This article examines the interplay among the environment, learning, leaders, and innovations in school systems. Six conditions that, together, have potential to shape an environment that supports organizational learning are illustrated with data from two leaders of innovation: one in an environment that resisted change; the other in a supportive environment. In one case, the environment limited what a leader of innovation could accomplish. In the other case, a supportive environment allowed the leader to influence widespread change, including a situation where one school's loss of good principals became a gain for the broader profession. Data suggested that modeling is a powerful way to lead and that innovations provide a natural springboard for organizational learning and the emergence of leaders. Findings also demonstrated the importance of innovations, risk taking, collaboration, and communication for organizational improvement.