Coaches have been shown to play key roles in the life-skills development and transfer process. The purpose of the study was to examine coaches’ approaches to teaching life skills and their transfer in youth sport. A multiple case study design was employed. Each case was composed of one coach and at least two of their athletes involved in youth baseball, rugby, soccer, and sailing. The data collection involved pre- and postseason interviews and in-season journaling with coaches, as well as postseason interviews with athletes. The results indicated that the coaches predominantly used implicit approaches, with just over half identified as using some explicit approaches to teach life skills. The coaches discussed several factors that influenced their decisions to use or not use explicit life-skills teaching approaches. The results have implications for future research and applied efforts aimed at maximizing the developmental gains athletes can derive from their participation in sport.