Relatively little is known about the relations between psychopathic traits and interpersonally-directed versus organizationally-directed workplace behaviors despite the implications of these traits for maladaptive (e.g., bullying, harassing, white-collar crime, slacking) and adaptive (e.g., improving the workplace, supporting others) workplace behaviors. In a sample of employed US-based community members (N = 352), we investigated the relations between the Triarchic Psychopathy Measure (TriPM) and an expanded version of the Levenson Self-Report Psychopathy Scale (E-LSRP), on the one hand, and interpersonal and organizational counterproductive behaviors and citizenship behaviors directed towards co-workers and the organization, on the other. As predicted, we found stronger positive associations between impulsive-antisocial traits (Disinhibition, Antisocial) and both interpersonal and organizational workplace deviance; however, these traits did not relate significantly to citizenship behaviors. We further found that interpersonal traits (Boldness, Egocentric) may play an adaptive role in the workplace, as demonstrated by increased citizenship behaviors. Affective traits (Callous, Meanness) were related to lesser engagement in citizenship behaviors and higher engagement in some interpersonally-directed counterproductive behaviors. In several analyses, statistical interactions among triarchic psychopathy traits, but not E-LSRP traits, predicted adaptive and maladaptive workplace behaviors. Our results suggest that employees’ psychopathic traits bear differential implications for both adaptive and maladaptive workplace behavior, and that these traits may operate in concert to increase the likelihood of such behavior.