The Leadership Reckoning Room with Stefani Okamoto

As CEO of Box of Crayons, Shannon Minifie has helpedthousands of leaders rethink how they show up — especially in a world reshaped by AI and rapid change. In this episode, Shannon breaks down why curiosity is no longer optional, how leaders can build cultures that learn faster, and whatit takes to stay grounded when everything around you is shifting. We also explore the emotional discipline behind trulycurious leadership — the willingness to question your own certainty, to sit with discomfort, and to create space for perspectives that challenge your defaults. Shannon brings a rare blend of sharp thinking and deep humanity, offering a roadmap for leaders who want to stay relevant, responsive, and real.This episode is a call to slow down, ask betterquestions, and lead with more humanity.

Sierra Slack is widely regarded as one of the greatest women’s lacrosse players in Occidental history - but her real legacy is what she’s building now. In this conversation, Sierra reflects on her journey from record‑breaking athlete to head coach, and the leadership lessons she’s learned along the way. We talk about standards, culture, the responsibility ofshaping young women, and what it takes to lead with both intensity and care. We also explore the identity shift from being the one who scores the goals to being the one who shapes the people - the quiet, often unseen work of coachingthat requires patience, conviction, and a deep belief in who your athletes can become. Sierra brings honesty, humility, and a fierce commitment to developing women who lead on and off the field.This is a masterclass in growing up, stepping up, andchoosing the kind of leader you want to be - on the field and far beyond it.

Chris Yates has spent his career transforming how people grow inside some of the world’s most iconic companies - leading learning and organizational development at Caterpillar, guiding global L&D at Microsoft, serving as Chief Talent Officer at Ford, and now shaping the future of talent as SVP at Equinix. He’s also a best‑selling author. But none of that is why this conversation matters. But the heart of this episode lives well beyond his career milestones.Chris is one of the most profoundly human‑centered leaders you’ll ever encounter - someone who listens with intention, leads with courage, and builds cultures where people feel seen, safe, and challenged to rise. He’s the kind of leader who changes you simply by how he shows up. The kind of leader I’ve learned from, trusted deeply, and would follow anywhere.This episode is a rare look inside the kind of leadership we need more of - honest, grounded, unpolished, and deeply human.

Welcome to The Leadership Reckoning Room! This is the podcast where leaders stop performing and start telling the truth. This is where we confront the habits holding us back, the blind spots we avoid, and the moments that define who we really are. If you’ve ever wondered, Am I helping… or am I the problem? - you’re in the right place.This podcast exists because leadership is lived in the small, human moments - how we show up, how we make others feel and how we choose to grow. In this room, we slow down enough to see ourselves clearly, to name what’s real, and to practice the kind of presence that lifts others. You’re invited to light the lantern for yourself and for the people who live in the wake of your leadership, so together we can lead with more intention, more humanity, and more light.