In this conversation, David Harlock, one of only two 3-year captains in the 100 year history of Michigan hockey, discusses what real leadership looks like, especially for a reserved personality like his; how college hockey compared to his experience winning a silver medal for the Canadian Olympic team, and playing for his hometown Toronto Maple Leafs in the NHL. Then he compares his career in hockey to his current profession in high-end insurance brokering and risk management. What translates, and what doesn’t? What advantages do former athletes have in the workplace? Traits like mutual accountability, teamwork, hard work, attention to detail, and countering failure, inevitable in any field, with persistence. He concludes by reflecting on his favorite teacher and the valuable lessons he learned from him.