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While educational leadership scholarship typically focuses on the roles that school and district administrators play in sustaining and improving public education, ways that community-based education organizations (CBEOs) contribute to these dynamics are underexamined. In this paper, we highlight our participatory action research study through which we collaborated with D-Justice, a Detroit-based CBEO, to assess organizational leadership and staff development needs. We highlight how D-Justice’s process to strengthen and sustain local leadership was driven by community-determined modes of learning and leading that provide pathways to liberatory futures and counter ongoing histories of dispossession and divisive politics that have influenced Detroit.