What Did This Year Teach You? 10 Self-Reflection Questions for Principals

Here’s something we certainly don’t have to tell you: the school year moves at lightning speed. From the first bell of the first day to the final send-off, principals are in constant motion—leading, navigating, and responding. 

We know summer isn’t a break for you as a school leader, but there is a slower pace. And with that pace comes the opportunity to pause, exhale, maybe unclench those shoulders, and ask yourself the questions that up until now, you’ve been too busy to consider.

But not just any questions. The ones that help you reflect with a level of honesty and depth about how the school year went, the challenges you faced, and how you’re going to shift and do things differently come August and September.

If that’s the kind of reflection that you’re interested in, we’ve developed a list of ten questions designed to help you grow—not just as a school leader, but as a values-aligned human operating in the world, looking to shape culture and community where others can thrive. 

Feel free to pair these reflection questions with whatever’s needed: a strong cup of coffee, a notebook and your favorite pen, or even a Zoom meeting for one so you can record your responses: 

Where did I lead with clarity, and where did I lead with assumption?

As author and speaker Brene Brown reminds us, “Clear is kind.” Clarity is a gift to everyone in your school community—your staff, parents, students, and external partners. But in the day-to-day whirlwind of your school, it’s easy to swap out clarity for assumption: assuming people know the larger vision, understand the “why” behind decisions, or feel safe speaking up when they don’t agree with something. 

Take stock of your year in communication: In which areas was your communication consistently clear and purpose-driven? Were there specific moments where confusion lingered too long? What might have been done differently in those moments? Your reflections here can inform how to model clarity as a leadership behavior. 

How did I handle feedback—both giving and receiving it?

Feedback is one of the most powerful tools a school leader has. When you’re able to give feedback to your staff, it’s a clear message that you believe in their abilities and want to help them further their craft. That said, it’s also one of the most emotionally-charged tools as well.

This summer, ask yourself: Did I create a culture of safety and candor? Did I have the right attitude, and did I develop the appropriate structure for feedback? Was I generous with specific, growth-oriented feedback? And when I received feedback from teachers, students, families, did I listen or defend? Your personal relationship and willingness to accept feedback often sets the tone for your entire school, so reflecting on how you approached it can give you clues for additional growth here. 

Were there situations where I prioritized urgency over importance? 

The Eisenhower Matrix is a great tool in theory for separating what’s urgent from what’s important—but as a school leader, how often do you really get that luxury? Fires need putting out, deadlines are real. So this is a great time to think about what meaningful work got sidelined this year in the name of urgency. 

Maybe it was building instructional leadership capacity. Maybe it was deep work around student belonging. Whatever it was, use this time to name what matters most, and build the systems or calendar space to protect it.

When did I feel most like myself this year—and when did I feel furthest away?

This question is all about alignment. Leadership isn’t about becoming someone else. It’s an opportunity to lead from your values, your humanity, and your unique lens on what makes a school a thriving community.

What moments over the past year made you think, “This…this is why I do this!” When did you lead with joy, purpose, and presence—and when did you feel performative or misaligned? Those moments where you felt both grounded and off-kilter can act as a compass to help you recalibrate how you’d like to keep showing up. 

What did I avoid this year, and why?

Avoidance is natural—yes, even for school leaders. We all do it. When you avoid something—a task, your feelings—it acts as a temporary reprieve from feeling uncomfortable. The key word is temporary. After all, unspoken tension doesn’t dissolve. Delayed decisions don’t make themselves. And the longer you wait, the heavier the avoidance becomes.

This question isn’t about shame, it’s about awareness. What conversation did you take a little too long to have with a teacher? What team dynamic did you quietly endure? What personal boundary did you ignore? Noticing the patterns is the first step toward shifting them.

Where did our school culture grow, and where did it fracture?

When a school community collectively feels cared for and valued, great things happen. Students are more engaged and feel more comfortable taking intellectual risks, educators and staff are more trusting and candid, and parents feel more confident. And that means that culture is so much more than an inspirational poster on a wall. It’s how people feel when they show up to your school building each day. It’s how decisions are made, how conflict is handled, and how people belong—or don’t.

Take a wide-angle view: What felt good about your culture this year? What shifted in the right direction? And where did you see signs of burnout, division, or disconnection? Your observations can shape everything from how you start the school year to how you invest in your leadership team.

How did I invest in the leadership of others?

You know that a strong school is never a one-person show. Whether it's empowering your assistant principal, teacher leaders, student leaders, or your office staff, your capacity grows exponentially when others are made to feel like they can lead, and have the agency to do so.

So ask yourself: Who did I intentionally grow this year? Where did I delegate well—and where did I hold on too tightly? What leadership moments did I create for others, and what structures need to change to support distributed leadership in a sustainable way?

What patterns are we carrying from past years that no longer serve me—or my school?

Sometimes we repeat decisions, schedules, or traditions simply because we always have. But leadership growth often means breaking patterns—not out of rebellion, but out of wisdom.

This summer, try a personal “Stop, Start, Continue” retrospective. What do you need to stop doing, because it’s outdated, draining, or no longer aligned? What do you want to start, because your current students, staff, and context call for something new? And what deserves to continue, because it’s still working, still grounded in your values?

Give yourself permission to revise the script. Growth doesn’t always mean adding more. Sometimes it’s about letting go.

How did I take care of myself this year, and what needs to improve or shift? 

This is not a “self-care” checklist. With that said, self-care is essential to leading well. Because even though it’s hard to keep in the forefront, the fact is you’re a person before you are a principal. And when you run on empty, it’s not just your health that suffers—it’s your presence, decision-making capabilities, and joy.

So, check in with yourself here: What practices or relationships kept me grounded this year? What drained my energy, and how did I come back from it? These aren’t just questions of wellness, they’re questions of sustainability. Reflecting now helps you build a rhythm for next year that supports your leadership, not just your output. 

What story am I telling myself about my leadership, and is that story true? 

We all have an inner critic. Maybe yours says, “I’m not doing enough,” or “I should have handled that better.” Maybe it tells you you’re alone in the work. Or maybe it downplays the incredible ways you showed up.

This summer, listen closely to your internal story. Is it rooted in truth—or in fear, comparison, or perfectionism? What would it sound like to rewrite that story with evidence, compassion, and perspective?

Make it a summer of reflection and recalibration

You don’t need to have the answers to all of these questions. But carving out time and space to answer them—honestly and with intention—can shape how you lead and how you connect with others (and yourself!) in the year ahead. 

So, reflect deeply. Lead bravely. And return in the fall more grounded than when you left.

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