Simulation-based training is increasingly being used for assessment and training of psychomotor skills involved in medicine. The application of artificial intelligence and machine learning technologies has provided new methodologies to utilize large amounts of data for educational purposes. A significant criticism of the use of artificial intelligence in education has been a lack of transparency in the algorithms’ decision-making processes. This study aims to 1) introduce a new framework using explainable artificial intelligence for simulation-based training in surgery, and 2) validate the framework by creating the Virtual Operative Assistant, an automated educational feedback platform. Twenty-eight skilled participants (14 staff neurosurgeons, 4 fellows, 10 PGY 4-6 residents) and 22 novice participants (10 PGY 1-3 residents, 12 medical students) took part in this study. Participants performed a virtual reality subpial brain tumor resection task on the NeuroVR simulator using a simulated ultrasonic aspirator and bipolar. Metrics of performance were developed, and leave-one-out cross validation was employed to train and validate a support vector machine in Matlab. The classifier was combined with a unique educational system to build the Virtual Operative Assistant which provides users with automated feedback on their metric performance with regards to expert proficiency performance benchmarks. The Virtual Operative Assistant successfully classified skilled and novice participants using 4 metrics with an accuracy, specificity and sensitivity of 92, 82 and 100%, respectively. A 2-step feedback system was developed to provide participants with an immediate visual representation of their standing related to expert proficiency performance benchmarks. The educational system outlined establishes a basis for the potential role of integrating artificial intelligence and virtual reality simulation into surgical educational teaching. The potential of linking expertise classification, objective feedback based on proficiency benchmarks, and instructor input creates a novel educational tool by integrating these three components into a formative educational paradigm.