Sport has the potential to foster the development of life skills, such as initiative, teamwork, emotion regulation, and goal setting, that transcend the fields and courts on which youth participate (Danish, Forneris, Hodge, & Heke, 2004). However, it is often acknowledged that this growth does not occur on its own. One factor that plays a central role in shaping positive sport experiences is the coach (Hellison & Cutforth, 1997). The purpose of this paper is to review the current literature on coaching strategies considered best practices for life skills development as well as to provide illustrative examples of many of these practices garnered from a case study of a model coach and the strategies he used in his high school tennis program. The paper concludes with additional practical considerations and recommendations for practitioners, coach educators, and scholars who continue to add to the body of knowledge regarding a coach’s role in positive youth development.