Sue Cunningham interviews David Dini, a longtime CASE volunteer, former CASE Trustee, who serves as the Eugene McDermott Headmaster at St. Mark’s School of Texas, where he has worked for more than 25 years. He came to St Mark’s to create a comprehensive advancement program in 1994 and was named headmaster in 2014. They discuss the challenges in managing crises as a leader through the unusual circumstance of facing both a devastating tornado that extensively damaged the school in the autumn of 2019 followed by the pandemic within months. They also discuss the path to school leadership through a career in advancement, and how that prepared him for his role, and the changing nature of his relationships with students, faculty, and the community of St. Mark’s supporters when moving from advancement to head of school. Finally, if you listen closely, you will hear a piece of advice that made a life-changing difference for Dini early in his career, which likely contributed to a similar result for St. Marks’s School of Texas.