The adoption and integration of work-based assessments by surgical units and training programs continues to increase, it is important to identify challenges in their implementation. The authors evaluated the barriers involved in the deployment of a supervisor assessment tool in Australia. A questionnaire was created based on existing literature from international, and non-surgical contexts. The questionnaire covered areas known to impact multisource feedback assessments. The questionnaire was delivered in September 2019 to 34 trainees and 25 supervisors. Participants then rated each item within the questionnaire on a Likert scale. During the survey period, 23 of 25 (92%) supervisors and 31 of 34 (91.1%) trainees completed the questionnaire. The results show that an assessment form is well received and there is a difference between trainees and supervisors on perspectives surrounding impact on trainee-supervisor relationships, how a trainee manages negative feedback, consequences of poor scores, the importance of anonymity, and acceptability of input from allied health and nursing staff. The results provide reassurance that the perception of supervisors who felt that negative ratings may affect trainee-supervisor relationships is unfounded. A digital distribution format of self-assessment and supervisor assessment forms is well received by participants. This method of assessment should provide trainees an additional source of feedback, and opportunities for self-reflection during their training.