I’ve been named a head of school three times and a finalist nine times. Granted, if I were a major league baseball player, I could be considered for the Hall of Fame with my “batting” average, but in no way am I an expert in securing a headship. Nonetheless, I have spoken to many search consultants, read hundreds of pages of position descriptions, been interviewed by several doctoral students writing about the path to headship, and been asked all sorts of professional and personal questions by search committees.
There are many pieces of advice that candidates are given as they approach headship for the first time: prepare your resume with the job in mind, have a succinct and authentic personal statement, consider what sort of school and what sort of philosophy will match your purpose. We hear these a lot.
There are other considerations that could provide an even deeper level of preparation. Here are five subjective observations that I’ve figured out about this process along the way. I hope they will help someone considering being a head of school.
Being a head of school is also one of the most dynamic, creative, nuanced, challenging, emotional, and fun servant leadership roles you will find. Leading independent schools is also really hard. We are working to balance two bottom lines: a financial bottom line and a mission bottom line. The intersection of these dual bottom lines can cause friction, but that friction creates incredible pearls that change their world.
I love being a part of supporting children in exploring their passions, their identities, and their sense of self as they launch into adulthood. It is my honor to work each day (and night) to support an incredible team of educators and support staff in delivering our mission and value proposition to our students. I am passionate about the role of independent schools in bringing people together around a shared set of traditions and expectations about the purpose of education and a life well-lived. And while I can imagine a life doing something else, I envision leading independent schools for many years to come. It’s a role that I hope more talented educators will consider, especially women and people of color. And I hope that sharing my personal experience and observations will be helpful to some of you in your journeys in independent school leadership. It truly is one of the best jobs on the planet.