Employment specialists play a pivotal role in assisting youth and adults with disabilities find and retain jobs. This requires a unique combination of skills, competencies and personal attributes. While the fields of career counseling, vocational rehabilitation and special education transition have documented the ideal skills sets needed to achieve desired outcomes, the authors characterize these as essential mechanics. What have not been examined are the personal qualities that effective employment specialists possess. Theorizing that these successful professionals exhibit traits and behaviors beyond the mechanics, the authors conducted a qualitative study incorporating in-depth interviews with 17 top-performing staff of a highly successful national program, The Marriott Foundation's Bridges from school to work. Four personal attributes emerged from the interviews: (a) principled optimism; (b) cultural competence; (c) business-oriented professionalism; and (d) networking savvy. In presenting these findings, the authors discuss the implications for recruitment, hiring, training, and advancing truly effective employment specialists, and offer recommendations for further research.