The transition from medical school to residency and from residency to fellowship involves working in new settings, with new roles and expectations, and with new colleagues. The task of resident and fellow orientation, therefore, involves introducing trainees to the program’s culture of work, education, and work/personal life balance approach. In this chapter, we present guiding principles for orientation to each of these components and provide sample orientation topics related to these principles. It is this chapter’s goal that the reader will take these ideas and apply them to their local program.