This case study explores adolescent well-being assessment, methods, and processes, drawing from the extensive social work research practices and impactful initiatives of NalandaWay Foundation, spanning the last 17 years. It examines the Monitoring, Evaluation and Learning (MEL) methodologies characterized by the application of participatory action and human-centric research methodologies, which recognize the non-linear and dynamic nature of adolescent development. The strength of this research approach lies in the flexibility and ability to capture nuanced aspects of well-being, moving beyond traditional assessments methodologies, authentically capturing the rich lived experiences, aspirations, and challenges of adolescents in various settings and contexts. The study affirms that NalandaWay Foundation has effectively adopted contextually appropriate and participatory methods such as Creative Elicitation Exercises, Peer Interviewing, Exit Slips/Tickets for Student Feedback, Observations and Activity-based Assessment of Socio-emotional Learning effectively. Further, the study, in particular, contributes to the discourse on human-centric practices in adolescent well-being assessments, emphasizing the importance of inclusive and contextually relevant interventions.