As advocacy communications professionals who work with educators, one truth is constant in the current conversations with superintendents, principals, teachers, parents, and youth advocates: Education conversations today are riddled with more land mines than ever before. In their current work at RALLY, an issue-focused communications firm, the authors attend focus groups, analyze quantitative messaging research, and engage with different audiences online to help look across the U.S. and across communication channels to identify patterns and strategies for communication that work. The authors find that four communications principles consistently help education and equity advocates navigate challenging waters, whether trying to de-escalate a situation with a concerned parent or convince colleagues to hold fast to their equity commitments. These principles transcend regional and political differences as well as urban, rural, and suburban contexts. The following four communication principles are presented in this article: (1) Ask thoughtful questions; (2) Lead with your values; (3) Seek common ground; and (4) Consider the context and choose the right messenger.