Health promotion programs designed specifically to support men to improve their lifestyle behaviours are required to improve men’s health. This study explored factors that influenced men’s experiences of, and engagement with, the Rugby Fans in Training—New Zealand pilot trial, a professional sport-based healthy lifestyle intervention for overweight men. Thirty-five men (mean age = 45, SD = 10 years) who completed the 12-week intervention participated in one of eight semi-structured focus groups. Using inductive thematic analysis, five themes represented the meanings in the data. First, a group of like-minded men all in the same boat recognised the importance of being in similar life situations and having similar reasons for joining the programme. Second, the men described the importance of the support and motivation provided by the team atmosphere created through the programme. Third, the motivational coach recognised the characteristics, skills and knowledge of the coach delivering the programme which created engagement with it. Fourth, the education sessions were valued for the knowledge gained and underpinning philosophies that guided them. Finally, the involvement of the rugby franchise influenced commitment to the programme and created initial interest. These results provide evidence for the key components that should be incorporated into the future development of and improvement to healthy lifestyle interventions for men.