This episode was originally released in May 2025 and remains one of the most relevant conversations I’ve had about how boards think about advancement today. With the holidays here, I’m re-releasing a couple of earlier episodes that continue to spark strong conversations with heads and board members alike.

In this episode, Mattingly Messina, Founder of Throughline and MoonshotOS Advisor, breaks down the potentially misaligned relationship between boards and fundraising in independent schools.

Drawing from his experience as a trustee, former director of advancement, and consultant, he explains why the traditional board committee structure no longer serves schools and how it’s holding back strategic progress.

Mattingly offers a fresh framework for embedding philanthropy across all board priorities, shares how heads of school can manage up with confidence, and challenges schools to stop apologizing for fundraising.

If you’ve ever said, “My board doesn’t know how to fundraise,” this conversation is a must-listen.

What You'll Learn from Mattingly Messina:

Fundraising is a Board-Wide Responsibility: Advancement shouldn’t live in one siloed committee. Because funding affects everything, philanthropy must be embedded across all strategic focus areas.

Shift from Function to Focus: Instead of organizing board committees around operational functions like finance or development, structure them around strategic priorities. This creates cross-functional collaboration and deeper trustee engagement.

Stop Apologizing for Fundraising: Heads and leaders should confidently speak about fundraising. When it’s treated as essential and mission-driven, not uncomfortable or transactional, it changes how trustees show up.

Manage Up with Courage and Strategy: Heads often try to fix advancement quietly behind the scenes. Real change happens when they name the dysfunction, invite the board into a new paradigm, and align with the board chair on a shared vision.

Relationship Before Ask: Fundraising isn’t about the ask but the connection. When trustees speak authentically about why they believe in the school, that personal story is often more powerful than any solicitation.

Is It Time to Rethink Advancement at the Board Level? (From the Archives)

Independent School Moonshot Podcast