Surveys indicate that practice and training in psychological assessment, and personality assessment (PA) to a lesser degree, has been stable or increasing over the past quarter century. However, its future arguably remains threatened due to changes in doctoral training programs and beliefs in the field concerning the utility of PA for treatment success. In order to increase interest in and use of PA, studies of training methods that include trainees’ perspectives are needed. This study evaluated the experiences of ten graduate trainees and their clients who were trained in and conducted a brief Therapeutic Assessment (TA). Qualitative responses to a self-evaluation administered post-TA were coded using directed content analysis. Results indicated that trainees’ viewed TA/PA as having clinical utility; they had positive feelings about TA/PA, and they desired or intended to use or continue learning about TA/PA. Clients’ responses reflected positive feelings about the TA, having gained new self-awareness or understanding, and having a positive relationship with the assessor. The findings suggest that teaching PA from a TA perspective could produce positive benefits for psychology trainees.