What does a basketball court have to do with leading a school district? More than you might think. In this conversation, we sit down with Chris Kennedy, West Vancouver’s Superintendent of Schools, whose earliest leadership lessons didn’t come from policy binders or strategic plans, but from coaching—reading a room, building trust, and knowing when to step in and when to step back.
We start with family roots in teaching and an unusually early path into leadership, moving quickly from classroom to principalship to the superintendent’s office. What kept that transition grounded wasn’t authority, but credibility—earned through listening, humility, and showing up consistently. Those same instincts still guide how decisions get made today. A big part of that transparency lives online. For years, this leader has been writing publicly on Culture of Yes blog—nearly 500 posts—using writing as a way to think, reflect, and invite conversation. It’s not about broadcasting answers; it’s about making the work visible. When people understand the “why” behind change, even hard shifts feel more human and easier to trust.
From there, the conversation gets practical. How do you lead a complex system without hovering? How do you introduce new tools without losing the relationships that matter most? And why is educator wellbeing no longer something we talk about after everything else gets done—but the work itself? We talk about autonomy, belonging, and the small conditions that make teaching feel sustainable again. On the student side, we explore British Columbia’s big-idea curriculum and what happens when you loosen the grip on rigid outcomes. The result is more room for choice, passion-driven programs like robotics and athletics, and learning that reflects local and Indigenous contexts instead of flattening them.
We also spend time on AI—not as hype or fear, but as a real tension educators are living with right now. We talk openly about privacy, equity, and environmental concerns, alongside practical uses that actually help: planning, drafting, and assessment support that gives teachers time back. The guiding idea is simple: technology should make schools more human, not less. The conversation widens to a national lens, asking what it would look like for Canada to build shared AI literacy and stronger networks between provinces—so we stop working in silos and start learning from one another.
If you’re trying to make schools ready for what’s next without losing the heart of teaching, this episode offers something rare: clarity without certainty, optimism without naïveté, and leadership rooted in trust rather than control.
