Apart from mandating the use of clearoff, I generally try to get the students doing a kind of mental gymnastics.
Taking cues from a certain event in flight. i.e. a radio exchange between another aircraft and a controller. Ask them where that aircraft was, when we will be likley to be closest to it.
While they are answering that ask them what our fuel load will be when we get there.
Then ask them what they will do if an oil light comes on and we are on a reciprocal track and 1000 ft above the other aircraft.
Then ask what mechanism triggers the oil light. etc etc etc.
It's basically making them really busy and taking them to different aspects of the entire picture. I feel it's important to keep a cohesive thread to develop an understanding of how these aspects relate to each other in the overall management of the flight.
Main thing I look out for is that they prioritise flying the helicopter. You can alter the priorities of the sequence by throwing in a hydraulic failure of something along those lines.
What takes them ten minutes to answer in the early days, comes in the blink of an eye later on.
An instructor's role is to turn out safe pilots who operate in a courteous and professional manner. You only have a hundred or so hours with them. I feel true judgement from good situational awareness can only come with common sense and experience.
Good question, Jolly Girl.