A Masterclass on the Changing Role of the Head of School
I've been thinking a lot about the conversations I've had with heads of school over the years.
The job feels heavier than ever, layered with responsibilities that stretch from vision and academics to enrollment strategy, fundraising, auxiliary programs, and investment oversight. And that list is only the beginning.
It's almost impossible to capture everything that lands on a head's desk, which is why the weight of the role is so deeply felt.
At the same time, that weight reflects the unique opportunity heads have to shape not only their schools today but their trajectory for years to come.
From Lead Teacher to Chief Executive
It's no longer just about being the head teacher in the traditional sense, focused on academics and culture. The headship role now carries the weight of running a complex institution.
Part of that complexity comes from the choices schools have made to stay competitive: expanding programs, investing heavily in facilities, and layering on services that raise families' expectations.
Why Schools Made These Choices
Those choices make sense in an environment where parents have more schooling options than ever: public, charter, magnet, micro, online, and homeschooling.
To remain relevant and compelling, schools expanded. They built things. They launched programs. They made commitments.
The Cost of Competitive Positioning
These expanded commitments and rising expectations come with a cost. Heads are under constant pressure to close the gap between tuition revenue and the true cost of running a school.
That means leading on enrollment strategy, philanthropy, auxiliary programs, and even managing investment portfolios. The business side of the job isn't a secondary concern anymore. For most heads, it's a daily one.
What Mark Crotty and I Talked About
This week on the Independent School Moonshot Podcast, I sat down with Mark Crotty, former executive director of NWAIS and now a partner consultant at Educators Collaborative, to talk about these pressures and how they've reshaped the headship role.
The episode, The Changing Role of Headship: Then vs. Now, is a deep look at why the job is both complex and complicated, and what that means for heads, boards, and aspiring leaders.
A Few Highlights from the Conversation
The headship role has become more institutional than pedagogical. Today's heads are responsible for an enterprise, not just a school community. That shift requires a different skill set than the role traditionally demanded.
Complex and complicated are not the same thing. Mark draws an important distinction between these two ideas, and why understanding the difference matters for how heads approach their work.
The loneliness of leadership is real. The top job can be isolating in ways that are hard to anticipate before you're in it. Intentional support systems aren't a luxury; they're a professional necessity.
Boards need to rethink how they hire and partner with heads. The expectations placed on heads have changed significantly. Board governance and support structures haven't always kept pace.
Aspiring leaders should ask hard questions before pursuing the role. Not every great administrator is the right fit for a headship. Mark offers a clear-eyed look at the questions worth sitting with before making that leap.
Why This Conversation Matters Now
Independent schools are navigating a moment of real pressure: enrollment competition, tuition sensitivity, facility debt, and the ongoing challenge of attracting and retaining great educators. The head of school sits at the intersection of all of it.
Understanding how the role has evolved isn't just useful for heads. It's essential for boards who are hiring, supporting, and evaluating them. And for aspiring leaders, it's a reality check worth having before stepping into the role.
Listen to the Episode
You can find the episode wherever you listen to podcasts:
If you're a head, aspiring leader, or board member, I think you'll find this one worth your time.
