This article examines how three Black tenure-track faculty from different academic disciplines prioritized and facilitated discussions on racism and racial violence with graduate students. Drawing on the process of facilitating difficult dialogues and racial battle fatigue as theoretical framing, we utilized case study methodology to illuminate the challenges that Black faculty face when engaging in these conversations. Our analysis yielded four themes: (1) deliberate and intentional preparation; (2) connecting current events on racism and racial violence to classroom lessons; (3) classroom management and decision making when dissonance occurs; and (4) reliance on trusted peers.