For the last two years, heads of school have been asking me about strategic planning.

And honestly? I never had a great answer.

Not because I didn’t believe in the work. I do, deeply. But because I hadn’t figured out how to approach it in a way that felt true to everything MoonshotOS stands for. I wasn’t going to offer something just because people were asking for it.

The answer came through the work itself.

What I kept seeing in the field

Running Business Model Retreats for private schools, I’ve watched boards and leadership teams interrogate their business model together, sometimes for the very first time, and seen something shift when they finally understand how the pieces connect. What’s driving revenue? Where costs are outpacing growth? Which enrollment assumptions haven’t been tested in years? Which opportunities are sitting right there, unacted on?

And working with schools on the School Operating System, I’ve watched leadership teams make real, visible progress toward their strategic priorities week after week. The rhythm of annual planning, 90-day sprints, and structured weekly meetings does something that good intentions alone cannot. It keeps strategy alive.

The more I did both kinds of work, the clearer one thing became: understanding your business model tells you where to go, but without a system to execute it, it’s really hard to get there.

Why the business model has to come first

Here’s what I mean by that, and why it matters.

Independent schools carry a set of financial and operational interdependencies that most traditional strategic planning processes treat as background noise. Enrollment trends, net tuition revenue, discount rate structure, staffing ratios, auxiliary revenue, competitive positioning. These aren’t just financial metrics. They are the architecture of your school’s ability to execute on any strategy at all.

When you do a rigorous analysis of that architecture before you build strategy, everything gets sharper. You can see where the strengths are and what’s worth building on. You can see where risk is accumulating before it becomes a crisis. You can identify which opportunities haven’t been acted on yet, and why. You can start to understand which strategic directions actually emerge from the foundation you have, and what realistic financial plans need to be built before you commit to them.

That last point is where a lot of strategic planning efforts come undone. Schools build beautiful plans, then discover the math doesn’t support execution. Or they commit to bold initiatives without fully understanding what the business model will and won’t sustain over a three-year horizon. Starting with the business model analysis closes that gap.

What MoonshotOS is now offering

That’s the thinking behind Strategy + The School Operating System.

It’s an eight-phase engagement that begins with aligning your board, moves through a rigorous analysis of your school’s business model, builds a three-year competitive strategy designed to win your market, and installs a leadership operating system that keeps your team executing against it week after week. Not a planning process with an end date. An operating system for your school’s leadership team.

I’m doing this work alongside David Hanson, the founder of Winthrop & Associates and former CFO at Phillips Exeter Academy. David has been conducting in-depth business model analysis for independent schools nationwide for years, and he is one of the most experienced financial strategists in independent education. His analytical depth, paired with MoonshotOS’s work in strategy, execution, and accountability, is what makes this engagement different from anything else in this space.

The point behind all of it

I believe independent schools change lives. And I’m committed to helping more of them stay strong enough to do it.

Strategic planning has been broken in this sector for a long time, not because the people doing it aren’t talented, but because the process usually starts too far downstream. It starts at vision and values when it should start at financial reality. It builds consensus when it should be building competitive advantage.

Strategy + The School Operating System is my answer to that. And it’s the fullest expression of why I founded MoonshotOS.

If strategic planning is on your radar for this year, I’d love to talk.

Learn more about Strategy + The School Operating System →