Purpose: In the wake of interlocking pandemics, educational systems are resetting in important ways, pursuing aims that are not exclusively instructional (e.g., social justice, well-being). As systems (re)build, they may vary in how they manage their institutional and policy environments, which may or may not be reorienting toward these same expanded aims and at a similar pace. Drawing on theoretical lenses related to coupling and the embedded agency of leaders, this article compares the work of system and school leaders as they reconcile system-level policies with their environments, and with teaching and learning in classrooms. Research Methods/Approach: Drawing on data from four elementary schools, situated across two educational systems (i.e., Montessori and International Baccalaureate) and two national contexts (i.e., United States and Canada), I highlight differences--between and within systems--in implementation of system-level policies. Findings: I find an educational system's "coupling orientation" provides context for the embedded agency of leaders and for the nature of their work as implementation agents. By orienting its leaders toward a certain coupling arrangement between macro (i.e., environment), meso (i.e., system), and micro (i.e., classroom) levels, a system can shape the type of work leaders do, and the degree of structure and agency they experience. Implications: In detailing differences in implementation between and within systems, this research helps scholars frame loose and tight coupling, structure and agency, along a continuum. For educational leaders, this article highlights necessary system knowledge for managing interactions between the environment, their system, and teaching and learning in classrooms.