This paper is an inquiry into the human factor in intermediation. We argue that we have not yet fully grasped the different roles, functions, and ways-of-being of the intermediary and that the concept of first- and second-order “wisdom” is helpful in understanding what it takes to succeed as an intermediary. Through a comprehensive inquiry into human intermediaries in a corporate strategic program for universityindustry collaboration in a global company, we develop a typology based on three fundamental roles: the “Power Promoter,” the Diplomat, and the Creative Integrator. On this basis, we argue that the wisdom of the intermediary involves mastering the different roles (first-order wisdom) and deciding between them in each individual situation of intermediation (second-order wisdom). As a result, we advance Hargadon and Sutton’s initial insight into the human factor in intermediation, thereby further humanizing the research on intermediation.