Case Study:
How Vail Mountain School Turned a Bold Strategic Plan Into Execution

Vail Mountain School had just completed a year-long strategic planning process. They had a clear vision, ten bold initiatives, and a leadership team that was already stretched. Here's how the School Operating System helped them do both: execute the plan and lead the school.

The Challenge: An Ambitious Strategic Plan Needing a Cadence for Implementation

After completing a year-long strategic planning process, Vail Mountain School had a clear vision and bold priorities. The challenge was not the plan itself. It was how to implement it in a school where everyone already felt stretched thin.

Leadership meetings were frequent and thoughtful, but time together often drifted toward urgent issues. Important strategic work competed with daily operational demands. For Head of School Steve Bileca, the question wasn't just how to move the strategic plan forward. It was about building a system that could help his leadership team operate well across everything, from long-term priorities to the day-to-day realities of running a school, without exhausting the people responsible for carrying it out.

Defining the Right Work: From Strategy to Annual Goals

Before changing how the leadership team worked day to day, the focus was on deciding what actually mattered.

The strategic plan outlined ten bold initiatives over ten years. The immediate challenge was not ambition, but focus: determining which priorities deserved sustained attention in the year ahead.

The leadership team identified a small, focused set of annual goals that reflected both the long-term direction of Learning Elevated and the realities of running the school. These goals became the filter for decision-making, sequencing work, and aligning effort across the leadership team.

Turning Annual Goals into 90-Day Action Plans

Once annual goals were clear, the leadership team broke them into 90-day action plans. Each plan included a defined set of projects designed to move the school forward in a manageable, focused way.

Projects were intentionally tied both to the strategic plan and to the day-to-day business of running the school. Working in 90-day cycles created momentum without overwhelm and made progress visible.

Leadership Meetings as the Engine of Execution

With annual goals and 90-day projects clearly defined, leadership meetings became the place where real work finally got done.

This was a high-functioning leadership team doing serious work. The challenge wasn’t commitment or competence. It was having a shared system that made execution reliable week after week.

Before adopting the School Operating System, leadership meetings surfaced important work, but the pace and pressure of school life made it hard to sustain focus from week to week. Decisions were made, but without a shared system, longer-term priorities were often overshadowed by what felt most urgent in the moment.

The operating system changed that.

Leadership meetings shifted from open-ended discussion to disciplined decision-making. The team came in knowing exactly what mattered, what needed resolution, and what progress was expected. Meetings stopped being a drain on energy and became the primary driver of execution.

Early on, this shift felt uncomfortable. Changing how a leadership team meets is real change. But as the system took hold, something important happened. Meetings became sharper. Decisions stuck. Projects moved. The leadership team left meetings aligned, clear on next steps, and confident that the work would actually move forward.

In a school where time and bandwidth are always scarce, this change alone fundamentally altered how the leadership team operated.

What used to be a weekly check-in became the primary way strategic decisions were made, advancing the school’s most important work.

Steve Bileca,
Head of School,
Vail Mountain School

What Changed for the Head of School

Before adopting the School Operating System, leadership meetings carried a quiet tension. Even with a strong team, it wasn’t always clear whether the most important work would actually move forward.

Once the system was in place, that changed in meaningful ways.

“The School Operating System channels my leadership so that our team can focus on the true substance of our plan and our mission, providing the assurance that our collective energy is being directed toward the work that matters most.”

“It serves as a constant anchor for our most ambitious aspirations, ensuring that our daily efforts translate into genuine, measurable progress toward our long-term vision.”

Advice to Heads of School

For heads of school considering a School Operating System, the biggest shift is not technical. It's behavioral.

A School Operating System isn't only about strategy execution. It's about how the head and the leadership team run the school, balancing long-term priorities with the daily demands that compete for attention. That's where most leadership teams struggle, and it's exactly what the system is designed to address.

For many heads, the realization comes when they see that execution no longer depends on them personally pushing every priority forward.

Adopting a system requires a willingness to slow down before speeding up, to be explicit about priorities, and to hold steady to a cadence even when the day-to-day pressures of school life push in other directions. The early work is about building discipline, shared expectations, and trust in the process.

The payoff comes when the leadership team no longer relies on individual heroics to keep things moving. Instead, the system does the heavy lifting across the board, from strategic priorities to the operational realities of running a school every day. Priorities become explicit, progress becomes visible, and accountability becomes shared. Leaders spend less time chasing follow-through and more time exercising judgment, building relationships, and focusing on the work that only they can do.

Steve Bileca

Head of School,
Vail Mountain School

“The School Operating System has really helped to ground me as a leader and align my leadership of this team with the goals we all agree are the right ones to focus our energy on.”