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There is a gap in the research on how fear, compliance, and leadership behavior intersect. We must interrogate ways our educational systems produce and perpetuate compliant or scared leadership. As we uncover deep-rooted issues embedded in U.S. public education, we must also name ways fear is institutionalized and rewarded. As James Baldwin reminds us, “not everything that is faced can be changed, but nothing can be changed until it is faced” (1962, p. 2). To carve a pathway toward courageous leadership, we must “face” and name the barriers and norms that keep us grounded in fear and compliance. This study utilizes Grounded Theory to explore and explain the relationship between fear, compliance, and leadership behavior in public education.