The increased weighting of digital natives in a fattening long tail has added complexity to organizational leadership, particularly during the global COVID-19 pandemic. Trends affecting the individual come from social, economic, and technological sources and affect leadership behaviors, and this in turn affects society. In order to understand this interconnection, lower-level influences and how they affect the higher-level visible signs are discussed. These lead to influences on behavior. Influences are felt as intensity and embeddedness of engagement, decision-management, feedback ability, and motivators. This chapter begins with a discussion of causes for this phenomenon and concludes with ways to work with the long tail, either from within as a member or externally as a leader. The chapter ends with a brief comment on future research based on findings discussed in this chapter.