Is Your School Ready to Change? Five Tests Every Leadership Team Should Run

Someone I worked with years ago recently asked me a simple question: What's the best part of building MoonshotOS?

I didn't have to think about it. The best part is building a community of schools that are genuinely committed to iterating their business models for long-term sustainability. That work matters, and being close to it is the part of this job I find most meaningful.

But here's what I've learned from sitting with schools through that process: wanting to change and being ready to change are two different things.

The Readiness Question

Any school contemplating meaningful business model change has to clear a set of hurdles before the work can actually take hold. The strategy might be sound. The case for change might be compelling. The data might be clear.

And yet the transformation stalls or never fully launches because the internal conditions aren't right.

When I talk with schools about this, I consistently return to guidance from Roy Ballentine, Chair of the Board of Brewster Academy. At TransformED 2023, an online conference I hosted, Roy shared five tests that schools should run before committing to significant change. His framework came directly from Brewster's own experience iterating its business model, a process that ultimately led to the launch of a network of campuses in Spain.

If you want to hear Roy walk through this directly, I made that session available as a free short course. It takes under 50 minutes and gives you a real feel for the kind of thinking that happens inside Moonshot Lab. You can access it here.

The Five Tests

These aren't a checklist you complete once and set aside. They're a framework for honest reflection, the kind of structured self-assessment that separates schools that successfully drive change from those that invest energy in a process that ultimately stalls.

Test One: Continuity of Leadership

Is there a long-term view with stable leadership in place to champion and sustain the change?

Meaningful business model transformation takes years, not months. If the leadership driving the work is likely to turn over before the initiative matures, the change loses its anchor. Schools that successfully navigate significant transformation almost always have a head of school and a board leadership structure that can sustain the vision over time, even when momentum is difficult to maintain.

This is also one of the core questions that informs the Strategy + School Operating System. Strategy built without stable leadership to execute it tends not to survive contact with the real demands of the school year.

Test Two: Cohesive Leadership Team

Does the school have a strong leadership team that works in unison toward common goals?

A compelling vision that lives only in the head of school's office doesn't move a school. Change at any real scale requires a leadership team that shares the same priorities, communicates clearly with one another, and pulls in the same direction even when the work gets complicated.

This test is worth sitting with honestly. A team that performs well in normal operations but fractures under pressure is a meaningful risk factor for any significant initiative.

Test Three: Board and Leadership Collaboration

How effective is the collaboration between the board and the school's leadership team?

This one surfaces more tension than the others in my experience. Boards and leadership teams that operate in silos, or where trust has eroded on either side, create a fragile foundation for change. The complexity of a significant strategic initiative tends to amplify existing dynamics, for better or worse.

Effective board and leadership collaboration doesn't mean the board and the head agree on everything. It means there's a productive working relationship where both sides contribute their distinct perspectives, the board governs rather than manages, and decisions get made with appropriate alignment rather than in opposition.

Test Four: Compelling Value Proposition

Can the school clearly articulate what unique value it offers families, and are families willing to pay for it?

This is a marketing and strategy question as much as it is a readiness question. Schools that can answer it clearly are in a very different position from schools that are still working through what makes them distinct in their market.

Brewster's global network expansion was grounded in a clear answer to this question. The school understood what it offered, who valued it, and how a new geographic footprint could amplify rather than dilute that value. That clarity was a prerequisite, not a byproduct, of the initiative.

The Business Model Retreat is often where this work gets done in a structured way, bringing leadership and the board together to build a shared, honest picture of the school's value proposition and competitive position.

Test Five: Willingness to Take Risks

Is the school community prepared to step outside its comfort zone and accept the uncertainty that comes with significant change?

This is the test that's hardest to evaluate from the inside. Schools, like most institutions, are culturally inclined toward stability and continuity. The people who are most invested in the organization are often the ones most attached to how it currently operates.

Willingness to take calculated risks isn't the same as recklessness. It's the organizational capacity to hold uncertainty, make decisions without complete information, and accept that the path forward will require adjustments along the way. Schools that have built this capacity, usually through smaller iterative changes over time, are substantially better positioned to drive larger transformation when the moment calls for it.

What Brewster's Story Illustrates

Brewster Academy's expansion into Spain wasn't a bold bet made on instinct. It was the outcome of rigorous self-assessment, careful planning, and a leadership team and board that had done the hard work of building the internal conditions that make change possible.

The five tests Roy outlined aren't just a reflection of what Brewster did. They're a framework for what any school needs to examine honestly before committing to significant change.

The schools I've seen navigate transformation most successfully aren't necessarily the ones with the most resources or the most favorable market position. They're the ones that were clear-eyed about their readiness, addressed the gaps they found, and built the internal alignment to carry the work through.

A Good Starting Point

If your school is contemplating significant change, or if you want to understand where your current leadership infrastructure stands, two resources are worth your time.

The Business Competency Self-Assessment gives you a baseline read on where you stand across the eight competencies that support this kind of strategic work. And Roy's session on Brewster's transformation, available as a free short course, is worth the 50 minutes it takes to get through. Access it here.

The question isn't whether your school should be thinking about its business model. In the current environment, that conversation is overdue at most schools. The more useful question is whether you have the conditions in place to do something productive with the answer.