This study examines four award-winning school leaders asking, "What makes a school leader effective?" A series of interviews were conducted with four award-winning school leaders (State Teacher of the Year, State Middle School Principal of the Year, State High School Principal of the Year, and State Superintendent of the Year), all of whom work within close geographic proximity to each other. The results were coded for themes and best practices for current school leaders who are preparing students for tomorrow's global society. The study sheds light on the perceived characteristics, skills, and best practices implemented by successful school leaders.