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Organizations in general operate in a top-down fashion, and policing is an example of such an organization. The paramilitary structure of policing establishes a chain-of-command wherein line-officers and detectives are responsible for adhering to decisions made by those in the upper echelon. Scholarly research on detectives is scarce and it is unknown how policy and changes in policy can influence their everyday work. The current study seeks to understand potential role conflicts and adjustments in the development of a detective within a paramilitary structure. Additionally, this study is interested in how a department can help better prepare an officer who may seek to transition into a detective role. The current study examines interviews with 21 detectives and officers who hold investigative positions to understand their progression into detective work and how the organization impacts that progression.