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Race is a difficult topic to discuss openly within college and university settings. Postsecondary educators who wish to facilitate dialogues about race and racism among students must take necessary steps to prepare for these discussions. Using data from a qualitative case study, this article discusses the strategies that educators employed to engage learners in these racial exchanges, including shifting from educator to facilitator, developing ground rules, considering students' comfort and developmental readiness, and structuring racially/ethnically diverse groups. Implications for practice are also provided.