This qualitative case study explores the experiences of former [Supplemental Instruction] SI leaders who worked at a four-year, private university in the Mid-Atlantic while completing their undergraduate degrees. The insights offered by participants through interviews and graphic elicitation reveal the ways in which serving as an SI leader prepares students for their post-graduation lives through the transferability of skills. This study also seeks to fill a void in research, as studies on academic assistance programs tend to explore benefits for student participants, such as increased retention and course grades, but fail to explore the development of the programs' student leaders.