In this research, I examine the concept of leadership as it is constructed in the youth-based organizations of Girl Scouts and Boy Scouts. How boys and girls are taught to lead as children in these single-sex, youth-based organizations has clear connections to prominent “masculine” and “feminine” styles of leadership, and I argue that these organizations assist in perpetuating gender inequality in the workplace in this way. Using historical content analysis and a modified grounded theory approach, I evaluate Boy Scout and Girl Scout handbooks printed over the past 100 years. I argue that through the process of “doing” leadership, the emotion work involved in becoming a boy or girl leader, and through promoting a sense of belonging, these organizations strategically strive to develop boys and girls with leadership styles that are gendered in nature.