The purpose of this article is to make visible collaborative pedagogical and research practices that opened space for community members to be co-educators and researchers with students and a professor on a youth violence assessment. We use Third Generation Cultural Historical Activity Theory (CHAT) as a conceptual framework to examine the learning that occurred in the boundary zone of our eight differently situated organizations. As we demonstrate through the inclusion of boundary dialogue excerpts, this process generated more authentic understandings of why racial inequity has persisted in youth violence outcomes. The assessment questions we asked, the key informants we engaged, the data analysis process we undertook, and the substantially different types of findings that emerged were a function of relationship building and radical listening in the boundary zone of our collaboration. We conclude that practices that foster radical listening in boundary work can reframe experiential learning for racial justice.