Rethinking the Head of School Position

Fall 2011

By James W. Wickenden

Having observed independent schools for years — first as dean of admission at Princeton University from 1978–1983, and then as president of an educational consulting firm since 1986 — I have noticed that the challenges of leading a school have changed dramatically. In consulting with more than 700 independent schools, often in a search for a new head of school, I’ve seen the head’s job become more complicated, with growing demands on his or her time and talent. This has led me to think about ways that a school’s board of trustees can ease the often untenable workload of the head and, in the process, create a more effective leader who is happier in the job and more likely to stay for the long run.

Heads Face Increasing Challenges 

The challenges and time drains facing school leaders are increasing these days, and putting additional pressures on the head of school. As a result, it’s getting more difficult for heads to sustain their energy and stay focused on the most important issues facing their schools. Consider the following pressures.

Increased Threat of Litigation 

When I began my firm, lawsuits against private schools were rare. Today, nearly every head has the school’s legal counsel on speed dial. Faculty and staff whose contracts are not renewed may sue. Parents whose children go before a school’s disciplinary board often threaten lawsuits, and school boards now have legal committees to contend with potential suits. Heads can no longer simply consider the best interests of students and the institution as they make decisions; risk-management strategies, human-resources protocols, and records-retention policies are also at play. All of these legal challenges translate into a new layer of demands placed on the time, energy, and emotional stamina of the head.

Maintaining Sound Financial Health

Although all well run independent schools have business managers, heads are ultimately responsible for the school’s financial health, which can be difficult to maintain in a down economy. Well-intentioned boards may have lofty goals of improving faculty salaries, increasing financial aid, and holding down tuition hikes. These goals are all noble, but they require the head to continually raise more money or to increase enrollment — in addition to running the school.

“Communicator in Chief” 

Whenever my firm launches a search for a new head, we always hear members of the school community say, “We need someone who is a superb communicator.” Today, virtually every constituent group — faculty, parents, students, trustees, and alumni — is looking for a head who is open and transparent, and who is unfailingly responsive to its concerns. This image of the head as “Communicator in Chief” has been further complicated by the explosions in email and mobile technology. Heads are barraged with electronic messages from the constituents, many of whom expect an immediate reply. The conscientious head may spend huge blocks of time responding. 

The Consumer Mentality

No one can deny that an attitude of entitlement has emerged with a vengeance among many independent school parents, who often introduce their demands by saying, “Since I am paying tuition, I expect the school to [fill in the blank].” Running a school is complex, of course, and decisions need to be made for the greater good of all, not just some, students — and yet many parents expect, and too often demand, special treatment. 

In addition, heads are expected to appear at just about every school-sponsored event — games, plays, recitals, etc. — and will log incredibly long hours during the course of the academic year. 

As psychologist Madeline Levine notes in her book, The Price of Privilege, there was once a time when parents worked in partnership with schools to discipline students who stepped out of line. Unfortunately, that is not always the case these days. Some parents may blindly defend their child when he or she engages in inappropriate behavior, which prevents that student from taking ownership of his or her own behavior, learning from mistakes, and developing a sense of responsibility. Parents who go to the head in an effort to protect their children from any consequences for their actions are not only making more demands on the time of the head, they are creating an environment in which the head feels under siege.

Trustee Turnover

Most schools have embraced term limits for board members as a way to bring in new blood and diplomatically cut ties with minimally effective trus­tees. This can be beneficial, but there is a downside, too. Boards need institutional memory, and there are obvious benefits to retaining trustees who have been generous with their wealth, wisdom, and willingness to work. When term limits require that valuable trustees step aside for a year, the school runs the risk of losing that patron to another nonprofit institution. To replace these extraordinary individuals is not easy. Also, key board initiatives often stall as a result. And guess who must lead the search for new trustees? Once again, major demands are made on the head’s time — both to find new board members and to bring them up to speed.

Cyber- bullying

Further complicating the life of an educational leader is dealing with cyber-bullying, which may or may not occur during school hours. The head of school is responsible for creating a healthy culture, and any phenomenon that has a negative effect on the community should rank high among the head’s concerns. While social networking sites such as Facebook allow students to stay in touch constantly with friends, these sites can also contribute to the fragmentation of a school community. Increasingly, schools are expected to handle incidents of cyber-bullying, where students with less-than-noble motives post controversial comments or photographs of their classmates on Internet sites.

Keeping Your Eye On The Long-Term

All of the above issues eat away at a head’s time. Besides being inconvenient, they take away time needed to focus on the long-term — to think creatively and strategically about the school’s next big challenge. While conventional wisdom suggests that the board should drive strategic planning, relatively few boards have the expertise to do this well — particularly when it comes to educational programs. It is much better to have an administrative structure that lets the head of school function effectively as “planner in chief,” devising productive strategies to address complex challenges, such as the following. 

Fierce Competition for First-Rate Faculty and Administrators 

With the retirement of veteran teachers projected to grow in the years ahead, schools that are committed to excellence can’t afford to approach this task haphazardly. Heads must spend time recruiting experienced teachers and thinking creatively about how to find candidates from nontraditional sources, such as engineering, business, the law, and the military.

Increased Competition for Students

Demographics indicate that there will be a decline in the number of students entering schools during the next decade and, as a result, the competition for able, motivated, and well-prepared youngsters will intensify. Paired with the latest research about the ways students learn, the shrinking school-age population will require many independent schools to position themselves in the forefront of educational innovation within their marketplaces. Parents are increasingly knowledgeable about advances in education and are likely to ask admissions officers and heads of schools about the services offered in specific areas.

Demands for Educational Programs in Globalism and Environmental Sustainability 

Institutions committed to globalism and going green will find themselves in the awkward position of revising their mission. “College prep” is no longer a mission that is either unique or inspirational. But if an institution is serious about going global and green, then its curriculum and the experiences it constructs for students will change. For example, schools committed to preparing students to become global citizens will find themselves developing a curriculum that addresses issues of universal applicability. Gone from the curriculum will be courses that are specific to a given location or culture. Taking their place will be courses in comparative politics, macroeconomics, comparative religion, and courses that address such global issues as water, energy, poverty, demographics, disease, climate change, and immigration. Furthermore, increased emphasis will be placed on the development of skills in math and science as well as in communication, critical thinking, creativity, problem solving, and teaming.

How Administrative Restructuring Can Help

So, how can board members help harried heads contend with these issues? In some cases, restructuring a school’s administration can help, as a way to reduce the head’s role in the day-to-day operation of the school, freeing up time to consider long-term issues and implement strategic initiatives. 

A successful administrative restructuring also lets a head spend less time at his or her desk responding to the immediate and sometimes unreasonable demands of parents and more time developing personal relationships vital to the school’s welfare, both within the school and in the surrounding community. Heads need to personally recognize faculty and staff members for their contributions — and not just by email, calls, or even handwritten notes, although all are important. The head must be visible and engaged in the one-on-one communications that build relationships; with these relationships comes mutual trust and respect (which helps to get buy-in for the changes that are part of the school’s strategic initiatives). 

In addition, the head must spend time cultivating potential donors, remembering the first rule of fund-raising: “People give to people to help people.” Heads should spend time forging relationships with potential donors, learning about their interests and helping them to understand how their contributions will have a significant impact on the school population. This cultivation is essential, because well-resourced philanthropists are besieged by people representing noble organizations, all asking for financial support. 

How To Restructure

Changing the administrative structure of the school can be initiated by the board, but planned and carried out by the head and the board collaboratively. One approach is for the trustees to authorize a study of the situation, consider a variety of alternatives in consultation with the head, and then approve a new structure.

The final outcome of any administrative restructuring exercise is difficult to predict. No single model fits all schools, and any restructuring should reflect the strengths and interests of the head of school, the challenges facing the school, and the skills and talents of the administrators already in place. And once the new structure is in place, both the board and the head must be disciplined enough to resist the inevitable attempts to draw the head back into operational matters that he or she has delegated to others. 

In any restructuring:
  1. Where possible, reduce the number of direct reports to the head of school.
  2. The new structure should enable the head to focus on the important — not just the urgent — challenges facing the school.
  3. Consider succession and mentoring. Giving junior administrators more responsibility may encourage talented individuals to stay with the school and advance. A well-managed sharing of leadership responsibilities should promote a healthier, more resilient school.
Undeniably, administrative restructuring can meet with resistance, particularly if some members of the administrative team lose direct access to the head. But resistance should not be an excuse to avoid restructuring. The demands on the time of the head of school have increased exponentially over the past few years, and they’re not likely to decrease anytime soon. Assuming there will continue to be just 24 hours in a day, the wise board of trustees will do what it can to prevent head-of-school burnout and provide a reasonable opportunity for his or her success and fulfillment.
James W. Wickenden

James Wickenden is founder and president of Wickenden Associates (Princeton, New Jersey), an educational consulting firm specializing in head of school searches. He can be reached at [email protected].