Purpose: The purpose of this study is to examine how context shapes leaders' caring approach in ways that influence organizational learning and the cultivation of professional capital. Design/methodology/approach: This exploratory study draws on case study data from two schools. Within each school, the authors draw primarily on semi-structured interviews with teachers and leaders. Findings: The authors found that school context and the accompanying leader beliefs shaped the structures and practices where organizational learning occurred, and thereby influence the diffusion of organizational learning in the school and the flexibility by which organizational lessons can be applied. Research limitations/implications: This research demonstrates that the context and place in which schools are situated influence how problems are apprehended and addressed. Leaders' relational approach, bounded by this context, influences how members of the school develop professional capacity. Larger scale studies would help clarify the nature of these effects. Originality/value: Although context has been shown to influence leadership, no study has examined the links between context, leaders' relational approach and organizational learning.