What Sets Successful CEOs and Heads Of School Apart | Jim Wickenden | 13 Min Read

September 5, 2022

The May-June 2017 issue of the Harvard Business Review (HBR) contained an interesting article entitled “What Sets Successful CEOs Apart.” As a consultant to independent schools for over 35 years, I decided to see whether or not the research done on CEOs might be applicable to Heads of Schools.  Despite the fact that not all leaders of independent schools see themselves as being in a business, they are.  That being said, the four significant behaviors mentioned in the HBR article that set successful CEOs apart are not uniformly applicable to Heads of School.  Thus, the purpose of this article is to define the following four behaviors and to explain which are and which are not relevant for Heads of School.  The four essential behaviors for successful CEOs are as follows:

  • Deciding with speed and conviction
  • Engaging for impact
  • Adapting proactively
  • Delivering reliably

Deciding with speed and conviction

While the authors of “What Sets Successful CEOs Apart” emphasize the need for those leading companies to be decisive, even when they may not have all the information needed to make wise decisions, making quick decisions is applicable on some occasions for Heads of School, but not always.  The following examples explain why this behavior is essential in some circumstances but should be avoided in others.

Examples requiring a Head of School to be decisive:

  • Emergencies:  When crises occur, school leaders must act quickly to ensure the safety of the students and staff.  Obvious examples are when a school must go into lockdown because of the presence of a dangerous intruder, when the fire alarm goes off, when Mother Nature dials up a hurricane, flood, or tornado, or when an earthquake occurs.  To prepare for such situations, effective school leaders must create systems for lockdowns and evacuations and practice them.
  • Sensitive admission decisions:  Most independent schools receive applications from youngsters who may not be stellar academicians, promising musicians, or great athletes but who come from families that have the wherewithal to make a transformative gift to the school.  While the decision to admit a youngster who falls into this category may not be applauded by the faculty or the coaches, those responsible for planning and delivering the school’s programs nonetheless appreciate a gift that might result, in an endowed faculty chair, a new theatre, improved science facilities, or a new gym.
  • Inappropriate behavior by faculty, staff, or students:  During the past four decades, newspapers have published stories about independent boarding schools where inappropriate relationships, often sexual, have occurred between faculty or staff members and some students.  Years ago, when this situation reared its ugly head, the practice of some Heads of School was to “sweep these incidents under the rug” as opposed to reporting them to the appropriate authorities.  Today, however, Heads of Schools know that they must notify the President of the Board and submit a report to the appropriate agency about any sexual misconduct between a school employee and a student.

Not all of the decisions a Head of School has to make are easy or likely to be popular.  Examples of those that require time, reflection, collaboration, and wisdom are as follows:

  • Non-retention of a faculty or staff member:  I’ve heard scores of stories about long-term members of the faculty who are not as effective or conscientious as their peers.  Those who fall into this category are usually well-known, but may not be well-respected.  However, when Heads decide not to renew the contract of a long-term employee, they may become the target of withering criticism.  When a decision is made to not reappoint faculty members, these folks usually remain at the school until the end of the academic year and in so doing are likely to receive sympathy from some of their peers, a few of whom may express incredulity about the decision of the Head.  Given the disruption that sometimes occurs when long-term faculty members are not retained, Heads must ensure that the teacher, coach, or staff member who is not being reappointed has been evaluated according to a defined and respected process.
  • Sensitive decisions regarding the expulsion of a student:  The flip side of a Head of School making the decision to admit “a development case” occurs when this leader decides to remove a student from the school community.  To avoid or at least minimize lawsuits, and to ensure that the school is doing the right thing, there should be a systematic review of a case and a thorough vetting of all involved to generate a sound decision.  A Disciplinary Committee can recommend to the Head of School a punishment for a student who broke a major school rule, but it is the responsibility of the Head of School to determine whether or not that youngster should be expelled.
  • Complicated disciplinary decisions:  [What follows is a true story.]  Several years ago, a couple who lived in an affluent community that could boast about having four well-regarded independent schools decided to take a vacation in Europe during the school year.  In so doing, the parents did not anticipate that their children would take advantage of their absence by planning a party.  Word of the pending party spread like wildfire amongst the students who attended the four local independent schools.  Not surprisingly, hordes of adolescents showed up at this unsupervised party.  When neighbors became fed up with the loud music and raucous behavior of those at the party, the police were summoned and once arrived quickly took control of the situation.  Because the students from four different independent schools contributed to the noise and disruption, the four Heads of School became involved.  Unfortunately, these Heads of School functioned independently of one another and in so doing meted out four different disciplinary decisions.  Once the local journalists learned about the party, the stories that were published turned out to be a public relations nightmare.  The issue was not whether one Head of School handled the situation appropriately while others did not.  Rather, the Heads did not communicate with one another to discuss whether or not there should be a degree of consistency with respect to the disciplining of the students who were involved.
  • Programmatic and curricular decisions:  With complex issues, Heads of schools who make quick decisions will be accused of being arbitrary rather than lauded for being decisive.  Four examples of complex issues follow.  In the past few years Heads of schools, with the blessing of their respective Board of Trustees, abolished their respective football programs.  Other independent schools have phased out the study of Japanese, Russian, and French because of declining enrollments in those languages.  We have also witnessed independent schools adding high-level courses to their curriculum while simultaneously eliminating certain Advanced Placement courses.  Finally, there has been a movement in the last two decades for some schools to offer the International Baccalaureate curriculum.  Because all of the aforementioned programs that were eliminated or instituted had their advocates, Heads of schools had to be prepared for pushback and criticism when these changes were announced.  Whenever a change occurs, someone loses.  Thus when major programmatic changes occur in schools, the Head needs to plan for the worst, hope for the best, and explain what led to those decisions.

Engaging for Impact

This behavior is essential for both CEOs and Heads of schools.

Just as CEOs must plan for the future, so Heads of schools must develop a vision and then  persuade the trustees, staff, coaches, parents, and alumni why this vision is appropriate for the future of the school.  To do so, however, the Head must have earned the trust of those in the different constituencies of the school.  This takes time and a genuine willingness to both acknowledge one’s mistakes and to give credit where credit is due. Those values are essential for a leader to know the importance of engaging others. However, having those values is necessary but not sufficient.  To engage others fully, Heads must be able to communicate well, listen and reflect, think strategically, and have developed or used a model for managing change.

Tips for both CEOs and Heads of schools regarding how leaders should engage others are as follows:

  • It is essential for the leader to get buy-in among employees and other stakeholders.
  • The leader must be a disciplined communicator.
  • Non-supporters should be identified and strategies developed to change their minds.
  • The leader’s confidence in a successful outcome reduces resistance to change.
  • The leader must be able to handle and respond effectively to conflicting viewpoints.
  • The leader cannot shy away from conflict.
  • While leaders should listen and solicit views, they should also be wary of defaulting to consensus decision-making.

While these tips are easy to understand, they may not be easily remembered.  To give Heads of School contextual information about how to engage others when executing change, a book worth reading is A Passion for Leadership by Robert Gates, formerly the Secretary of Defense, the President of Texas A & M, and the Director of the CIA.

Adapting Proactively:

Leaders who adapt proactively possess the following four traits:

  • They are able to deal effectively with situations not in the playbook;
  • If they spend half of their time thinking about the long-term, in so doing they are able to identify early signals;
  • They recognize the need for flows of information; and
  • They acknowledge their mistakes and learn from their setbacks.

Heads of School regularly have to respond to situations that are not in the playbook.  Examples include, but are not limited to, the unexpected death of a beloved faculty member, the suicide of a student, the struggles of an adolescent when the parents are going through a divorce, the lawsuit filed by a former student who claims to have been sexually molested by a school employee 30 years ago, the discovery of a drug distribution ring led by the son of a trustee, a cheating scandal involving juniors and seniors, or the withdrawal of a seven-figure pledge by a family who for years has been a loyal contributor to the school.

All of these situations must be handled with compassion, grace, dignity, thoughtfulness, wisdom, and the willingness to communicate.

To enable a Head of School to think about the long-term, several conditions must be met to give the leader the time to think, reflect, research, and plan.  Thus effective stewardship by the Board of Trustees should ensure that:

  • The number of direct reports to the Head should be limited to five to seven.  Stated another way, the larger the number of direct reports, the greater the likelihood of Heads of School being anchored in their offices.  The more time they spend in their offices, the less they will be visible on campus or be able to cultivate prospective donors.
  • The Board needs to monitor the organizational structure of the school to counter direct-report creep.  With respect to this issue, the Heads of schools may be their own worst enemy if when they add another direct report to manage a new function they don’t arrange for an administrative restructuring by demoting someone whose effectiveness has declined.
  • The annual goals of the Head that are mutually developed by the Board and the Head should be limited to those that can be reasonably accomplished in an academic year.  In essence, the more Heads are asked to do, the less time they have to think, read, reflect, plan, be visible on campus or cultivate potential donors.

Heads of School will need to manage the broad flows of information addressed to this office.  The issue is not the amount of information that flows to that office, but the source.  If the Head of School’s office is the repository of complaints from the faculty members who believe that they are overworked and underpaid, from parents who question the grade of an essay given to their child, from a coach who is lobbying for a new athletic facility, from a sports fan who believes the starting quarterback on the football team should be replaced, from a disgruntled alumnus who questions the lack of emphasis on the Classics, from the health-conscious folks in the school community who lobby for more nutritious food and less homework because students need more sleep, little time will be available for the development of strategic initiatives that will solidify the foundation and reputation of the school.  In sum, the Head must be willing to delegate and be advised by trusted colleagues on how the aforementioned issues will be handled and why their recommendations are consistent with the mission of the school.

Delivering reliably

As is the case with the second essential behavior, namely engaging for impact, both Heads of Schools and CEOs must be able to deliver reliably. I am not going to differentiate between what CEOs and Heads of schools must do to deliver reliably.  Rather, I will focus on making recommendations to Head of School search committees to assess what they should do to ensure that the candidates are prepared to deliver reliably.

Having conducted hundreds of searches for Heads of School, I have learned that Heads who are reliable and who deliver what they promise are far more respected than Heads who make a concerted effort to befriend as many people as possible.  In asserting this, I am not suggesting that the Board of Trustees hire an ogre; rather, I believe that an organized, thoughtful, hard-working, collaborative, and forthright leader is far more effective than extroverts who may be able to draw laughs from a crowd but who are more impulsive than structured in how they approach the job.

The following questions deserve attention when independent school search committees are evaluating finalists for the Head of School position.  I recommend that Head of School search committees ask each finalist to:

  • Describe a significant and mission-appropriate contribution to the school where they work.
  • Give an example of what they have done to develop a reputation of trustworthiness.
  • Describe the process they would use to communicate expectations.
  • Describe what they have done to assess the extent to which those they have supervised have fulfilled their commitments.
  • Give examples of the process they used to delegate tasks and the methods they used to follow up.
  • Ask them what is most important when building a team.

Concluding Comments

I’ll conclude with four points.

  1. Leading a school is different from leading a corporation.  I’m not arguing that leading one is more difficult than leading the other; they simply are different.
  1. While leading a school is different from leading a corporation, effective leaders of both must have developed specific behaviors.  Specifically, they must be able to be decisive when the situation requires such.  They must be given time to think about the future and have the courage, determination, and interpersonal skills to manage change.
  1. Both corporate boards and boards of trustees must seek out and appoint leaders who can communicate effectively with their respective constituencies.  Furthermore, these leaders must be mature enough to realize that critical decisions will not always be applauded and that necessary confrontations will rarely be appreciated.
  2. Those leading independent schools must acknowledge that in order to survive and thrive, the school has to compete for students, faculty members, coaches, and money.  This means that goals must be established and fulfilled, standards must be formulated and honored, and those responsible for delivering the school’s services and programs must be held accountable.

You may also be interested in reading more articles written by Jim Wickenden for Intrepid Ed News.

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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