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Considering the substantial upcoming transfer of leadership to younger generations, it is critical to study the unique trait, skill, and behavioral associations of youth leaders. The purpose of this two-phase study was to quantitatively examine the relationship between positive psychological capacities (PsyCap), personality, and empathy with leadership skills in youth. Regression results from both phases revealed cognitive empathy and academic PsyCap as significant predictors of youth leadership life skills. These results follow earlier research that identified trait-based emotional intelligence as a significant predictor of leadership skills in youth. The combined results offer important considerations as leadership scholars and practitioners attempt to accurately predict and plan for the leadership transfer landscape over the next two decades. These combined results also serve as helpful considerations for youth leadership practitioners as program outcomes, learning objectives, and activities targeting the development of cognitive empathy and PsyCap will perhaps allow for more productive youth leadership development efforts and better documentation of their impact.