It sounds there is still a lot more communication that needs to go on. Rather than trying to get it going in the heat of the moment (which could easily put him in an uncomfortable position), have you tried sitting down and talking this over with him? He may be very uncomfortable with the idea. Not to mention that such a rapid shift in the power dynamic isn't something that most find easy to transition through without practice, even when it they know it is expected of them. Trying to bait someone into doing something totally new tends to not be very effective.