Whether life skills are developed through sport greatly depends on how coaches create suitable environments that promote the development of youth (Gould & Carson, 2008). The purpose of this study was to examine, using Gould and Carson’s (2008) model of coaching life skills, the philosophies and strategies used by model high school coaches to coach life skills and how to transfer these life skills to other areas of life. Interviews were conducted with both coaches and their student-athletes. Results indicated that coaches understood their student-athletes preexisting make up and had philosophies based on promoting the development of student-athletes. Results also demonstrated that coaches had strategies designed to coach life skills and educate student-athletes about the transferability of the skills they learned in sport. Although variations were reported, coaches and student-athletes generally believed that student-athletes can transfer the skills learned in sport to other areas of life. These results are discussed using Gould and Carson’s model and the youth development literature.