Supplemental Instruction (SI) is a peer-led academic support program in which SI Leaders help students develop study habits and note-taking strategies as well as facilitate test preparation. While the effects of SI on students receiving the instruction have been thoroughly investigated, there have been far fewer studies that have assessed the impact of SI on its Leaders. Furthermore, research on Leaders has yet to adequately consider community colleges or Hispanic-Serving Institutions (HSIs), or to employ qualitative methodologies. Thus, this paper details an SI program developed at a two-year HSI and the impact of the SI Leaders’ experience via qualitative data analysis of structured, open-ended interviews. The majority of Leaders described shifts in long-term goals or changes in learning styles from individual learning and a desire to “look smart” to one that embraced asking for help, peer learning, and belonging. The data indicate a shift in academic mindset among Leaders, particularly among minority male and female adult learners and Latino males.