Your Head of School Search: Five Considerations for a Candidate’s Deep Preparation
By Jack Hall, Head of the Walker School (GA)
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
As you look at the school’s dashboard data for the last five to ten years, what are the most concerning indicators and what are the current approaches to addressing them?
What does success for the next head of school look like in year one?
Identify two or three key wins that would constitute a successful first year.
Define the concept of what rest means for a head of school.
Please articulate your vision for what the head of school / board relationship should look like.
Please describe how the head of school is involved in the selection of trustees.
If an anonymous donor suddenly gave the school a gift of $1 million (or whatever figure you choose) and only 10 days to decide how to use it, where would the school choose to spend the money?
What is the most difficult decision the board of trustees and head of school ever made? Describe how the board and head worked together to work through this challenging decision.
What are the two or three most important expectations the board has for the next head of school? Describe the evaluation process for the head of school.
What are the two or three most pressing issues which the next head must address in the early part of their tenure? And, to what extent do the board and faculty have the appetite for leaning into those issues?
Describe the last known conflict that existed at the board level or in the community at large. How was it resolved and what role did the head of school play in the process?
Given that search firms help schools develop a list of characteristics and skills desirable in the next head of school that often reflect areas the current leader does not possess, please share what aspects of the currentleadership skills and capacities are valued in the organization.
Rationale: Oftentimes a future head of school sees the list and says "that's me ... pick me" while there is a hidden list of capacity and skills of the current head of school that bring value, are important, and the community will grieve. The next head of school should have BOTH the desired list of skills as well as the key skills of the current head to be successful. The skills of the current head of school may often be taken for granted and almost unrecognized, particularly if the departing head has served for quite some time.
Will the board support the head in finding time and energy to devote to those parts of school life that bring great joy?
This question grows out of a conviction that boards must give school heads time and space to do those things that lift them (e.g., teaching, advising, or coaching), thus increasing their energy and capacity to deal with difficult issues heads must resolve on a regular basis.
Conclusion 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.