Leading with Curiosity and Connection

Reflections on guiding schools with empathy, purpose, and openness

I’ve been thinking deeply these past few weeks (perhaps even more than usual) about what it means to be a school leader right now. Being away last week at the annual NYSAIS Heads of School Conference gave me the space to step back from the daily rhythm of Parker and reflect on the larger landscape of education and leadership today.

The world feels particularly charged at the moment. Everywhere we turn, issues that once seemed neutral or shared have become politicized: how we teach, what we teach, even what kindness or community means. For those of us leading schools, this presents both a profound challenge and an opportunity to hold steady to our values while keeping our communities open, curious, and compassionate.

At Parker, our mission—joy and discovery unite our community in deep intellectual engagement that nurtures confidence, compassionate citizenship, and a sense of belonging—isn’t just a statement on the wall. It’s a compass guiding everything we do. In times when division seems to dominate, we are called to be the counterbalance, a place where children learn to listen, to think critically, to empathize, and to engage respectfully with difference.

But this isn’t easy work. It asks educators, parents, and leaders to model what we hope to see in our students and in the compassionate citizens we aim to help them become: to stay curious when it would be easier to close off, to seek understanding when disagreement feels personal, and to lead with both clarity and humility.

At the conference, we heard from the inspiring President of Oberlin College, Carmen Ambar, who shared about a program called Sustained Dialogue. In this initiative, student-led groups meet regularly for honest, vulnerable conversations across lines of difference, not to persuade or agree, but to listen, connect, and understand. Through these dialogues, students are learning how to engage with empathy and curiosity, even when they disagree. Programs like this remind me how essential it is for schools to create spaces where young people can practice true listening and build bridges of respect in a divided world.

I found myself surrounded by other heads of school who are navigating these same tensions. The conversations were honest and deeply grounding. Many of us spoke about the challenges of leading schools in times of polarization, as well as the strength that comes from returning again and again to the core purpose of our work: to nurture thoughtful, compassionate young people who can help build a better world.

Being a school leader today means holding complexity with grace. It means knowing that our influence reaches beyond curriculum or policy; it extends into the kind of tone we set, the conversations we invite, and the example we model for our students and our communities.

As I return to campus next week, I feel renewed in my commitment to that work. The world may be noisy, but our schools can still be places of calm, of inquiry, and of connection—places where young people learn that belonging and difference are not opposites, but partners in the shared work of learning and living together.