Our society continues to be plagued with rampant acts of racism, sexism, xenophobia, transphobia, misogyny, and hate crimes. More so than ever before, engaging in difficult dialogues across differences is imperative. Counseling psychologists are equipped with a multitude of skills that make them uniquely suited to be leaders in effective dialogue engagement. This article provides an overview of a time-limited social justice training opportunity for emerging counseling psychologists called Community Conversations. Community Conversations are designated brave spaces where small groups of college students from varying backgrounds are invited to engage in facilitated interactive and experiential dialogues that explore difficult topics related to power, privilege, and marginalization. The current study examined the multi-tiered impact of the Community Conversations Initiative on both graduate student facilitators and undergraduate participants. We discuss results and practical implications.