Questions to Ask Babysitters
For the stage where you have three or four sitters to choose between and need questions that actually separate them, rather than ones any reasonable person passes. They are comparative on purpose: how many families they already juggle, which ages wear them out, how their last arrangement ended, what they would do if something better landed on a night you had booked. Once you have picked someone, a full hiring interview covers the detail of your own house.
The questions
Open any question for the note
How many families are you sitting for at the moment?
Why ask it
This tells you where you would sit in the queue. Someone with four regular families is clearly trusted and also likely to be booked on the Saturday you want; someone with none may be new, or may have recently lost a family for a reason worth finding out.
What nights are you generally free, and how far ahead do you like to book?
Why ask it
Ask early, because it can end the conversation kindly. A sitter who needs a fortnight's notice is no use for a Thursday emergency, and one who only works weekends will not cover a weeknight parents' evening.
How do you get to a job, and how late are you happy to stay?
Why ask it
Transport quietly decides reliability. A sitter relying on a last bus will start looking at the clock at ten, and one you have to drive home changes what a late night costs you. Better to know before you book a table for eight thirty.
Which ages are you happiest with, and which do you find hardest?
Why ask it
The second half is where the answer lives. Most sitters have a real preference, and someone who admits toddlers wear them out is being useful. Anyone who says all ages are the same has probably not spent long with a two-year-old.
Tell me about the last family you sat for: how did it start, and are you still with them?
Why ask it
You are listening for how arrangements end. Kids grew up, family moved, term finished: all ordinary. A story that stays vague about why it stopped is the one to gently return to later in the conversation.
What is the most children you have looked after at once?
Why ask it
Numbers change the work more than ages do, because two children in different rooms cannot both be watched. If you have three and their ceiling is one, that is not a small gap to bridge on a first booking.
What does a good evening look like from your side?
Why ask it
Sitters answer this honestly because it sounds like small talk. Some describe a calm house after bedtime, some describe playing until they are exhausted, and the answer tells you what they will optimise for once you leave.
Would you rather have a written list of instructions or a quick rundown at the door?
Why ask it
A practical fit question with no wrong answer, only a mismatch. If you are a note-leaver and they only take things in verbally, expect the note to be skimmed and plan a two-minute handover instead.
Have you ever had to say no to a family about something? What was it?
Why ask it
Sitters who can decline a request, an extra two hours, an unfamiliar pickup, a job outside their comfort, are safer than sitters who agree to everything. Agreeing to everything is how someone ends up out of their depth with your children.
How do you feel about a family having a camera or a monitor in the living room?
Why ask it
Whether or not you have one, the reaction is informative. Calm acceptance, or a straightforward preference to be told where cameras are, is what you want. Strong discomfort is worth exploring rather than dismissing, and so is total indifference.
What is the longest stretch you have been alone with children?
Why ask it
A three-hour evening and a ten-hour Saturday are different jobs. Lunch, naps, boredom and two meltdowns arrive in the long one, so if you need full days, someone whose experience is all bedtime slots is untested for what you want.
What would you do if we were an hour later back than we said?
Why ask it
It will happen. You want to hear that they would expect a text and stay, not that they would call their mum for a lift or start messaging you at 11pm. This is also the moment to agree what you pay for the extra time.
If one of the children told you something you thought I ought to know, what would you do?
Why ask it
Deliberately open, because the answer shows their instinct about loyalty. Sitters who would tell you, without making a drama of it in front of the child, are the ones who will also tell you about the small things.
Have you given a child medicine before, and how did you check the dose?
Why ask it
The checking is the whole answer. Reading the label back to the parent, or texting to confirm, is what you want to hear. Confidence without a checking step is the thing to be wary of, even from someone experienced.
Do you see tidying up as part of the job?
Why ask it
This is the most common unspoken resentment on both sides. Some sitters clear up automatically and some consider it outside the role, and both are defensible. What you cannot afford is each of you assuming the other's answer.
Which families do you keep going back to, and why do you think that is?
Why ask it
The reasons they name tell you what they need from you: clear instructions, being paid on time, kids who already know them, a family who does not run four hours late. Now you know whether you can offer it.
Has a family ever done something that made you not want to sit for them again?
Why ask it
Asking a sitter to review parents rebalances the conversation, and the answers are usually reasonable: paid late, came home much later than promised, played down a sick child. Listen for whether their complaint is about respect or about work.
What is your rate, and does it change after midnight or for extra children?
Why ask it
Ask for the whole structure now, not just the headline number. Minimum bookings, per-child additions and a late-night rate are all normal, and finding out about them at the end of an evening is what sours arrangements.
If you had a Saturday booked with us and something you would rather do came up, what would happen?
Why ask it
Put plainly like this, most people answer honestly, and the honest range runs from "I would never cancel" to "I would tell you as early as I could". The second is fine. What you are testing is whether they would go quiet.
Who could I call who has had you in their house?
Why ask it
Ask for two families, ideally with children close to your kids' ages. Hesitation, an offer of only relatives, or a reference from four years ago all mean you should slow down before the first booking.
Comparing several sitters
Practical guidance for the conversation itself
Screening before you meet anyone
Do the logistics on the phone first
Availability, transport, notice and rate rule out most candidates in four minutes and cost nobody an evening. Only meet the people who could actually cover the nights you need.
Ask the same three questions of everyone
Pick the ones that matter most in your house, perhaps hardest age, phone use, and what happens if you are late back. Identical questions make the answers comparable, which is the whole difficulty when you are talking to five people.
Write down the phrase that stood out
After three calls the candidates blur. One sentence each, in the sitter's own words, is enough to remember who said their favourite part was bedtime and who said they mostly get asked to keep an eye on things.
Aim for two or three, not one
A single sitter is a single point of failure
Exams, illness and other families' bookings all arrive at once. Two sitters your children know, used regularly enough that neither is a stranger, is worth more than one excellent one you can never get.
Match the sitter to the job
A teenager who is wonderful with an eight-year-old after school is not the person for a full Saturday with a toddler. It is reasonable to keep one for short evening slots and another for long days.
Pay the going rate and pay it promptly
Sitters ration their availability towards the families who are straightforward. Paying on the night, at the rate you agreed, is most of what keeps you at the top of the list.
The first booking
- Book a short, easy slot first: two hours before bedtime rather than a wedding you cannot leave.
- Overlap for twenty minutes so the children see you being relaxed with this person.
- Leave one sheet on the counter: your mobile, a second contact, the address, allergies and doses.
- Say what time you will actually be home, then be home then.
- Ask your children the next morning what they did, and listen to what they mention first.
What to be careful about
Hiring on warmth alone
Being lovely with children in front of you and being reliable on a wet Tuesday are different traits. Someone your kids adore who cancels twice a month will not work, however good the first meeting was.
Skipping references because the interview went well
A confident conversation is not evidence. Two short calls to families who have actually left this person alone with their children is the only part of the process that tests the rest.
Leaving the awkward topics for later
Visitors, phones, driving, tidying and money are all easier to raise before the first booking than after something has gone wrong. Ask, say your own answer, and confirm the important ones by text.