I have a simple question for you: Who do you turn to when things get hard?

Not when you need information. Not when you need a decision made for a committee. When you genuinely need someone to help you think through something difficult, push back on an idea you've become too attached to, or remind you that you're on the right track when the pressure is building.

For most heads of school, the honest answer is: not enough people.

That's the problem I want to talk about today.

The Isolation Problem in School Leadership

Being a head of school is one of the most complex leadership roles in any sector, not just education. You're running a mission-driven business with tuition-dependent revenue, a faculty culture that requires constant care, a board you report to, parents who have strong opinions, and a community that expects you to be steady regardless of what's happening behind the scenes.

And you're often doing it without a true peer in the building.

That isolation isn't unique to school leadership, but it's more pronounced than people realize. I've heard it consistently across the interviews I've done with heads of school, and it came up again during the ACIS Leadership Conference recently. Leaders who appear confident and capable from the outside often operate with very little real support on the inside.

This is exactly why I spend so much time thinking about the eight essential business competencies for independent school leaders. Building business fluency matters, but so does building the right support structure around you. One without the other leaves you exposed.

What a Personal Board of Directors Actually Is

I first encountered the phrase "personal board of directors" a couple of years ago, and it clicked immediately. As I reflected on it, I realized I'd had one for years without naming it that way. I'd always surrounded myself with people who gave me honest feedback, pushed me when I needed it, and supported me when things were difficult.

The concept is straightforward: a small, trusted group of people in your life whose job is to help you grow, hold you accountable, and offer perspective that you can't generate from inside your own head.

They're not people who report to you. They're not your board of trustees. They're not your leadership team. They're people who have enough distance from your day-to-day to offer genuinely objective input.

Why This Matters More in Independent Schools

Running an independent school requires fluency in areas that most educators were never formally trained in: financial strategy, enrollment modeling, board dynamics, marketing, and operations. That's a lot to navigate, and much of it is learned on the job, under pressure, in real time.

Having the right people around you doesn't just help you feel less alone. It actively improves the quality of your decisions.

How to Think About Who Belongs on Your Board

When I started to examine my own personal board more intentionally, I found it helpful to think in roles rather than names. Here's how I've structured it.

The Accountability Partner

This is the person who keeps you honest about your goals. They're not there to validate you. They're there to make sure you're doing what you said you were going to do and to challenge you when you start rationalizing your way out of hard commitments.

Accountability is one of the core functions of the School Operating System I build with school leadership teams. The same principle applies at the individual level. Without someone holding you to your own standards, it's easy to drift.

The Mentor or Coach

You need at least one person on your board who has navigated the road you're on. Someone who has made the hard calls, survived the difficult board relationships, led through financial pressure, and come out the other side with perspective.

This person doesn't need to have all the answers. What they offer is pattern recognition. They've seen versions of your problem before, and they can help you see it more clearly.

The Supporter

Every board needs someone who is simply in your corner. Not unconditionally, but genuinely. Someone who reminds you of your worth when self-doubt creeps in and who helps you maintain perspective when you're in a hard stretch.

For many people, this is a spouse, partner, or close friend. The key isn't the relationship type. It's the quality of the trust.

Your Board Should Be Bigger Than Three

Those three roles are the foundation, but a strong personal board of directors expands from there. You want people who bring varied perspectives, different areas of expertise, and different relationships to risk and change.

Think about who in your life challenges your assumptions in productive ways. Who has domain expertise you lack? Who has led through something you haven't faced yet? Who tells you the truth even when it's uncomfortable?

A strong board isn't a collection of supporters. It's a collection of people who make you sharper.

Two Things Worth Doing Now

Once you've started mapping out who's on your personal board, two actions matter.

First, tell them. Most people don't know they're playing this role in your life. Naming it changes the relationship. It signals that their input matters and that you're paying attention to it. That clarity tends to strengthen the dynamic in ways that benefit both of you.

Second, ask yourself how you're showing up for others. The best version of this isn't a one-way support structure. Think about who has named you as a trusted advisor, even informally. Think about where you're equipped to offer accountability, mentorship, or honest feedback to someone else. Building these relationships is reciprocal work.

Where Moonshot Lab Fits In

One of the things I designed Moonshot Lab to do is give school leaders a structured version of this kind of peer support. Members gain access to a community of independent school leaders navigating similar challenges, a cohort of other heads of school for peer accountability, and direct input from nine advisors who deeply know the independent school context.

It's not a substitute for your personal board. But for many members, it becomes part of it.

If you're a head of school who feels like you're operating without enough of the right people around you, that's worth paying attention to. The role is hard enough even with support. Without it, every decision carries more weight than it should.

One Question to Sit With

So, who's on your personal board of directors?

Take a few minutes this week to actually write it down. Who fills the accountability role? Who offers mentorship and pattern recognition? Who is genuinely in your corner?

And then ask yourself: are there gaps? Are there roles you've been filling alone that would be better served by the right person?

You don't have to solve it all at once. But naming it is a better starting point than hoping the right support shows up on its own.

If you're curious how the eight business competencies framework applies to your own leadership development, the self-assessment at that link takes about ten minutes and gives you a clear picture of where you stand.