For the past four years, the team working on the “Ed Ruscha, Streets of Los Angeles” project at the Getty Research Institute has worked to establish a framework for leveraging the benefits of collaboration and conversation between groups of people who work in different areas of expertise and communities of practice. Facilitating sustained conversations among art historians, art librarians, and technical specialists has proved a successful framework of mutual consultation between Getty staff and external collaborators. These conversations helped external collaborators better understand the kinds of metadata generated through the archival process and how it might be useful for investigating their particular research questions. In turn, Getty staff gained a better understanding of the kinds of metadata helpful to researchers, which helped determine our own priorities for this work. Moreover, new avenues of inquiry emerging from this collaborative project have outlined a path for articulating best practices in digital art history projects to come.