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Mentoring skills are valuable assets for academic medicine faculty, who help shape the professionalism of the next generation of physicians. Mentors are role models who also act as guides for students’ personal and professional development over time. Mentors can be instrumental in conveying explicit academic knowledge required to master curriculum content. Importantly, they can enhance implicit knowledge about the “hidden curriculum” of professionalism, ethics, values and the art of medicine not learned from texts. In many cases, mentors also provide emotional support and encouragement. The relationship benefits mentors as well, through greater productivity, career satisfaction, and personal gratification. Maximizing the satisfaction and productivity of such relationships entails self-awareness, focus, mutual respect, and explicit communication about the relationship.In this article, the authors describe the development of optimal mentoring relationships, emphasizing the importance of experience and flexibility in working with beginning to advanced students of different learning styles, genders, and races. Concrete advice for mentor “do's and don'ts” is offered, with case examples illustrating key concepts.