This study focused on the experiential learning experiences of eight trainee educational psychologists (school psychologists in the United States) from Singapore who participated in three role-play sessions during a two-day Basic Counseling Skills Training Program. Data collected from transcriptions of video-recorded sessions, a focus group discussion session, and responses to qualitative questionnaires were analyzed using Strauss and Corbin's Grounded Theory. The results of this study revealed that Western-style counseling andragogies such as realistic role-plays and immediate instructor feedback could be used effectively to teach Singaporean trainee educational psychologists basic counseling skills, and to broaden their understanding of the role of an educational psychologist. The study also revealed that the experience of failure in a role-play could be a motivator to change their practice both within and outside the classroom.