As the literature is far from being unanimous in regards to the psychosocial benefits of sports practice, we conducted a preliminary qualitative study with nine teenagers who participated in a group sporting challenge to better understand: (1) youths’ perceptions regarding the program’s most important dimensions and (2) its effects in the physical, psychological and social spheres of their life. Following these results, we highlighted six driving principles we consider to be significant to interventions involving sports as a tool for psychosocial development: (1) cooperation amongst youth; (2) facilitators’ discipline, direct involvement and positive attitude; (3) moving the youths beyond their physical, psychological and social comfort zones; (4) the interplay between enjoyment and effort; (5) constant innovation in training content; (6) risk as a driving force for cohesion and social ties.