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Racism within school systems will not change unless leaders reflect and redress them (Diamond & Gomez, 2023). Within a research practice partnership, the authors of this study asked the leadership teams at two urban high schools to each identify a policy problem: one examined a token economy policy, while the other chose to examine their grading policy. The leadership teams then used an anti-racist policy decision-making cycle of inquiry protocol (Authors, 2021) to reflect on how the policy may perpetuate racial inequities and what changes could remedy them. Although both schools’ leadership teams deepened their reflections about the racial impacts of the policy problems, there were distinct differences in the teams’ capacities to resolve them.