As vehicle automation increases, drivers' roles shift from active operation to passive monitoring, making it challenging for drivers to effectively take over when automation fails. While a growing body of research focuses on providing assistance to improve driver monitoring behavior and takeover performance, these approaches have been mostly linked to the takeover event. The current study proposes to facilitate drivers' awareness during automated driving by adopting strategies from natural conversations, specifically, asking driver questions while monitoring the vehicle. In this simulated driving study, we investigated how different types of questions affect monitoring behavior and takeover performance with or without takeover notifications. Our preliminary results suggest that the driving-related questions could improve drivers’ takeover performance, especially when the takeover notification is absent.