The Leadership Check-In Before a New School Year
By Molly McGee Hewitt, PhD, CAE
Every school district has a process for evaluating performance for leaders and the team that reports to them.
During my tenure as a district employee and administrator, I have received and given more evaluations than I care to admit and while for most of my career they were positive and went as expected, there were some that surprised both myself and the person on the other end.
I understand the value of evaluation and accountability, but I also recognize that many times evaluations are done in a fleeting manner and do little to recognize true accomplishments and dedication of any one individual. As a matter of fact, there were many moments where I noticed the evaluation rubric was designed in a way that did not allow for any celebration!
This article is meant isn’t meant to change your views on district evaluations, it is meant to look deep inside yourself and reflect with purpose. Before another school year begins, I encourage you to conduct your own leadership check-in – one that’s not tied to a rubric or a rating scale, but to your own growth, purpose, and aspirations for the year ahead.
If possible, give yourself one (or two) hours of alone time. It does not have to be in the perfect setting – all you need is a pen and paper or an electronic note taking app and a quiet place (nothing fancy – this can be done at work, in your car, or even your kitchen table).
I use a pen and paper to get my thoughts out and turn them into a digital working plan.
The only requirement is that you need to be able to focus inward.
Once you have given yourself the time and space to do this, you begin the process.
The process is simple, but honest reflection rarely is. Here are a few practices that have helped me over the years. I hope they’ll help you, too.
- Brain Dump- I make an extensive and detailed list of all my projects, personal needs, and professional obligations. This allows me to set a realistic foundation for the current and future timing of my life and what will be required of me to move the needle forward. I spend time doing this first and often come back during the process to edit or add items. Seeing the future in front of me is enlightening…sometimes even scary!
2. Calendar review (a reality check)- next I look month by month at the year behind me and the year ahead. I use last year as an opportunity to remind myself of what occurred and how we handled it. I look for anything I can delete or change as I move forward. Always asking myself, what is the best use of my time. As I look ahead, I try to make sure my calendar is complete, both personally and professionally.
3. Deep dive questions-
a. Am I happy in my current position? Why or why not?
b. Do I have the support I need to do my job? Explain yes or no.
c. Does my supervisor support me? Explain?
d. Do I keep up to date professionally? How?
e. Do I actively support and build my team? List examples of how.
f. What are my greatest accomplishments?
g. What are my greatest challenges?
h. What are my greatest areas for improvement?
i. What do I wish my supervisor recognized about me?
j. Where do I want to be in 3-5 years?
k. Where do I want to be in 10 years?
Now add your own. They are meant to be a starting point to think about and get clear about the future! Brutal self-honesty makes this process dynamic.
Once I complete this, I prepare a summary document for myself with goals, an annual schedule and priorities for self. While you may choose to keep this self-evaluation private, I have often shared it with my supervisor, my colleagues or even my team. For me, it keeps me more accountable and generates some great feedback and discussions.
In the coming days, buses will leave the yard, students will fill the seats, radios will come alive, and another school year will officially begin. Like every year, there will be challenges you can’t predict and successes you couldn’t have imagined.
The best way to prepare isn’t simply by inspecting buses, reviewing routes, or finalizing schedules. It’s by taking a few quiet moments to prepare yourself – to set your intention for the leader you want to be when that first bus rolls.
After watching our members over the years, I know the heart, humility, and dedication you bring to this profession. You don’t just move buses – you move students safely toward their future. That’s a tremendous responsibility and an extraordinary privilege. So before the first bus rolls this school year, make one final stop. Invest an hour in yourself. I think you’ll discover it’s one of the most valuable preparations you’ll make all year.

