The School for Student leadership (SSL) provides a unique educational experience for Australian Year 9 secondary school students at a time when parental expectations may not necessarily be in alignment with student engagement and motivation. Yet there are often concerns amongst both students and their parents about spending time outside 'traditional' educational settings and the potential impact on development and achievement. This paper discusses part of a longitudinal project between Monash University Gippsland and the SSL, investigating how parents and students experience their involvement with the school through focused reflection over time. Initial findings suggest that parents have broader concerns than their adolescent children but that both acknowledge significant positive developmental changes. Interestingly, there was no concern expressed in relation to missing a term of traditional academic schooling by either parents or students, with suggestions that the social-emotional development that occurred far outweighed the loss of a term of schooling. The project will continue to conduct followup research to determine whether the reported benefits are sustained over time.