A Year of Strategic Wonder: Creating Space for Curiosity in School Leadership
Independent schools pour tremendous energy into leadership, yet senior administrators rarely have what they need most: space. Space to reflect, question, imagine, and explore—without having to solve a crisis, approve a hire, adjust a schedule, or navigate disagreement.
Most administrative meetings are dominated by decision-making mode, where urgency rules and consensus is required. What almost never appears on the agenda is time to wonder.
This year, I have the privilege working with a school whose head of school made a different choice. Their goal is not to prepare for strategic planning or generate a list of initiatives. They simply want to give their leadership team the gift of structured spaciousness—and the experience has been quietly transformative.
Why Wonder Matters
Strategic wonder offers something school leaders almost never receive: freedom from the tyranny of the immediate.
When administrators are not solving today’s problems, they can ask bigger, more revealing questions:
Who are we becoming as a school?
What do families find truly compelling?
Which assumptions deserve to be challenged?
What possibilities emerge when no decision is required?
What external forces are shaping us—whether we acknowledge them or not?
Wonder isn’t an escape from decision making. It’s how leaders deepen the insight and shared understanding that make future decisions wiser. And importantly, wonder has inherent value, even when it leads to no plan at all.
A Year of Strategic Wonder: What It Looks Like
For this engagement, we designed an eight month experience rooted in deep inquiry, broad conversation, and slow thinking. Across many topics such as identity, enrollment, culture, and programming, the guiding principle remained the same:
No decisions. No votes. No action items. Just disciplined curiosity.
Our wondering has taken us through several rich arcs:
Listening for Identity: Conversations with leaders, faculty, parents, and students; campus walks; and reflective dialogue to understand the school at its best.
Exploring What Should Endure and What Might Evolve: Considering traditions, structures, and rhythms: what remains essential, and what might look different if the school were founded today.
Examining External Forces Without Urgency: Demographics, college value perceptions, student life pressures, and enrollment trends explored with attention—not alarm.
Introducing New Lenses for Institutional Thinking: Understanding how academics, finance, advancement, and enrollment intersect; using SEM as one lens among many.
Understanding What Families Find Compelling: Parent interviews and internal reflection to surface the attributes that genuinely drive enrollment decisions.
Imagining Multiple Futures: Not predicting what the school will become, but considering what it could become—each scenario revealing identity, aspiration, and possibility.
The Value of Strategic Wonder
Strategic wonder delivers powerful benefits:
Clarity – Surfacing truths that daily operations bury.
Alignment – Building shared perspective across administrative roles.
Renewal – Reenergizing leaders by escaping crisis-driven thinking.
Insight – Revealing patterns and possibilities otherwise overlooked.
Culture-Building – Strengthening trust, curiosity, and collaboration.
Wisdom – Encouraging long-horizon thinking in a rapidly changing landscape.
What It All Means
Strategic wonder is not preparation for something else; it is a powerful experience in its own right. It invites leaders to slow down, look closely, think generously, and imagine boldly. And when a leadership team spends a year in disciplined curiosity, the effects linger long after the conversations end.
At 20 More Students, we believe deeply in the value of this work. While enrollment strategy is at our core, helping schools cultivate a year of strategic wonder is one of the many ways we support leadership teams across the country. If your school is interested in exploring what a year of wondering could make possible, we’d be glad to help you begin.
