How Did You Lead This School Year? A Checklist for Leaders

May is a weird time for school leaders.

You’re sprinting to the finish line, but somewhere in the back of your mind, next year has already started.

Maybe you’ve jotted down a few summer goals. Or perhaps you’re tweaking your master schedule or adjusting staffing roles. Some leaders are just hoping to survive testing and Awards Day first!

Before you shift into planning mode, let me suggest something that I try to do intentionally every year. Take some time to reflect on last year before committing to any big initiatives for the next.

May is one of the only times in the school year when you can really look both ways.

You have a fresh experience with what just happened and you have time to predict what’s coming next. That’s why reflection is so important.

Below is the exact framework I am using this May to process the year.

I don’t want to get bogged down in the stress of the end of the year. Instead, I want to look at the whole year holistically.

I want to think about how I led, what I learned, and what I want to be different going forward. 

At the end, there’s a downloadable version you can print, use with your admin team, or use in your own quiet time.

Four Focus Areas for Reflective Leadership

These 13 questions are broken into four categories. Each category is focused on a different aspect of school leadership.

1. Systems and Strategy

How well did the school run, and what do I need to adjust?

• What worked this year that I want to double down on?

• What systems broke down under pressure—and why?

• What is one thing I said “yes” to that I wish I had said “no” to?

2. People and Culture

How did I lead and support my staff and students?

• Who rose to the occasion as an unlikely leader on my team?

• What culture wins am I most proud of?

• Which students did we really reach? Which ones did we miss?

3. Personal Leadership

How did I grow as a leader?

• Where did I grow personally as a leader?

• Where did I avoid hard decisions, and what were the consequences?

• What is something I need to let go of to lead better next year?

4. Vision and Momentum

What am I building toward next?

• What excites me most about the year ahead?

• What do I want to be true about my school next May that isn’t true right now?

• What is a bold move I’ve been avoiding that I need to reconsider?

• How will I lead differently next year?

A Few of My Own Answers

You don’t have to answer all 13 questions in one sitting. Start with the ones that make you pause. Here are a few of mine:

What systems broke down under pressure, and why?

One in particular that comes to mind is the peer observation initiative.

At Sebastopol, we implemented a system of having teachers visit other classrooms to support one another and to learn from each other. We had an easy way to keep track of the observations, and we used a Google Form for teachers to give positive feedback.

While this seems great on paper, it had unintended consequences of making some teachers feel micromanaged and others feel the stress of “one more thing to do” while their plates were already full.

I believe next year we will use peer observations much more selectively.

New teachers may need to see our veterans in action, and some of our best teachers need to share their tips and tricks with everyone. But no one should feel overwhelmed because of it.

What culture wins am I most proud of?

We celebrated our first ever Level A rating with a huge party at the park, t-shirts, a staff luncheon, “A+” pins to wear on our lanyards—you name it, we did it. Everyone got a chance to celebrate their part in our success. 

I am also proud that our student council stepped up and took over our video morning announcements. They do a fantastic job, and it is great to see students in leadership.

Where did I grow this year?

This year, I gained a broader perspective on leadership thanks to my experience in the Mississippi School Board Association’s Prospective Superintendent Leadership Academy (PSLA).

Being a part of this cohort pushed me to think beyond my own school and consider the bigger systems at play, such as district-level strategy, school board dynamics, and funding. 

I have started to see how district decisions ripple out across school campuses and how important it is to lead with both vision and political awareness. Now, when I make decisions, I can think about them as an advocate for my school as well as an important part of the district.

What excites me about next year?

I am excited about the opportunity to refocus and strengthen the culture we've worked so hard to build.

Every school year brings change, and with that comes a chance to re-center our culture, align our team, and set the tone early.

Last year we focused a lot on setting appropriate boundaries around our time, and that has really benefited our staff. I definitely want that to continue and to do even better at it. 

I’m also excited to support our new staff and to set a few challenging (but attainable) goals that will help us grow together. 

Download the Checklist

If you want to keep this framework handy or to use it with your leadership team, you can download a one-page printable version here:

Four Focus Areas for Reflective Leadership.pdf

Download PDF • 25KB

Before you rush into summer planning, take a moment to finish this one with reflection.

Is this checklist helpful for you? Let me know in the comments below!