Mentoring is inarguably the most critical element for faculty advancement. However, most mentoring programs focus on early career surgeons, and too frequently mid-career surgical faculty receive little feedback or formal mentoring. Mentoring a surgeon at the mid-career level has unique challenges that are more complex. There are several roles that need to be fulfilled by a mentor and there are various strategies for mentoring. This chapter explains these challenges and the mentoring roles necessary to address them. We provide strategies on how a mentee can build an effective mentoring team. At times, it is even necessary to redefine your career path, and this chapter will describe the steps necessary to start this process. At the senior administrator level, we delineate steps toward building an effective mentoring program at your institution.