The Hidden Pitfalls of Headship—and How Strategic Leaders Avoid Them
Written by LAURA FULLER - TEG SEARCH CONSULTANT & EXECUTIVE COACH
New heads of school are typically selected after a prolonged and carefully structured search process led by trained consultants. This process is designed to identify the candidate best suited to the school community. Community-wide surveys are administered, consultants and the search committee conduct multiple rounds of interviews, and a broad range of constituents have opportunities to engage with the finalists. Their feedback—organized through a well-developed rubric—helps the committee assess each candidate’s qualifications. The search requires months of diligent work and aims to build a deep understanding of the skills, talents, and experience each candidate offers. Notably, the rubric used during this process often emphasizes operational experience, references, and evidence of tactical success—precisely the competencies that frequently motivate candidates to pursue headship.
As complex as the search process is, the true test of fit begins when the new head of school (HOS) enters the transition period and ultimately assumes the role of the school’s de facto CEO. Many new heads rise through faculty or administrative ranks, where operational competence propelled their advancement and where they feel most confident. The challenge is that the work of a head of school is fundamentally strategic, not operational. The transition requires the largest professional leap of their career—shifting focus toward relationship-building and enterprise-level leadership. Ironically, the very strengths that helped secure the headship can become liabilities if they draw the new HOS back into operational territory. Lacking experience in strategic leadership, new heads may gravitate toward familiar managerial tasks, which can lead to early perceptions of micromanagement.
During the critical transition period—when relationships are forming and faculty and administrators are particularly attuned to the new leader’s behavior—a head of school can unintentionally create strain by overemphasizing operations and processes. At the same time, they may overlook the importance of forging a strategic partnership with the board to establish clarity of mission and vision. New heads must recognize that adding value no longer means doing the operational heavy lifting. Responsibility for accurate and effective daily work is now shared across the administrative and faculty teams. Tactical execution properly belongs to the team, not the HOS.
Strategic leaders understand that their highest value lies in setting a clear vision for the school and communicating it effectively to all constituencies. The HOS must articulate priorities and ensure the community understands their “why, how, and what.” This is essential for building buy-in and cultivating the growth mindset necessary for the school to thrive in a competitive environment. Heads ensure that the conditions are in place for others to do their best work—providing resources, professional development, and alignment with the strategic plan.
The new head must also shift from leading a single functional area to stewarding the entire enterprise. Success is no longer measured by personal accomplishments but by the environment they create for others to excel. This requires balancing competing priorities across diverse constituencies and understanding how each decision may have ripple effects across the community. New leaders must focus on long-term institutional health rather than short-term operational wins.
It is easy for school leaders to become consumed by immediate challenges, but doing so risks neglecting their responsibility to prepare the institution for the future. New heads must discipline themselves to prioritize long-term gains over daily operational problem-solving. They must also trust administrators—many of whom they barely know—to manage daily operations while they set the strategic tone and direction.
Woven throughout all of this is the essential need to build strong, positive relationships with students, faculty, staff, administrators, parents, and ultimately the board of trustees. This requires patience, energy, and a well-planned communication strategy that emphasizes visibility and accessibility—especially during the first years of headship. While it may be tempting for new heads to focus on decisions within their functional expertise, such as specific curriculum offerings or program structures, these early “wins” are far less important than being present in classrooms, attending school events, and meeting individually with members of the community. Though relationship-building may not yield immediate or measurable outcomes, long-term success as a strategic leader depends heavily on the HOS’s early investment in cultivating trust and connection.
