Background: Employers consider strong leadership skills among highly desirable qualities for new hires. To meet the needs of today's complex workforce, colleges and universities have increased opportunities for experiential learning for students. However, it is not known how students make meaning of these experiences in context with their personal backgrounds and experiences. Purpose: This study examines how women and men in college make meaning of leadership and leaders through experiential community-based mentoring participation. Methodology/Approach: A two-step qualitative content analysis of reflective journals, with a sample of 20 students utilizing the constant comparative method, is used to generate overarching themes. A second qualitative analysis compares how men and women understand leadership differently. Findings/Conclusions: Findings reveal that, despite a shift in the leadership literature away from hierarchical or trait models toward transformational, relational models that are typically more inclusive of women, our participants still made meaning of leadership and leaders in ways that were more closely aligned with antiquated understandings of leadership. Implications: Recommendations including use of experiential learning as a tool to intentionally increase leadership development and efficacy for women and men in college are discussed.