In addition to traditional roles, educational developers increasingly find themselves considering their involvement in issues of institutional change. However, this evolution leads to new challenges as educational developers attempt to discern whether and how to be involved in particular organizational change efforts. This chapter provides a framework that can help centers of all types reflect on the broader risks and rewards of institution-level leadership. Through a series of context-based reflective questions, the authors hope to promote strategic thinking among educational developers (particularly center directors) and to spur new questions and research as our field continues to evolve.