Why Being a Head of School Might Be the Toughest Job I Know
Over the years, I've come to deeply appreciate the people who sit in the head of school's seat.
But the more I work alongside school heads, the more convinced I become: this isn't just one of the most challenging jobs in education. It's one of the hardest jobs, period.
The complexity is staggering. Heads of school juggle multiple constituencies, revenue streams, retention challenges, fundraising, academic programming, strategic planning, and more. It's the kind of role that could make your head spin on any given day.
And yet, the heads I know manage all of this with incredible grace and deep care for their communities.
The Learning Curve No One Fully Prepares You For
That grace doesn't mean the path to the seat is easy. There are steep learning curves, especially on the business side of leadership.
I hear it regularly from heads who are newer to their roles: the financial skills required caught them off guard. Managing up, particularly with the board, was something they expected but weren't quite ready for in practice.
This isn't a reflection of their capability. The head of school role has expanded faster than the support structures that exist to prepare people for it. The business side of the job demands financial acumen, strategic thinking, and operational clarity that most career paths in education simply don't build along the way.
If that resonates, the MoonshotOS Business Competency Self-Assessment is a useful place to start. It covers eight competencies that matter most to independent school leaders and takes about ten minutes to complete.
A Conversation Worth Having: What Boards Are Actually Looking For
That's why I'm excited to share this episode of the Independent School Moonshot Podcast: What Boards Look for in Today's Heads of School.
This episode features our sponsor John Farber, Managing Director at RG175 and former head of school. John has led close to 40 head of school searches and brings a perspective you rarely get access to: what boards are actually evaluating, and what candidates are consistently underprepared for.
It's a conversation I think every head, aspiring head, board member, and senior administrator should hear.
The Five Things That Came Up Again and Again
Here are the top takeaways from our conversation:
Business acumen is no longer optional. Every search committee John works with wants it. Not at a CFO level, but at the level where a head can read a balance sheet, understand enrollment economics, and talk credibly about the school's financial health.
Strong board relationships can make or break a head's success. It's not just about managing up. It's about building a working relationship with the board that creates clarity, trust, and shared direction from day one.
Many aspiring leaders are ready to lead, but haven't had the chance to build their business skills. This isn't a character flaw. It's a structural gap in how school leaders are developed. The good news is it's addressable.
Strategic clarity is essential for execution and alignment. Boards aren't just hiring someone to manage the school. They're hiring someone to lead it somewhere. If you can't articulate a clear direction, that lands hard in a search process.
Cultural fit matters more than geography or resume pedigree. Schools have distinct identities. Boards want someone who gets theirs, not just someone who checks every credential box.
What This Means If You're Preparing for the Head Role
If you're an aspiring head working toward your first opportunity, John's perspective is a gift. You now know what the search committee is looking at.
The business side is the one place most aspiring leaders can get ahead of the curve before they're sitting across from a board for the first time. That means building fluency in financial statements, enrollment modeling, and how a school's business model actually works.
The Moonshot Lab was built for exactly this. It's a membership community where independent school leaders at every stage build business fluency through expert coaching, peer accountability, and practical frameworks. Aspiring heads use it to close the skills gap before the opportunity arrives. School leadership teams use it to build shared language around strategy and operations.
What This Means If You're Already in the Seat
If you're a sitting head, the takeaways here aren't just about the search process. They're a useful diagnostic for your current reality.
Are you and your board operating from the same strategic picture? Is there clarity between you on priorities, direction, and the health of the business model? If not, that's worth addressing before it becomes a governance problem.
Starting with the Business Model
One of the things I've come to believe strongly is that strategic clarity in independent schools has to start with an honest look at the business model. Not mission. Not programming. The underlying economics of how the school operates, where it's healthy, and where it's exposed.
That's the starting point of the Business Model Retreat, a single-day facilitated session I run with school leadership teams. It gives you the diagnostic picture that should sit underneath any meaningful strategic conversation.
For schools ready to go further, the Strategy + School Operating System takes that business model analysis all the way through a full strategic planning process and installs the execution infrastructure to make the strategy actually run.
Listen to the Full Episode
If you're a head of school, aspiring head, board member, or just curious about what it takes to lead a school today, I think you'll find this conversation worth your time.
John has a perspective most people never get access to. He's been on the other side of nearly 40 searches and speaks candidly about what he sees, what boards want, and what candidates consistently get wrong.
Listen on your preferred platform:
Or visit the full episode page for additional takeaways and supporting resources:
