Adolescent Medical Decision Making (aMDM) is frequently discussed but presents a significant challenge in practice, especially in cases of adolescents with life threatening or life limiting illnesses. In this paper, we present a case that explores the importance of aMDM, the difficulties for providers when engaging adolescents in these discussions, and how certain skills may be incorporated into pediatric practice. Literature suggests that patients of this age group, while being legally without capacity, have meaningful insights into their care. However, unless physicians feel comfortable and competent engaging adolescents in a manner that honors their developmentally appropriate understanding of their illness, these insights can be lost.