Consistency, consistency, consistency!
Try to do the same thing each time you go in, so he'll come to expect it and know what it means. Same words, same actions. What we would do is walk in and say, "Lie down, go to sleep". At first, she wouldn't lie down, so we'd put her down if she was standing. We'd keep only saying those words if she popped back up again. And we also say the same thing when we put her down for the start of the night (Although I add, "good night, sweetie") If she was really crying when she wakes overnight, we'd comfort briefly, but put her right down as soon as she stopped crying (sort of weaning her away from longer comforting - like you and the hand holding, etc). But you're aiming to just walk in, say the words, and he'll lie down, without touching him at all. Then you leave. If he fusses or cries again, then go in and repeat the words - calmly but firmly. Once you start doing the wi/wo, try to avoid caving in to the old habits, because then he'll come to expect that. Does he have a lovey - that can help A LOT! HTH!
