One of the most important distinctions I have learned as a school leader is the difference between a plan and a strategy. Schools are very good at making plans. Calendars fill quickly, initiatives multiply, and activity becomes a substitute for direction. Strategy requires something more difficult: choice.

True strategy is about deciding what a school will prioritize and, just as importantly, what it will not. This idea is captured clearly in the Roger Martin video, A Plan Is Not a Strategy, which challenges leaders to move beyond lists of projects and toward disciplined thinking about positioning and purpose.

I have seen schools mistake motion for progress. Without a clear strategy, even well-intentioned initiatives can pull an organization in competing directions. Strategic planning is the moment when leadership slows the pace, asks harder questions, and aligns effort around a shared vision.

During Oak Hill’s strategic planning process, we spent significant time resisting the urge to simply catalog everything we wanted to do. Instead, we asked where the school needed to focus its energy to thrive over the long term. That required honest reflection, open conversations, and a willingness to name tradeoffs.

This distinction matters deeply for boards and Heads of School. A plan without strategy creates exhaustion. A strategy without discipline creates frustration. When strategy is clear, it becomes a filter for decision-making. Leaders can explain why certain opportunities are pursued and others are deferred, not based on preference but on purpose.

For me, strategic leadership means helping communities understand that strategy is not about doing more. It is about doing what matters most, consistently, over time. When schools embrace that mindset, they move from reactive planning to intentional growth.