Ensuring a Smooth Head of School Transition

Wickenden Associates
September 7, 2019

Few, if any, aspects of trusteeship rival the Head of School search for sheer challenge, hard work, and potential for reward. The fruits of a successful search are magnificent to behold: an outstanding new leader for the school as well as a renewed and energized school community, excited about the future and dedicated to the pursuit of a shared mission.

The search for new leadership in a school is like a stone cast into a pond: The resulting ripples can either strengthen the school culture or heighten existing tensions. Because the completion of the Head search marks both an end and a new beginning, it is an appropriate time to reflect on the school’s condition and plan for the future. The search provides the Board with an opportunity to:

  • Review the school’s mission statement and either affirm or refine a vision for the school’s future.
  • Articulate near and long-term goals.
  • Review and, if necessary, improve communication with and among the various constituencies of the school.
  • Strengthen the Board’s own performance and renew its commitment to the school.

When the Board embraces these opportunities, the search is far more likely to succeed than if nothing is done. The school constituencies are likely to feel confident in their new leader; the new Head will enter the position with understood expectations and goals; and the Board will have developed a set of criteria upon which to evaluate the new Head’s performance in the years to come.

This is also an appropriate time to review the key initiatives under consideration at the Board level to determine which should be fast-tracked and which might be better tabled until the new Head’s arrival. Examples might include a languishing strategic planning process, facilities upgrades or land purchases, a capital campaign, settlement of a lawsuit, etc. The Board leadership should also work with the outgoing Head to defuse any landmines that might explode later if not resolved now. Items in this category might include necessary austerity measures, tuition hikes, or the dismissal of under-performing employees.

While a well conducted search will go a long way toward promoting a successful transition to new leadership, ensuring the best possible start for your next Head of School is a task that should not be delegated solely to the Search Committee and consultant. There are some specific steps the Board can take to help ensure a smooth transition for the new Head:

  1. Define the challenges the school needs to address.
  2. Review, update, and distribute a revised job description for the Head of School.
  3. Review and, if necessary, revise the evaluation process for the Head of School.
  4. Publicize on the school website the criteria by which the Head will be evaluated.
  5. Craft and disseminate to the faculty and staff (and possibly parents, depending on the items) a Charge to the new Head.
  6. Ensure that the Chair of the Board will function in that capacity for at least one year after the new Head takes office.
  7. Unless the school is in crisis, instruct the new Head to study the school for the first year and then inform the Board of the changes he or she would like to make during the following year.
  8. Provide the new head with needed coaching, mentoring, professional development, and/or the opportunity to join and build a network

Boards concerned about the longevity of their school leaders should consider altering the parameters of the Head’s job through administrative restructuring, reducing the number of his or her direct reports and enabling the Head to focus on the important—not just the urgent—challenges facing the school. No one 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.

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