AbstractAddressing difficult, controversial, or sensitive issues with employees is a critical component of effective leadership, but discussing uncomfortable topics with subordinates can be daunting, even for those with structural power. Distinguishing between the structural power that supervisors hold, and their situationally felt personal sense of power, we consider here how a supervisor's personal sense of power relates to his or her inclination to confront, or to avoid, difficult conversations, as well as to offer social support in such contexts. Integrating a social role theory perspective, we further consider the role of gender. Across an initial study (N = 588), and a follow‐up replication study (N = 567), we show that personal sense of power predicts supervisor's inclination to confront (and not to avoid) difficult issues in the workplace, as well as to offer social support to the target of conversation. We also consider whether such effects vary across male and female supervisors, finding inconsistent results across studies. In Study 1a, we found that power had less of an effect on the avoidance and support intentions of women than men, such that women (but not men) were more likely to constructively confront the difficult issue head on as well as to offer support, even when they felt low in personal power. These effects did not emerge in Study 1b. However, in both studies, we find a main effect of gender on social support such that women were more likely to provide social support when confronting difficult issues. We speculate about reasons for this inconsistency, and further theorize about the role of personal sense of power and gender in explaining supervisor's engagement in difficult conversations.