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This study examines how system-level equity leaders in K–12 public and independent schools navigate the paradoxical demands of promoting equity within institutions that often resist change. Drawing on interviews with 27 equity directors, we develop a leadership framework grounded in tempered radicalism (Meyerson & Scully, 1995). Equity leaders employed a range of strategies—from covert, internal actions to public, collective efforts—shaped by their organizational and political contexts. These included upholding principled commitments, mapping the terrain, exerting quiet pressure, coalition building, and establishing broad-based support. Our findings illuminate the complexity of equity leadership amid rising backlash against DEI. We contribute a nuanced understanding of how equity leaders sustain themselves and advance change, offering practical and theoretical insights for leadership in contentious educational contexts.