"What Moneyball Teaches Boards and Heads" - Jim Best Delivers Keynote At ACIS Conference

VAIL, COLORADO — October 15, 2026 — What can the film Moneyball teach independent school leaders about effective governance?

Quite a lot, according to Jim Best, co-founder of The Leader Network, who delivered the keynote address, The Work Behind the Work, to 150 Heads of School, trustees, board chairs, and school leaders at the two-day Association of Colorado Independent Schools (ACIS) Leadership Conference in Vail.

Drawing on a memorable scene from Moneyball, Best described how Billy Beane, played by Brad Pitt, challenges his baseball scouts to stop focusing on replacing lost players and instead ask a more fundamental question: “What's the problem?”

It's a generative question—and one that school boards too often overlook.

Having served as a Head of School, trustee, and board chair, Best brought a unique perspective to the challenges facing today's independent school leaders.

When a headship struggles, he explained, what appears to be a performance problem is often a partnership problem. Strengthening that partnership requires three essential practices:

Work through the modes: First identify the real problem (Generative), then determine a course of action (Strategic), and finally ensure responsible oversight (Fiduciary).

Design the partnership: Establish clarity around roles, responsibilities, and decision-making authority.

Invest in relationships: Build the trust and mutual understanding that sustain effective leadership.

Throughout the keynote and subsequent workshops, Heads and trustees worked side by side, applying these principles to real leadership challenges and examining a deceptively simple question: Where does this decision live?

The sessions emphasized that effective school governance depends not simply on the performance of individual leaders, but on the quality of the partnership between them.

"Jim brought our Heads and trustees into the same conversation—and gave them practical tools to strengthen their partnership. And he did so in an engaging, insightful, and entertaining manner. It was exactly the right message for this moment in school leadership."

~Alan Smiley, Executive Director, Association of Colorado Independent Schools

Best's central message was clear: Name the real problem. Design the partnership. Lead it together.

That's the work behind the work—and the foundation of effective school leadership.