Four generations of employees have now merged in the workplace, creating a work environment with diverse ethics and organizational perspectives. In a law enforcement environment, as in any organization, differences in organizational perspectives and work ethics among employees and supervisors can create tension, especially between an employee’s need for autonomy and a supervisor’s need for enforcing department regulations. Police agencies generally adopt a paramilitary organization, which can be difficult for younger employees who have generally experienced a less rigid supervisory style in the past. The author offers several recommendations for bridging the need for employee autonomy and the need for strict supervision; these recommendations focus on department purpose, character and reputation, department work standards, intensity of supervision, supervision consistency, and department turnover. The author recommends that supervisors adapt the core components of these recommendations, including the need for repeated emphasis on the importance of character and reputation to the functioning of the police department, to working with their employees. It is the responsibility of the police supervisor to create a productive and satisfying work environment while ensuring the highest professional quality. The challenge for supervisors is to respond to inevitable workplace change with creativity and flexibility. A table offers a summary of the workplace perspectives of four different generations.