manager wants to match outfits, in trouble for a text sent outside of work, and more — Ask a Manager

here are the 10 best questions to ask your job interviewer — Ask a Manager

It’s five answers to five questions. Here we go…

1. Does my manager want to match outfits with me?

I know this is almost definitely a joke, but it’s a reoccurring and oddly specific one.

I’ve been at my current office job for about a year and a half. When I was a few months in, I wore a red plaid dress and thought nothing of it, until the next day when my boss (who I hadn’t seen the day I wore the dress) told me she was also wearing red plaid and joked we matched. At the time I thought nothing of it, but every few weeks or months similar things happen. One day I wore what I thought was a plain black and white striped cardigan, and my boss immediately said she had to have one, and asked where and when I bought it and how much it cost. It seemed like a lot of details for a joke, then she mentioned matching again.

She’s made a few more comments and then today I was wearing a green skirt and an autumn orange shirt, and she said she loved those colors and needed to start wearing them again soon. I said something like, “I hope you’re not talking about matching again” and she started saying how funny it would be if we did match, and I said, “If you start copying my outfits, I’m going to start wearing crop tops.” My boss laughed for a good while and I left. I don’t think I’m in trouble as we work in a casual small office and joking is a quite common. I’ve also been told I’m funny and friendly, and I kept my tone friendly as I said it, so I think it was fine.

But all the comments about matching are starting to bother me and I don’t know what to do. I’m turning 30 this year and my boss is about the same age as my mother. The only explanation I can think of for this is that this is my first office job and my taste in clothes is very girly and vintage, so sometimes I’ve asked my boss if certain outfits are OK to wear to work. My boss has approved of all my outfits — again, we’re very casual — so maybe this is just her way of saying what I’m wearing to work is fine? Also, I don’t usually wear heels or make up to work or do my hair, but today when she made the comment I was wearing make up. Is she trying to tell me to dress more fancy or is she just trying to be funny? What, if anything, should I say the next time she brings up matching outfits?

You are reading way too much into it. Your boss is just joking around and maybe likes your fashion sense. You’ve talked with her about clothes before, so she might figure you have a camaraderie on the topic or that it’s a shared interest. It’s very unlikely that she actually wants to wearing matching clothes; she’s just being friendly. (It’s also not uncommon for people, usually women, in an office to joke about accidentally matching. She may have just latched on to this as a point of connection.)

is it weird to start dressing like my boss?

2. How can I tell the new owner of my company how crucial I am?

I work in an office of a family-operated business with less than 10 employees. I am the only one not related to the family. I love my job and am really good at it. I am involved in or manage all aspects of it. The owner has decided to sell the business and I am the only one that has been asked to move to the new business.

I recently met with the person who will be buying the business and, while they are in the same field, they have less experience than me. It was very apparent that I would have to train them on multiple aspects of the business, including products and systems. To say I am concerned is an understatement. While I thought it was a meet and greet, they used it more as a new employee interview. It became apartment to me while speaking that they did not understand the extent that I run the business day to day and the work that I do. To be frank, if I didn’t move to the new business, I don’t think it would stay afloat. Though comments they made, it became apparent they were trying to justify my wage.

I guess my questions is how to navigate this big change and make sure that I am not coming across as arrogant or demanding but also make sure that they know that my wage and hours are really not negotiable and that while I have no interest in purchasing the business from the owner, I basically run it. Any insights or advice would be helpful.

It makes sense that they treated the meeting more as an interview than a meet and greet; most people in their shoes would want to assess the person in your position before they start working with you. But it’s reasonable for you to assess them right back and figure out if you want to work for them and whatever their vision is for your position. If you’re getting vibes that they might be skeptical of your pay, hours, or role, that’s something you should try to explicitly hash out now — unless you’re willing to just take it as it comes after the ownership change, even you turn out to be really unaligned. (To that point: are you sure you want to stay on?)

Meanwhile, can you talk to the current owner and ask what conversations they’ve had about you, and how much the new owner has been told about what you do? They’re better positioned that you are to explain that you’re crucial — and if they don’t think the business would stay afloat with you, they should tell the incoming owner that. But it would also be smart for you to prepare a detailed description of what you handle and the amount of time involved in each piece. In other words, don’t tell the new owner that you’re crucial — show it.

3. I got in trouble for a text I sent to a coworker/friend outside of work

I was venting to a coworker who I thought was a friend and said that sometimes my other coworker made me want to high five her in the face. She took a screenshot and sent it to our manager. Can my employer write me up for something I said in text to a friend while I was off the clock and off job premises?

Yes. You were talking to a coworker (friend or not) about another coworker and you said, basically, that you wanted to slap her in the face. It doesn’t matter that it was outside of work hours or off work premises; things you say to and about coworkers are fair game for your employer to take action on if they consider it a problem for your workplace.

That said, writing you up is silly. Your manager should have just talked to you, said it’s not acceptable to talk about colleagues that way, and asked what’s going on that was behind it.

4. I don’t know whether I’m going on a trip or not

I’m trying to figure out whether to follow up on an exciting work opportunity that was hinted att and then just sort of … dropped.

In the last six months, I began a new role that I absolutely love and have gotten great feedback about my work and abilities. I feel that I’m proving myself, and when my boss suggested that the organization might like to send me on a trip to provide logistical/operational support for an upcoming event with an exciting international partner, it was validating! However, that conversation was a month ago and I have heard nothing since. One part of me wants to ask whether our shop is still in need of my help and whether I should plan my tasks and meetings around this (soon approaching) event or not. Another part of me thinks that it would be gauche and presumptuous for me, a brand-new and low-ranked employee, to follow up about participating in a glamorous international work trip. I’m still trying to establish myself as a reliable, effective, and grounded team member, so should I ask, or should I just assume that it was not a serious suggestion, and leave it alone?

It’s not gauche or presumptuous to ask about it. They mentioned it! It’s reasonable to go back to your boss now and say, “You’d mentioned last month that you might want to send me to X for Y purpose. Since the event is getting closer, I wanted to check back with you and see what you’re thinking about it.”

5. My doctor won’t sign off on an accommodation

I have chronic neck pain that I have never solved. Sitting or standing at a desk is the worst thing for it, and I have considered changing careers because of it (but this hasn’t been financially possible). My MRI shows arthritis and bulging discs, but I know some people have those and feel no or less pain (or probably more, for some). I manage it with a combination of yoga, physical therapy, muscle relaxers/painkillers and frequent medical massage. I’m probably in pain eight days out of 10. Recently I’ve decided to be more proactive and sought an accommodation from my company, who is a large employer known for being good about this. An HR person immediately set up a meeting and gave me the paperwork for my doctor to sign. Yay! Right?

Except … my doctor won’t sign it, writing me back to say she’s “not sure this qualifies.” And now I feel foolish in front of my boss, who knew I was seeking this accommodation. The accommodation is to work 1-2 days in office instead of 3+ (being able to take breaks to lie down/stretch helps me). I already have an ergonomic setup at home and at my office, so that won’t help.

I feel that the root of the problem is that I appear fit and healthy, and I’m youngish. But it’s a very real problem that often has me in tears by the end of the day. What should I do, other than changing careers or trying to find a new doctor, I guess? Am I being unreasonable in requesting this accommodation? I know a lot of people have neck pain. Is that why it isn’t seen as a condition to accommodate? I’m just so frustrated.

Your doctor’s role isn’t to say whether your condition qualifies for accommodation under the law; her role is to say what you need to perform your job safely and comfortably. If she believes that’s less in-office work, it’s appropriate for her to say that.

But is she tell you that she doesn’t believe less in-office work is necessary? I wouldn’t be surprised if she’s dealing with a lot of patients seeking her sign-off on work-from-home accommodations in cases where she doesn’t actually think it’s necessary, and that might be what’s going on here. In that case, you could have a conversation with her to try to better understand her perspective and share yours (specifically, the relief you’ve found from being able to lie down and stretch throughout the day). If you’ve otherwise found her to be a caring and responsive doctor, that conversation is worth having. But if she’s not taking your pain seriously, you’re better off finding someone who will.

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