Although many conceptions of leadership focus on the power of a single individual or “great man,” leaders often work together in pairs. In pairs such as a President and Vice President or a superhero and sidekick, one leader often possesses more power while the other plays a more supportive role. What factors influence people’s expectations about who holds leadership roles in such pairs? How might a leader’s traits and gender influence perceptions of how well-suited that leader is for each position within a pair of leaders? To examine these questions, we presented adults (N = 236) and adolescents (N = 67, ages 12-15) with a narrative about a fictional town led by a pair of leaders: the “first leader” and the “second leader.” Between-subjects, we varied the gender and position of an existing leader (first, second) and presented participants with four prospective leaders (i.e., agentic boy, agentic girl, communal boy, communal girl) who were interested in the other role, which had been left vacant. Adults and adolescents preferred agentic leaders, regardless of gender, over communal leaders, supporting a strong association between agency and leadership and demonstrating that adults and adolescents prioritize agency over other traits. Participants were also asked about their own preferences for the two roles. Adolescents viewed both first and second leader roles as more desirable than did adults. Whereas adolescent girls and boys rated both roles equivalently, adult men viewed the first leader role as more desirable than did women. Implications and future directions are discussed.