Where was this CEO coming from, and would you work for her again?

May 8, 2022 2:23 PM

I recently assisted at an event on a contract basis for a former employer. The CEO is new and was hired after I left my job with the former employer. The event was plus-one, so I brought a "date" who is really just long-time friend I've know since I was ten years old. The next day, the CEO had me meet with her for what I assumed would be a quick debriefing of the event. Instead, basically all she said to me was, "Was your guest last night your brother? He seemed really nice."

I thought it was a bizarre question, and a question that was way too personal. What may have been her motive? I am told she is happily married, and even if she were not, it seems that it would be wildly inappropriate, considering that I don't even know her and this was a business setting, for her to go through me to pursue anything with my friend. And what if he hadn't been just a friend; what if he had been my husband? That would have made her question even more unacceptable, in my opinion. What do you make of her? Would you consider doing contract work for her again?

posted by SageTrail to Work & Money (23 answers total)

I’m very confused why you see this question as inappropriate. It seems like small talk to me? If she said something more (“what’s his number?” or whatever) ok maybe, but otherwise it seems like you’re reading a lot into some small talk.
posted by dorothy hawk at 2:31 PM on May 8, 2022 [39 favorites]

Unless your plus-one was playing the field a bit and the CEO wanted you to know that your plus-one was on the prowl, I'd chalk it up to awkward small talk.
posted by kimberussell at 2:33 PM on May 8, 2022 [1 favorite]

To me, calling you in for a meeting just to ask who your plus-one was seems weird, but the question itself reads as extremely innocuous - like, the smallest of small talk. Unless, like, she asked for his number or something? Although even that would have been only a little bit boundary-crossing, in my opinion.

If she had asked and your plus-one had been your husband, you would have said, "What! Oh my gosh, no, we're married!"

Unless you're leaving something out, this seems like casual small talk. If people asking any questions at all about your personal life feels inappropriate and boundary-crossing to you, you should probably not bring people from your non-work life to work events in the future.
posted by mskyle at 2:34 PM on May 8, 2022 [14 favorites]

I would definitely be weirded out if that was the entire content of the meeting, as you said. But I don't know that that would stop me from doing another event for her, just charge more because you know she's weird.
posted by Lyn Never at 2:39 PM on May 8, 2022 [4 favorites]

Where is the implication that she was interested in him?
posted by saturdaymornings at 2:56 PM on May 8, 2022 [2 favorites]

Best answer: A CEO making a subordinate meet with them just to ask this question is NOT small talk. It does seem inappropriate to me, but I don't know what the significance is. I would feel uncomfortable that a superior at work was essentially requiring me to tell them about my personal life. I would be as vague and brief as I could get away with.
posted by Flock of Cynthiabirds at 3:01 PM on May 8, 2022 [10 favorites]

Maybe she thought you two looked like siblings and wanted to satisfy her curiosity. Still weird, but relatively innocuously weird.
posted by ssg at 3:03 PM on May 8, 2022 [3 favorites]

"Was your guest last night your brother? He seemed really nice."

In my culture this is slightly overly-friendly small talk. To me it's a compliment about the person you brought and maybe an opening for you to say "Oh no that is my longtime partner" or "Nope just a friend. He had a good time I think the event went well." It's fine to be weirded out by it but I think different office environments have different levels of formality and informality and to me this is pretty informal but it doesn't seem inappropriate unless you are leaving out more about how the conversation developed.
posted by jessamyn at 3:11 PM on May 8, 2022 [8 favorites]

How a skilled entrepreneurial CEO of a smaller business thinks and operates might, in some aspects, not be completely dissimilar from operating as a matchmaker: be open to and interested in everyone you meet, try to learn a bit about them, what they want or need, and what they can offer to other people. Then be open to thinking of how each person might be matched with other people in one's network, and pitch win-win or win-win-win opportunities to, er, "unlock the value".

CEO might not have been asking on behalf of herself, but might have a network of acquaintances or friends who could potentially be interested in your friend, if your friend is open to opportunities of one form or another.

This kind of thing could be very inappropriate if there is a continuing professional relationship between your friend & the CEO's business, professional power imbalances, etc, but if that isn't the case & your friend is unlikely to interact professionally with CEO in future, what's the harm in giving a little information to people who made a new acquaintance?
posted by are-coral-made at 3:13 PM on May 8, 2022 [2 favorites]

I wonder if what happened is that she was surprised you brought a '+1' at all, given that you were (I think?) staffing the event rather than a guest at it.
posted by kickingtheground at 3:27 PM on May 8, 2022 [65 favorites]

It sounds like this might have been a somewhat awkward attempt to get to know you better. She may have ended the conversation because you seemed weirded out. Ideally someone at that level would have been able to make it less uncomfortable but CEOs can be socially awkward too. It doesn’t seem sinister to me.
posted by lunasol at 3:52 PM on May 8, 2022 [2 favorites]

I think it is weird that she called a meeting with you if that was all she asked about, but I don't think the question itself is wildly inappropriate and I don't agree that your additional scenario is "even more unacceptable", either.

I would not work for her again if I felt as put-off by this as you seem to be.
posted by sm1tten at 3:59 PM on May 8, 2022 [2 favorites]

I interpret this as the CEO indirectly expressing discomfort or surprise that you brought a guest to an event you were being paid to work at.
posted by latkes at 4:52 PM on May 8, 2022 [50 favorites]

Married people sometimes have single friends.

Sometimes people set up meetings because they think they'll have questions but actually all those questions got answered in the intervening time.

The situation you describe seems a little unexpected but does not send up red flags for me.
posted by brainwane at 5:00 PM on May 8, 2022 [3 favorites]

I'm generally pretty uncomfortable sharing my personal life at work but even so the question itself seems like pretty normal small talk to me.

It *is* odd that that was the only thing in the meeting, but I can think of several reasonable explanations, which other people have offered already. I'd chalk this up to a bit of social awkwardness, think no more of it, and not factor it into whether to work for this client again.

The one possibility that would concern me: Depending on context around the event I might interpret it as a gentle "I was surprised that you brought a plus one to an event you were staffing" nudge. So if I did work another event I'd make sure to get very clear on whether I could bring someone.
posted by Stacey at 5:08 PM on May 8, 2022 [4 favorites]

The only other alternative read I could offer is: your friend presents as rich / confident / well connected and she was trying to suss out how you could possibly roll with such folk.
posted by St. Peepsburg at 5:28 PM on May 8, 2022 [2 favorites]

Best answer: As for whether you should work for this CEO again? Did your invoice get paid on time? Were the requirements reasonable and within agreed upon boundaries?

If the CEO may have seen you as a peer rather than subordinate - given that you are a contractor, this is unclear - I can see this as an awkward attempt at networking with you and trying to make a more personal connection. That’s very much pushed towards women as “leaning in” and can be weird when it doesn’t seem natural.

But I would judge the business relationship on the business things. Unless she was terrible in some other way, this reads as socially awkward and probably fine. I might have my guard up a little bit, but unless she has a reputation for boundary crossing or drama this wouldn’t put me off a business relationship.
posted by Bottlecap at 5:32 PM on May 8, 2022 [7 favorites]

There’s a certain management personality that just shoots the breeze if they think everything went well. Consider her debriefed and move on.
posted by michaelh at 5:54 PM on May 8, 2022 [5 favorites]

I think you’re leaving out some pertinent details. What was the event? Was it a fundraiser or something that cost the company significant cash? Were there costs associated with attending? Like was it a fancy plate dinner?

Was she running numbers afterwards and wondering why they didn’t make as much as planned and saw that contract staff were allowing guests that were not immediate family or spouses?
posted by miles1972 at 7:49 PM on May 8, 2022 [3 favorites]

It's possible that her assistant or admin set up the meeting as a default next step after the event and the CEO realized too late to cancel that she didn't really have anything significant she wanted to follow up with you about. So she figured she'd ask a small talk question, shoot the shit with you for a couple minutes and cut the meeting, but then you were clearly weirded out by her small talk question so she ended the meeting figuring, why throw good time after bad.

At least if this CEO were me I can definitely see this playing out this way. Of course there's a reason nobody's asking me to be CEO of anything lol
posted by potrzebie at 9:26 PM on May 8, 2022 [1 favorite]

My first thought was that she was taking a soft (or passive-aggressive, you decide) approach to asking why you as a contractor brought a plus-one, especially having never mentioned a spouse. But you will obviously have the details my mind is filling in.
posted by kapers at 10:23 PM on May 8, 2022 [6 favorites]

I recently assisted at an event on a contract basis for a former employer. The CEO is new and was hired after I left my job with the former employer. The event was plus-one, so I brought a "date" who is really just long-time friend I've know since I was ten years old.

I am confused, were you working at the event you brought the plus-one to? In your industry is this normal? What had you been contracted to do? In other words, were you being paid to attend?

I think it was her way of figuring out why you brought a plus-one to an event you were contracted to work at.
posted by 15L06 at 11:16 PM on May 8, 2022 [26 favorites]

My gut is that she was motivated by surprise that you brought anyone as a +1 to the event since you were working the event and not actually an invited guest. I suspect she was gently poking around about who he is and why you brought him.
posted by whitewall at 2:29 AM on May 9, 2022 [8 favorites]