When the Superintendent-District Fit Isn't Right
June 16, 2026
Author
We don’t become school district superintendents overnight.
Most of us have spent many years as highly accomplished building or district administrators prior to our first superintendent position. We are used to being very successful, so when we do not experience the same level of success we are accustomed to, it can be a huge blow to our confidence, pride, and ego. Immediately, thoughts of the “Peter Principle” begin to creep in. Many times, it is a matter of fit. A superintendent not being the right fit for a district does not make that leader a failure.
When Success No Longer Feels Like Success
Deciding to retire from public education was very bittersweet for me. On one hand, I was excited to see what new adventures were available, but I couldn’t shake the feeling of being a failure. When I began this superintendency – my first – the plan was to retire from this district in ten years, not four. I bought a house and began growing roots in the community. While my transition came sooner than we originally envisioned, I believe deeply that people are placed where they are needed at the right moments in life.
I believe deeply that people are placed where they are needed at the right moments in life.
Our district faced a major challenge in the first month of my tenure. I leaned on my mentors and my team and handled it as best I could at the time. More major challenges arose over the next couple of years. For the first time in my career, I could feel something was not right. I realized that district dynamics are often more complicated than they appear.
Similar to most superintendents, I spent a lot of time reflecting, overanalyzing every decision, and owning each challenge we faced. I came to the difficult decision that it was time for me to retire from public education. Had I lost my ability to lead? At the AASA conference a few months ago, I began talking with colleagues about my feelings and was shocked to learn that I was not alone. Many superintendents were, or have been, in a similar situation. That is when I determined that I needed to write this blog post.
The Difference Between Failure and Fit
There are many reasons, with varying causes, that a particular district and superintendent are not, or no longer, the correct fit. Countless superintendents worked for only a few years in one or more districts before finding the right fit where they experienced long-term success. We often read that the average length of superintendency is only 3.5 years. Superintendents I spoke with attributed this mostly to superintendents moving districts in search of the right fit, not leaving the profession.
Leadership mobility is much more common outside of education. Bill Belichick struggled mightily during his first stint as an NFL head coach before growing into one of the most successful coaches of all time.
Advice From Other Superintendents
Superintendents I spoke with provided me with some outstanding advice.
One superintendent who was seemingly in a perfect spot, but didn’t have full board support, told me to not be afraid to pull the rip cord. They are now experiencing a fully supportive board and great success in a different district. I was also reminded that a major part of the job is to “trust, but verify.” We have to trust the professionals on our team, but not forget to verify their work, since we are ultimately responsible.
Another superintendent who had a similar experience told me, “Remember who you are as a leader and don’t let someone else ever impact your confidence. You sit where you do because of your years of proving your strengths as an educator and leader, so you need to hold your head high and keep doing what is best for students.” I definitely took this to heart.
A supportive board and cabinet are integral to a district’s and superintendent’s success, as is a strong, trusted network to lean on.
Another piece of advice I received from a superintendent colleague was, “Reach out to your network and find solace with other superintendents who have ALL felt this way. People expect you to know the answer to every question and there is just no way that is possible. You must rely on your network to help you navigate difficult situations, to help you feel like you are enough, and to give you a sense of belonging in a very lonely world.”
What I've Learned
As I have reflected on my four years as a superintendent, there are things I would have done differently given another opportunity. I learned that we are not superhuman or infallible. This is a lonely job, but we cannot do it alone. I also learned that there are always multiple perspectives from which situations are viewed, and each one is valid for consideration.
Ultimately, this position is extremely relational, not individual. Strong leaders can struggle in the wrong environment, with the wrong timing, or without the necessary relational alignment and support. A supportive board and cabinet are integral to a district’s and superintendent’s success, as is a strong, trusted network to lean on. Don’t be afraid to reach out to others, offer to help when you can, and build a supportive network.
