Unlike more traditional institutions of higher education, Empire State College situates the mentoring relationship at the center of almost all organizational and pedagogical decisions. As Empire State College mentors know, our role goes beyond that of the college advisor who informs students what courses they need to take to fulfill requirements. The mentor-mentee relationship is complicated by demands on time, assumptions about what counts as academic activities, race, class, gender, prior learning experience of both mentor and mentee: the list is endless. Sometimes, the complexity of these relationships gets overwhelming, since presumably we have a unique relationship with each unique student. In this essay, we propose that skills learned by social workers and other human services professionals can positively add to how mentors go about the business of advising and guiding students. We specifically focus on approaching the mentoring relationship from a “strengths perspective,” using key elements of reflective practice.