boss is dating his former assistant, colleague is openly rude, and more

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

1. My boss is dating his former assistant, who still works here

I have been an assistant for over a decade. I love the work I do. In January, I started a new role supporting the CEO of a mid-size company — definitely not a small family business, but not a Fortune 100 corporation either. I was told the position was open due to a promotion the previous assistant received, which was a great thing to hear!

Upon getting here, I noticed the vibe between the CEO and his former assistant to be … different. They constantly talked during the work day about personal things, spent lunch together, and when one of them would leave for an errand or for the day, they would talk on the phone. At first, I chalked it up to a close personal relationship between an exec and his former assistant, but after seeing something private happen between them one day, I quickly accepted that they were in fact in a relationship.

My question is, how weird is this? I told myself I wouldn’t make it a “thing” unless it impacts my work. In general, it doesn’t, but I find myself holding back on asking him or telling him things because I don’t want to interrupt what is clearly a boyfriend and girlfriend in a deep personal discussion. It feels weird to me, but I don’t know if I’m being sensitive. They clearly started the relationship before her promotion and her assignment to a different manager, but does that matter?

I don’t want to go to HR about my concerns because our HR person has seemed to turn a blind eye to it. The office does not acknowledge it publicly, but at least eight coworkers have brought it up to me to share how inappropriate they find it. I guess it’s top of mind to ask you now because of the recent dismissal of the Nestle CEO due to an undisclosed romance with a subordinate!

Man, the Coldplay guy must be relieved that the Nestle CEO has already displaced him as the first example people think of when they think of inappropriate work relationships.

And this is inappropriate. I mean, it’s good that she was assigned to a different manager, but he’s the CEO which means he still has plenty of professional power and influence over her, which means that there is still a legal liability for the company, as well as major practical concerns (will people be hesitant to report issues with her because she’s dating the CEO? will her new manager feel comfortable holding her accountable if there are problems with her work?) and perception concerns (will colleagues wonder if the promotion was a result of the personal relationship?). None of it is good for either of them, none of it is good for other employees, and none of it is good for the company.

If the HR person is deliberately turning a blind eye to it, that’s a problem. The power dynamics limit what she can do (he’s her boss) but she has an obligation to inform the board (which is his boss). Who knows, maybe she has. Maybe their “solution” was the job change. It’s not enough, if so.

All this said, you shouldn’t let it prevent you from interrupting their conversations when you need your boss’s attention. Be matter-of-fact about it — “Hi Jack, can you grab me when you’re done so we can go over this week’s schedule,” “Sorry to interrupt, I need to get your sign-off on this before 3 pm,” etc.

2. My coworker is openly rude to me

What do you do when your coworker acts like a teenager for a while and says “whatever” to your statements and/or actions at work after you apologized for your mistake? How long and how much space should you allow for her rude attitude towards you?

I acknowledged my error/misbehavior that had upset her, so I owned the fault and sincerely apologized for it. While giving her some space, I also tried showing in actions (doing extra hard work to help her workload).

Although her unprofessional attitude persists, the work productivity stays relatively steady/manageable. If she doesn’t disrupt my work, do I let it go and let her keep giving me the attitude/continue with the unprofessional behavior? Or do you have any suggestions to cope with her?

This is interesting because normally I’d want to know what the mistake was and how it impacted your coworker in order to put her reaction in context — but it sounds like she’s being so openly rude that it doesn’t really matter. It would be different if she were simply being less warm than she used to be, but responding with “whatever” is rude and unprofessional, and it’s not okay regardless of what led to it (particularly if it’s become her go-to response to you now). Part of having a job is that people need to maintain a baseline level of civility with their colleagues, regardless of what one’s personal feelings about them might be.

Depending on exactly what the rest of the rudeness looks like, one option is to calmly and matter-of-factly name it and ask her to stop. For example: “I understand that you’re upset with me, but we do need to work together civilly so I’m asking that you not speak to me that way.”

But if that doesn’t work or if she’s routinely hostile or goes beyond just a little snippy, loop in your manager since at that point it’s a work problem that she should be aware of and addressing.

Related:
how to deal with a coworker who’s rude to you

3. My coworker and I are applying for the same job, and she’s really bad at part of it

My team is going through a restructure. Two of us will be applying for the same role, as currently we split the role half and half. However, I’m noticing that this other person, Billie, is missing things.

There’s a legal aspect where we have to make sure we have certificates online and she’s historically struggled with this. I’ve also been noticing things like:

• She ignores emails about data requests.
• She doesn’t send over material and misses deadlines.
• She forgets meetings and has said “forgive me, I forgot to do my homework!” when I asked why she didn’t show.
• She didn’t clear a report that went to a big standards board, which was a big enough deal we got a departmental email about how to avoid it happening in the future.

However … she takes on things like putting us in a regional celebration, which isn’t a legal responsibility but is very glittery and plays well with the standards board, and she set up a work-related discussion club. I’m worried that when the time comes to interview, her experience and her flashier stuff will trump my quieter wins of getting the legal stuff done. She did a qualification a few years ago so I think that also shields her.

We currently have different bosses so I don’t feel like I can go to her manager and let them know about all the stuff she’s not doing. Our management is pretty ineffectual and she’s also pretty good at sucking up to our (male) bosses. I’m not. I’m quiet and just get on with things.

Talk to your own manager! Say these issues have been ongoing and you feel like it’s relevant to the hiring decision but you’re wary of looking like you’re just trying to boost your own chances for the job, and ask for his advice on the best way to handle it. If he hears enough of the details about the problems with your coworker, he’s well-positioned to raise the issues himself with your coworker’s boss and/or with whoever is hiring for the combined job.

Separately from that, make sure that you go into the interview really well-prepared with concrete examples of how you’ve been excelling at the work, including your responsiveness, consistency, and reliability at meeting deadlines. Don’t assume anyone who’s interviewing you knows much about your work (even if they do or should); make the case for why you’d be great at the job, regardless of what you think they might already know or have seen. And you should also think about who might be well-positioned to champion your candidacy, too. For example, if you have colleagues who clearly appreciate working with you over your coworker because they know you won’t ignore their emails or miss their deadlines, ask them if they’d share their feedback about working with you with the hiring manager. (You don’t need to frame it as “talk about why Billie sucks”; frame it as “share how I’ve been good at the job.” If that spurs them to also share with the hiring manager that their experience with Billie has been less positive, so be it! I know if I heard two coworkers were going for the same position that affected my own work and one of them was easy to work with and one wasn’t, I’d jump at the opportunity to share my input.)

4. Do I have to be on LinkedIn?

I am job hunting for the first time since pre-Covid. As a senior manager looking for a lateral role, do I really need to have LinkedIn? And if so, does it hurt me to take down my profile picture?

I graduated college when LinkedIn was relatively new and we were all urged to make accounts, and I’ve had mine ever since. I’m connected to a few people from my past jobs, but don’t use it to keep in touch with anyone. I absolutely hate it and I have had concerns about data privacy for a long time, which are being compounded by AI, but I have always thought (and been told) that I had to have it in order to be taken seriously as a job applicant. I recently deleted all of my other social media, and I am wondering if LinkedIn is really necessary in 2025? If it is, what are some good data protective measures to take?

There are some fields where it will look at little odd not to have any LinkedIn presence (for example, recruiting), but they’re more the exception than the rule. There are a ton of people with no LinkedIn profile who are successfully employed. You’d probably know if you were in a field where it really mattered.

That said, if you’re open to keeping it, it can be a good idea to. It’s an incredibly useful way to track down former managers and other colleagues in the future, and you might want them for a reference or networking lead at some point even if you haven’t wanted to keep in touch with them previously. That also goes both ways; it lets people find you if they want to ask you for a reference or about a job at your company. But if you feel strongly about it, in most fields you don’t need to have one.

If you do keep it, you can go into the privacy settings and turn off all kinds of things.

5. My new job made me take a medical exam

I finally got a job offer and its from a large university/hospital. I have signed the offer letter and was given almost every test today except for a pap smear! They took fingerprints and urine, did an eye test, weighed me, and asked me all my medical stuff and medications I take. I get this is a hospital, but the job I applied for is a switchboard operator.

Is this legal in the U.S.? I did kinda ask about it and she said they need to make sure I am healthy enough to do the job. When I told them I have epilepsy, they are making my doctor give me a release to work.

It feels very much like a relic from another time, but it’s legal.

Employers can’t require job candidates to take medical exams (or answer medical questions), but once they make you an offer, they can condition it on you passing a medical exam. If they do that, legally they have to do it for all employees in your job category (they can’t pick and choose who they ask it of). They also can’t pull the job offer because of information about a disability revealed by the exam, unless the reasons for the rejection are “job-related and consistent with business necessity.” Weirdly, though, the exam itself doesn’t have to be job-related and consistent with business necessity! For most jobs, it’s extremely strange.

After you begin work, they can’t ask you medical questions or require an exam unless they need medical documentation to support your request for an accommodation or they have a bona fide concern that you’re not able to perform the job safely for medical reasons.

Related:
my new job sprang a surprise medical exam on me

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