Welcoming a new head of school is a moment filled with optimism, hope, and excitement—an energy that every board hopes will be sustained for years to come. And yet, data from NAIS continues to show a troubling trend: head of school tenures are growing shorter, and the number of “unexpected” transitions increases each year. While there are many contributing factors, one essential practice stands out as a kind of “insurance policy” during those first critical years: a systematic, clearly defined, and meaningful evaluation process for the head of school—one that is aligned with a thoughtfully designed transition and entry plan. 

Too often, however, we hear stories of heads arriving at their new schools only to be swept into the speeding train of opening days without a plan for growth and evaluation. This can be either because the trustees would like to develop a plan collaboratively to build trust and connection, or because it is at the bottom of a long to-do list. Regardless, clarity around what success looks like, how feedback will be given, and what growth is expected is critical to ensure that the board and head share understanding of purpose and process. 

In our years as practicing heads and now as coaches and advisors to heads and boards, we’ve come to believe that a well-constructed head of school evaluation process is one of the most powerful—and underutilized—tools for successful leadership transitions and long-term school health. When done well, it meets the needs of both the board and the head, strengthens trust, clarifies shared goals, and fosters meaningful professional growth. When neglected or rushed, it can fray the relationship at the heart of the school’s leadership and contribute to instability and shortened tenures. 

Here are six core principles that can help boards and heads build an evaluation process that is useful, lasting, and human-centered. 

1. Growth, Feedback, and Evaluation Are Not the Same 

“Evaluation” often becomes a catch-all term that flattens the nuances of leadership development. A robust evaluation process should be one strand in a broader developmental arc—one that includes self-reflection, regular feedback, and opportunities for professional growth. Just as we do with students, we must distinguish between summative assessment (are goals being met?) and formative development (how is the head growing?). The head should be actively involved in setting goals, gathering feedback, and reflecting on progress. Trustees, in turn, should assess outcomes and contribute to goal-setting, not just evaluate performance. The aim is not only to measure results but to support the head in becoming a stronger, more effective leader. 

2. Use the Process as a Form of Education for the Board 

The head of school role is uniquely complex. It blends instructional leadership, strategic planning, personnel management, crisis response, community-building, and external relations—often all in a single day. Most trustees come from other sectors and may not fully grasp the intricacies of school leadership. That’s why the evaluation process should include time for board education. When a head reports on their year, it’s not just about outcomes—it’s an opportunity to illuminate the complexity of the role. Boards that understand the head’s work are better equipped to offer insight, support, and appropriate accountability. 

3. The Process Evolves at a Predictable Pace 

A strong evaluation process should be established before the new head arrives and systematized with a calendar and set of activities for a defined term—ideally three years. A predictable annual rhythm, built collaboratively between the head and board leadership, reduces stress and misunderstanding. A dependable process, customized to the school’s mission and the head’s stage of development, sends a powerful message: we are building something steady and sustainable, grounded in the belief that growth is ongoing. 

4. Encouraging Internal Feedback

Effective heads don’t just respond to external evaluation—they actively seek internal feedback. Whether through online tools, faculty/staff surveys, or regular leadership team check-ins, great heads create mechanisms for reflection and input. Boards should encourage these practices and be open to incorporating internal feedback into the evaluation and goal-setting process. A strong evaluation isn’t just about looking at the head’s work—it’s about empowering the head to look within the organization and themselves. 

5. School Culture and Needs Should Inform the Structure 

The head of school role includes both quantifiable goals (enrollment, fundraising, revenue) and qualitative outcomes (culture, trust, tone). While the former are easier to measure, the latter are equally important. Evaluation structures should reflect the current climate of the school. For example, selective interviews with a representative cross-section of faculty, staff, or parents can offer valuable insights. The key is to tailor the evaluation to the school’s unique context and needs. 

6. A Robust and Transparent Process Builds Trust and Connection 

A thoughtful evaluation process can be much more than a compliance task—it can be a strategic asset. Communicating the process to the candidate during the search and to the community early in the head’s tenure signals the board’s commitment to transparency and partnership. It sets a tone of trust and openness that strengthens relationships across the school community. It also models what learner-driven growth looks like and how a board/head partnership can support that growth for everyone. 

Ultimately, a head who feels genuinely supported by a clear evaluation process becomes its strongest advocate. You can spot these leaders—they are confident, reflective, and deeply engaged. They model a culture of growth, trust, and shared purpose. And in doing so, they help build schools where leadership is not just about outcomes, but about relationships, learning, and long-term success.