Gaining access to diverse knowledge and expertise is often the primary motivation for collaboration among different professionals and organizations. Extant approaches have focused on communication dynamics during collaborative processes—where participants have already accepted the value of one another’s knowledge/expertise—and narrowly presumed transfer-integration as the successful outcome of collaboration. I argue that gaining a more complete understanding of collaboration requires investigating how collaborators’ knowledge/expertise are differently implicated in their communicative efforts to break in, maintain, and leave collaboration. Further, conceptualizing collaboration as a cyclic process adds complexity to current theories by considering how collaborators’ communication impacts and is impacted by their previous and/or future collaboration. I support these arguments by providing evidence from field studies of long-range regional planning, which involves collaboration among various organizations to bring diverse inputs for envisioning the distant future of their region. Through a set of three studies focusing on different components of a collaboration life cycle (the beginning, middle, and end), the findings reveal communicative dynamics that enable and constrain productive engagements among diverse organizations with distinct knowledge/expertise.