The aim of this study was to gain a deeper understanding of coaches’ perceptions of their role in the development of life skills in adolescent athletes in two different sport contexts. Semistructured interviews were held with 24 coaches: 12 coaching high school basketball and 12 coaching community swimming. All coaches followed a holistic, athlete-centered approach. Coaches described the life skills they taught, their motivations, and the strategies they used to foster life skills development in practice. Although some differences between the two contexts were identified, the overall results indicate that all coaches fostered the development of life skills through various teaching and transfer strategies, and that coaches had two main motivations: athletes’ needs and their own values. The main results are discussed in light of the literature on life skills in sport and positive youth development, and in terms of methodological considerations. The study concludes with some practical recommendations for coaches.