Through customized strategic retreats for Board and administrative leadership teams, 20 More Students partners with remarkable schools to create powerful breakthrough experiences that position schools to successfully navigate an array on institutional challenges.

This day-long retreat invites administrative leaders and trustees into a guided experience of strategic wonder—an immersive opportunity to step back from day-to-day pressures and engage deeply with the school’s identity, market realities, and future readiness.

Examples of Exercises Included in the Strategic Wonder Retreat

Push–Pull–Habit–Anxiety Mapping

Leaders identify what is pushing the school to change (pressures and frustrations), what is pulling it toward the future (aspirations and opportunities), the habits that create inertia, and the anxieties that make change feel risky. This structured dialogue surfaces unspoken tensions and helps the group name what feels most urgent — and most within their power to address.

External Forces Deep Dive

Using current demographic, economic, workforce, and market data, participants assess how well the school’s internal systems are positioned to respond. In small groups, leaders evaluate whether their institution behaves like a “living system” — sensing change early and adapting deliberately — or whether it reacts episodically to external pressure.

The Black Swan Scenario: The Compressed Choice Moment

Participants are presented with a plausible 8–10 year future scenario in which demographic contraction, economic shifts, and intensified competition compress enrollment decision-making. In response, leaders consider: What should we double down on? What assumptions may no longer hold? What might we need to reimagine — or release? This exercise is not about fear; it is about strengthening foresight and institutional resilience before pressure mounts.

Together, these and other exercises create a disciplined but imaginative space — one that helps boards and leadership teams think clearly about identity, distinctiveness, sustainability, and the systems required to thrive in the decade ahead.

If you’re looking to create a powerful strategic experience for your team, but can’t find the time, 20 More Students is glad to handle all of the details. Book a call anytime to discuss your needs.

Through a sequence of facilitated conversations and exercises, participants explore what makes the school most itself, where tensions exist between preservation and evolution, and how external forces—demographic shifts, family economics, workforce challenges, and changing expectations of schooling—are reshaping the landscape. The retreat moves from reflection to foresight, asking leaders to examine whether the school’s systems function as a living, adaptive organism or remain optimized for a less volatile era, culminating in a carefully constructed “black swan” scenario that pressure-tests assumptions about enrollment, value, and sustainability.

By the end of the day, participants leave with a shared language, clearer identity anchors, and a stronger sense of what the school must double down on, reimagine, or release in order to remain distinctive, resilient, and mission-aligned in the decade ahead.