Introduction: There are few opportunities for mentorship of practicing surgeons and no evidence to guide the design of such programs. This study explored outcomes and barriers associated with the design of surgical mentorship programs. Methods: Interviews were held with organizers, mentors, and proteges of 2 programs. Data from 23 participant interviews and 23 nonparticipant surveys were analyzed thematically. Results: Participation was greater in the program where planning was participatory and mentors visited proteges. Scheduling was a key barrier, and existing relationships enabled mentorship. Most nonparticipants said they were already trained or had no interest in the skill. Mentorship was valued for exchange of tacit knowledge, hands-on learning, and real-time feedback. Mentorship prompted participants to realize gaps in skill; several said they already adopted the new skill, and many were interested in ongoing mentorship. Discussion: Several beneficial outcomes appear to be associated with mentorship, but longitudinal evaluation is required. Telementoring and train-the-trainer models may promote participation in surgical mentorship. Participants suggested that technical training be integrated within pre- and postmentorship education and follow-up. Such programs can only be implemented if issues of sponsorship and funding are addressed. (Contains 2 tables.)