Posted by Ask a Manager

https://www.askamanager.org/2025/12/vote-for-the-worst-boss-of-2025-round-2.html

https://www.askamanager.org/?p=34650

It’s round 2 of the Worst Boss of 2025 voting. In the first round we narrowed the pool from eight nominees to four (see results here). The four winners from round one are paired off in two match-ups below, as we move closer to declaring a winner.

1. Repulsive Rivals – The Nominees:

• the CEO keeps asking young male employees to try her breast milk
• my boss said I’m threatened by his “masculine energy”

2. A Loathsome Line-up – The Nominees:

• my boss told me to stop having sex with my boyfriend or quit my job
• my company makes summer interns wear bikinis

If the voting isn’t showing up for you, you can also vote directly here: pair 1, pair 2

The post vote for the worst boss of 2025: round 2 appeared first on Ask a Manager.

https://www.askamanager.org/2025/12/vote-for-the-worst-boss-of-2025-round-2.html

https://www.askamanager.org/?p=34650

Posted by Ask a Manager

https://www.askamanager.org/2025/12/new-job-wont-let-me-wear-my-wedding-ring-bringing-snacks-for-your-coworkers-when-youre-new-and-more.html

https://www.askamanager.org/?p=33490

I’m on vacation. Here are some past letters that I’m making new again, rather than leaving them to wilt in the archives.

1. My new employer won’t let me wear my wedding ring

I’m getting ready to start my new job in a fast-moving but rather conservative industry. I’m starting as an assistant but have the possibility of advancing up to management throughout my career here. Last week, I had a meeting with the woman who is going to be my supervisor and we finalized things like my salary, work hours, etc. She also spent a significant amount of time making sure I understood the dress code, as it is very strict, even stricter than many other offices. There were things like only certain colors of clothing, absolutely no nail polish, minimal makeup in only natural colors, no heels over two inches but no “casual” shoes either, etc.

One of their rules is that, while some jewelry is allowed, it can only be either gold or silver in color and absolutely nothing else. Here’s the thing: My wedding ring is purple (amethyst encrusted). My husband got this ring for me because he knows I dislike gold and silver jewelry and prefer colors, and it’s also my birthstone. My supervisor pointed it out during our meeting and said, unfortunately, I wouldn’t be able to wear it during work hours. I was a bit taken aback but did not argue.

Now that I’m getting ready to start, I don’t know what to do. On one hand, rules are rules. On the other hand, it’s my wedding ring and it’s very precious to me and I never take it off. I also don’t want to go out and buy some arbitrary silver ring to wear in place that means nothing to me. It would seem silly to give up this great job over a ring, but I just don’t know. If it were any other piece of jewelry I wouldn’t care, but not this one. What should I do?

That’s a ridiculous rule and I cannot fathom any legitimate business need for it, other than that they have a need to be overly controlling.

I’m curious to know what would happen if you say, “I understand your rules about jewelry, but this is my wedding ring and I don’t take it off. I’m certainly willing to abide by the dress code, but it’s not an option for me to remove my wedding ring. What’s the best way for me to proceed, given that?” They may say that yes, they’re going to require you remove the ring if you want to work there, but I’d like to make them say it out loud because it’s ridiculous.

But if they do, then you’ll have to decide if you’re willing to remove it for work every day (and also if you’re willing to work for people who give adults rules for rules’ sake).

– 2018

2. How to tell an employee to stop cc’ing my boss

I’m a new manager and I have an employee who consistently copies other people on emails I’ve directed specifically to her. What is confusing about this is that sometimes the emails are related to situations that may not have been well handled by her. I’m trying to be supportive and encouraging and make these things teachable moments instead of “you’re in trouble” moments, but when she then turns around and copies my boss in her response it makes me look bad for not immediately reporting the issue to him.

I don’t know how to explain this to her without making it sound like I want her to hide things from my boss. Do I just cc my boss every time I think her judgement may have been off to get ahead of the problem? That would probably get her in trouble more, which I don’t want either. I don’t have a problem with her telling my boss about an issue that has come up in her area, but when I’ve responded saying something like, “You used your best judgment in the moment; let’s figure out how to fix it together,” it’s a little jarring to then discover that she’s included my boss in her response.

The good news here is that you’re her boss so you can just direct her to stop doing this. I’d start, though, by asking what her thought process is when she does it. For example: “Jane, I’ve noticed you’ll often cc Fergus on a response to me when I’ve initially sent the email only to you. How come?” She’ll presumably respond with “I thought he should be in the loop on X” or something similar, and then you can explain why that’s not the case: “Actually, Fergus doesn’t need to be involved in that. If I decide that he does, I’ll of course loop him in, but part of my job is fielding this sort of thing so that he doesn’t need to spend time on it.” And then give the clear direction to stop: “Going forward, please leave Fergus off emails about this kind of thing. I’ll loop him in if I think he’d want to be informed or be able to give input.”

I think you’re feeling weird about saying “don’t tell Fergus things,” but that’s not the message; it’s “Fergus has other things he needs to focus on. He and I are aligned about when to bring him into the conversation, and I’ll do that when it’s needed.”

(Also, I wouldn’t assume that you’ll look bad to your own boss for not immediately reporting issues to him, unless they’re truly big enough that he’d want immediate notification. Your employees will make mistakes. You only need to loop your boss in when those mistakes are big ones that will impact things he needs to know about, or when it’s enough of a pattern that you’ve developed serious performance concerns about an employee and need your boss’s buy-in on your plan for handling it.)

– 2016

3. Bringing snacks for your coworkers when you’re new on the job

People like to nibble at work, especially if it’s free food. What do you think of newbies bringing in nibbles in order to curry good feelings? Yes, it’s sucking up, but is it okay?

I once brought in coffee candies that the boss couldn’t keep their fingers away from when I was working in a small store. But for a more professional office environment, is it okay to curry favor in the fashion?

There’s nothing wrong with bringing in food for the office when you’re new. But I wouldn’t do it in order to “curry favor.” The way you make a good impression on your new coworkers is by being warm and pleasant, interested in the work and what they do, not being rude/annoying/arrogant, and doing a good job yourself. If you don’t do those things, no amount of brownies or candy will change that. And if you do, no brownies or candy will be necessary.

That said, if you’re having trouble meeting people in your new office, I could see bringing something in after a month or so and letting people know to stop by your office if they’d like some. But I’d do that to meet people, not to ingratiate yourself with them — and not right off the bat.

– 2013

4. A misbehaving coworker doesn’t know I’m about to become his boss

I’m in a tricky spot — I was recently granted a promotion that will put me in charge of my current team. Because we have a big project launching a month from now, my boss has concluded that it’s best to keep everyone focused, and not announce the restructuring (and my new role) until after this project wraps. The issue is that I already have tension with and big concerns about one coworker who will report to me (let’s call him Jeff), and the situation is rapidly getting worse.

I don’t think it’s a personal beef with me: Jeff has made some big missteps in the past year and received a lot of criticism for it, so I suspect he’s just feeling defensive and disengaged. But in recent meetings he’s been combative and curt with me, and another coworker recently divulged that he’s taking regular time out of the office to interview at other companies, offloading major components of his job onto an unqualified freelancer, and hiding out in conference rooms where he watches baseball games on his laptop instead of working.

Jeff is clearly looking for an exit, but in the meantime, his behavior is impacting our team and he’s not taking pains to hide it from me because he doesn’t know I’ll soon be his manager. How can I intervene right now, seeing as the promotion won’t be public for another month?

You probably can’t. You just don’t have standing or authority to do anything about it right now. However, you can talk to your boss about the situation so that he’s in the loop, and to ensure that he’ll have your back in dealing with the situation right out of the gate when your promotion takes effect.

For now, you’re getting the benefit of getting a really clear look at a problem you’ll have to deal with soon though, and it sounds like you’re seeing more of it than you’d see if Jeff knew you were soon to be his boss. You’re not obligated to tip him off in order to protect him from himself (especially since that would mean divulging information you’re not authorized to divulge yet). And it might actually be useful that when you do become his boss, he’ll realize that you know the situation; that could make it easier to have a candid “you’ve got to cut this out” conversation with him.

(And meanwhile, you can hope that one of those interviews turns into a job offer, which sounds like it would be the best thing for everyone.)

– 2018

The post new job won’t let me wear my wedding ring, bringing snacks for your coworkers when you’re new, and more appeared first on Ask a Manager.

https://www.askamanager.org/2025/12/new-job-wont-let-me-wear-my-wedding-ring-bringing-snacks-for-your-coworkers-when-youre-new-and-more.html

https://www.askamanager.org/?p=33490