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This qualitative study investigates the hiring side of the principal labor market in Chicago Public Schools. The goal of the study is to understand how the recruitment and selection processes may facilitate or impede getting effective principals into high-needs schools. We examined how hiring decision-makers think about which principal competencies and qualities best match their school needs and how recruitment efforts align with those conceptualizations. We used two primary sources of data (1) principal job postings and (2) in-depth interviews with hiring decision-makers. Understanding hiring processes – both the recruitment and selection of candidates – is important so that districts and schools serving students who have been historically marginalized, are better able to attract and select highly qualified candidates.