Peer mentoring is widely recognized as a high-impact practice in higher education, particularly for supporting first-year students’ academic transition, sense of belonging, and social integration. First-year students benefit from guidance, reassurance, and relationship-building with experienced peers who help normalize challenges and connect them to campus resources. Effective mentoring programs foster inclusive communities that promote engagement and persistence, but research consistently emphasizes that positive outcomes depend on intentional program design and structured mentor preparation to meet the diverse needs of new college students. This pilot study examined the experiences of junior and senior students serving as peer mentors for first-year students enrolled in a leadership seminar. Mentors completed structured training grounded in the R.I.S.E. (Respect, Influence, Support, Empower) Model, which emphasizes values-based, relational mentoring centered on first-year students’ identities, growth, and agency. A mixed-methods design was used with Kirkpatrick’s Evaluation Model guiding the assessment of mentor development. Level 1 (Reaction) examined mentors’ perceptions of their preparedness, confidence, and satisfaction with the training, while Level 2 (Learning) focused on the knowledge, skills, and mentoring strategies mentors reported gaining to effectively support first-year students. Data were collected through pre- and post-training reflections and surveys and analyzed using descriptive statistics and thematic coding. Findings indicated that mentors felt confident and prepared to support first-year students and articulated clear intentions to build trusting, supportive relationships. Mentors emphasized empathy, communication, and individualized support as essential for helping first-year students navigate their transition to college. Mentees echoed the sentiment that this mentoring relationship provided individualized support and a sense of belonging. Training strengthened mentors’ ability to guide conversations, provide structured feedback, and empower mentees to reflect and set goals. Recommendations include edits to the mentor training program based on mentor feedback and replication of the study to glean additional insights on peer mentoring training and program facilitation.