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This paper highlights wisdom from a collective case study of 30 semi-structured interviews with award-winning principals, specifically national views on principalship and diversity. Attention on diversity is significant as principal demographics do not reflect student populations (U.S. Department of Education, 2022). School leaders mentioned a variety of structural inequities in schools, and followed up with solutions spanning motivation, recruitment, student experiences in schools, and intentional programming. Significant was how participants’ identities influenced their critiques and solutions. White participants articulated less assuredness and preparation to respond to the challenges of injustice. Implications from this research reveal the danger of white deference, avoidance, and individuality, and reveal how a multi-pronged approach is necessary to heal the wounds of systemic racism.