Many Heads of school arrive at the role through a traditional and deeply meaningful pathway. I did. I began as a classroom teacher, moved into school administration, and eventually stepped into headship. That journey provides an invaluable, holistic understanding of students, teaching, families, and the daily life of a school. You know what it means to be in the trenches, and that perspective matters.
What changes dramatically, however, when you become a Head of School is the scope of the role. As a division head or assistant head, I was primarily an educational leader. As a Head of School, I became both an educational leader and the chief executive of a complex organization. The skill set required expanded quickly, particularly in the area of financial management.
I was fortunate in two important ways. First, I had long been interested in personal finance and investing, which gave me a baseline level of comfort with financial concepts. Second, early in my leadership career, I was intentional about learning. When I became an Assistant Head of School in Lake Forest and knew that headship was a future goal, I sat down with our CFO and asked him to teach me everything he could about independent school finances. We met reguarly over a number of months and that decision proved foundational.
There is a great deal about a school’s financial life that remains invisible until you are sitting in the head’s chair. I learned about managing bond obligations, understanding loan covenants, negotiating leases, planning for capital improvements, working with insurance carriers on comprehensive coverage, and understanding how fundraising fits into the broader financial strategy. I gained experience thinking through tuition increases, staff compensation, long-term sustainability, and how financial decisions ripple through culture and mission.
Later, working alongside exceptional CFOs, I continued to ask questions and deepen my understanding. Over time, I found myself entering finance committee meetings not with trepidation, but with curiosity and confidence, able to engage thoughtfully alongside trustees with deep financial expertise.
For aspiring and new heads of school, I strongly encourage intentional learning in this area. Resources like Peter Baron’s Think Like a Head of School course does an excellent job of demystifying the independent school business model.
Strong financial leadership is not about being a CFO. It is about understanding the system so you can ask thoughtful questions, make principled decisions, and steward the school’s resources with care. That understanding is essential to leading a healthy, mission-aligned school over the long term.