Unemployment rates remain high among individuals with psychiatric disabilities despite growing evidence that supported employment programs (SEPs) can help such individuals to obtain and retain competitive employment. A complete understanding of factors that may facilitate or hinder the success of such supported employment efforts is urgently needed to increase the efficacy of SEPs and move more individuals with psychiatric disabilities from welfare to work. This exploratory study provides insight into potential facilitators and barriers to employment among individuals with psychiatric disabilities from the perspective of job coaches. Twenty-eight job coaches from 14 SEPs in a Northeastern state reported on their experience with four recent clients, two who were successful in obtaining employment and two who failed, through a semi-structured mail survey. Findings suggest that job coaches use similar strategies to assist clients, but in each case try to tailor specific strategies to client's needs and characteristics. Factors that influence successful job placement and research and policy implications are discussed.