The supervision of personality assessment can be likened to the process of teaching art. Much like artistic training, supervision of personality assessment is a complex process that calls for creative integration of different working processes, some more technical and formal and others broader and more complex. On the surface, compared to psychotherapy supervision, supervision of personality assessment is fairly structured and centered on specific tasks such as scoring, making a diagnosis, or determining personality organization. Nevertheless, principles of psychodynamic psychotherapy such as parallel processes are relevant as well. We discuss the process of integrating intersubjective and psychodynamic elements into personality assessment supervision and argue that this integration helps the supervisory work to proceed effectively. We present the role of knowledge, the institution, and parallel processes in the supervisory work.