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To explore the mentor–mentee relationship with a focus on determining the characteristics of effective mentors and mentees and understanding the factors influencing successful and failed mentoring relationships.The authors completed a qualitative study through the Departments of Medicine at the University of Toronto Faculty of Medicine and the University of California, San Francisco, School of Medicine between March 2010 and January 2011. They conducted individual, semistructured interviews with faculty members from different career streams and ranks and analyzed transcripts of the interviews, drawing on grounded theory.The authors completed interviews with 54 faculty members and identified a number of themes, including the characteristics of effective mentors and mentees, actions of effective mentors, characteristics of successful and failed mentoring relationships, and tactics for successful mentoring relationships. Successful mentoring relationships were characterized by reciprocity, mutual respect, clear expectations, personal connection, and shared values. Failed mentoring relationships were characterized by poor communication, lack of commitment, personality differences, perceived (or real) competition, conflicts of interest, and the mentor’s lack of experience.Successful mentorship is vital to career success and satisfaction for both mentors and mentees. Yet challenges continue to inhibit faculty members from receiving effective mentorship. Given the importance of mentorship on faculty members’ careers, future studies must address the association between a failed mentoring relationship and a faculty member’s career success, how to assess different approaches to mediating failed mentoring relationships, and how to evaluate strategies for effective mentorship throughout a faculty member’s career.