8 Questions to Ask a New Babysitter

When Toby was a newborn, I felt totally overwhelmed by the process of finding a nanny. How do you even begin? I wondered. Thankfully, over the past four years, we’ve figured out how to find wonderful caregivers, including 8 questions to ask…

Here’s how we found great nannies (we have a more casual search process for date-night sitters):

Step 1: Scout potential sitters
This is the hardest part, I think! We’ve found potential nannies through word of mouth from friends, as well as online parenting forums in our neighborhood. (We’ve never used a service, like sittercity.com or care.com, although they seem good. Have you?) Once we find a handful of people, I set up phone interviews.

Step 2: Ask enlightening interview questions
For the phone interview, I’ve found that these eight questions have helped me learn a lot about someone’s personality and decision-making skills:

1. Please tell me about yourself and your experience with children.
2. What do you think kids like about you?
3. What’s your favorite age child to take care of?
4. What kinds of activities do you like doing with kids of different ages?
5. Have you ever had a philosophical difference with parents you’ve worked for, or is there something they asked you to do that you would have done differently?
6. How have you handled discipline with kids you’ve cared for?
7. Can you tell me about an emergency situation you’ve been in while babysitting, or something that scared you?
8. What questions do you have for us?

Step 3: Talk candidly with references
References are usually overarchingly positive, so in an effort to speak candidly, I always make sure to ask, “What did you NOT like about this person? What are some things you found bothersome?” Then you’re much more likely to get a direct and straightforward answer, and you can decide if that thing is a deal breaker or not.

Step 4: Meet the nanny for a playdate
After narrowing down the list to my favorite two or three candidates, I’ll meet each of them in person with the boys. Since we’ve already done the phone interview, we won’t have to talk about anything major and can just chitchat and play with the boys and spend time hanging out. It’s great to see their personality and if everyone has a good vibe!

Step 5: Trust your gut
To me, one of the most surprising things about hiring nannies is how much it’s like dating! When we’ve interviewed potential nannies, sometimes they’ll look perfect on paper (tons of experience, glowing references), but something won’t click, or I’ll just have a funny feeling that something’s not quite right. It’s such a personal and intimate relationship, and you want to find someone whom you and your children will fall in love with—and whom you can trust. Another surprising thing is how much I’ve loved the sitters we’ve worked with. Our sitters have become part of our family, and we adore them so much more than I ever thought possible.

And an aside: My heart is breaking into a hundred little pieces because our beloved nanny Brady recently told us that she’s moving back to Colorado this December. We’re so sad (I cried when she told us), but it’s a great decision for her and of course I want the best for her. But still. Heartbreak.

What’s your childcare situation? Do you have a babysitter or nanny you love? How did you find him or her? Did you ask any other interview questions that worked well? Have you ever had a negative childcare experience? Did you choose a daycare instead? I’d love to hear…

P.S. 5 tips for sibling rivalry, and 10 tips for traveling with a baby. Plus, mothers talk openly about work/life balance.