Letting Go: The Current Head’s Role in the Search Process

Letting Go: The Current Head’s Role in the Search Process and Moving On

Carole Everett | February 15, 2025

The search for a new Head of School is one of the most pivotal moments in the life of a school. For the outgoing Head, it can be a time of mixed emotions: pride in the work accomplished, sadness at leaving a community, and perhaps anxiety about what the future holds. It is crucial that the current Head navigates the search process thoughtfully, playing an active but respectful role that supports the work of the Search Committee while also setting the stage for a successful transition to the new leader. This process requires a balance of involvement, patience, and, ultimately, letting go.

The Role of the Current Head at the Start of the Search
The Head of School’s involvement in the search process begins when the search is officially launched. Typically, the school will hire a search firm to guide the process, and it is at this stage that the current Head must prepare to engage in a constructive, candid conversation.

During the first meetings with the search consultants, the current Head should share vital information about the state of the school, including its strengths, challenges, and opportunities for growth. This is the time to offer insight into the school culture, the academic and financial health of the institution, the composition and effectiveness of the Board of Trustees, and any other key elements that the new Head will need to understand. The current Head should provide context for the search, but should resist the temptation to get overly involved in shaping the exact characteristics or preferences for a successor. The search consultants will take this input into account and, together with the Search Committee, begin drafting the leadership profile that will guide the search.

This stage is also an opportunity for the outgoing Head to communicate any personal reflections or considerations they feel are important for the search team to know. It can be helpful to talk openly about what the current Head sees as the “next chapter” for the school and the direction in which they believe the institution should move. However, it is important to remember that the future of the school, and the choice of the new Head, is not about personal legacy but about ensuring the continued vitality and success of the institution, and both are the responsibility of the Board of Trustees.

During the Search: Trusting the Process
Once the Search Committee begins meeting, reviewing candidate dossiers, and narrowing the field to semi-finalists, the current Head must step back. This phase requires patience and discipline, as the outgoing Head’s curiosity about the process can be a temptation. It’s important that the current Head trust the Search Committee to do its work without interference. This means refraining from reviewing candidate dossiers, inquiring about or discussing specific candidates, or engaging in conversations with the Search Committee unless asked a direct question.

The Search Committee is entrusted with the responsibility of identifying the right leader, and while the current Head can offer helpful background and insights, it is vital that they respect the Committee’s role in the process. By maintaining a healthy distance, the current Head allows the Search Committee to make decisions based on their own observations and assessments, without undue influence or bias. The Search Committee must also vigilantly uphold confidentiality and know that it is not out of disrespect for the current Head that he or she is not involved, but for the integrity of the Committee and process.

For the current Head, this can be one of the most challenging aspects of the process. After years of leadership, it’s natural to want to be involved in every aspect of the search. However, the goal is to make sure the new Head is selected based on the needs of the school, as determined by the Board, not on the personal preferences of the outgoing leader. The Search Committee needs space to do its job, and the current Head must be confident in the team’s ability to make the right choice.

Meeting the Finalists: Selling the School
When the finalists for the position of Head of School are invited to campus, the outgoing Head’s role shifts once again. This is a critical moment where the current Head can help “sell” the school to the finalists and help them understand why it is such a wonderful opportunity for leadership.

During the finalist visit, the current Head should focus on welcoming the candidates and showcasing the strengths of the school. This is an opportunity to highlight the unique aspects of the community, the culture, and the school’s vision. The current Head should be transparent about the challenges ahead, but also emphasize the tremendous potential for growth and innovation. It’s important to frame the opportunity as one that will enable the new Head to build upon a solid foundation, with a strong staff, dedicated families, and a robust academic program. The outgoing Head should take care to demonstrate a sense of pride in the work done and confidence in the future direction of the school.

At the same time, this is a time to step aside and let the candidate establish his or her own connection with the community. While the outgoing Head is participating, it is essential to remember that this is now about handing the baton over to a new leader who will bring their own approach to the role.

Transitioning Leadership: Supporting the Successor
The Head is still the Head! Once the Head-elect has been appointed, however, the transition phase begins. This is a time for the current Head to shift gears and prepare to relinquish control. It is important to remember that, while letting go can be an emotional and difficult process, it is not about you as the current Head — it is about the future of the school and its ongoing success.

A successful transition requires ongoing communication and collaboration between the current Head and the Head-elect. Ideally, the outgoing Head should meet with the Head-elect regularly during the transition period — at least once a month — to share insights, provide guidance, and offer support in preparation for stepping into their new role. The outgoing Head is still the Head until the end of his or her contract. Often faculty and staff may need to be reminded of this. (I had to send out “the opera is not over until the fat lady sings” memo to remind people of this so that they would not make end-runs to the Head-elect or Board members!).

Importantly, the current Head should include the Head-elect in major hiring decisions during the transition. While the current Head will still have a hand in hiring, it is essential that the new Head feels empowered and included in decisions that will have an impact on the future leadership of the school. This helps foster a sense of ownership and continuity and ensures that the new Head has the opportunity to shape the school’s leadership team from the outset, if that opportunity presents itself.

Letting Go for the Future
Ultimately, the Head’s role in the search process is about facilitating the transition to a new leader who will carry the school forward. It’s about ensuring that the institution remains strong, vibrant, and poised for success long after the current Head has moved on. While this process can be emotionally challenging, the key to a successful transition is recognizing that the future of the school is paramount.

The current Head’s ability to “let go” — to trust the Search Committee, to support the new Head, and to step aside when the time comes — is a vital part of this process. It requires humility, patience, and a deep understanding that the ultimate goal is the continued success of the institution. It means that the outgoing Head does not visit the school during the first year of the new Head’s involvement, unless by invitation, so that the new person can establish him or herself. By embracing this role, the outgoing Head ensures that the school remains strong and that the next phase of its journey is one of growth and success.

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