In this article, authors Deborah Helsing, Annie Howell, Robert Kegan, and Lisa Lahey argue that today's educational leaders face a host of complex demands as they strive to implement lasting, meaningful change in their school environments. As these demands often require a level of personal development many adults may not yet have, there is a need for professional development programs that are genuinely developmental. This article describes one such program that provides the opportunity for participants to make qualitative shifts in the ways that they understand themselves and their work. Using case study methodology, the authors explore the psychological development of one participant as she increases her capacity to determine, and be guided by, her own theories, values, and expectations of her personal and professional relationships and responsibilities. (Contains 5 notes.)