E58: Joe Connolly on Leading So Others Can Flourish

Dr. Reda Othman sat with Joe Connolly, Executive Director of the Saint Thomas More Chapel and Center at Yale University, to explore what servant leadership looks like when it's lived — not just taught. Joe has spent decades leading at the intersection of healthcare, community service, and mission-driven work, and in this conversation he opens up about how he discovered his calling, how he builds cultures where people genuinely belong, and the discipline it takes to keep your leadership grounded when the calendar fills up and decisions pile on. Two moments stand out: Joe describes the long discernment process that brought him from sixteen years in Catholic healthcare to Yale — not a single breakthrough, but a deliberate elimination of what he didn't want until the right opportunity landed in a very small bullseye. He also shares how his team at St. Thomas More learned something surprising from their own students — that in a world saturated by screens, the thing students valued most was walking into a space that had none. This is a conversation for any leader trying to align mission, culture, and daily practice — especially those navigating complex institutions where staying true to purpose requires both conviction and flexibility. Key Takeaways 1- Discover why defining what you don't want can be the most powerful step in a career transition — Joe used elimination to find clarity after sixteen years in healthcare. 2- Learn the three decision-making frameworks — my decision, your decision, or our decision — and why making the framework explicit prevents decisions from getting bogged down. 3- Understand how the integration of personal values and professional life creates what Joe calls a true calling, not just a job. 4- Apply the "Pray, Study, Act" model as an organizing framework that keeps a wide range of programs aligned under one clear mission. 5- Rethink what belonging actually looks like — from a receptionist who sets the tone, to food that drives community, to the deliberate choice to keep screens out of a space students call home. 6- Recognize that servant leadership is easy when everyone is aligned — the real test comes when individuals project personal preferences over the mission. 7- Protect space for reflection by proactively carving it into your calendar — because if you don't, the fire just keeps burning.