The day will come when the head of school is ready to move on, or when the board determines it’s time to make a change in leadership. In the best circumstances, head transitions are planned and agreeable, and both the board and head have a year or 18 months to craft a smooth transition. At Telluride Mountain School (CO), we experienced a smooth, planned transition during the 2017–2018 school year. Nonetheless, as the outgoing head, I dreaded the shift in focus from advancing the school to the tricky business of changing heads. Prior to my headship, the school had been through two short-term headships, one interim and one external hire, and there was a lot of anxiety about the next head. As excitement about the school’s future builds, it’s natural for the board to turn its attention to the new head search. That generative energy is an essential component of the transition, but it’s important to remember that the outgoing head still has important work to execute, and the board has particular responsibilities to them. I have served on two search committees as an administrator and have moved from head of school to retirement. Those experiences taught me a number of ways the board and head can maintain a strong relationship and remain forward-looking during the transition period. Teamwork and communication are essential throughout this phase. With good analysis, organization, and execution, the board and head can craft a strategic plan to help the school maintain its momentum. Prepare for the Best During a transition, it’s easy to lose sight of the ordinary protocols and procedures that allow for the effective division of responsibilities between the board and head. It’s the board’s responsibility to hire and support the new school leader and prepare the community for the transition. The outgoing head must prepare faculty, staff, and programs, maximizing the school’s potential for success. At times, the head may have to remind the board about principles of governance. Trustees may grow anxious about the transition and start to assume responsibilities that are still the purview of the head, or they may become so consumed by the search that they overlook their ordinary responsibilities, which then fall to the head. It’s easy to press pause on big initiatives, such as fundraising campaigns or capital projects, during a transition. But now is the time to maintain the flow of ordinary work. The regular work of the board and head will provide the necessary stability. While I did not participate in the search for the new head or the development of the school profile at my school, I met regularly with the transition committee to discuss the school’s perceived needs, strengths, and challenges in relation to the search. As the head and board prepare to announce the head’s resignation, they can reflect on the important themes of stability and growth and identify the actions that will promote both goals over the coming year. Even if the head is not on the transition committee, he or she can be an important resource for developing the school profile and job description, as well as an excellent sounding board to help make sense of the range of qualities that constituents desire in the new head. While it is natural for many board members, faculty, staff, and parents to suggest qualities opposite to those of the sitting head, the head’s voice may temper the tendency to swing too far in the opposite direction when choosing the next school leader. Shore Up the Team Just as the outgoing head can counsel the transition committee, the committee can support the outgoing head with its perceptions and advice about the strategic needs of the school and the outgoing head’s ongoing role in fulfilling them. The transition period represents valuable time to shore up the school, so it can weather the inevitable bumps that will accompany a new school leader’s journey. The outgoing head should take a hard look at the condition of the school to identify potential weaknesses that change could exacerbate. The first thing for the outgoing head to examine is the current administrative team. What skills and knowledge will leave with them? What weaknesses or gaps exist in the current staff? It’s important to structure a team that is strong in all areas of administrative activity before the new head arrives. The outgoing head can identify gaps in both specific knowledge about operations and broad areas of function, such as fundraising or program leadership. Now is the time for the outgoing head to make any final administrative hires or assignments that can contribute to the administrative team’s long-term success. The winter before the head’s final year is a great time to see if any faculty members are ready to take on administrative or leadership roles. With the existing faculty taking on new program responsibilities, the administrative team has the capacity to absorb additional roles or tasks that the new head will not be managing. Outgoing heads can also cultivate faculty leaders, such as mentor-teachers and division or department heads, and put in place multiyear plans for faculty development to guarantee continuity in teaching. While the new head may want to make changes down the road, all this preparation should provide smooth sailing for the first year or two. The outgoing head should also confirm that academic and extracurricular programs are in a good state. There should be a plan for the cyclical review of the school’s programs with a familiar system for the faculty and their leaders. Incoming heads are better supported when instructional leaders and department and division heads are familiar with their responsibilities for overseeing and recording curriculum and pedagogical approaches. Consider the Strategy Mix If the succession is orderly, the head and board can ensure that the school’s strategic plan is current and provides the right mix of goals-in-progress and flexibility to allow the new head to uphold the school’s mission and create new plans for advancement. At my school, our mix included not only lots of accomplished goals but also a selection of “low hanging fruit,” or clear objectives, for the new head to pursue. We also planned a fall retreat to review and update our strategy formulation. The right mix depends on the individual school. As a school develops its profile and the characteristics it desires in a new leader, certain themes will emerge, and the existing strategic plan can reflect the school’s taste for both change and stability. If the school is seeking a disruptive leader, then the plan should allow for greater flexibility and build in plans for close collaboration among the new head, the board, and key constituents to develop a new vision and roadmap. But if the board believes that the school is moving in the right direction, the strategic plan might include goals that extend current objectives to ensure stability and a smooth runway for the new head. The school’s most recent accreditation report, especially the major recommendations, will also provide a lot of insight. The new head will feel well supported when the board and its chair are familiar with the school’s current status with its accrediting body. Then the first-year goals for the new head can flow naturally from the report’s recommendations without the head feeling that the board is overstepping its role. The outgoing head can do much to pave the way for the school’s success by working closely with the board on the strategic plan and by familiarizing the chair and the new head’s evaluation committee with the broad outline of recommendations. In the end, my board—with my enthusiastic recommendation—determined that an internal hire of our associate head was the best match. Through ongoing attention to the cooperation between the board and head, a clear strategic outline for the new head, and my preparation of the faculty, administration, and programs, we were able to lay the groundwork for a successful transition. And that’s something to celebrate.