the year.

4. How can I support you more effectively next year?

Great principal supervision is built on trust, clarity, and continuous improvement. Asking for feedback models the kind of reflective practice we hope to see in principals themselves, while providing valuable insight into how the supervisory relationship can become more effective. These kinds of reflective conversations are the result of intentional principal supervision that prioritizes principal growth and development.

The strongest principal supervisors know how to move beyond check-ins and compliance conversations to coaching conversations that promote reflection, growth, and action. They know how to ask thoughtful questions, listen deeply, and help principals turn insights into meaningful changes in practice.

That’s the work at the heart of Transformative Principal Supervision (TPS). For more than a decade, Transformative Principal Supervision has helped principal supervisors develop the skills, structures, and habits needed to support principal growth and improve outcomes across schools. By helping supervisors focus their time and attention on principal development, TPS strengthens school leadership and creates the conditions for continuous improvement across a district.

As you look ahead to the coming school year, these four questions are a good place to start.