The employees of the authors’ university, like employees of many large organizations, receive hundreds of pieces of information weekly through bulk emails from the university’s central offices. The employees are overwhelmed by the volume. At the same time, the senders feel frustrated because their messages are not getting employees’ attention. Employees, senders, management, and even the organization itself all have different interests in what messages should be sent to whom and read by whom. This multi-stakeholder problem is a common challenge for socially embedded agents in organizational contexts. These agents cannot succeed by focusing on only one stakeholder’s perspective. In this chapter, we use this case study to explore the design challenge of an organizational communication agent to address such a multi-stakeholder problem. We show in detail how an analysis of the various stakeholders’ perspectives and the entities of the system can lead to a representation of the problem space that can be optimized. We find this case study useful to motivate designers of other workplace agent systems to consider how to incorporate the perspectives of different stakeholders in their designs.