This study assesses the relative importance of environmental, intraorganizational, and contextual factors that explain the process and outcomes of organizational learning in six Manitoba schools. Based on the data provided by 265 teaching staff and their principals, the present findings verified that transformational leadership, supportive school culture, and flexible school structure were persistent factors in accounting for organizational learning and adaptation. Environmental variables acted as motivational forces that served to break away from individual and organizational inertia. The effect of contextual factors reasserted the idea that schools were unique and that changes could not simply be transplanted without considering the characteristics of staff and their schools.