Internet Dating for Parents and Caregivers Part 2: Blind Dates


This is part 2 of a 4-part series about finding a nanny. Part 1 is here. It was authored by my friend and one of the baddest mamma jamma lawyer moms around, Shylie Bannon.

Once you’ve posted the personal ad for a nanny and the applicants start rolling in, you get to start evaluating potential candidates!

It’s just like Tinder—should I swipe right or left?

You should pay attention to the detail contained in the response. Did the candidate personalize her response, or did it seem like she copied and pasted the same message she sent to 20 other jobs? Did she proofread her response before sending it? And although it sounds shallow—how does this person look in her profile picture? Do you want someone who thinks that posting a sultry “duck lips” photo on their caregiving profile to be responsible for your child?

Check out the candidate’s social media pages if you can find them before deciding whether to respond. I found one candidate who looked great in the care.com app who posted racist memes and got involved in fights with “baby mama drama” on her Facebook page. No thanks.

You should perform a Google search, and you may also want to do a quick court records search in the county in which you and/or the nanny live if you have enough identifying information for the prospective candidate. We weeded out several candidates based on domestic violence injunctions, misdemeanors, and an overwhelming number of evictions/collection actions.

If the candidate seems like a potential winner based on her initial message, set up a phone interview. Good phone interviews typically last about 30 minutes, and you should make sure you are in a place where you will not be easily interrupted, and that you have a notepad handy during the interview. Pay attention to when the candidate agrees to schedule the phone interview—if she is currently employed with another family and “sneaks away” to take a call with you, that may say something about how much attention she will pay to your kids when she’s watching them.

The phone interview will be the most important part of your interview process. If you invest yourself in the process, you will figure out very quickly whether someone is a viable candidate for the position, or is destined to be a bad fit. And like all matchmakers, the best advice you will get is, “when you know, you KNOW.” If conversation flows easily, if you feel like you can communicate well, that is the most promising sign for the next step. Conversely, if the conversation is stilted, stiff, or you get an off feeling, things likely won’t work out.

During these phone interviews, it is tempting to do most of the talking, but you will learn a lot more about the candidate if you do very little talking, at least at the outset of the call. The first question you should ask is simply, “Tell me about yourself.” Listen to the substance, but also the manner in which the candidate answers the question.

Is she forthcoming? Is she well-spoken? Is she focusing on her experience in childcare, how she came into the field, or is she telling you about a traumatic experience with her ex-husband? Is she able to easily carry the conversation?

If she hasn’t already told you, the next question should be designed to find out why this person is seeking a job in childcare, and then, if she is already in childcare, why she is looking to switch jobs. The answers we heard the most often were, “My kids are grown up and I just love cuddling babies,” or, “I’ve been a babysitter before and always loved kids.” Consider what these answers mean to you. We did not feel that someone who wanted to “cuddle babies” would be a good fit for us because our son is a busy little boy and not much of a cuddler.

The best practice is to ask a lot of neutral, open ended questions that do not suggest an answer to the candidate. If you ask the candidate “what has a typical day looked like when you’ve taken care of a six month old before” and she gives a cursory answer that is vague and seems to cover only the basics (“play, eat, change diapers”) without giving specific examples, you may want to ask more specific questions about her answer.

“What kind of play did you do with Baby Jane in your last position?” “What kinds of strategies/games did you use to help Baby Tom learn to crawl?”

Other questions you may want to ask include, “Can you describe the most recent family you worked with, and why did that job end/why is it ending?” “What is your favorite age to care for and why?”  “What type of family/employer are you looking to work with?” “How do you prefer to communicate with parents about the baby’s day?” and “What do you do to keep calm when you are having a hard day?”

Over time, there were certain aspects of answers that I learned I needed to “dig deeper” on. If a younger candidate told me she had been a nanny before, I made sure to ask her about the details of the position. I found there were a lot of candidates who described themselves as full-time nannies, but then discovered that often the mother was in the home with them the majority of the time they worked. Likewise, I learned to ask whether they had ever nannied for someone who was not a relative or a close family friend.

And lastly, it was important to me that the applicant ask me at least one or two questions about my son relatively early in the conversation. Be leery if the candidate bad-mouths prior families she worked with or easily shares gossip about their private lives, as that’s the #1 sign she’d do the same about you.

If you feel like a candidate is promising after hearing about her background, moving into more specific questions and information-giving is important. Even if you already mentioned the “non-negotiables” in your online posting, verbally review the specifics of the job and these non-negotiables again, asking the candidate to confirm that she is 100% ok with each one of those things. Time is valuable when you are a mama, and the last thing you want to do is spend an hour on the phone with someone who sounds like your personal Mary Poppins to find out at the last moment that she is allergic to your French bulldog furbaby.

For many women, discussing salary is the most uncomfortable part of this process. Some candidates will bring up salary as one of the very first topics in the conversation. I don’t blame candidates for bringing it up early, but if it’s the very first question the candidate asks, it raises questions about whether the caregiver is applying to the “highest bidder” or whether she is looking for the right family dynamic. You don’t want to hire someone you’re worried will jump ship the moment she gets a higher-paying offer. If possible, you should try to start the conversation by asking the candidate what she is looking for in terms of a salary. If the candidate is looking for something higher than what you are willing to pay, keep in mind that she may be interested if you offer other benefits, such as paid vacation or holidays, cell phone reimbursement, or more convenient hours than other families.

If your phone interview goes well, then you should ask the candidate for references and set up an in-person meeting. Try to get at least two or three references, particularly other families for whom she has worked. When you call the references, make sure you ask detailed questions to corroborate information the candidate provided you, and to convince the reference to give you a complete picture of the candidate. Find out whether the caregiver stays in touch with her former employers, and whether she still babysits for them on occasion. I also tried to do a little research on the references to determine whether the reference was someone whose opinion I would value. When I researched my nanny’s last employer, I discovered that she and her husband got married at the same venue my husband and I did, lived very close to where we lived, and is a Vice President with one of my firm’s biggest clients. What she had to say mattered a lot to me. It was an even better sign to know that the candidate still watches their kids on the occasional weekend.

For us, in-person meetings were largely a formality after good phone interviews. Some people prefer to have these meetings in a public location like a Starbucks. We held several of these interviews in our home, and I always let the candidates know that they were welcome to bring their husband or a friend to the interview with them to make them feel more comfortable about coming to a stranger’s home. Try to schedule the interview at a time when you will be able to speak with the candidate both with and without your child present—for us, interviews were often scheduled toward the tail end of naptime, so we could talk privately first and then we could see how the candidate interacted with our son.                 Finding a caregiver is hard, emotional work. There will be times that you are disappointed by candidates, and feel like you will never find someone “good enough” to watch your child.

But I promise, just like in dating, there is someone out there for everyone, and when you know, you know. Once you find that person, it’s time to have “the relationship talk.”

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