Various studies have found positive and negative associations of Machiavellianism with job performance, and the meta-analytic relationship between the two is weak. We sought to resolve these inconsistencies by comprehensively testing Socioanalytic theory, which suggests that social skill (i.e., political skill) and reputation are integral to how personality (i.e., Machiavellianism) is expressed in behavior evaluated by others (i.e., job performance). Moreover, the newly developed Five-Factor Machiavellianism scale also assisted in this clarification, because it properly characterizes Machiavellianism as strategic and shrewd, as opposed to prior measures that portrayed it as impulsive and lacking ambition. In the present study, targets (N = 550) provided self-rated Machiavellianism and coworkers (N = 1127) rated target political skill, reputation, and job performance. Our results demonstrated that, (only) when lacking political skill, individuals high on Machiavellianism developed poorer reputations with coworkers that result in reduced job performance assessments. Whereas, those high on political skill did not suffer such negative work consequences from their Machiavellianism, suggesting that political skill can function as a protective factor for dark personalities. The findings provide insight into the Machiavellianism – job performance relationship, and they indicate various directions for future research. •We study Five-Factor Machiavellianism (FFM) and job performance.•We test full Socioanalytic theory of personality in a multi-source design.•We use political skill (PS) as moderator of the personality-performance relationship.•We use reputation as mediator of the personality-performance relationship.•At low PS, FFM negatively predicts job performance mediated by reputation.