This dialogic chapter focuses on leadership preparation that addresses injustices through critical perspectives and social justice. The authors theorize about cultural dialogue in educational and public spaces as social justice advocacy. Their thesis is that difficult cultural dialogue cultivates leading, learning, and teaching for a more just and equitable world and that cultural dialoguers promote improved leading, learning, and teaching. They support their stance by exploring practices in the university classroom to support such commitment and that foster value for cultural dialogue within and beyond this context. These notions, which are intricate beliefs about the value of dialogue as advocacy, inform their work as educational leadership professors in doctoral-granting US institutions. Stimulated by the mold-breaking, textual dialogues of scholars from different disciplines, they describe pivotal concepts and support these with illustrations in social justice literature. They explore the role of dialogue and debate in expanding consciousness and building community, with untapped transformative effects for individuals and their communities. Conversational snippets from dialogue with doctoral students imbue these concepts with detail. Their students, who reflected on their struggles, were currently K–12 public school leaders and teachers in Texas and North Carolina. The authors attempt to bring cultural dialogue alive in the social justice contexts of engagement, community, and transformation relative to the complex processes and effects that occur educationally and publicly. Situating themselves and their students as cultural dialoguers, they adopt educationalist Freire’s concept of “dialoguer” by adding “culture” to it. The authors see this work as their ethical responsibility to extend the pedagogy of a democratic theory in action by communicating widely with audiences.