Now widely accepted as an independent field of specialization, the practice of supervision is viewed as the most important element in the development of counselor competence in career counseling. The bulk of our knowledge however, concerning the process of supervision has grown out of the psychology literature and this has guided the practice of supervision. The goal of this research is to extend the supervision research by investigating different aspects concerning the nature of the perceived supervisory working alliance and by investigating the possible relationship between the supervisory working alliance and impact (proposed as a variable predictive of outcome), as well as investigating whether supervisee shame-proneness could be found to be significantly related to the supervisory working alliance and impact. The participants in this research included 43 supervisees and 13 supervisors undergoing a 5-session supervisory process. The Internalized Shame Scale (ISS) was administered to the supervisees prior to the start of the supervision sessions and following the last supervision session as a measure of shame-proneness. The Supervisory Working Alliance Inventory-Trainee (SWAI-T) and Supervisor (SWAI-S) versions were used to measure the strength of reported supervisory working alliance and the Session Evaluation Questionnaire (SEQ) was used as a measure of impact immediately following each of the supervision sessions. Results from this research serve to highlight the importance supervisees place on having a safe and trusting environment for their supervision to be beneficial and suggests supervisors pay particular attention to this aspect of their supervisory alliance building for any meaningful learning to take place as well as to diminish the possible negative impacts of supervisee shame-proneness. Furthermore, this research suggest that the supervisory working alliance perceived by supervisees may be an important predictive factor for the outcome of supervision arguing for the importance supervisors should place on building and strengthening this process variable.