This case outlines a dilemma encountered by an assistant professor and graduate teaching assistant teaching within an educational leadership preparation program. The case offers a detailed illustration of a race-related conflict occurring in a course focused on preparing school leaders to address issues of social justice within diverse settings. Addressing race-related issues within the classroom are of the utmost importance for today's leadership preparation programs, as the influx of traditionally marginalized populations within public schools continues to rapidly increase. Implications for the development of school leaders include the purposeful examination of issues related to race, diversity, social justice, positionality, and the facilitation of critically-oriented conversations.