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

In this episode, John Farber, former head of school and current managing partner at RG175, shares hard-earned insights from conducting over 60 leadership searches.

He dives deep into the evolving expectations for heads of school, especially the growing demand for business acumen and strategic thinking.

From managing up to building strong board relationships and financial fluency, John explores what aspiring heads must understand to thrive. He also candidly reflects on why tenure has shortened and how boards can better support heads.

This is essential listening for anyone exploring or supporting the headship path.

What You'll Learn from John Farber:

Business acumen is no longer optional. Heads must understand budgets, financial levers, and how to partner with their CFO and board.
Managing up is a critical leadership skill. Strong board relationships enable heads to lead with confidence rather than fear.
Most aspiring heads are underexposed to key responsibilities. Strategy, governance, and operational leadership are often learned on the job.
Strategic clarity supports execution. When schools socialize their strategy and use it as a North Star, decisions are easier, and leadership alignment improves.
Cultural fit is essential for success. Heads who align with the school’s culture have greater longevity and fulfillment.

Discussion Prompts

How does your board currently assess business acumen during head or leadership searches?
What support structures exist for new heads to develop their financial and operational fluency?
How can your school better educate faculty and staff about the board’s expectations of the head?
What would building a truly supportive board-head relationship at your school look like?
How can you help aspiring leaders at your school get real exposure to board dynamics, finance, and governance?

What Boards Look for in Today’s Heads of School (From the Archives)

Independent School Moonshot Podcast