Supplemental Instruction (SI) is an internationally recognized learning assistance program used in higher education to support traditionally challenging classes by offering regularly scheduled, peer-led, group study sessions for the students enrolled in the targeted course. This study explored the administrative hours spent on specific SI program constructs (training-related, observation of sessions, planning support, and administrative tasks) and program funding and their relationships with program outcomes (attendance rate for the program, the difference in the average final grades between SI session attendees and non-attendees, and the difference in the rate of Ds, Fs, and withdraws between the SI session attendees and non-attendees). This quantitative study collected data from SI programs at institutions across North America (N = 63). Multiple linear regression and correlation were used to examine the relationships between the variables. The regression models and correlation analyses were statistically insignificant, except training-related hours per SI leader was significantly related to the attendance rates for the entire SI program. This result might suggest that training-related hours assist leaders in developing high-quality sessions, thereby increasing attendance percentage. This finding indicates that SI program administrators should enhance their training-related responsibilities per SI leader to increase attendance rates for the program. These findings were limited by small sample size and focus on supervisory constructs while ignoring other factors such as institutional characteristics that may influence program outcomes. Future studies should explore each supervisory construct individually while controlling for aspects of SI programs that may affect program outcomes and collect larger sample sizes.