Purpose: A recurring frustration in educational research is the tendency for school leaders to implement reforms in ways that prioritize compliance over more substantive improvements to practice. Drawing on new institutional theory and sensemaking theory, this article explores the different ways leaders respond to continuous improvement (CI) reforms and why they frequently privilege external compliance over the perceived needs of their schools. Methods: This study used interviews, observations, and artifacts to analyze how six leaders across two midwestern school districts led the implementation of a CI method. Data analysis involved an iterative process of identifying emergent themes, refining themes based on existing research, and evaluating their usefulness in explaining differences within and across school leaders, in order to understand the different ways leaders responded to CI and what factors caused them to prioritize compliance over substantive improvement. Findings: Findings illuminate six different responses to CI that vary across three dimensions: whether leaders prioritize bridging or buffering, the form or the function of reform, and concerns for external legitimacy or internal improvement. Leaders’ professional identities, their beliefs about the usefulness of CI, and their perception of district regulation contributed to whether they implemented CI in a way that prioritized concerns for legitimacy over improvement. Implications: These findings trace the shallow reach of recent reform efforts to the ways leaders make sense of the complex institutional and technical demands of their role, offer an integrative typology of leaders’ different approaches to implementation, and identify factors that support more productive responses to district reform.