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The purpose of this qualitative study was to explore the perceptions and experiences of PK-12 Principals (n=15) and District-level HR Administrators (n=10) when selecting AP candidates through the lens of person-job fit theory and person-group fit theory. Study findings align with Division L, Section 5 by addressing issues related to human capital development and staffing strategies in educational leadership. Additionally, this work aligns with the overall conference theme and this particular unit by reimagining these elements beyond technical solutions to address evolving social, political, and institutional realities of developing and staffing the administrative workforce in schools.