Society lives in perilous times for educational equity. The progress made in desegregation, culturally responsive pedagogy, and social justice is threatened by backlash legislation and protests in defense of the status quo. The pushback is happening at structural levels and very personal levels. There is an urgent need for professional learning that prepares educators to stay the course and lean into difficult conversations about race and equity. To help students navigate tensions and respond to difficult conversations, educators need to build their own skills first. In their work with educators, the authors apply strategies and tools designed to facilitate challenging conversations. This article highlights these to help other educators in their own conversations and challenging situations.