Mentorship is an important aspect of student growth and development. Students who are mentored have been shown to have superior outcomes on leadership and cognitive skills. Using data from the 2011 Multi-Institutional Study of Leadership, analyses were conducted to see how personal characteristics and types of mentor influenced mentoring outcomes among a sample of 482 students at a university in the Caribbean. The study design used Astin’s Input-Environment-Output model of student assessment. Hierarchical regression analysis was used to assess how the input variables age, sex and first-generation student status were correlated with the mentoring outcomes scales. In addition, the college experience variable, type of mentor, which included faculty/instructors, student affairs staff, employers, and other students was examined to see how the type of mentor influenced outcomes on the mentoring scales. Type of mentor was an important predictor of mentoring outcomes. Student affairs staff had the greatest impact on outcomes by a statistically significant margin. The study has implications for how a structured approach to mentorship, and the requisite training of mentors, can improve outcomes on leadership empowerment and personal development.