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This chapter examines the tensions inherent in conceptions of social justice as they relate to educational administrator preparation programs. In order to determine how social justice is conceptualized in K-12 administrator preparation in Ontario, Canada, we conduct a document analysis of publicly available information related to provincial leadership preparation programs. We identify an ideological bias toward managerial and transformational leadership paradigms which favor externally mandated outcomes that unintentionally reinstate hierarchical management paradigms and democratic forms of racism (Henry, Tator, Mattis, & Rees, 2000). Drawing on critical democratic and antiracist literature and our own research and practice, we propose an approach to leadership preparation that can support diversity and transformative praxis while working within a mandated transformational paradigm.