The psychiatric chief residency year is a stage in professional development during which a psychiatrist-in-training is assigned roles of both administrator and trainee. Negotiating the responsibilities of these two positions simultaneously leads to a particular set of opportunities and dilemmas. The varied characterizations of the roles of the chief resident highlight its potential: the chief resident has been described as “boundary phenomenon” (1), “double agent” (2), “broker for excellence” (2), “staff therapist” (3) “middle-manager” (4), and “role model” (5), among other things. Several articles have recognized the chief resident’s role as ambiguous (1, 4, 6, 7) and pointed to the value of making the roles of chief residents explicit and directly delegating specific powers to them (4, 6, 8). This has apparently become the norm: Lim and colleagues (9) found in a 2006 survey that 71% of programs now provide written job descriptions of the chief residency and that these are considered useful in anchoring chief residents in their position. The literature is sparse, however, on formal training for psychiatric chief residents (see Table 1 for a list of articles that mention training for chief residents; most offer few details).