System, methods, and other embodiments described herein relate to engaging a driver of a vehicle about driving behaviors. In one embodiment, a method includes computing predicted controls according to at least a defined skill level of the driver. The predicted controls indicate how to control the vehicle to maintain the vehicle along a driving path on a roadway. The method includes, in response to receiving manual control inputs from the driver, generating control feedback to the driver about the manual control inputs based, at least in part, on a difference between the manual control inputs and the predicted controls.