A diverse health care workforce is essential to meeting the health and wellness needs of society. Nursing programs are aware of this need but struggle to attract and retain culturally diverse students. Educators in the academic setting should be equipped to effectively engage students of all ages, ethnicities, cultures, religions, socioeconomic standings, and gender identities, often in an impersonal lecture hall or a virtual classroom. How do academic faculty introduce difficult conversations all while providing supportive, culturally competent education to large, diverse student populations? One strategy is to engage students in candid, instructional conversation. This strategy involves presenting materials that may be difficult and/or uncomfortable to discuss in the class as a whole and then breaking into smaller discussion groups. In a virtual learning scenario, this strategy can be applied by using breakout rooms. Breakout rooms are ideal for discussing the highly charged topics at the forefront of nursing, such as race, gender identity, and how they impact patient care. Students can explore their experiences and biases with their peers in a nonthreatening environment. Breakout rooms provide safe places for difficult conversations and set the stage for finding similarities and understanding differences. Students get the sense that their voice matters and values are appreciated. Collaboration with peers decreases isolation and helps students build a support system, which is a critical component of success. This combination of investment, recognition, and collaboration can improve the retention of diverse students.