A phenomenological study was conducted to gain knowledge of the lived experience of three master’s level counseling supervisees, with a doctoral student supervisor, utilizing the Enneagram, an ancient personality classification system of nine core personality types, throughout 15 weeks of supervision. This study explored the use of the Enneagram and its impact on the supervisory relationship. Emergent themes included: (a) self-awareness; (b) other awareness; (c) relationship and rapport; and (d) professional identity and role induction. The use of the Enneagram within supervision during early stages of counselor development appeared to be helpful to these students in fostering growth and learning