In a world of infinite resources, program directors could ask for and receive everything that residents and faculty need. Outside Utopia, program directors must ask for resources, decline requests that are not educationally valuable, mediate disputes, and build and maintain relationships. Fortunately, there are several different effective approaches to preparing for and conducting negotiations, two of which are presented here. We will discuss various scenarios in which a program director may find the need to negotiate and suggest approaches for such negotiations. We hope that this chapter will increase program directors’ knowledge of negotiation and their appreciation of the benefits of skillful negotiation. We encourage all program directors to practice their negotiation skills, with a view to ensuring that their department has the highest quality program possible and that residents have the very best educational experience.