What to ask a babysitter before the first evening

Background checks, references and first aid training answer an important question: is this person safe? They’re necessary, and you shouldn’t skip them.

They don’t answer the question most parents are actually anxious about on a first evening, which is quieter and harder to name. Will my child be all right? Will this person notice what I would notice?

That one is answered by a conversation, and it takes about twenty minutes.

Ask about situations, not qualities

“Are you patient?” gets you a yes from everyone. Instead describe something real and ask what they’d do.

• “She refuses to go to bed and starts crying for me. What do you do?”
• “He says his tummy hurts. How do you decide whether to call me?”
• “They’re fighting over the same toy and one has just hit the other.”
• “She asks for a snack that isn’t on the list I left.”

You’re not marking answers against a key. You’re listening for whether they’ve clearly been in the situation before, whether they stay calm describing it, and — most tellingly — whether they say I’d call you at a point that matches when you’d want to be called.

That last one is the real compatibility test. Some parents want to hear about everything; others would rather not have their evening interrupted over a scraped knee. Neither is wrong. What matters is that you and the sitter agree, in advance, where that line sits.

Watch the first meeting, not just listen to it

Have the sitter meet your child before the first booking, with you present, and pay more attention to behaviour than to answers.

Do they greet the child directly, or talk about them over their head? Do they get down to the child’s level? When the child ignores them — which is normal — do they take it personally or just carry on, available?

Children are not reliable judges of character, but they are very good detectors of adults who are interested in them versus adults who are being polite to a parent.

The handover that prevents most problems

Most difficult evenings trace back to something not said. A short written note beats a long conversation at the door, because at the door you’re leaving and they’re absorbing nothing.

Worth writing down:

• Bedtime, and what it actually looks like. The story, the particular toy, the hall light left on. The ritual matters more than the time.
• Food: what they can have, what they can’t, and allergies stated explicitly, not implied.
• What’s normal for this child. That he always says he’s not tired; that she goes quiet when she’s upset rather than loud. This is the information nobody thinks to pass on and the sitter most needs.
• When to call you, when to call someone else, when to call emergency services.
• One nearby contact who can be there in ten minutes.

Fair expectations in the other direction

Reliability runs both ways, and sitters consistently report the same frustrations: getting home much later than agreed without warning, unclear payment, a house where the rules change between visits.

Being clear about finish time, paying promptly at the agreed rate, and being honest if your child is having a hard week — all of it makes you the family that a good sitter keeps free in their calendar. In a market where reliable sitters are the scarce thing, that is worth more than a slightly higher rate.

The thing worth remembering

The anxiety doesn’t fully disappear on the first evening, and it isn’t supposed to. What helps is knowing you asked the questions that mattered, that the sitter knows the small specific things about your child, and that you both agree on when the phone rings.

After that, go out. Leave the phone on. It will almost certainly be fine, and the second evening is much easier than the first.

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MatchSitters connects parents with vetted, certified childcare professionals. More at matchsitters.com.