Urban schools often experience rapid turnover among teachers and leaders. Yet, research and practice highlight the importance of sustained leadership over time as an integral component of school improvement. Successful leadership requires principals who operate in multiple dimensions at once, moving from individual capacity to group empowerment, to whole school improvement and back again. It also requires that principals be given time and support to hone these skills. In most urban schools, however, principals are left on their own and face increasing district and public scrutiny. This case highlights one principal who learned to distribute leadership through individual and organizational learning, and built systems to ensure continued improvement as he plans to transition out of the school after 11 years. How did his leadership evolve? The case uses an appreciative inquiry approach to explore the creation of community and organizational structures that lead to sustained school improvement.