After more than 80 conversations with heads of school across the country, a clear picture has emerged.

Almost every leader I've spoken with brings up the same pain: hiring is harder than it used to be, and keeping great people is even harder. The instinct is to treat this as an HR problem, a compensation problem, or a culture problem. And sometimes those factors are in play.

But in reflecting on these conversations, I've come to a different conclusion. The difficulties schools face with staffing are not isolated issues. They are direct symptoms of deeper pressure on the traditional independent school business model.

That distinction matters because the solution depends entirely on how you diagnose the problem.

The Promise Independent Schools Make

Independent schools make a significant promise to families: a meaningful, developmental experience for their children, whether academic, social, athletic, artistic, or some combination of these.

I know this firsthand. I benefited from that kind of experience, and it's a big part of why I've spent my career working in and around independent schools.

That promise is real. And it is worth fighting for.

But the environment in which schools fulfill that promise has changed substantially. Families have more choices than ever: public schools, charter schools, online learning, microschools, homeschooling cooperatives. The competitive pressure on independent schools to stand out has intensified.

The natural response has been to add. More programs. More services. More offerings to attract and retain students. And in many cases, those additions have made schools genuinely better.

The challenge is that additions rarely come with proportional increases in revenue. And that gap creates real strain on staffing.

Adding Value Without Adding Capacity

Here is where the business model pressure becomes most visible.

When schools layer on new programs and responsibilities without adjusting the revenue model, the burden falls on the people doing the work. Teachers and staff are asked to do more. In many cases, things are not removed from their plates to make room for the new priorities.

This is not a judgment on school leaders. It is a structural problem. The instinct to expand value for families is correct. The issue is that the business model has not kept pace with the expanded scope of what schools are trying to deliver.

The result is predictable. Workloads grow. Expectations increase. Burnout follows. And talented people leave.

If you want to understand why retention is hard, start there.

The Changing Relationship with Work

There is another factor compounding this challenge, and it is not going away.

The workforce has changed. Millennial and Gen Z candidates approach work differently than prior generations. They value flexibility, autonomy, and alignment between their values and their employer's mission.

Some of that shift actually works in independent schools' favor. Mission-driven work is compelling to this generation. But the flexibility piece creates friction. Remote and hybrid arrangements are genuinely difficult to offer in a school setting where presence is fundamental to the experience.

That reality shrinks the applicant pool. And it makes the hiring conversation harder, even when everything else about the school is strong.

This is not something schools can solve with better recruiting alone. It requires thinking about how the school is structured, what it asks of people, and whether the model supports long-term sustainability for those working within it.

When the Model Can't Support the Mission

The core of the dilemma is this: the traditional independent school business model was not designed for the environment in which schools are operating today.

Tuition-dependent revenue with rising discount rates, fixed cost structures dominated by compensation, and limited non-tuition revenue streams create an inherently fragile financial situation. When that fragility meets an expanded program scope and a more demanding labor market, something gives.

Usually, what gives is the people.

This is why I keep returning to the business model as the starting point for any meaningful conversation about staffing sustainability. You cannot build a long-term retention strategy on top of a model that cannot support it financially. And you cannot make smart decisions about what to add, what to cut, and where to invest without first understanding where your model is strong and where risk is quietly building.

The MoonshotOS Business Model Retreat was designed for exactly this. It is a single-day working session that maps your school's business model, surfaces pressure points, and identifies real opportunities. Many schools use it as the starting point for a more intentional conversation about sustainability and growth.

A Collective Challenge, Not an Individual Failure

One thing I want to be clear about: this is not a story about school leaders doing things wrong.

The heads I have spoken with are talented, committed, and working hard in a genuinely complex environment. The job has expanded faster than the support structures around it. That is a sector-level challenge, not an individual one.

What it calls for is an honest look at the model, not a harder push within the existing one.

The path forward requires leaders to step back and ask the structural questions. What are we actually promising families, and is our model built to deliver it sustainably? What are we asking of our faculty and staff, and have we removed anything to make room for what we have added? Where are we generating revenue, and where are we leaving it on the table?

These are not easy questions to answer alone. That is why I built Moonshot Lab: a community of independent school leaders working through exactly these challenges together, peer-informed and built around the belief that schools do better when they are not figuring this out in isolation.

Diagnosing the Problem Is the First Step

The optimism I carry into this work comes from what happens when school leaders clearly name the business-model problem.

Once the diagnosis is honest, plans can move forward. Decisions become clearer. Priorities get sharper. And the work of building long-term faculty and staff sustainability becomes possible in a way it is not when you are treating symptoms rather than causes.

If your school is wrestling with hiring and retention, start with the model. Not with the job descriptions, not with the compensation benchmarks, not with the exit survey data. Those things have value, but they will not show you the underlying dynamic.

The model will.

If you want a structured way to do that work, the Business Model Retreat is a good place to start. And if you are looking for a longer-term framework for applying what you learn, the School Operating System provides the infrastructure to move from insight to action.

What I Would Love to Hear From You

These conversations have shaped how I think about this problem, and I want them to continue.

What are you seeing at your school? Are there hiring or retention dynamics that feel unique to your context? Have you found approaches that are actually working?