This study examines whether and how self-monitoring moderates the relationships between two personality traits (agreeableness and conscientiousness) and counterproductive work behavior directed toward the organization (CWB-O) and toward other employees (CWB-I). High self-monitors strive to attain personal goals related to status and prestige enhancement by adjusting their behavior to what the situation requires or allows for. We propose that the status enhancement motive can take on two different yet related forms—impression management (interpersonal potency) and opportunism (win-at-all-costs)—depending on relevant situational cues. We hypothesize that in public, interpersonal settings where their behavior is visible to others, high self-monitors' desire to enhance their status by looking good to others suppresses the natural expression of low agreeableness via increased engagement in CWB-I. Conversely, we hypothesize that in private, non-interpersonal settings where their behavior is rarely visible to others, high self-monitors' desire to enhance their status by doing whatever it takes to get what they want intensifies the natural expression of low conscientiousness via increased engagement in CWB-O. On the basis of two independent samples of participants, results of moderated multiple regression analyses provided support for the hypotheses. Copyright © 2013 John Wiley & Sons, Ltd.