Mentorship is one of the cornerstones of surgical education, providing students with the tools to navigate the challenges of the transition from a trainee to a surgeon. Our study aims to describe the characteristics of successful mentorship of medical students who successfully matched into surgical fields, and to provide medical students practical information on how to successfully find and maintain successful mentoring relationships. In this multi-center cross-sectional observational study, 2 surveys; 1 for mentees, defined as junior surgical residents (medical students who matched into surgical specialties), and 1 for mentors, defined as staff surgeons, were used to collect data between August 1, 2020 to November 1, 2020. The study was retrospective in nature and did not directly assess survey participants while they were in medical school, but rather while they were residents, retrospectively answering regarding their experiences as medical students. The surveys contained 24 questions pertaining to demographics, the dynamics of mentor-mentee relationships, qualities sought in a mentee, and barriers/benefits to mentorship. A total of 111 attending surgeons and 138 surgical residents completed the surveys. Seventy-eight percent of surgeons had mentored at least 1 medical student, while 74.6% of residents had at least 1 mentor during medical school. The top three mentee qualities reported by mentors were willingness to learn, being a hard worker, and curiosity. There was a significant disparity between mentors' and mentees' perceptions of the importance of scientific curiosity as a mentee trait (p < 0.05). Mentors and mentees have different perceived barriers to forming successful mentorships. While the majority of students have experienced fruitful mentoring relationships, the differences in perception of mentors and mentees still represent barriers to be overcome to allow mentorship in surgery to flourish.