Dr. Jen Fry’s favorite mistake is a disagreement with her best friend of over ten years — a small miscommunication that led to eight months of silence. Neither of them knew how to reconcile it. Then Jen’s mother passed away, and her friend sent a card. That single act of reaching out changed how Jen thinks about conflict, reconciliation, and the kind of people worth keeping in her life.
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Jen is a sports geographer, tech founder, TEDx speaker, and author of I Said No: A No-Nonsense Guide to Setting Boundaries, Speaking Up, and Having a Backbone Without Being a Jerk. In this conversation, she draws on her background as a college volleyball coach, tech founder, and conflict expert to break down what leaders and teams get wrong about conflict, feedback, and boundaries.
We dig into why niceness gets weaponized to keep people quiet, why kindness requires accountability, and why people pleasing quietly ruins reputations and results. Jen explains why conflict-avoidant bosses create conflict-avoidant cultures, why anonymous feedback does more harm than good, and the critical difference between being defensive and defending yourself. She also shares what she saw on a high school volleyball video that she wishes she could burn — and what it taught her about being a better teammate and leader.