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 confidence and knowledge to manage the problems that migrate to the Head’s desk. 

Some aspiring Heads are fortunate enough to work for a supervisor who functions as a mentor. Most Heads of School take pride in preparing their faculty and staff to assume leadership positions either in their own school or in other independent schools. Some Heads, however, make an effort to keep their administrative turnover low. They don’t promote aspiring Heads quickly; they don’t contribute to the professional development of this cohort by sending them to workshops or national conferences or by encouraging them to cross-train with other school leaders. In essence, aspiring Heads of Schools working in a low or non-existent growth culture must take the initiative to learn as much as possible about the issues associated with leadership, finance, fundraising, and governance. How do you do this with a Head of School who is not oriented to mentoring direct reports? I’ll answer that question in the form of a memo… 


No aspiring Head will be an expert in all fields. There will be faculty members at your school who are better teachers, better artists, better coaches, and better counselors. Because search committee members know that few, if any, polymaths will be in the applicant pool, they are likely to place more emphasis on a candidate’s ability to be an effective leader than on being a superstar in one area. 

A successful Head of School must develop a wide range of skills to lead the school’s different constituencies. Undeniably, the various concerns of the students, parents, faculty, staff, coaches, and trustees will differ. How one juggles the disparate issues that are important to the different constituencies requires a leader who ideally is intuitive, intelligent, ethical, compassionate, respectful, honest, persistent, and patient. Those qualities do not emerge full-blown at birth. Rather, they are developed over the years by those who think seriously about preparing themselves for a leadership position. Given that, it is essential that aspiring Heads think about the principles that contribute to successful leadership and how they can develop them.

Aspiring Heads should reflect on their journey, on how they have grown and will continue to grow as a leader. What contributed to their becoming more adept in the areas of judgement, decision making, motivating others, and wisdom? At the risk of being hyperbolic, the answer to the leadership question is one of the most important a candidate will give when being interviewed by the Head of School Search Committee. 

In addition to reflecting on the principles that guide successful leaders, it might be worthwhile for candidates to consider what Willink and Babin wrote in their book, Extreme Ownership: How U.S. Navy Seals Lead and Win. Some of the principles Willink and Babin noted are as follows: 

  • For leaders, the humility to admit and own mistakes and develop a plan to overcome them is essential to success. 
  • It is not what you preach. It is what you tolerate. 
  • Leaders should never be satisfied. They must always strive to improve, and they must build that mindset into the team. 
  • Leaders do not make excuses. 
  • When leaders issue orders that are too complicated, people do not understand them. Prioritize and then execute. 
  • Leaders must be able to earn the trust of those on their team. 

Willink and Babin also wrote about the dichotomies of leadership. These, too, warrant consideration. A good leader must be: 

  • Confident but not cocky 
  • Courageous but not foolhardy 
  • Competitive but a gracious loser 
  • Attentive to details but not obsessed by them 
  • Humble but not passive 
  • Aggressive but not overbearing 
  • Quiet but not silent 
  • Calm but not robotic. 


For Aspiring Heads who have not studied accounting or who have not worked in a business prior to pursuing a career in education, the following advice might be helpful:

  1. Make appointments to meet with the Chief Financial Officer of the school where you work. Once you have arranged tutoring sessions with the CFO: 
    • Ask what a Head of School should know about building and managing the operating budget;
    • Ask which line items in the budget should be watched like a hawk because they can vary from month to month;
    • Ask what aspects of the job keeps them awake at night.
  2. Obtain a copy of your school’s operating budget, the most recent audited statements, and a copy of the auditor’s management letter. Study these documents and then make an appointment with the CFO to obtain answers about issues you do not understand.
  3. Make appointments with the Head of School, the CFO, and the Chair of the Finance Committee of the Board to talk about the partnership between governance and management in building the case for the four main budget drivers: tuition, salaries, physical plant, and financial aid. In addition ask the Chair of the Finance Committee about the financial policies that are or should be codified, how tuition, salary increases, plant maintenance, and financial aid levels are set, and what process would be used if the Board decides to reduce the operating budget by five percent.
  4. Make an appointment with either the Head of School or the CFO to become familiar with financial missteps.
  5. Ask the CFO what they would expect an Aspiring Head to know about the construction and management of the operating budget before applying for a Head of School position..


Because the majority of Aspiring Heads have not been significantly involved in fundraising, the following suggestions might be helpful in preparation for when this subject is brought up in an interview with a Head of School Search Committee:

  1. Prior to applying for a Head of School position, inform the Director of Development that you want to learn about the elements of fundraising by participating in a meaningful way in some function of that office. Taking the initiative to learn a new skill will impress a search committee even though you may not be an expert in this area.
  2. Remember that people give to people to help people.
  3. Remember that fundraising is a relationship business and that by virtue of your being in education for decades youve had extensive experience building relationships.
  4. Acknowledge that the Head of School is, in fact, the fundraiser-in-chief even though they may not have had extensive experience in this area.  


Of all of the aforementioned issues to be discussed with a Head of School, none will be as challenging for you as preparing for the questions about governance. Once again, my recommendation is that you do your homework prior to submitting your papers to a search committee. For example: 

  1. Ask your Head of School to assign you to one of the standing committees of the Board of Trustees. The insights you’ll gain doing the committee work should help you to respond thoughtfully to their questions about governance.
  2. As part of your homework, read some books on governance. Possibilities include three books authored by Richard Chait: The Effective Board of Trustees, Improving the Performance of Governing Boards, and Governance as Leadership. Other options include William Bowen’s book, Inside the Boardroom, and John Carver’s book, Boards that Make a Difference. Undeniably, there are other books and articles on governance you might read. If you prefer articles to books, subscribe to “Board Source.”
  3. Always remember that the Head of School is in the paradoxical position of leading the Board. If given the opportunity, ask your current Head of School how he or she has been able to manage this.


In closing, I want to encourage those of you who aspire to be a Head of School to remind you that this journey is a learning experience. If you are not selected, one of the biggest mistakes you can make is to wallow in depression or convince yourself that those making the decision are negatively biased against you. Plagued by such an attitude, the chances of improving your odds of winning will be negligible. However, if you reflect on your answers, commit yourself to being as prepared as possible, and come up with better examples in your responses, your chances of being successful will increase significantly.

Read other articles written by James W. Wickenden.

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.

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