The Head of School’s Fundraising Playbook: Unlocking Donor Engagement & Strategic Giving

How can independent school leaders embrace fundraising as a core leadership skill, even without formal training?

In this episode, Jill Goodman, Jill Goodman Consulting, a consultant with decades of experience in independent schools and development strategy.

Jill breaks down how school heads can shift their mindset around fundraising, build stronger donor relationships, and ensure that development is not an afterthought but an integral part of school leadership.

Whether you’re a new head of school or a seasoned leader, this conversation offers actionable insights to strengthen your approach to development.

What You'll Learn from Jill Goodman:

• Fundraising Requires a Leadership Mindset – Heads of school must embrace bravery and curiosity to engage with donors effectively rather than viewing fundraising as an intimidating task.
• The Power of Vision in Development – A compelling vision fuels fundraising success by aligning donor passion with the school’s strategic priorities.
• Heads & Development Directors Must Work Together – Development directors should have a seat at the leadership table, ideally reporting at board meetings to build trust and align donor strategies with institutional goals.
• Avoid the ‘Big Fish’ Trap – Schools often chase high-profile philanthropists rather than focusing on cultivating relationships with their most dedicated supporters.
• Donors Aren’t an ATM for Budget Shortfalls – Treating donors as a quick fix for financial gaps can damage long-term relationships. Instead, schools should diagnose and address the root cause of financial challenges.

Discussion Prompts

• What are the most significant barriers that keep independent school leaders from embracing fundraising as part of their leadership role?
• How can school heads shift their mindset from fear to curiosity regarding donor relationships?
• Why is it essential for development directors to have a seat at the leadership table, and how can schools facilitate this?
• What are the risks of relying on donors to cover budget shortfalls rather than addressing systemic financial issues?
• How can schools better engage their existing donor base instead of chasing high-profile philanthropists?