Researchers increasingly identify virtual reality (VR) simulations as a potentially effective professional development tool. However, simulations used in education and behavior analysis typically require active oversight from technicians and instructors. "Smart" VR integrated with artificial intelligence could independently administer simulation components, alleviate logistical challenges associated with high-quality professional development such as behavioral skills training (BST), and provide trainees with opportunities to extensively practice skills across a range of disciplines. The limited research in this area has yet to demonstrate a functional smart VR application with the ability to provide instruction related to a primarily vocal skill. The current study used a randomized, combined multiple probe across behaviors and participants design to examine a smart VR application's ability to deliver components of BST and assess participants (n = 2) acquisition of a mathematical questioning strategy designed to examine covert student problem solving in general education settings. Results suggest that automated assessment of participants corresponded with results of direct observation. Although insufficient to demonstrate a functional relation between training and participant performance, the iterative experiment provides qualified support for the use of automated BST as a tool for skill acquisition. Findings indicate smart VR represents a promising means of improving professional development and a fruitful area of interdisciplinary collaboration.