Businesses and organizations operate as a group at some point or another. They may be permanent groups, ad hoc groups, virtual groups, or just-in-time groups. In any field, there will be some grouping, and for these groups, there are key components to develop and become effective, efficient, integrated, and high-performance groups. Globalization has added new dimensions, and as the world continues to globalize, the workforce is becoming more and more diverse. Added to this is the generational issue that has played and will continue to play a significant role in organizations for years to come. Not only are individuals working longer; some are also retiring and then returning to the workforce. Organizations, therefore, need to promote a multicultural environment that leverages multi-generational leadership to achieve growth and sustainability. Hence, adopting a qualitative approach, this chapter discusses and deliberates on the compass and connotation of multigenerational leadership in the contemporary multicultural workplace.