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We argue that leadership development is inevitably affected by on-the-job context. We define context as including the elements of a work and organizational setting that influence behavior. Especially important are those elements in the immediate work setting that are controlled by one’s supervisor. We call this local context. To be effective, leadership development efforts must explicitly address and include supervisory support and engagement as an intentional part of the development process. To highlight the vital importance of the supervisor in leadership development, we examine five phases of supervisory involvement in development over the past 75 years. We advocate Phase Five Leadership Development in which the supervisor takes an active and supportive role as a steward of the development process.