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

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.
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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.