Why the Increase in Head Of School Turnover? | James Wickenden | 8 Min Read

In 1942, my father was appointed Headmaster of Tabor Academy, a school in Marion, MA, with an enrollment of 42 boys. (The job title “Head of School” was not used at that time.)  For 36 years my father and his colleagues gradually increased the enrollment to 550.   Also of note was the fact that during the last seven years of his Headship, he refused to accept a raise, preferring instead to have whatever monies were available to go to the faculty.  Why do I begin this article by mentioning my father?  After 36 years of leading Tabor Academy, the Board of Trustees informed him that he would be replaced.  Although age, not a pandemic, was responsible for that change, the issue of turnover amongst Heads of School is not a recent phenomenon.

It is now over 45 years since my father was informed that he should retire. Because my memory of his being relieved of his responsibilities still lingers, that combined with multiple stories during the 2020-21 academic year about the turnover amongst the Heads of several independent schools, prompted me to write an article that would not only describe how challenging the job of a Head of…

Register Now
You may use your member school or partner discount code !!!

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.