The quantum growth of remote work has caused both managers and employees to reconsider where and how to work. This often takes the form of negotiations between an employee and manager as they attempt to resolve differing views on how best to carry out remote work. The multi-issue negotiation role-play exercise described here encapsulates these often opposing views through the negotiation of seven issues related to working from home. The issues are designed to reflect different types of negotiation approaches and include those that are distributive, integrative, and compatible between the parties. Furthermore, the design of issues reflects differing values assigned to each role, in order to foster student engagement and a greater appreciation for how to achieve trade-offs. Through this exercise and ensuing discussion, students learn how to better analyze and carry out negotiations, and enrich their understanding of the complexities of setting up remote work arrangements.