Central to the ability of successfully facilitating sport participation toward positive developmental outcomes is the youth sport leader. Youth sport leaders are responsible for addressing the many stressors and risk factors that youth encounter in both sport and life. However, a majority of youth sport leaders do not receive coaching education or training, especially in regard to youth development. The purpose of this study was to gain a greater understanding of the various factors, which affect youth sport leaders, their team, and the community in which they coach. The four key areas of team building/teamwork, parental influence/involvement, sportsmanship, and teaching life skills emerged. By better understanding the issues within youth sport, researchers will be more aware of the most relevant issues to guide future research and to inform the development of coaching education. Moreover, youth sport leaders will be better equipped and prepared to maximize youth development through sport participation.