This chapter explains why dialogue is the primary mode of interaction that the Toolbox Dialogue Initiative uses in its workshops. The chapter first describes what dialogue is not and then offers a definition of what dialogue is. This definition emphasizes the participation of at least two people in conversation that aims at a shared goal. After defining dialogue, the chapter shows how it can have both informational aspects—dialogue as argumentation—and relational aspects—dialogue as human association. The chapter goes on to discuss how these aspects bring benefits to both individuals and groups. For individuals, these benefits include enhanced learning about ill-structured problems and cultivation of reflexivity and perspective-taking; for groups, improvements are seen in collective metacognition and in the production of creative responses to research problems. However, there are caveats: despite its array of benefits, dialogue is neither necessary nor sufficient for some forms of team success. The chapter concludes by showing how Toolbox workshops use particular forms of participant stance, structure, and facilitation to encourage dialogue that benefits both cross-disciplinary teams and individuals.