Background Confidence is a crucial trait of any physician, but its development and relationship to proficiency are still unknown. This study aimed to evaluate the relationship between confidence and competency of medical students undergoing basic surgical skills training. Methods Medical students completed confidence surveys before and after participating in an introductory workshop across 2 samples. Performance was assessed via video recordings and compared with pretraining and posttraining confidence levels. Results Overall, 150 students completed the workshop over 2 years and were evaluated for competency. Most students (88%) reported improved confidence after training. Younger medical students exhibited lower pretraining confidence scores but were just as likely to achieve competence after training. There was no association between pretraining confidence and competence, but confidence was associated with demonstrated competence after training (p < 0.001). Conclusions Most students reported improved confidence after a surgical skills workshop. Confidence was associated with competency only after training. Future training should investigate this relationship on nonnovice samples and identify training methods that can capitalize on these findings.