Strategic Planning Depends on Middle Leaders

At some point this Summer, many senior leaders' will begin pondering how to get everything done next year, especially those things labeled as strategic. Strategic planning often begins at the senior leadership or Board level, but it succeeds or fails in the middle.

Middle leaders are the people who translate strategic priorities into daily practice. They notice where expectations are clear and where they are confusing. They see which initiatives are gaining traction and which are becoming noise. They understand how teachers are experiencing change, how families are interpreting decisions, and how students are being affected by the systems adults create.

That is why any evidence-based strategic planning process needs to consult middle leaders carefully.

I am currently supporting a school through a strategic planning process that is intentionally taking time. This is not because the school lacks urgency. It is because the community holds very different perspectives about what the school is becoming, what it needs to protect, and what it now needs to develop. Moving too quickly would risk narrowing the inquiry before the school understands the full nature of the challenge.

The process has been iterative by design. We have used divergent tools to surface assumptions, then gathered evidence to test those assumptions and consider alternative explanations. As new perspectives emerge, the questions become sharper.

Some of those questions are about teaching consistency from the earliest years through graduation. Others are about community connection, admissions narratives, financial sustainability, student agency, wellbeing, facilities, and future readiness. At first glance, this can feel too broad. Leaders may reasonably ask: where is the target?

But in a school community, the target cannot be chosen only by reducing a list of priorities. Each question will be understood differently by teachers, parents, students, senior leaders, Board members, admissions teams, and alumni. Middle leaders are often best positioned to help interpret these differences because they sit close to both strategy and practice.

They can help senior leaders understand where change is likely to meet momentum, resistance, confusion, or fatigue. They can identify the pivot points where a shift in practice, communication, structure, or support could influence several parts of the school at once.

As schools prepare for a new year, one of the most useful questions senior leaders can ask is: how are we preparing our middle leaders to lead the strategic work ahead?

This means more than sharing the plan once it is finished. It means involving middle leaders in the inquiry, helping them understand the evidence, clarifying what they are being asked to lead, and giving them practical tools to support their teams.

Strategic change depends on coherence. Coherence depends on the people who help others make sense of the work.

For schools that want to strengthen this layer of leadership, Middle Leaders must have the clarity of strategic focus, within which they need to act. For those ready to act, we offer The MiLL, Middle Leader Lab, designed to help middle leaders move from managing tasks to leading strategic change. Through practical tools, live learning, peer connection, and focused leadership development, The MiLL helps schools empower the leaders who turn strategy into meaningful practice.

​Join the MiLL waitlist if you haven't already.