Few career counseling theories have had the long-standing background of Hollands RIASEC theory. His theory, which espouses that job satisfaction increases when there is congruence between individuals interests and environments, has resulted in many practical, reliable, and valid inventories, such as the Self-Directed Search (SDS). The majority of Hollands tools and related studies have focused on high school, college, and adult individuals, with a paucity of studies reporting on the use of SDS with middle school students. The purpose of this paper is to provide information on the processes and outcomes of using a theory-driven assessment tool, i.e., the Self-Directed Search Career Explorer (SDS-CE), with middle school students. Based on the results of 14 separate career counseling groups utilizing the SDS-CE and the statistical analyses results it is concluded that the SDS-CE is a useful tool with a test group of African American middle school students; its use is enhanced when coupled with Cognitive Information Processing theory. (GCP)