Notes from The Head Search Frontier

At GLP, we are always interested what transitions are taking place in the independent school world, particularly as we are continuing our New Heads Leadership Lab program. 

With that slight introduction, I want to report on a recent conversation Greenwich Leadership Partners had with Jim Wickenden, the veteran president of Wickenden Associates and a seasoned expert on the leadership search environment for independent schools. Throughout the independent school world, Jim is held in high regard for the firm’s successful work and his reputation for experience and understanding of the ever-evolving issues of school leadership and governance. I first met Jim as a teacher when he came to The Taft School to scout out early aspirants for leadership. Jim’s commitment to understanding not just his business but also the independent school world was impressive, so after becoming the headmaster at Blair Academy, I made one of my first off campus trips to meet with Jim in Princeton. Going to Wickenden Associates was sort of a pilgrimage both to pay respects and to glean as much as possible about the lay of the land for independent schools in New Jersey. That early venture proved quite valuable, and from that time forward Jim and I have kept in touch.

Stephanie Rogen and Monie Hardwick, both of whom helped guide the questions for Jim and expand upon the issues, joined and helped lead this discussion. What follows is an excerpt of our recent conversation.


GLP: As you know, we are involved in a new approach to leadership transition for new heads, and have just completed work with our first cohort, all of whom seem to be off to a positive start. What qualities do you see as key to a successful transition for new heads?


  • First and foremost, the new head has to love the work; taking this position should not be driven primarily by compensation or status.
  • Second, the new head has to understand what will make him or her effective as a leader and have the wisdom and courage to seek support for that success. Schools tend to be resistant to autocratic leadership, meaning that new heads have to tread both strategically and with sensitivity.
  • Third, new heads need to adopt an effective leadership philosophy with self-expectations regarding communications, being able to listen carefully, and having a work ethic that sets the bar high.
  • Fourth, successful new heads are fueled by high energy and a willingness to be seemingly omnipresent for the school community—around the campus, in the hallways, the dining hall, dormitories (if at a boarding school), and at school events. While learning to know the names of the faculty, staff and students requires concentration and effort, it is nonetheless important.
  • And lastly, heads must recognize that effective leadership is a highly moral act. As a result, heads must understand their values and live by them.

GLP: How well prepared are new heads of school for their leadership role?

JW: In the 30 years that I have been in the Head of School search business, it has been impossible not to recognize that the demands have increased and the job has become more complex. Not surprisingly, new heads are not as well prepared as they need to be. New heads do not know what they don’t know. Further, as they confront unfamiliar challenges, some are hesitant to ask for help or reveal their uncertainty to their board chair.

GLP: What is the overall climate of the search business today?

JW: I am optimistic about the leadership search climate. My optimism is based not only on the volume of the work and business vigor we are experiencing, but also because new schools are being founded and there seems to be a recognition among trustees that a school could benefit from the professional support of a search firm that is knowledge about both the aspiring heads and the schools where they work. I have never been busier. We are busy in the fall during head of school searches and then again in the spring when other administrative positions have to be filled.

GLP: How involved are you in the transition of new heads?

JW: Certainly we stay in touch with the school and the new head, but because they start in July, we are in the middle of our new search season. As a result we are not hands-on in the first two or three months. With respect to the transition process, I have written a paper on this. Included in this paper is the strong recommendation that all boards develop ‘The Charge to the Head” and make that available to the faculty, staff and parents. Rest assured that if board chairs reach out to us for support, we do our best to advise and guide them.

GLP: What are key areas of support that a new head needs?

JW: Obviously, honest, constructive, and regular feedback is important. New heads always want to know how they are doing and need t occasional course corrections. The feedback needs to be well intentioned and truly useful, preferably coming from a trusted board chair or someone the head can trust. In my experience, day schools heads receive lots of feedback; boarding schools heads not so much. Both can be an issue. I always recommend a structured calendar for communication, and I know GLP’s work is designed to support a feedback process for new heads.

GLP: Any final thoughts on transition and preparation issues?

JW: The central issue in successful transitions concerns the relationship between the governance structure and the head’s leadership progress. If the Board is open, patient, and pro-active in supporting the head, and if the head is an active communicator and an enthusiastic learner, then a pathway for success can be established in the first year.

GLP: Thank you, Jim.


What struck us most about our conversation with Jim Wickenden was the steep cliff that new heads step off as they begin their first headship. Clearly a great deal of time, energy, and expense goes into the search process, and there are inevitably great expectations for the new head. However, the crucial first year for that head is likely to be under-supported, under-planned, and filled with unanticipated challenges. Certainly boards need to think strategically about this transition and leadership establishment period, taking the first year as seriously as they took the search process. A smooth start and strong first year for the new head can cement the purpose of the search and set the stage for an extended, successful tenure. Every board’s top priority is securing successful leadership, and thus attention to this transition period should be considered as important as the search process.