The purpose of the study was to identify the roles and skills of present-day faculty association leaders (FALs) within Illinois’ public four-year universities with a collective bargaining unit and distinguish tangible actions of these individuals as they exercised their everyday roles in this professional capacity. A qualitative research design was used to gather data and explore perceptions and life experiences of twelve FALs. A personal interview was conducted with each participant with the assistance of a researcher designed interview guide. FALs view their role as that of a contract manager: one who interprets, negotiates, and defends the contract in conjunction with informing their constituents to contractual matters of concern. The ability to communicate effectively was identified as the primary professional skill required of FALs. The ability to be an empathetic listener with the capacity to be open-minded and flexible to circumstances on-hand was identified as the foremost personal skill best suited for FALs. This research advances the contextual understanding of FALs as they go about fulfilling their daily roles and their need for preparatory training.