Start about 2-3 months before they will need care to start to transition their child to a daycare day routine. That means waking them and feeding them breakfast as if they were going to work, that means the naptime the child has in the morning is what the caregiver will be doing too so you can tell her what time seems to work. Have the child nap in a playpen in a room other than their bedroom. Put them down awake and without toys - we are not to have stuffed toys, etc in playpens during naptime. Let them get used to going to sleep. As soon as possible let your child start to do things for themselves such as feeding table foods, trying to hold a cup or at least holding their own bottle. You can cuddle with your child but let them hold it not you. Switch from on demand feeding to scheduled snacks and meals similar to a daycare day. Let your child learn to play for themselves and with themselves. It is fine to show them what a rattle can do or how to stack the blocks but then retreat and let them make the blocks do what they want them to do. Do not take your child for a walk so they can nap - outside time is playtime not sleeptime and is akin to rocking your child to sleep. Take your child to playgroups where there are other children and it is noisy so they learn that they can be ok in such an environment. Basically the closer you can make your child's day to what they will face when they start daycare the easier the transition will be for everyone. The caregiver you choose should be able to help you look at their schedule and decide where changes will need to be made and you can look at changes especially to the morning routine which of course effects the rest of the day's routine. It also makes the transition to work easier for mom if she is used to getting up and getting ready to go out the door even if she doens't actually go out the door.