The head of school search process has been described as a delicate dance, with both prospective candidates and boards or search committees putting their best foot forward in hopes of making a strong match. The search committee comes to the interview with carefully crafted questions, and the candidate responds with thoughtful, well-prepared answers. Both the committee and candidate have a goal of presenting themselves in the best light. 

But that neat, one-sided approach doesn’t always lend itself to finding the best fit. For both a search committee and a candidate to feel confident they’ve found a great fit, a deeper dialogue is necessary. A search process that includes thoughtful, important, and even challenging difficult questions from the candidate is much more likely to produce a clearer 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.

Jack Hall, partner at CarterBaldwin Executive Search and former head of school, has years of experience participating on both sides of the interview table, working closely with school boards, search committees, and heads of school candidates throughout the search process. He was recently asked for his input on the questions a candidate should ask to gain a more intimate understanding of the state of the school, its challenges and opportunities, culture and nuances, and the type of relationship its board has with its head. He reached out to several colleagues to find out what they felt were some of the most important (and revealing) questions an aspiring head of school should ask, as well as those the board or search committee should be prepared to answer.

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. Instead of skirting around potential issues, questions of this nature help both the candidate and school engage in transparent conversations that lead to a partnership that endures.

Question 1: What are the most concerning indictors from the school’s data over the last five to ten years, and how is the school addressing them?

Question 2: What are the two or three most important expectations the board has for the next head of school, and how is the head evaluated?

Question 3: Will the board support the head in finding time and energy to devote to those parts of school life that bring great joy?

Question 4: What specific achievements define success for the next head of school in the first year?

Question 5: How would you define rest for a head of school?

Question 6: What is your vision for the head of school and board relationship

Question 7: How does the head of school participate in the selection of trustees?

Question 8: 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?

Question 9: 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.

Question 10: What are the two or three most pressing issues that 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? 

Question 11: 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?

Question 12: 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 current leadership skills and capacities are valued in the organization.  

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.

On April 15, 2024, Jack will explore this topic further at SAIS’s New and Aspiring Leaders Institute. With the lens of both an interviewer and interviewee, Jack will dive deeper into how to create a robust dialogue that provides a truly transparent understanding of the current state of the school and helps all parties find a great match.

Jack Hall is a partner at CarterBaldwin Executive Search and leads the firm’s independent K-12 practice. His understanding of and affinity for independent K-12 schools are grounded in a lifetime of experience in the space – first as a boarding school student, then as a teacher, coach, administrator, head of school, and trustee. Prior to CarterBaldwin, Jack served as head of school at The Walker School, from 2011-2022. He also spent twelve years as head of school for Augusta Preparatory Day School and eleven years as a teacher, coach, and administrator at The Westminster Schools in Atlanta. Jack served as chair of the head of school search committee and board chair at The Stony Brook School, giving him yet another valuable perspective on school leadership and governance.

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Melissa Murray joined CarterBalwin in 2019. An Ohio native, Melissa has a broadcast journalism degree from Bowling Green State University and spent more than 12 years in healthcare public relations. CarterBaldwin is an executive search firm that partners with corporate, nonprofit, and academic clients to build exceptional leadership teams. Originally founded with a focus on corporate clients spanning the gamut of private, public, and private-equity backed companies, CarterBaldwin has built a complementary nonprofit practice leveraging best practices learned and developed in their corporate work. They pride themselves on having a highly experienced staff, an unrivaled search process that delivers excellent results for clients on time and on budget, and an exceptional candidate experience.