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Assistant principals comprise the main pool from which principals are hired and they are essential to effective schools. Students of color, especially, benefit from diversity among school leaders (Grissom, et al., 2017). However, women and people of color are less likely to be “tapped” for leadership opportunities despite possessing equivalent qualifications and evincing similar aspirations as their male colleagues (Glass, et al., 2001). At present, the practical and cognitive components of effective principal preparation—especially for women and nonwhite candidates—are primarily captured through qualitative approaches. This study contributes methodological rigor to complex questions regarding who tends to be successful in reaching the principalship and what combination of personal, professional, and cognitive factors contributes to that success.