So, because of my responsibilities at various jobs I've had, I’ve conducted many, many interviews in my life. Despite this experience, I did not feel adequately prepared to meet with potential caregivers for my kiddo when the time came to find one. And coming up with serious interview questions for nannies? I barely knew where to begin. I mean, this was my son we were talking about. How the hell was I supposed to even scratch the surface on the many things I needed to know about this person before entrusting them with my actual baby?

Perhaps the thing that threw me off about these meetings were that they blended the professional with the personal — the really personal, including my child and the inner workings of my marriage and my home — in a way like no other ever has. Not only did I want to make sure this potential nanny was capable, caring, and safety-conscious, but I also wanted to make sure she (or he, though all our finalists were female) got a good impression of our family, too. When we were conducting interviews, our appearances were neat and clean, our son was napped and fed, and my husband and I were doing our very best to be super-friendly and respectful.

The conversations went well enough, but we've yet to actually call on anyone we interviewed just yet, not because they weren't awesome, but because we've yet to bite the bullet and decide, "YES, this thing we want to go do is important enough that even if my mother-in-law can't come over to watch our son, we will still do it." It's a big deal to leave your kid with a sitter, or a nanny, or in daycare for the first time. Maybe I would feel better if I'd asked every real question I had on the matter? Perhaps, but most of them weren't exactly interview appropriate. So, instead, I'll share them with you all:

"Will You Please Send Me Pictures Of My Child Every 8-10 Minutes?"


Is that unreasonable? I’d be willing to consider every 15-18 minutes if that’s important to you. Also, I’d like a 30-second video every hour, except when he’s napping in which case I’m OK with one taken as he falls asleep and then as he wakes up (you’ll be able to catch it; just watch his cues). Also, I’d also appreciate regular updates via text about his meals, snacks, energy level, diapers contents, and changes of clothes.

"How Much Of Our Food Do You REALLY Think You'll Eat?"

I mean, it's fine. You will have your run of the kitchen, that's part of the deal. I'm just hoping to prepare myself for the chance that I might get home and find zero apples or (God forbid) an empty Cheez-It box. It's important that you be very honest in this matter.

"How Much Do You REALLY Like Nannying?"


See, I need to know you’re here for the right reasons, sort of like the women who go on The Bachelor, but “here” as in “my house” and not as in “national television show that will make you semi-famous for one to eight weeks.”

"True Or False: You Will Look In The Cabinet Under The Bathroom Sink."

This is a bit of a trick question because the answer should be TRUE if you are looking for medicine for the kiddo, but FALSE if you are trying to figure out my deepest, darkest health-related secrets.

"Have You Ever Attempted To Seduce One Or Both Parents That You Nanny For?"


How did it go? (I'm not judging. I mostly just want to hear the gossip.)

"Have You Ever Worked For A Mom That You Couldn't Stand? Why Did She Bug You? "

Perhaps most importantly, did you ever complain about her on social media?

"Are Any Sketchy Photos Or Videos Of You Floating Around Online?"


Look, I'm not shaming your journey, nor am I discriminating against any choices that have been made and/or filmed. I just want to know in case anything surfaces and reporters come ask me about it.

"If You Could Get Rid Of Any Task Related To Nannying, What Would It Be?"

Hint: if "taking care of kids," that would probably be a red flag for me.

"On A Scale Of One To Ten, How Nosy Are You?"


We’ll say that one is "discovers secret diary and doesn’t read it" and 10 is "steams opens our mail and then reseals it?"

"If You Notice Something About My Parenting You Think You Can Help Me With, How Honest Would You Be With Me?"

Since my own toddler is the only one that I've ever cared for, and the nannies I've talked to have worked with many more, I understand they may have a few tips and tricks up their sleeves. It's a tricky question to ask someone though, and I didn't have it in me to bring it up with either potential nanny that I've talked to.

"If You Notice Me About To Leave The House With Toddler Goobers On My Sleeve, Would You Tell Me?"

What about two different shoes? I've been known to make questionable fashion choices when running low on sleep. It's a group effort over here, is what I'm saying. I need to know if you're just in it to keep the kid alive, or if you're really down to be part of the team.

"How Can We Ensure That My Kid Becomes Your Favorite Of All That You Nanny For?"


I mean, that’s the real issue at hand, right? Because I want this to be a mutually-beneficial relationship and I see the full potential of that if you can like him more than anyone else in the world for a few hours at a time for an appropriate hourly rate.

"Do You Know Any Shortcuts For Getting Toddlers Into Their Snow Clothes?"

Actually, this one is serious. I thought I'd ask, just in case.

"I Want You To Like Us As Much As We Like You!"


This isn't a question so much as something I came really, really close to shouting at our favorite candidate. Playing it cool is hard.