Background Trainers in surgery have an educational obligation to train trainees in performing operative procedures. Objective We hypothesized that poor concordance manifests as discrepancies between the trainee and the trainer, with an associated reduction in satisfaction with the training experience, perception of training quality, and completion of workplace-based assessments (WBAs). This study also aimed to validate the novel Supervised Training Operative Procedure (STOP) online tool. Method We developed an online proforma (STOP online tool) and conducted a prospective, single-blinded study of 53 orthopedic operative procedures with 53 trainees between January 19, 2019, and August 27, 2019. Results Forty-four (82%) trainees were listed as the primary surgeon. The overall mean trainee satisfaction (on a 0-10 Likert scale) was 8.25 (range: 3-10), and the mean trainer satisfaction was 8.28 (range: 4-10). A preoperative discussion between the trainee and the trainer occurred in 96.2% of the cases. Forty-eight (91%) trainers preoperatively established trainees' objectives and 91% (n = 48) of the cases showed postoperative completion of objectives. Forty-four (83%) trainers anticipated workplace-based assessment (WBA) completion for trainees, and this translated into 41 (77%) completed WBAs. Overall, 47 (92.9%) trainees felt that the STOP tool would be useful as a surgical training checklist and in the completion of WBAs. Conclusion The STOP checklist is useful in understanding qualitative and quantitative measures of the overall trainee performance of an operative case. This holistic approach will enable us to establish a structured perioperative surgical training checklist, as trainee and trainer requirements are dependent on one another.