Over the course of eight audio files, Dr. Anthony Conelli, Chair of the Bank Street Department of Leadership, facilitates a critical dialogue that explores the concept of democracy in schools and classrooms. Participants shared a story about a time they participated in a democratic experience, explaining what happened, how they felt, and what they learned. The Progressive Leaders Group is designed to provide a snapshot of practice regarding the experience of Bank Street alumni and other progressive leaders throughout the tri-state area. To this aim, these leaders analyze and discuss the challenges that school leaders grapple with in schools and organizations.