We propose that guilt proneness is a critical characteristic of leaders and find support for this hypothesis across 3 studies. Participants in the first study rated a set of guilt-prone behaviors as more indicative of leadership potential than a set of less guilt-prone behaviors. In a follow-up study, guilt-prone participants in a leaderless group task engaged in more leadership behaviors than did less guilt-prone participants. In a third, and final, study, we move to the field and analyze 360° feedback from a group of young managers working in a range of industries. The results indicate that highly guilt-prone individuals were rated as more capable leaders than less guilt-prone individuals and that a sense of responsibility for others underlies the positive relationship between guilt proneness and leadership evaluations.