E.W.
I have an 11 month old that I just moved out of our bed. The first night was kinda rough but the rest have been ok. The first night I put her in her crib, she was sooo sleepy she did not wake up immediately. However, she woke up 30 minutes later. She refused to lay down so I let her cry for 5 minutes then I went back to lay her down. She refused again so I let her cry for 10 minutes. She went to sleep within that 10 minutes. I hated hearing her cry but I was sooooo sleep deprived from her being in our bed since birth that I went through with the crying. Miraculously she slept all night. The following nights were different. But I think she learned that her crib was a place for her to sleep. The second and remaining nights, when I laid her down, she let me rub and pat her back while she looked at me through the rails (no tears!!!). I stayed with her until she fell asleep (couldn't bear letting her cry again). She fell asleep in about 5 minutes. She woke up the fourth night a few times but I didn't take her out of the crib. I just sat down next to her (on the floor) and rubbed her back. I believe that "crying it out" doesn't work for every parent or every baby and is not necessary for a successful transition. However, in my case, I think it taught my DD that the crib was a comfortable place for her to sleep. And when I am with her, rubbing her back and looking at her, she falls asleep pretty quickly. Also, you may want to start a routine before bed that somehow ends with him going in the crib. We have been doing the same routine since she was like 3 or 4 months so she knows bedtime is coming up. We actually finish the routine in her room now (with her in her crib) since she sleeps in the crib (rather than our bed). I hope this helps. Good luck!