Using interpretative phenomenological analysis and Robert Kegan's constructive-developmental theory, this study investigated how developmental stage shaped the subjective experiences of 13 adolescents (M[subscript age] = 15.92 years, 54% females) in a developmental coaching and outdoor adventure education program. Participants were drawn from socioeconomically disadvantaged schools in Sydney, Australia, and represented Asian, Middle Eastern, and European ethnicities. A single, semi-structured interview was conducted with participants postprogram, following protocols approved by an institutional ethics committee. Interview data were used to investigate participants' meaning-making structures as evidence of constructive-developmental stage both at the time of interview and program participation. We found that, despite being similar ages at program commencement, participants displayed a range of constructive-developmental stages. The data demonstrate how participants at different stages of meaning-making experienced the same activities differently, including what they experienced as challenging and supportive. Furthermore, our findings suggest that there is a valuable role for developmental coaching in scaffolding program challenges to stimulate constructive-developmental growth. Constructive-developmental theory provides a novel framework for understanding the different ways in which adolescents make meaning of developmental programs. We hope the findings from this study will help those who design and implement these programs to appreciate constructive-developmental differences in their participants to better target interventions aimed at facilitating developmental growth.