is it OK to compliment coworkers’ nails or haircuts, saying I’m leaving my job due to its rigid culture, and more

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

1. Is it OK to compliment coworkers’ nails or haircuts?

I believe that comments on people’s bodies are totally inappropriate at work, and in life in general. But if someone has changed their hair or has some cute nails (I myself do not do these cute things but notice them), is commenting on them in the same category as body stuff? Technically it is part of their body, but it doesn’t seem as bad to be “oh the magenta highlights are cool” or whatever. Should I stop commenting on haircuts and nail design?

One school of thought is that it’s fine to comment on things that are obviously a deliberate choice — like a shirt or a haircut or nail design — but not things that are an inherent part of the person’s appearance, like their weight or their eyes. It’s not a bad rule, although in reality someone creepy can make comments on nail color sound creepy too.

I think a better litmus test can be whether you’d say it to a gender you weren’t attracted to — so like if you’re a straight man thinking about complimenting a female coworker’s haircut, are you going to say it in the exact same way you’d say it to a man with a new haircut? If so, it’s likely fine. If not, you should skip it.

2. Should I tell interviewers I’m leaving my job because of its overly rigid culture?

I am currently at a desk job that’s mostly fine, but very rigid. There’s absolutely no work from home under any circumstances, no deviation from hours allowed even when it doesn’t affect job performance or coworkers’ workload, and not a lot of sick or PTO time to make up for it. It’s very “this is the way things have always been done and we are never going to change.” But I know that other companies tend to allow people in my position to have flexibility and some work from home. In my understanding, this rigidity is abnormal in the Year of our Lord 2026.

If I were to look for another job, how do I explain why I’m looking to switch without sounding like an entitled millennial brat? If they ask why I’m looking for a new job, is it okay to say the rigid corporate culture and I don’t vibe, or that I’m looking for more flexibility? Will it sound like I’m looking to shirk responsibilities at a new job?

When I took this job, I was in dire straits to get out of a toxic nonprofit. I’ve been here over three years already, toughing out five days a week in office while my peers in other companies get at least three days in, two days WFH. I know I could keep going, the pay is good, the work is easy, the people are generally nice, but the boomer work mentality is insane and unfair.

There are still a lot of companies that operate the way yours does. If it’s not for you, there’s nothing wrong with disliking it, but they’re not necessarily as out of step with other companies as you’re painting them as! They might be — if the PTO is really low, that would sway me — but the rest of it isn’t especially outrageous and you’ll find it in a lot of places. That doesn’t mean you shouldn’t change jobs over it — you definitely can! — but it’s helpful to calibrate your sense of how abnormal it is so that you make sure to confirm the next place will be different. (Although even that isn’t foolproof — lots of people who had work-from-home jobs are being told to return to the office five days a week.)

As for interviewing: in general your answer about why you’re applying to a new job should focus on the appeal of the new job to you, far more than what you don’t like about the old job. In your case, you’ve been there for three years; it’s beyond reasonable to just be looking to take on something new, and then you can talk in specifics about what appeals to you about the job you’re applying for. You should still use the interview process to dig into what their culture is like and how much flexibility they have, but it shouldn’t be the focus of this particular question.

Related:
do I need to give interviewers a great reason for why I’m looking to leave my current job?
can you say you’re looking for a new job because you want “a new challenge”?

3. My job won’t implement any of my ideas, but won’t give me a clear no

I’ve been teaching in this school for several years now, and I have a problem. Every time I ask to do something fairly typical for a school, I hear, “That’s a great idea,” only to be told a week later that it’s not feasible this year. Again, these are typical things in schools: for example, adding a new class (one that is technically required by the state, no less) that I am the only person at the school qualified to teach, starting a club with several students expressing interest, or taking on a class that I have taught before here.

I know partly why I am in this position. My sister died four years ago, and for the entire year after that, I was an atrocious teacher. I probably should have been fired, but there was a massive teacher shortage at the time. And then the year after that, I did better, but I was also pregnant for most of the year. I’m doing great now by most measures, and they keep adding things to my plate … but never the things I ask for. I ask at the very beginning of the year and get told, “I’ll get you the paperwork.” I send out reminders, and it never comes. Then, once they’ve put me off, I get told, “Not this year. Try next year.”

I’m guessing they mean no, even though they’re saying to try later, but I honestly wish they would either just tell me no and give me any kind of reason why, or tell me how I can change things.

Can you change schools? Fairly or not, sometimes it’s just very hard to get people to see you differently after they’ve fallen into seeing you a certain way. And even if you’re wrong about what’s going on, it seems clear that — for whatever reason — this is just how it’s going to go at this school. It might be very different if you can make a fresh start somewhere else.

4. My boss keeps asking about progress on a personal project I’m not doing

I’m a new grad a few semesters out of college and landed a full-time role in my dream industry with a probationary period. It is a very small company and I report directly to the founder. Two weeks in, she told me she was not satisfied with my work, heavily implying I would be let go after the probationary period (at the end of May).

She then suggested I make a specific project that would aid in my job hunting, framing it as trying to help me join a company I was truly passionate about. I nodded along with no real intent to go through with the project, thinking that would be the end of it.

Since then, she’s asked me every single week how said project is going. I’ve dodged it for the most part, saying I’ve been brainstorming and planning, but not sure how long I can keep it up. I have no intention of making this project as I’m working on other projects for said upcoming job hunt, but my boss is insisting that this will be the key to my dream job and is very dismissive if I suggest otherwise, I simply nod along because I am a fresh grad and she is in the industry.

I’m also very non-confrontational and I need to keep this contract until it ends to support myself; I’m not sure how to deal with this weekly nag about a project when it is my fault for even letting it go on for a few weeks. Proper HR does not exist at this company.

Can you just tell her that you’ve spent some time playing around with it but you’ve decided not to pursue it for now because of ___? What you fill in the blank with will depend on the specifics, but it could be anything from time commitments outside of work to deciding you’d rather focus on some other aspect of the work. You could add that you really appreciate her making the suggestion.

If you think that will just cause more issues, you could go with something vague like, “Yes, still sketching out ideas” or “still at the thinking and exploring stage” or similar … but you’re probably better off just more clearly telling her it’s not something you’re pursuing.

5. Applying for multiple jobs at the same company with only slightly different cover letters

I was laid off recently, and one employer I’m focusing on applying to is a very large healthcare organization. Its application tracking system has you upload only one resume (per candidate profile) and only answer most of the applicant questions once, but then has a section at the end to upload up to 10 different cover letters (you’re supposed to put the job ID number in the cover letter document title when you upload). When I look at my candidate profile, I see my resume at the top and then multiple cover letters beneath. (I’m applying for a lot of very similar administrative openings, so it’s not like I’m just scattershot applying for random things. But I do really want to work for them.)

From the HR/hiring manager’s side, how much does it matter if there’s some repeated phrasing in multiple of the cover letters? I do write a new cover letter for each one, and try to keep it warm and pertinent, but I do have some sentences I reuse in the opening/conclusion of each letter — otherwise it would take forever to apply for these very similar roles, if I’ve already used up the points I’m making about myself. Will HR care/compare them, or is it not worth worrying about?

You’re fine. Ideally the letters shouldn’t all be identical, but they’re not; you’ve switched up some of your phrasing to make them each a bit different. They’re unlikely to bother comparing them, but even if they did, you’re fine.

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