The head of school search process has been described as a delicate dance, with each side putting its best foot forward in hopes of making a strong match. The search committee presents carefully crafted questions while the candidate shares thoughtful, well-prepared responses. The goal is to present both the school and the individual candidate in the best possible light.
It has been my experience that such an approach does not lend itself to finding the best fit. A search process that includes thoughtful, important, even difficult questions is much more likely to yield a transparent understanding of the current state of the school as well as the strengths and weaknesses of the candidate, both of which are crucial to a successful partnership down the road. Recently, a colleague shared that she was a finalist in a head search and asked for advice about questions to ask in that final round. Rather than share just one, I reached out to a cross section of educators and asked, “What one question would you recommend a finalist for a head of school ask of the search committee or board of trustees?”
The questions below, each from a different educator, offer a balanced, thoughtful, and discerning approach for a prospective candidate aimed at getting both parties to talk about key issues that speak to alignment and match. Rather than dancing through a process that obscures red flags, questions of this nature help both the candidate and school engage in transparent conversations that lead to a partnership that endures.
Head of School Finalist Questions for Search Committee/Board of Trustees
This is a time for future heads of school to be bold and unafraid to turn down a job. Likewise, boards should be focused on the candidate who is the best fit for the school and truly understands the school’s strengths, weaknesses, and the culture he or she will be adopting. With the anticipated turnover in independent school leadership ahead, this notion of fit will become even more crucial in the years ahead.
Jack Hall is head of the Walker School in Marietta, Georgia, where he has served since 2011. Before joining the Walker School, he served as head at Augusta Preparatory Day School in Augusta, Georgia, from 1999 to 2011. He will be retiring from the Walker School in 2022.