Machiavellian leaders have a strong propensity to advance their personal interests, which may unknowingly precipitate their employees to behave in a similar manner through the exercise of upward influence tactics as a representative of political behaviors. Machiavellian leaders can be broadly described as displaying strategic and self-serving, misanthropic and agentic orientations. Thus employees may find it hard to work with such leaders and, subsequently, recognize the relevance of exercising social influence in order to facilitate their supervisory relationships. Accordingly this chapter examines the effects of a leader’s degree of Machiavellianism on employees’ use of upward influence tactics, and further examines how the moderating roles of the gender of the employee and their perceived leader similarity come into play. In so doing, this chapter addresses the dearth of research examining the effects of Machiavellian leaders on employees’ performance of political behaviors. More specifically, it develops a better understanding of how Machiavellians may influence employees’ choices of upward influence tactics, and identifies some relevant conditions that may impact the exercise of social influence.