A mentor serves as role model, counselor, and advocate for an understudy or protégé. The art and science of mentoring have been investigated most thoroughly in the educational literature, yet there are unique situational and individual considerations in the surgical arena that may warrant special consideration. The general attributes of successful mentors are not foreign to academic surgeons but may require deliberate cultivation to optimize mentorship in the context of academic medicine. Moreover, the stages of productive mentoring may be counter to the learned adaptive behaviors and instinctive personality traits of some accomplished surgeon educators. Indeed, examples of failed mentorship are common in our medical centers and, specifically, in surgical training programs. The behavioral adaptation that supports surgical decision-making under conditions of incomplete data and unusual stress often devalues succession planning and derivation of satisfaction from the success of other members of the team. Accordingly, fostering effective mentoring relationships in academic surgery will require a concerted effort to develop appropriate behaviors conducive to the mentoring process. The personal and professional growth of our students as well as the succession planning for our specialty are dependent upon the successful creation of an environment conducive to mentoring in academic orthopaedics.