Trainees develop surgical technical skills by learning from experts who provide context for successful task completion, identify potential risks, and guide correct instrument handling. This expert-guided training faces significant limitations in objectively assessing skills in real-time and tracking learning. It is unknown whether AI systems can effectively replicate nuanced real-time feedback, risk identification, and guidance in mastering surgical technical skills that expert instructors offer. This randomized controlled trial compared real-time AI feedback to in-person expert instruction. Ninety-seven medical trainees completed a 90-min simulation training with five practice tumor resections followed by a realistic brain tumor resection. They were randomly assigned into 1-real-time AI feedback, 2-in-person expert instruction, and 3-no real-time feedback. Performance was assessed using a composite-score and Objective Structured Assessment of Technical Skills rating, rated by blinded experts. Training with real-time AI feedback (n = 33) resulted in significantly better performance outcomes compared to no real-time feedback (n = 32) and in-person instruction (n = 32), .266, [95% CI .107 .425], p < .001; .332, [95% CI .173 .491], p = .005, respectively. Learning from AI resulted in similar OSATS ratings (4.30 vs 4.11, p = 1) compared to in-person training with expert instruction. Intelligent systems may refine the way operating skills are taught, providing tailored, quantifiable feedback and actionable instructions in real-time.