May 17, 2022
Having conducted over 350 Head of School searches during the past three decades, I can say without hesitation that the odds of any given candidate being appointed in their first foray into the Head of School sweepstakes are not high. While I do not want to discourage candidates from applying for a Head of School position, I feel obligated to state the obvious, namely that there is only one ‘winner” out of the theoretical pool of 50 or more applicants in a given search.
Because of the standard competition, I want to emphasize the importance of being prepared. This memo is for educators who have made a decision to seek a Head of School position in an independent school. I have identified four issues that aspiring Heads should address before taking the next step in their careers. These four issues are leadership, finance, fund-raising, and governance.
Moving up the career ladder in independent schools requires hard work, conscientious preparations, and more than a dollop of luck. Competitive candidates must have an advanced degree, interpersonal skills, a moral compass, the skin of an alligator, and a broad set of relevant experiences to provide them with the requisite…