District-level directors, principals, and human resource personnel can bring important viewpoints and information in assisting the school board and superintendent during the teacher negotiations process. Unfolding in this case study are the myriad pressures brought forth to the key players in the process, the negotiating process of interest-based bargaining (IBB), and the unique perspective of administrators who served as both labor negotiators and management negotiators in different settings. Also emphasized is the work of school boards and how fractious relations can lead to unintended consequences, as well as the key role of the superintendent in the negotiation process.