Memo to Aspiring Heads of School | James W. Wickenden | 7 Min Read

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…

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Jim Wickenden

Jim is a Principal at DRG and Founder of Wickenden Associates, an affiliate of DRG. Having been the CEO of one of the premier education executive search firms in the United States, Jim brings unparalleled experience and networks to best serve clients. With over 30 years of experience identifying and guiding Heads of Schools and other senior administrators of schools across the country, Jim approaches each search with flexibility and openness that responds to the individual needs and concerns of schools and their leaders. Before founding Wickenden Associates, Jim served as the Dean of Admissions at Princeton University and Director of Student and Alumni Affairs at the Harvard Graduate School of Education. A graduate of Tabor Academy and Princeton University, Jim holds a master’s degree in Counselor Education from Rutgers University, a master’s degree in the General Purposes of Education from Harvard University, and a doctorate in Counseling Psychology from Boston University. As a former member of eight boards of independent schools with a wide range of missions and resource levels, Jim also knows firsthand the responsibilities shouldered by today’s trustees; and knows how to guide boards through tough transition processes and on good governance practices. Jim lives in Princeton, NJ, and when he is not at the office he enjoys reading enlightening books.