So I'm not a new working mom at all but I've been incredibly fortunate to share a nanny with neighbors of ours in the same building ever since our oldest (nearly 4) was born. They are moving and we'll no longer have the arrangement. When my 4-year-old started "school" a year ago, he was already sleeping in a bed so transitioning to a sleeping bag (which we originally bought for our very rare camping trips) at daycare was no big deal. DS2 sleeps in a crib or pack n' play, which they don't have anymore for older toddlers at their day care. Any advice on a sleeping bag? I'm seeing these sleeping mat things - are they better? I'm really worried there's no way they're going to get him down in a roomful of kids with no pack n' play.
In general I really don't know how we're going to prepare him because while he's speaking I don't think he understands complex sentences - he's going to go from being with our nanny ever since he was three months to school with total strangers :-(. DS 1 at least left for school with the same girl he'd been doing the nanny share with. I may have a bigger issue with him, since the girl will be leaving school as well (our neighbor's second daughter is younger than our DS2 and I don't think that "breakup" will be as hard on him).
Re: Getting 2-year-old prepped for first time in daycare
Personally, I think your daycare will figure it out. They are used to this and will know how to handle the transition. My son went from the baby room to the toddler room and sleeping from a crib to a cot. I think it took a couple days, but they figured it out. I always think.. they're the experts and they know what to do. I don't think there's anything you can do to "prepare" him. He'll be fine.
Otherwise, I have no other tips for the other parts of the transition, since my son has been in DC since 6 months old. But honestly, I would just keep communicating with them, ask them what they recommend and how it is going, etc.
Be kind, for everyone you meet is fighting a hard battle. -Philo
Baby N conceived after 1 miscarriage and more than 2 years of TTC. Diagnosis was low sperm count. We found success after 3 months of anastrozole to increase DH's testosterone and one IUI.
Some charts
I'm stupid. You're smart. I was wrong. You were right. You're the best. I'm the worst. You're very good-looking. I'm not attractive. - Happy Gilmore
No advice on the naps, DS started going to daycare again at 20mos, but only PT, so we left it up to them to whether they wanted to try to get him to nap (and possibly disrupt the sleepers) or just go have quiet time.
As far as transitioning, we just told him he was going to play with some new friends and once we learned some names, we would throw those in as well. I have to be honest, he cried at dropoff every time for a while, but there was always at least one kid excited to see him (and every other kid that walked through the door LOL), so that helped.