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Key Takeaways

• Effective school leadership depends on a capable team of administrators with complementary expertise, not just the head of school.
• Financial planning, enrollment, faculty development, advancement, and student life require coordination across departments.
• Shared purpose helps ensure that individual departments work toward the school’s broader mission and long-term goals.
• Trust and constructive disagreement allow leadership teams to challenge assumptions and make better-informed decisions.
• Distributed leadership strengthens institutional continuity and reduces a school’s dependence on any single individual.

Randall Dunn has served as Head of School at Rye Country Day School in Rye, New York, since 2022, drawing on more than 30 years of experience leading independent schools. He previously spent over a decade as Head of School at Latin School of Chicago, a PK-12 institution with roughly 1,200 students and 250 faculty and staff, where he advanced diversity and inclusion initiatives, adopted a social and emotional wellness program, and led a $50 million endowment campaign. Randall Dunn also held leadership roles at The Roeper School in Michigan, Landon School in Maryland, and Derby Academy in Massachusetts, after beginning his career as a sixth-grade teacher and coach at The Potomac School in Virginia.

He holds a Master of Education in Human Development and Psychology from Harvard University and a Bachelor of Arts in Psychology from Brown University, credentials that inform the discussion below of why strong school leadership depends on more than one person at the top.

Leadership in education has become a team sport. The head of school remains responsible for setting direction and ensuring that the institution fulfills its mission, but the scope of that responsibility has expanded well beyond academic programming. Financial sustainability, enrollment, faculty development, advancement, facilities, technology, and community relations all require specialized knowledge.

A school’s ability to navigate those demands depends in large part on the strength of the team surrounding its head. Recent research from the National Association of Independent Schools illustrates the breadth of contemporary school leadership.

In a 2025 study of reporting structures at independent schools, the most common roles reporting directly to heads of school included the chief financial officer or business officer, enrollment leader, advancement officer, and division head. The research also found substantial variation in how schools organize these responsibilities, with structures often reflecting the size and circumstances of the institution.

Effective leadership teams require a clear understanding of how individual responsibilities fit together. Decisions about enrollment, for example, can affect financial planning, staffing, student life, and long-term strategy.

A new academic initiative may require additional resources or changes to the schedule. A major facilities project can influence both finances and the student experience. When leaders understand these connections, specialized expertise becomes an institutional asset rather than a collection of separate functions.

Shared purpose is equally important. Harvard Business Review’s recent examination of high-performing teams emphasizes the importance of a common purpose and a commitment to working collectively toward ambitious goals.

The same principle applies in schools, where departments can otherwise develop priorities that make sense individually but do not necessarily advance the institution as a whole. Clear authority helps turn alignment into action.

NAIS’s research found that traditional hierarchical structures remain common among independent schools, particularly those undergoing changes such as enrollment growth, capital campaigns, or administrative restructuring. Such structures can provide clarity about who is responsible for what, while more established schools may have greater flexibility to organize leadership around their particular missions and cultures.

Trust within the leadership team is another essential ingredient. Senior administrators need enough confidence in one another to raise concerns, challenge assumptions, and acknowledge when a strategy needs to change.

Without that openness, teams can become overly cautious or protective of their individual areas. Productive disagreement, by contrast, allows different forms of expertise to improve a decision before it reaches the wider school community.

A strong leadership team also gives a head of school room to focus on the work that only the head can do. Rather than serving as the final decision-maker on every operational question, the head can concentrate on institutional direction, relationships with the board, long-range planning, and communicating the school’s mission.

NAIS’s principles for heads of school specifically call for an effective leadership approach that appropriately involves administrators and faculty in decision-making. The result is more than greater efficiency; distributed leadership builds institutional capacity.

When responsibility, expertise, and authority are developed throughout the senior team, a school is less dependent on any single individual and better prepared to sustain its priorities through periods of growth, transition, or uncertainty.

Great schools require strong leadership at every level. A capable head of school provides direction, but a well-designed leadership team provides the collective expertise and continuity needed to turn that direction into lasting institutional progress.

FAQs

Why is teamwork important in school leadership?

Schools face complex responsibilities involving academics, finances, enrollment, staffing, facilities, and community relations. A strong leadership team brings together the expertise needed to manage these areas effectively and support the institution’s overall mission.

What roles typically report directly to a head of school?

Common senior positions include the chief financial officer or business officer, enrollment leader, advancement officer, and division head. The exact reporting structure varies depending on a school’s size, needs, and organizational priorities.

How does shared purpose improve a school’s leadership team?

A shared purpose helps administrators align their departmental decisions with the institution’s broader goals. It also encourages collaboration and reduces the risk of individual departments pursuing priorities that conflict with one another.

Why should school leadership teams encourage constructive disagreement?

Open discussion allows administrators to raise concerns, challenge assumptions, and consider different perspectives before making important decisions. This can improve strategic judgment and help teams adapt when existing plans need to change.

How does distributed leadership benefit a school?

Distributed leadership gives qualified administrators meaningful responsibility and allows the head of school to focus on institutional direction, board relationships, and long-term planning. It also builds organizational capacity and helps the school maintain continuity during leadership transitions or periods of uncertainty.

About Randall Dunn

Randall Dunn has served as Head of School at Rye Country Day School in Rye, New York, since 2022, bringing more than 30 years of experience in independent school leadership. He previously spent over a decade as Head of School at Latin School of Chicago, where he advanced diversity and inclusion efforts and led a $50 million endowment campaign, and also held leadership roles at The Roeper School, Landon School, and Derby Academy. He holds a Master of Education from Harvard University and a Bachelor of Arts in Psychology from Brown University.