The overall purpose of this study was to examine parents' role in the development of character among young athletes, with a particular focus on life skills development across learning contexts (i.e., sport, family, school). Participants were 20 parents (13 mothers, 7 fathers, M[subscript age] = 46.8 years, SD = 4.6) and 24 children (14 girls, 10 boys, M[subscript age] = 14.3 years, SD = 1.3) who competed in a variety of youth sports. Each participant completed an individual semistructured interview. Interviews were transcribed verbatim, and data were analyzed using thematic analysis. We identified five strategies that parents used to facilitate their children's life skills development: reinforcing values and consistency; giving perspective and guiding; seizing teachable moments; instructing, reminding, and encouraging; and promoting independence. These findings highlight parents' role in character development among young athletes, and show that life skills are developed and reinforced, across learning contexts.