A superintendent’s career path often goes something like this: Successful teacher earns administrative certification, becomes an assistant principal or principal, starts working on a doctorate or further administrative certification, moves into the central office, then makes the jump into the top position. Students at Pennsylvania’s Bucknell University take a class on “The Superintendency” before they start applying for positions. The course addresses many fundamental aspects of the superintendent’s role, but one has been overlooked: “How do I negotiate my first contract once I have been offered a position?” Students in a recent class tackled this question by developing a research project that focused on the contract development process and the content of superintendent contracts in Pennyslvania. What they found sheds light on the issues of contract development, compensation, and the superintendent’s relationship with the board.