When asked what he looks for when hiring employees, Dr. Paul Orehovec, Vice President of Enrollment Management at University of Miami responds, “Somebody who wants my job” (personal communication, September 25, 2010). He further explains that the heavy demands of higher education administrative positions require people who are self-motivated and driven. These professionals need mentoring relationships to help them establish appropriate career and professional goals. Mentors often have valuable knowledge to share with their mentees on these topics, but do not always know how to effectively share their expertise. Mentoring relationships occur in a number of settings in academia, but there are few frameworks to guide the establishment of these mentoring relationships. The purpose of this article is to demonstrate how the six phases of the Appreciative Advising model (Bloom, Hutson, & He, 2008) can be adapted to help higher education administrators mentor and nurture the careers of future administrative leaders. The Appreciative Advising model is being utilized on a number of college campuses to help students identify their dreams for their future and devise a plan to make those dreams come true (Bloom et al., 2009). This article proposes adapting this model to be used with academic staff to help them achieve their career and personal goals