Aspects disclosed herein provide an operator training system that can train an operator about basic machine movements, operations, and applications, such as asphalt compactor rolling patterns, paving-by-numbers, milling-by-numbers, etc. with the use of a virtual reality headset at any point or time on a work site. The operator training system uses data received from the virtual reality headset and associated hand controls to guide the operator via training scenarios. The operator training system also includes providing immediate feedback on the outcome of the training scenario and may also identify one or more areas of improvement.