The Head of School's Job: What Lies Beneath
August 5, 2025
As a long-time educator and a former Head of School, I've had countless conversations about the role of school leadership. From the outside, the Head of School's job seems clear: leading assemblies, shaking hands at school events, delivering a compelling commencement speech, and being the public face of the institution.
However, after decades in the profession, I've come to believe that the Head of School's job is like an iceberg—only a small, visible portion of it is seen by the public, while the vast and more critical part remains hidden beneath the surface.
The Visible Tip of the Iceberg
The public sees the "face" of the school. They see the leader at the podium, in a social media post, or cheering on the sidelines of a game. This visible work is crucial; it builds trust, inspires confidence, and communicates the school's values to the community. Parents, students, and faculty see the Head's presence in classrooms, their communication in the weekly newsletter, and their active engagement in school life. This public-facing role is what most people identify as the "job."
The Unseen Mass Below the Surface
What the community doesn't see, however, is the immense and often challenging work that lies beneath the surface. This is the heavy lifting that makes the visible part of the job possible. It's a world of complex, nuanced, and often difficult work, including:
Financial Stewardship: Managing a multi-million-dollar budget, navigating financial aid, planning for capital improvements, and ensuring long-term institutional health—a constant exercise in balancing mission with fiscal responsibility.
HR and Personnel Management: Leading a large and diverse faculty and staff, conducting performance reviews, managing interpersonal conflicts, and making tough personnel decisions that impact lives and livelihoods.
Strategic Planning: Working tirelessly with the Board of Trustees and key stakeholders to develop and execute a long-term vision that will guide the school for years to come. This involves data analysis, market research, and difficult conversations about the future.
Crisis Management: Navigating unexpected crises, from a public health scare to a student safety issue, with calm, clarity, and compassion. This often happens behind the scenes, demanding swift, decisive, and confidential action.
Pastoral Care: Serving as a counselor, mentor, and spiritual guide for students, faculty, and families in moments of personal crisis or emotional need—providing a listening ear and a steady hand in the most challenging of times.
Legal and Regulatory Compliance: Ensuring the school complies with an ever-growing list of local, state, and national regulations, from employment law to accreditation standards.
The Importance of a Complete Understanding
Understanding the full scope of the Head of School's job is not just an academic exercise; it's a critical component of successful governance. When a Board of Trustees, a search committee, or a new Head of School grasps the true depth of the role, it leads to:
Realistic Expectations: An appreciation for the time, energy, and emotional toll of the job, preventing burnout and fostering a more supportive partnership.
Strategic Partnerships: A relationship built on trust and a clear division of labor, where the Board handles governance and the Head handles the day-to-day operations.
Effective Candidate Selection: A search process that looks for a leader who possesses not only public-facing charisma but also the unseen skills of financial acumen, personnel management, and crisis leadership.
The best leaders are those who can perform both the visible and invisible work with equal grace and skill. They are the ones who understand that the small, visible tip of the iceberg is only possible because of the immense, unseen mass that provides its foundation.