Preparing for a Headship: Pointers from the Field | James Wickenden | 10 Min Read

During the past 35 years, I have worked with over 360 search committees for new Heads of School. By attending the interviews that the search committees conducted with various semifinalists, I’ve learned what issues generally are of concern to those making the selection. I’ve also heard the responses—some good, some not so good—of those being interviewed. 

After observing over one thousand interviews, I decided to use the information I gleaned from these sessions to write about what aspiring Heads of School should do to prepare themselves for their first headship. 



At some point in the Head of School search process, someone will ask candidates about their philosophy of education. Clearly, you should be prepared for this. The issue is how. When submitting your papers to a search committee, include a one- or two-page statement of your educational philosophy. While you can include in this a statement of ideas gleaned from readings you have done and experiences you’ve had, the document must reflect your beliefs, not a reflection of the beliefs of others. Next, make certain that your comments during the interview process coincide with the written Statement…

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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.