The role of the chief resident in internal medicine is examined through the eyes of an organizational psychologist who, over a 3-year period, met with each of 6 groups of chief residents for an average of 1 hour a week over the 12 months of the job. Based on this experience, the chief resident job is conceptualized as a middle management role with 4 distinct types of tasks: up work, down work, lateral work, and internal work. Core challenges facing the chief residents at each stage of the chief resident year are also identified. The paper concludes with a description of "lessons" learned in 5 areas (sliding up or sliding down, losing contact, splitting, scapegoating, and losing sight of the system) for improving the effectiveness of the chief resident role.