As present-day organizations respond to global competition, much attention has been given to the multigenerational workplace. A ripe environment for both knowledge sharing and collaboration, organizational development leaders have in recent years extolled the merits of reverse mentoring as a knowledge sharing mechanism designed to further engage younger employees, who often are challenged in finding their footing within an organization. To stave off attrition of the organization’s younger generation, this capstone project aims to explore the mentor relationship through the lens of knowledge sharing practices, delving deeper into reverse mentoring as a social exchange exercise that not only engages all members of the organization, if executed with intentionality, but aids in inclusion, organizational restructuring, improved communications, and retention. A review of the extant literature provides a framework by which human resource leaders can replicate and evaluate reverse mentoring programs, introducing the knowledge sharing initiative to multigenerational organizations with the goal of cross -collaboration, trust building, and skill development. A review of both the challenges and opportunities of reverse mentoring are detailed as the author seeks to pilot a bidirectional learning program at the University of Baltimore.