As the nation's personal, social, and political divides deepen and become more contentious, administrators, faculty, staff, and students face the challenge of navigating this division. Issues of human rights, free speech, and college and university policy converge with remarkable contention, leaving many higher education professionals believing they do not have the knowledge and skill to facilitate civil discourse. On some occasions when dialogue is broached, parties hold fast to their positions staunchly without care or empathy for the other's perspective or lived experiences. This environment can perpetuate even deeper divides. This article will review how to cultivate a culture of care to set thoughtful expectations of all campus stakeholders, provide a foundation for empathy and compassion from which to hold meaningful conversation, and explore the notion that a both/and approach to difficult conversations can be far more useful than an either/or method of discourse.