As today’s police officers grow to take on leadership roles, the intergenerational relationship between millennial commanders and Generation Z (Gen Z) personnel will determine the organizational success of law enforcement agencies. Current administrators and leaders need to recognize the importance of proactively fostering this working relationship to establish a viable succession plan. The competing interests and value structures of these two generations could potentially create a divide in the workforce that hinders progress and cohesion; however, a clear understanding of each generation’s motivations and shortcomings allows leaders to establish mutually beneficial areas of interest where collaboration can be found. If done correctly, an organization will continue to run smoothly into the future as one leader or leadership group is replaced by an experienced and skilled successor.