This paper examines interactions between educational systems and environments, focusing on the stance leaders take toward instructional guidance in their environment. After analyzing interview and focus group data from 49 school and system leaders across three systems (i.e., Montessori, International Baccalaureate, Catholic), we found differences by system in leaders' stances toward their environment. These stances provided context for the educational infrastructure of each system and for the challenges leaders faced. Rather than taking it as a given that instructional practice is loosely coupled to educational policy, these findings help to illuminate a variety of relationships between systems, environments, and classroom practice, and suggest such variety has implications for school and system improvement.