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 of Philosophy that accompanied your submitted credentials. Be true to yourself. You should also make certain that your philosophy of education does not conflict with the mission of the school. In fact, if your philosophy of education conflicts with the school’s mission, you should not apply for the Headship of that school. 


It has been my experience that leadership in schools is more exercised than discussed. Whether that is your experience is not the issue. Virtually every Search Committee with whom I have worked has indicated that leadership was one of the most, if not the most, sought-after qualities. While leaders have different traits and personalities, those who are effective are able to formulate a vision, communicate that vision, and then persuade others to pursue that vision. However, making that statement to a search committee is not likely to generate gasps of astonishment. Thus, you have to do more than state the obvious. 

What might you do to prepare for addressing the leadership issue? It would be helpful for you to read about the issue of leadership; based on those readings and on your experiences, you could identify four to eight principles that drive your leadership behavior. Above all, make certain that those principles are consistent with your personality and values. Thus, when asked about your leadership style you can talk about principles that are important to you rather than simply presenting a bland generalization about the need for leaders to formulate a vision. 



In 1991, Wickenden Associates sent a questionnaire to Heads of School asking them to identify the skills needed to perform their job effectively. At the top of their list was “Developing a close working relationship with the President of the Board.” Next was “Developing an effective working relationship with the Board.” Nothing I have observed in the past 35 years has led me to believe otherwise. Unfortunately, it is difficult for an educator who is not in the top spot to gain critically important experience in the area of governance. What might be done to offset this disadvantage? An obvious answer to that question would be to set aside time to discuss governance issues with your Head of School and with trustees you know well. Ask them the following questions: 

  • What interferes with an effecting working relationship with the Board? 
  • What should the Head and the Board President do to create a team approach to governance? 
  • What should the Board do when confronted by a rogue trustee? 
  • What standing committees should be created or eliminated? 
  • What are the advantages and disadvantages of an all-parent Board? 
  • How should the Board evaluate itself? 
  • How should the Board evaluate the Head? 

Any aspiring Head of School should also read about governance. As a starter, I’d recommend the NAIS Trustees Handbook. It’s a good summary of traditional governance issues and, obviously, is geared to independent schools. Other books about governance that I have found helpful are those written by Richard Chait, John Carver, Cyril O’Houle, and William Bowen.


Although you may not have asked someone for a major gift, remind yourself that fundraising is a skill. Remind yourself that motivated bright people can develop skills. Also, according to a former Head of the Dalton School in New York City, “The critical elements of successful fundraising are: 

  • Articulating the mission and current vision of the school; Defining the means to fulfill the vision of the school and the resources needed to implement those means; Having the ability to develop a good relationship with potential donors; Being consistently responsive. 
  • Even though you may not have cultivated a major donor, remind yourself that if you are applying for a Head of School position, you have developed skills that would prepare you to be successful in raising money. For example, one must be able to communicate well. Having spent time in the classroom, give yourself credit for being able to “Make the case.” 
  • Your knowledge of schools gives you an idea of what is and what is not being done well in an institution. Because you have extensive experience in education, you are accustomed to working collaboratively. Thus, pairing up with a trustee to “Make the Ask’ should not be an unusual challenge for you. 
  • Finally, to learn more about the mechanics of fundraising, you should arrange a meeting with a Director of Development you know and respect. That person should be able to give you advice about what should be done to prepare for a capital campaign, build an endowment, and how to launch a planned giving program. An experienced Director of Development would be able to describe what the role of a Head of School should be in fundraising. 


Heads of Schools have built budgets and monitor how the dollars have been spent. Furthermore, Heads of Schools have experience adjusting the line items in the budget as unforeseen events occur or as Boards instruct the Head to “find the money to fund an initiative the trustees find appealing.” While none of these tasks requires a Ph.D. in Economics, I readily acknowledge that experience in this area is helpful. 

What then might an aspiring Head of School do to offset a lack of experience in budgeting? For a quick course in budgeting, I recommend that you meet with the Chief Financial Officer of the school to learn how the budget is constructed, identify the critical line items in the budget, and learn how to analyze the monthly reports generated by the Business Office. 


Certain issues that cross the desk of a Head of School can be handled by relying on one’s experiences. Other issues may be resolved by relying on one’s values. And finally, there are the “Moving Targets” that need to be addressed but which defy easy resolution. These include issues that relate to the recruitment, supervision, and professional development of the faculty, how technology can enhance learning, improve communications, and increase productivity. In addition, one might have to tackle how diversity, equity, and inclusion are defined and managed, and how the school contributes to the moral development of the students. Each of these “moving targets” should be considered before you are interviewed by a search committee charged with evaluating Head of School candidates. 


Schools will have to respond creatively and aggressively to manage the impending teacher shortage. Relying on referrals from teacher placement agencies and responses to ads will not suffice. Think about what you might reasonably do to take an aggressive posture in the faculty recruitment process.  

The longer that I worked with schools, the more I am convinced that schools that generously support professional development not only boost the morale of the faculty but also improve the quality of their pedagogy. The issue, then, is not whether one supports professional development, but how one plans and manages it. Your position on professional development might reflect the changing needs of the faculty as they age, as their interests change, as new research on learning is communicated, and as technology continues to offer new ways of accessing and presenting information. 


Although I have heard search committees ask candidates about how technology is used in their respective schools, I have yet to hear an educator say, “We know exactly how to use technology at every grade in every discipline.” In fact, I never expect to hear that statement. Technological advances are continuous, and the resistance of the “chalk and talk” faculty members is not going to quickly disappear

Because technology is going to be increasingly a factor in how schools function, it would be wise for any aspiring Head of School to define how technology can enhance learning, improve communications, and increase productivity. 

Finally, my visits to schools have taught me that if a school moves aggressively into technology, it must ensure that resources—human and financial—are allocated to make certain that the expectations are clear, the training sound, and the support readily available. Thus, do research on how this aspect of schooling should be staffed and be prepared to define your position on this issue before you venture into the Head of School sweepstakes. 


Richard Light, a professor at Harvard University, published a book in 2001 entitled Making the Most of College. For 10 years, Professor Light and his colleagues interviewed over 1600 undergraduates at different colleges and universities to determine what experiences contributed to effective education. His findings on the issue of diversity bear repeating. Professor Light learned that an overwhelming majority of undergraduates had a very positive reaction to the diversity that exists at their respective campuses. The students, however, added that it was not sufficient just to create a diverse community. Efforts must be made to structure interaction among those from different backgrounds. In Light’s words, “Learning from people of different backgrounds does not always happen naturally, Campus atmosphere and especially residential living arrangements are crucial.” 

Assuming that the findings of Richard Light are valid, then those who are aspiring to Head of School positions might evaluate the extent to which students from different backgrounds are given the opportunity at their respective schools to interact and learn from one another. It might also be wise for one to think about what a Head of School might do at another school to foster this interaction. Given the current climate surrounding this topic, consider very carefully what you have accomplished at your current school and emphasize that any plan to address DEI is very school-specific.


Although I have never heard a student say, “I want to go to School X because it will contribute to my moral development,” parents are increasingly concerned about this issue. I have also noted that while many schools include in their mission statement a commitment to the development of “the whole child,” few schools have programmatically defined how they intend to address the issue of moral development. 

Given the importance of moral development to those seeking a school to educate their child and given the responsibility of the trustees to ensure that the school fulfills its mission, I recommend that aspiring Heads of School be prepared to explain the programmatic steps a school should take to foster character development in the students who attend. Aspiring Heads of School should also be prepared to explain to a search committee how the discipline system of a school could be used to contribute to the moral and social development of the students as well as the possibilities for restorative justice programs. 


The concept of being prepared is far from profound. Despite that, too many aspiring Heads of School seem to take the attitude that they will learn on the job rather than developing the skills and/or knowledge base prior to being appointed. While search committee members may be polite when listening to someone who thinks his personality will overcome his lack of knowledge, rarely do trustees appoint someone based solely on charm and enthusiasm. Thus, if you are serious about becoming a Head of School, do your homework. Develop a coherent philosophy of education. Read about leaders and leadership. Talk to your Head of School, your school’s trustees, your Business Manager, and your Director of Development about tasks the Head must perform but which you have yet to learn. Finally, do enough research to enable you to take positions on such complex issues as faculty development, technology, diversity, and moral development. In sum, don’t assume that osmosis is going to prepare you for a headship.

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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