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The author’s purpose in this paper is to engage in an examination of Dewey’s (1916) Democracy and Education in consideration of democratic leadership preparation. The author examines the problematic nature of preparing education leaders for the work of creating more democratic schools. In particular, the author focuses on the need for pedagogical considerations in leader preparation that are grounded in democratic ideals and that foster democratic dispositions. Four primary elements were determined that shape the democratic imperative for leader preparation: democratic knowledge (as socially constructed and contextual), democratic pedagogy (as experiential and authentic), democratic practice (as inquiry), and democratic culture (as communicative and community based).