As people step into independent school leadership, particularly if they aspire to become a Head of School, one of the most important and often undervalued aspects of the role is fundraising. For many new leaders, fundraising can feel intimidating, uncomfortable, or even misaligned with why they entered education in the first place. In my experience, it does not have to be that way.
Throughout my career, I have been fortunate to work alongside exceptional development directors and Heads of School who helped reframe what fundraising is and what it is not. One of the most important lessons I learned early on is this: fundraising is not about asking people for money. When I share that, it often gives new heads pause. If you are not asking for money, then what are you doing?
Fundraising is about creating a culture of philanthropy, or more simply, a culture of giving. At its core, it is about helping people connect their intrinsic desire to give back with work that feels meaningful and aligned with their values. Most of us feel a deep pull to support causes we believe in. My wife and I have long supported organizations that resonate with us, not because we were asked, but because we felt inspired to contribute to something larger than ourselves.
Several years ago, I read The Generosity Network, and it profoundly shaped how I think about fundraising. The book reinforced the idea that generosity is not something to be extracted, but something to be activated. When people are invited into a vision they believe in, giving becomes a natural expression of shared purpose rather than a transactional exchange.
The role of a Head of School in fundraising, then, is to articulate a clear and compelling vision for the school and to invite others to participate in bringing that vision to life. When fundraising is grounded in purpose, authenticity, and trust, it becomes deeply relational. You are not asking for money. You are inviting partnership.
This shift in mindset is transformative. It allows school leaders to engage confidently and honestly with families, alumni, and community members. It also creates space for generosity to emerge naturally, rather than from pressure or obligation. When schools lead with clarity, mission, and heart, philanthropy follows.