How to Talk to Your Boss’s Kids at the Office

“OMG she is soooooo cute!!!$#@ She totally has your nose.” Holy shit, no. I know before I even look. Someone’s child is in the office and they are near my desk. My brain looks something like this:


I have no idea what to say when a co-worker brings their child into the office, so I decided to go to the source. I asked two mom-of-the-year candidates and mothers of two, Debby Robertson and Shea Gilliam, questions about how myself and other talking-to-kids-challenged humans can be less awkward.

Meet the moms:

Debby Robertson:

About: "Loves reality shows, soap operas and cheesy pop music, much to the chagrin of my husband."

About: “Loves reality shows, soap operas and cheesy pop music, much to the chagrin of my husband.”

Shea Gilliam:

About: "I can tie a cherry stem with my tongue. Which is probably why I'm now a mother of two...."

About: “I can tie a cherry stem with my tongue. Which is probably why I’m now a mother of two….”

Hopefully their answers, along with a few potential questions I brainstormed based on their insights, can help you be ready next time you hear, “She is absolutely adorbs!!!”

Q: What do you like to discuss with other people about your kids?

Debby: Usually, the latest stuff they are doing. It can range from full on bragging of how wonderful and adorable I think they are to how much my oldest one is driving me crazy. Dylan, my oldest is definitely the product of his parents – feisty, inquisitive and stubborn as all get out, but so sweet too. I think he gets the sweetness from me, and the stubbornness from his dad. 🙂

Shea: Probably their personal progress. My 19 month-old, Naomi, is constantly learning new things or saying a new word, so it’s fun for me to be able to tell stories about her latest new feat. I also like talking about how it is that I became a mother, because it’s probably not like everyone else – but a lot of people think it’s TMI…so…yeah.

*See “Shea’s India Story” at the end for the conception deets.

Me: Ok, ok, that makes sense. Questions I could ask:

  • What’s your child’s latest feat? Anything crazy he’s done?
  • How often does she remind you of yourself?
  • Shea, how was this little guy conceived? (I love you already.)

Q: What question can people (guys especially) reasonably ask about a baby that you would appreciate?

Debby: I think anytime anyone shows any real interest makes a mom feel special. It would have to be a natural conversation though. I can smell bullshit from a mile away so if someone is just asking to suck up, I’d be like, “WTF?”

But an easy question is just to ask, “Do you have a picture of the baby?” Parents like to show off pics.

You could also ask about the name of the baby. Ask how the parents chose it. What’s the middle name? Is he/she named after anyone?

If the kids are older you could ask some of the following:

  • What grade is you son/daughter? Do they like it? Do they behave differently in the class then they do at home? Do you like the school/teacher?
  • Do your kids participate in sports? What? How did they get involved in that? Is it competitive?
  • You can always ask about certain holidays – special occasions like Christmas/Santa, Halloween, birthday parties, movies that are coming out, etc.

Shea: Haha….this is kind of a tough one. If a guy who was single ever asked a question about my children that made sense I would think he was a complete freak of nature 🙂 But I appreciate them trying! I guess a guy could ask me just about anything that showed he was interested, such as:

What was the last cool thing your baby did?”

  • Oh, you’re house hunting, does this mean you have to consider school districts too?
  • What do you normally feed your baby?
  • When does potty training happen? Because I have no idea…

Me: I see the light!

Q: What do you like to talk about most about being a mom?

Debby: It’s usually about how I feel guilty about being away from them or not spending enough time with them because I’m working. I usually make a joke about it to play it off. I find a lot of times, moms commiserate over stories by complaining about things – what they’re not doing, what their husbands aren’t doing, what their husbands just did that made you crazy, etc. I’m usually bitching about how busy or tired I am or just thankful I got a nap in.

Me: I almost have too many questions in my arsenal. I need to talk with a mom ASAP. For example:

  • So you’re pretty busy these days huh?
  • How’s your husband doing?
  • Is your husband overly-protective? Excited to play sports with child?

Q: What do co-workers say to you about your kids that drive you insane?

Debby: This is a generality and not indicative of the larger group, but it drives me crazy when good intentioned- people want me to stay out with them versus going home to my kids, like I’m missing out on something by not partying. I’ve spent a spent a lifetime partying, and while a night of partying can be fun, so is going home and being with two kids who tell you over and over how much they love you. Don’t get me wrong. I love a night out just as much as the next person, but there are times, when I’d rather be home and it doesn’t make me feel like I’m missing out on anything – except maybe a hangover.

Shea: I don’t like when people take good things that my kids do and credit it as “lucky.” For example…both of my kids are excellent sleepers. So when I tell people that, they’re like, “Oh you’re so lucky you got good sleepers.” No, I’m not lucky. I’m anal about their schedules and sleep. Okay…one more example: My 19 month old is a pretty well behaved little girl. I hate when people are like, “You’re so lucky you’ve got a calm kid.” She’s not calm. She is like any other (almost) two year old. She wants to run and scream (and does when it’s appropriate), but we don’t let her get away with that crap in public. We lovingly teach her that it’s not okay to act like a brat!

Me: Noted. And Noted.

Q: What’s a common mom-with-kids problem that someone could bring up that would lead to discussion?

Shea: This is hard because it completely depends on the age of the baby. Newborns: Sleeping! Ask how that is going. 4-8 month olds: Feeding! They are just learning to eat, so ask if they have started feeding them solids and if so, how that is going. 12-16 month olds: Walking or being mobile! 16 months – toddler: Ask what new development they are working on. At this age, they might have a new sibling at home. If so, ask how that transition is going.

Q: Closing Advice?

Debby: Overall, I think the biggest issues tend to be when people treat you awkwardly because you have kids. If you can relate to the mom/boss as a person, just ask the person normal questions. The more real you can be, the better. If you feel like you are forcing the conversation, then don’t do it. And as long as you don’t ask about sore nipples, sex after baby or anything else that’s inappropriate with a co-worker, you should be fine.

Me: The world is now a better place. Group hug?

*Shea’s India Story:

Naomi was conceived while we were travelling in India. But funny story – we went to a village church one Sunday with our friends who lived there (we were volunteering.) After the service, Usha explained that this would be our last day in the village and they should say goodbye. All of the sweet old Indian women came and laid hands on me and were giving me blessings. When I asked Usha what they were saying, she said that they were praying for me to one day return to India and when I did, I would have a baby to bring with me. I laughed and said, “Could they maybe pray for something I could use, like winning the lotto?” Three months later, I took a pregnancy test and the rest is history….

Side note: 6 months later, Usha emailed me and said that the same village church was still praying for my return, but now they were praying for a brother or sister for Naomi. Three months after that I found out I was pregnant with Indiana. I have since emailed Usha and told her that they now needed to start praying for a college fund for both of my children since it was their fault I had that to worry about now!


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