We weren't sure if he was ready to actually sleep in it, but decided we would try. At first Joshua moved his teddy bear back to the crib to get ready for bed. But with encouragement he eventually moved to the new bed, sitting with his back against the headboard. We expected him to come out of his room after a few minutes and ask to move to the crib, but we never heard even a peep from him.
I checked on him after an hour and he was fast asleep, curled up at the head of the new bed with his back still against the headboard and his feet on the wall. I guess this means he likes his new bed ... I just don't know how you teach a two year old to sleep in a more traditional position.