Given the stance of education-based sport entities (i.e., NFHS) that sport participation leads to leadership development, this article aims to provide coaches and practitioners several strategies to teach leadership skills anchored in principles from skill acquisition literature. The principles explored include (1) identification of skill abilities, (2) demonstration, (3) verbal instruction, (4) specificity and (5) feedback. Following a continuum describing life skill acquisition (including structuring the sport context, facilitating a positive climate, discussing life skills, and practicing life skills), examples are provided of how to enhance leadership skill development.