Survival 101: Three Tips for New Heads

Jim Wickenden, Founder, Wickenden Associates
September 18, 2019

No new Head of School is fully prepared to handle all that he or she will face when picking up the leadership reins of the school. What new Heads are least prepared to deal with are those activities and tasks unique to headship. In that vein, here are three tips for every new independent school Head.

Tip #1: Develop a Healthy Working Relationship with the Board

A new Head must focus on developing a healthy working relationship with the Board. The critical relationship, of course, is with the Board Chair. Of almost equal importance, a good working relationship must be formed with the Chair of each of the standing committees, especially the Executive Committee. Last, but far from least, the new Head must make every effort to get to know each member of the Board.

  • The new Head of School and President should make and honor arrangements to communicate on a weekly basis. The Head should ask the President about major issues that should be addressed, as well as controversial issues to be avoided until the new Head builds credibility within the school community.
  • The new Head of School should make an appointment to meet with the Chair of each Standing Committee to learn what the expectations are of each
    Chair, as well as the goals of each Committee.
  • The new Head of School should make a concerted effort to meet with every member of the Board of Trustees to find out what has worked well in the past, what might be changed or improved, and what each trustee would like to see happen at the school in the next 5-10 years.

At the first meeting of the Board, the new Head should review his or her goals for the year, along with the metrics that will be used to evaluate achievement of these goals. Also at this meeting, the Head should request that the Board charge him or her with conducting a study of the school in order to present findings in the following spring about the strengths to be maintained, the challenges to be addressed, and a vision for the next 5-10 years that might be considered.

Tip #2: Prepare for the Unexpected

Prior to becoming a Head of School, an aspiring Head has likely taught, coached, advised, chaired committees, directed an office, department, or division, and perhaps served on a standing committee of the Board of Trustees—all valuable experiences. However, new Heads will be expected to manage situations for which they may not have had any direct experience. For example:

  • Tragically, a teacher, trustee, parent, or student passes away
  • A trustee or major donor’s child violates a major rule that could result in expulsion
  • A parent verbally abuses a teacher whose only “indiscretion” is the enforcement of the school’s rules
  • A hostile town council needs to be convinced that the school should be awarded a permit for a construction project that will impact the traffic pattern of a neighborhood

Managing scenarios like these takes leadership ability, judgment, wisdom, and courage. It helps to have a trusted and experienced mentor with whom the new Head can discuss responses to these scenarios well before they occur. Often a supportive Head in his or her current school will gladly fill this role. Having an idea about how to approach problems is likely to give the new Head confidence when the unexpected crisis occurs, while reducing the tendency to panic, overreact, or be forced to make an unwise decision.
In addition, prior to the opening of school, the new Head should meet with his or her administrative team to discuss strategies and processes for emergency scenarios, and in doing so, codify the guidelines to be used when the unexpected occurs.

Tip #3: Manage Litigation Judiciously

Sometimes the unexpected involves the threat of legal action. Thirty years ago, lawsuits against independent schools were relatively rare. Today, Heads may have their legal counsel on speed dial. Faculty and staff whose contracts are not renewed may sue. Parents whose children go before the school’s disciplinary board may threaten lawsuits. The following problems that have recently confronted Heads of independent schools should make new Heads aware of the multiple legal challenges that come with the job. Each poses a different question of how to protect the school while doing what is right.

  • A Catholic elementary school is sued by a family when the Head refuses to move a child out of a class taught by a Muslim.
  • The son of a Trustee and major donor attacks and hospitalizes a classmate.
  • A highly-respected and long-term department chair is accused of sexually abusing a student.

Any time something occurs which involves legal action, the Head’s first call should be to the President of the Board, and the second call should be the school’s lawyer. Once the President and the school’s lawyer have been informed, the new Head should convene the administrative team—or the crisis management team, if one has been put in place for this purpose. Often, an official statement needs to be issued, sooner rather than later. Legal counsel, as well as the school’s communications officer should work together to craft an appropriate response.

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