This study asked a group of coaches about the major challenges they encounter in their coaching experience. The study was conducted with a group that had recently completed an introductory coaching course, but they had widely varied coaching experience, and coached male and female athletes in a variety of sports at multiple levels. We were interested in the extent to which the challenges were specific to the coaches’ context, or varied according to the age, education or experience of the coach. Our results showed that coaches face multiple challenges, but dealing with parents was commonly cited as the most challenging in all contexts, indicating that a generic coach education program on this topic could be effective. Other challenges tended to be associated with specific contexts and generic coach education programs may not be able to effectively prepare coaches for those challenges.