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This article explores how leaders in two public school districts shape their school’s organizational culture to challenge harmful social ideologies and culture. The exanimation of systematic district leadership—Culturally Responsive District Leaders—featured in this article demonstrates the importance of intentional, consistent, and long-lasting relational engagement of minoritized communities as an opportunity to prepare formal systems for crises. The two district case studies will demonstrate the importance of systematic actors in preparing systems, like schools, to be resilient, sensitive, and accountable when complex and diverse incidents systematically construct disparate realities for their organization members. Likewise, this article explores a new concept, “Organizational Stress Tests,” a process that entrepreneurially builds upon past organizational incidences to function under severe or unexpected pressure.