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Despite the urgency of addressing race, class, language, and other disparities in K-12 student outcomes, few processes and tools support the development of equitable organizational leadership. This comparative case study examines how leadership teams engage in collective learning with tools, including the Leadership for Equity Assessment and Development (LEAD) Tool, to change policies and practices to mitigate disparities. Using Engeström’s expansive learning theory, we analyze observations, interviews, and documents to identify: 1) how teams describe their collective growth, 2) whether and how practices and equity outcomes change, 3) how teams engage with tools, and 4) what contextual factors shape growth. Findings have implications for improving organizational policies and practices to promote equitable student outcomes as well as leadership preparation.