The opportunity for high-achieving university students to take on leadership roles in mentoring and peer learning contexts is perhaps underutilised. Peer Assisted Study Sessions (PASS) programs are an example where the role of the peer leader, who facilitates the study session, is crucial to the success of the program. The implementation of PASS programs is motivated by, not only a desire to address issues of transition and retention within universities, but also a desire to provide learning support for students studying targeted and difficult subjects with large student cohorts. This paper uses Brookfield’s framework (1995) of critical reflection to consider multiple ways in which PASS programs can embed opportunities for PASS Leaders to reflect critically upon their practice.