The goal of this qualitative study was to understand middle school principals’ perceptions of leading a transition from traditional grading to standards-based grading (SBG). Using a multiple case study approach six middle school principals who work in a school district that had successfully implemented SBG in elementary school, but not in middle schools, participated in the study. This study took place during the COVID-19 pandemic, thus the study also sought to understand how principals perceived the impacts from COVID-19 on their leadership of SBG. A demographic survey was sent to each participant and semi-structured interviews were conducted with each principal. Using the constant comparison method, four themes emerge: (a) misalignment between PLC practices and individual teachers’ grading practices exists, (b) a lack of district level SBG report card grading progressions from elementary school to middle school has created confusion and frustration, (c) parents and teachers expect traditional grading in middle school to prepare adolescents for high school, and (d) leading SBG was not a priority following the COVID-19 pandemic. This study also used Bandura’s Social Cognitive Theory (SCT) as a framework to understand how principals’ self-efficacy impacts that of their teachers and how collective efficacy can be improved by increasing the principals’ self-efficacy as an instructional leader. Implications of this study include suggestions for principals to increase their knowledge and self-efficacy through professional development, collaboration, and district level supports. The unique role of middle school culture, including grading practices is discussed.