<p>Adolescence is a developmental stage characterized by increased engagement in risk taking, which can serve adaptive functions such as identity exploration and social integration. However, most existing research has focused on negative risk taking, with limited attention to how positive and prosocial risk taking contribute to adolescents’ leadership development. Moreover, previous studies on adolescent risk taking have predominantly relied on cross-sectional designs, leaving within-person developmental processes underexplored. This study utilized three-wave longitudinal data (<i>N</i> = 554; mean age = 13.35 years, <i>SD</i> = 0.35 years; 50% girls) to examine the relations among positive risk taking, prosocial risk taking, and prosocial leadership. Participants were assessed at three time points: July 2020 (T1), January 2021 (T2), and July 2021 (T3), each wave separated by six months. The Random Intercept Cross-Lagged Panel Model (RI-CLPM) was applied to distinguish within-person effects from between-person effects. Results indicated that, at the within-person level, both positive risk taking and prosocial risk taking predicted subsequent increases in prosocial leadership, which in turn, predicted further increases in positive and prosocial risk taking. Conversely, negative risk taking was not significantly associated with prosocial leadership at the within-person level. These findings suggest that participation in positive and prosocial risk-taking activities facilitates the cultivation and reinforcement of leadership skills among adolescents.</p>