Purpose: While school leadership literature has searched for practices with the largest effect on outcomes, we know little about how these behaviors vary by context. Further, recent shifts to include teachers in leadership have prompted a need for purposeful distinction between teacher and principal perceptions and roles. Person-centered statistics offer a means to study differences in how teachers and principals perceive leadership by context, how these perceptions interact, and the extent to which this interaction influences teacher decisions, such as whether or not to remain at their current school. The paper aims to discuss these issues. Design/methodology/approach: This study applies a two-level latent class analysis (LCA) with a cross-level interaction to the 1999-2000 Schools and Staffing Survey (SASS), n = 35,560 teachers across n = 7,310 US public schools. SASS includes a comprehensive set of leadership measures, not found in other surveys, collected when US schools restructured to include teachers in leadership. Multilevel LCA helps to identify different types of teachers and principals in leadership, the distribution of teacher types across principal types and to test the extent that these types predict teacher retention decisions. Findings: Teacher and principal types were best defined by the survey items that addressed their own role not the role of the other. The highest and lowest responding teacher types were evenly distributed across principal types. Teacher types who reported the lowest principal-directed leadership were more likely to leave their school regardless of principal type. Originality/value: This study provides evidence for how leadership differs across perceptions and context and, in turn, influences teacher retention.