Managing business relationships is challenging because people with boundary roles do not have any authority over others in the network. That is why various forms of persuasion play an important role in building socially embedded business relationships. Firms do not usually pay deliberate attention to how their people with boundary roles communicate when interacting with other firms’ representatives. This chapter presents a tool to evaluate the rhetoric of people with boundary roles within firms when they interact with the other firms’ representatives. Based on Aristotelian rhetoric—broadly defined as the art of persuasion—we developed and tested a tool that enables evaluation and development of boundary-spanning behavior in inter-organizational relationships.