Totally just went through this about 5 months ago, and actually am still registered at Care.com because I want to find a good back up sitter in case our new main one doesn't work.
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I found that you really need to think about what's most important for YOUR peace of mind - what things are you most worried about? Find ways to ask them about it. I also found it VERY interesting to watch them respond to my dd. The sitter we ended up liking best and using was one of the last I interviewed, and while she was attentive to my questions, she almost kinda ignored me and was totally focused on playing with dd. I didn't even get through half of my questions before they were playing and I kinda drifted to the back of the house to just listen to how they interacted. I did ask all my questions before it was all over, but despite what everyone had written in their care.com profiles, this sitter's ability to engage my daughter immediately, go along with the games she wanted to play, plus some other things I noticed about her, that all was more important than the verbal answers to my questions.
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For me safety - not just child safety but neighborhood/house safety is very important. I liked that the sitter was leaving after the 1st interview, then rang the bell a few minutes later to ask if I knew the guy in the car across the street because he'd been there for awhile. I REALLY liked that she noticed that and was concerned. Turned out not to be an issue, but it was good to me that she noticed.
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I guess the point of all this is that the PP's post about "mothers helper sessions", i.e. paying a sitter but staying home and trying to stay in the background for a couple visits, that will give you a lot of info.
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Likewise, it was more how other sitters did (or didn't) interact with dd that ruled the rest of them out. The one who looked best on paper was actually one of our least favorites after meeting her a couple of times.Â
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Then there's the nudist, former model babysitter who I ruled out as much because she was super late for the appointment as I did because on the 2ned visit she told me she was a nudist, didn't lock her doors (we live in a big city!), and seemed too interested in my husband... but that's a story for another thread LOL!
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One question I did find useful to ask each one: tell me a time when a child was injured while you were watching them and tell me what happened/how you handled it. I didn't assume everyone had had a child injured, but I asked it just like that to kinda take the pressure off of them lying and saying "Oh, no child's ever been injured with me". Every single sitter had a story and I learned a lot from them. I also asked how they dealt with toddler tantrums, since dd is 2. I learned a lot from their answers, though I learned more when dd melted down in front of a few of them and I just asked them how they'd handle it while she was melting down.
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Btw make sure you're very clear up front with prospective sitters that you're looking for someone who's avail on short notice. Also make sure you're clear with yourself, and then clear with them, about how often you expect to need someone. You can always adjust it if you need to, but being clear about expectations up front saves you and them a lot of precious time.Â
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Good luck finding someone!