Self-awareness represents an important aspect of leadership. However, past research on leader self-awareness has focused on one component of self-awareness, self versus others’ ratings, leaving the second component, the ability to anticipate the views of others, largely neglected. We examined this second component of self-awareness by focusing on women leaders who have been found to under-predict how others rate them. In two studies, we measured how women leaders anticipate the views of their bosses in regard to their leadership. In Study 1, 194 leaders rated their leadership, were rated by their bosses, and then predicted how their bosses rated their leadership. While we found that women under-predict their boss ratings compared with men, we did not find that boss gender or feedback played a role in this under-prediction. In Study 2, 76 female leaders identified (via open-ended questions) possible reasons and consequences of under-prediction for women in organizations. Results from Study 2 reveal the following: (1) the reasons for women’s under-prediction include a lack of self-confidence, differences in feedback needs, learned gender roles, and self-sexism; and (2) the perceived consequences of under-prediction are negative for both women and the organization.