What tools do student leaders need to teach their peers about complex issues of identity, diversity, and social justice? How can student leaders help build positive school culture? For several years, New Haven Academy has partnered with Facing History and Ourselves, an international educational and professional development organization, to train student leaders to facilitate conversations with their peers around difficult topics in advisory and other school forums. We will discuss benefits and challenges of this model and how it fits into a whole school Facing History and Ourselves approach. We will share topics, tools, and training from our experience to help participants plan for their own schools. Middle and high school teachers interested in Facing History or student leadership are encouraged to attend.