This qualitative case study of two middle schools explored the principal's role of monitoring to ensure student achievement predominantly of minority students who characteristically underperform on standardized assessments. When standardized test data continues to show achievement gaps for Hispanic and African American students widening when compared to their White and Asian counterparts, the nation looks to site level leadership to ensure equitable educational opportunities aimed to narrow this gap. Interviews with teachers and principals from two middle school sites within separate large urban districts formulated insight into the complexities of ongoing monitoring. The interview data illuminated the challenges that principals face as they juggle site demands, district initiatives, and operational expectations. Using a multiple case study approach, classroom observations, interview transcripts, and artifacts triangulated the data. Analysis of the data collected resulted in the identification of six leadership practices which served as the lens to anchor the study's findings. Outcomes revealed that effective use of formative assessments to improve student achievement required guidelines for how to use the data to create systems to support students based on the formative results. In this study, the principal most effective at navigating educational systems experienced better results in sustaining staff motivation and maintaining growth goals. Recommendations to assist middle school principals serving predominantly minority students include providing opportunities for staff collaboration between successful and less successful sites as well as ongoing monitoring of the site principal's purposeful and sensible blending of their operational and instructional work while they strive to promote student achievement.