In an age of instantaneous information sharing and increased interdependence, today’s leaders must learn to work collaboratively, leveraging the strengths, skills, and experiences of those around them, in order to address the challenges they face. The Center for Collaborative Leadership is uniquely situated in the College of Management at the University of Massachusetts Boston. The purpose of the Center’s Emerging Leaders Program is to challenge and inspire the adult participants in the program to act collaboratively, identify and rethink boundaries, build purposeful relationships, and become better leaders and citizens. In this brief, the authors reflect on how this program is changing not only the individual leaders but, as importantly, the organizations and communities to which they belong. They offer insights on lessons learned that may be beneficial to others who teach graduate students and professionals.