The complexities of Graduate Medical Education require a Family Medicine Residency Program Director to work with multiple stakeholders, including educational and hospital leadership teams, faculty, residents, clinical staff, and community partners. The ability to negotiate and collaborate will enhance the Program Director’s ability to develop a successful program, meeting the needs of regulatory and accrediting agencies, the residents, and the sponsoring institution. This chapter will explore the various styles of negotiation, the basic elements in a negotiation, and common scenarios that a Family Medicine Residency Program Director may expect to encounter. In addition, we will examine how collaboration can be effective to reach the desired outcomes using the resources of others around us, and how to develop the skills to enhance our collective work together for the benefit of a successful program.