Experienced music educators rate their senior class of musicians by often using the terms exceptional, talented, average, limited, unremarkable or apathetic. This summative evaluation considers class size, academic results, willingness to participate in extra curricula musical activities or post secondary school career choices in the music industry. Such characterisation by teachers raises the question: To what extent does this determination depend on the individual traits of the students, their musical experiences or the personal influence of their music teachers? This pilot study examined this question by comparing six cohorts of senior musicians over the six years of their secondary school music education within an action research context. Through the use of the Boy’s Music Ecosystem model (Collins, 2011) and interview results, the study revealed six themes that point to successful practices in boys’ music education and the possible benefits of a longitudinal view across a boy’s entire secondary school music experience.