Drawing upon cognitive-motivational-relational theory, we offer a framework for understanding the mechanism underlying the effect of negative workplace gossip about supervisors (NWGS) on employees as gossip senders. We propose that NWGS can elicit two negative emotions, namely, anxiety and guilt, which further lead to employee behaviors that reflect avoidance and approach tendencies, respectively. We first tested these proposals in a survey study of graduate students (Study 1) and then replicated our findings among employees in the workplace (Study 2). In both studies, we found that NWGS is positively related to both anxiety and guilt, which in turn are linked to further avoidance-related workplace deviance and impression management directed toward the supervisor, respectively. Our results also show that the effects of NWGS on employees’ impression management through guilt are significant only when the employees score high on supervisors’ approval contingent self-worth. We discuss the implications of these results for managing workplace gossip in organizations.