It shouldn't be hard for someone to ride as Steve's domestique, and punch a hole in the air for him, at the right sort of speed, responding to calls to speed up and slow down until they have it.
Unfortunately, Steve will have seen plenty of shocking group riding on UK audaxes, so I can understand his reticence. And, given that this is a mental challenge as much as a physical thing, the most important thing is for him to feel comfortable with all aspects of his ride.