Numerous studies have documented the transition difficulties that health care students experience when they move into paid professional practice. Addressed in this paper are three questions that challenge post-secondary educators. (1) What might a successful transition look like for a "new" health care professional? (2) What individual actions could we, as educators, initiate to promote successful transitions for our students? Should we accept mentoring as an effective strategy to support students' transition, and if so (3) What might demonstrate effective mentorship? The evidence suggests that the process of transition into professional life for health care workers may be facilitated when post-secondary education experiences include the development of strong professional networks, the provision of supportive learning opportunities, supports for developing self-confidence in their new roles are provided and mentoring continues after graduation. [Articles in this journal were presented at the University of Calgary Conference on Postsecondary Learning and Teaching.]