Although many studies indicate that mentoring is an effective approach to developing leadership skills, there is no empirical research that provides support for the idea that mentoring can be effective in the cultural context of the Saudi system of higher education. The present study elicited the views of twelve university administrators participating in a year-long mentorship program. The study employed qualitative data collection methods through interviews and journals. Findings illustrate that mentees benefitted from the program when trust was established. Mentors, on the other hand, sometimes confused their mentorship role with that of supervising, rather than guiding, their mentees. Power relations, gender differences, age gaps, and other cultural-related issues were identified as factors that contributed to the program's (in)effectiveness.