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Over the past decade, data-informed decision-making has become a major aspect of school reform agendas in both federal and state accountability policies. Despite its growing recognition, we know relatively little about what forms of data school leaders use, how they matter for students’ learning, and which school contexts matter for such leadership practices to be successful. Using hierarchical linear modeling with the survey and administrative data from Florida, this study finds students from schools where their leaders ground their decisions on benchmark test results tend to score higher on their reading and math tests. Such beneficial leadership practice is more likely to arise in schools characterized by supportive relationship among staff. Results provide recommendations for leader development and policy implications.