my coworkers have a crush on my boss … and are taking it out on me
Nov. 11th, 2025 06:59 pmI’m off today so here’s an older post from the archives. This was originally published in 2020.
A reader writes:
I’m the executive assistant for a small company. I’m the direct support for the VP of human resources, “Dave,” who is very charismatic and likable and a generally nice guy. He’s also very good looking. However, he’s very professional with great business boundaries. I enjoy working with him.
Two managers in particular, “Karen” and “Nancy,” need to meet with him all the time. All. The. Time. Their departments aren’t undergoing any HR issues, they don’t have any staffing needs, and they’re not hiring or firing anybody right now. They call to schedule multiple meetings a week, drop by to see if he’s available for 1:1s when his schedule doesn’t have a single second free, and call him multiple times a day. Dave always routes them back to me to take a message or schedule them with him. Nancy gets angry with me when I tell her he’s not available and blew up at me last week that I’m “not his chaperone.”
Dave has noticed it and so have a few other execs. Dave’s been very clear about making both of them go through the same process other staff members go through to schedule with him. Just the same, other staff have started calling them his “fan club” and me the “bouncer.”
When I was working with the other assistants and operators on a training, word about his “fan club” had gotten around and one person mentioned that Karen calls me names and tells the other staff I’m in love with Dave and don’t want other women near him, which is why I never let her schedule with him. She even showed me a few emails in which Karen advised her department support professional to go over my head to see Dave and that I wasn’t the “keeper of his zipper.”
I’m not sure how to approach this. I’m more angry than I am embarrassed. I’m also bothered because the support staff report to me, and some of my staff have reported both Nancy and Karen as being difficult to work with and unpleasant in other aspects of the day-to-day, not just in regards to the Dave thing. Where do I start with this?
This is so gross!
If Karen and Nancy were simply trying to meet with Dave all the time, that would be annoying but manageable. Even then, though, at some point Dave would probably need to shut it down more firmly than he has. (Not that he’s at fault here! It sounds like he’s managing an uncomfortable situation pretty professionally — but needs to hear how it’s gone off the rails.)
But this is more than Karen and Nancy trying to get a weird amount of Dave’s attention. Blowing up at your for doing your job, calling you names (!), spreading rumors that you’re in love with him, and ever uttering the words “keeper of his zipper” in a work context is … ugh, so over the line and gross and violating. To you, and also to Dave.
It’s time for you to talk to him. It’s going to be awkward and uncomfortable, and you need to do it anyway. (Remember that the awkwardness is 100% on Karen and Nancy, not you.) He needs to know the full extent of what’s happening, how out of control it’s become, and how it’s affecting you.
If you’re hesitating to do that because it feels uncomfortable or you don’t want to burden him with this or you feel like you should be able to deal with it yourself … you still need to talk to him, for three key reasons. First, he deserves to know what’s being said about him so he can decide for himself how he wants to handle it. It’s not right to let this happen behind his back without informing him. Second, as your boss he needs to be aware that you’re being harassed and mistreated. Third, as the VP of HR, he has a professional obligation to intervene and ensure this is shut down — his job in the company requires it (and there’s a point where not acting will make people question HR’s competence, and how seriously HR would take it if someone else were facing similar issues).
So talk to Dave. Tell him all of it — the name-calling, the yelling at you, the rumors, the undermining you, all of it. And I’m sorry to say, you’re going to have to repeat the “keeper of his zipper” line because that makes it clear just how over the line this has become.
You can tell him you’re embarrassed to have to repeat all this, but it’s important that you tell him it’s happening, and that you tell him it’s at the point that HR needs to intervene and shut it down.
If Dave is as great as he sounds — really, even if he’s only sort of okay — he’s going to be grateful you told him and will deal with it so you don’t have to. It’s his job! Let him have the info he needs to do it.
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I made a gift guide for each employee on your team
Nov. 11th, 2025 05:42 pmIf you’re the boss, finding the right gifts for your employees can be fraught with questions: How much do you spend? Should you spend the same amount of money on each person? And if you don’t know someone well, how do you make sure they like the gift while still keeping it professional?
For the record: managers don’t have to give their staff members gifts, but it’s a nice gesture if you want to do it, and in some offices it’s expected. (Although here is your obligatory reminder that because of the power dynamics involved, gifts at work should flow down, not up. Managers should never expect or encourage gifts from employees.)
A while back, New York Magazine asked me to put together a gift guide for bosses buying for employees, and I’ve updated it for 2025.
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my coworker is blackmailing me not to take time off for my honeymoon
Nov. 11th, 2025 03:59 pmI’m off today so here’s an older post from the archives. This was originally published in 2020.
A reader writes:
I work in an office where I’m the only person who can do 75% of my job, but there’s a second person who can do essential functions. We have a policy that only one of the two of us is allowed to request advance time off at a given time (so one of us is always in, barring emergencies).
I’m getting married in October, and in relation to that requested — and was approved for — two days before the wedding and the two weeks following. I don’t take much time off and have more than enough “in the bank” to cover that with some left over. It was approved immediately by my supervisor.
Since then, my close coworker (Jane, who covers some of my essential duties) first started asking if I really “need” that much time off. She then dropped a bit of a bombshell on me and said that she “really needs to go to Florida the following weekend (after my wedding) for a cousin’s wedding” so asked if I could be in for the second half of that week as well as the following Monday. I told her that my plans weren’t certain yet, but that I didn’t want to commit to that and leave those requested days open.
That was met with a tirade about how she “always looks out for me” and that I need to “do this one thing for her.”
We normally have a cordial, if not especially friendly, relationship but she has turned nasty and threatened to blackmail me over a a sick day where she claims I “wasn’t really sick.” She had seen me at the grocery, where I was mostly picking up a prescription but also doing general grocery shopping, but don’t have a doctor’s note if push comes to shove. When she brought it up, she said, “That day I saw you at the grocery store, I know you weren’t really sick but were just goofing off for the day. I’ll report you for that.” I responded with, “I was there to pick up a prescription, even though I bought some other things because I didn’t have anything at home that sounded good.” She responded, “If you don’t let me have this, I’m still going to report it.”
(For context, this happened during the work day, probably around 1:00 in the afternoon. Sometimes one of us will go to the store to buy work supplies during the day. When I saw her there, I had just come from the doctor’s office, which is literally right across the street, and was shopping for other things while waiting on a prescription to be filled at the store pharmacy.)
This has gone on for a week and she’s not dropping it that I need to be in those specific days, and I’m not relenting.
There’s a possibility that — for a variety of reasons — I won’t even be working there in October, but at the same time I don’t know how to handle this. I mentioned it in passing to my supervisor, who wasn’t overly interested and he indicated that I was “okay” since I’d requested the time 9+ months in advance. Still, though, I feel that the battle isn’t over yet, and it’s negatively affecting my ability to actually do my day to day job as Jane is refusing to do the small part of her job that I don’t have the proper training/credentials/ability to do.
In addition, there are the logistics that if our supervisor agrees to let us both off, I’m no doubt going have two dozen calls/texts a day on my honeymoon from people who are persistent enough to call me 10 times in a row if I don’t answer. Needless to say, that’s NOT a situation that I want to deal with, but it happens any other day when both of us are off (heck, it happens when I’m off just because of the sheer volume of stuff that she doesn’t care to learn to be able to answer).
Jane is a jerk.
But not a very smart jerk. She thinks she has way more power here than she does! And I think you think she does too.
You requested time off for your wedding and honeymoon nine months in advance. It has been approved. Your manager reiterated that your time off is secure.
Jane’s blackmail attempt is embarrassing — for her. It has no teeth at all. You don’t have anything to hide because you didn’t do anything wrong. You’re allowed to pick up prescriptions when you’re sick. You’re also allowed to buy yourself groceries when you’re sick. But if your manager really doubted you for some reason (which is unlikely), you could always contact your doctor’s office to get documentation that you did indeed have an appointment that day. It probably won’t come to that, though. But if you needed to, know that you could get the back-up you need.
Unless your boss is a complete fool, I can’t imagine he wouldn’t be at least slightly interested in knowing that one of his employees is (a) attempting to blackmail another (b) into altering her wedding and honeymoon plans (c) that have already been approved and (d) is refusing to do part of her job because of a personal vendetta.
I strongly suggest that you talk to him and say this: “Jane is harassing me about the time off I had approved for my wedding and honeymoon. She wants some of those same days and told me that if I don’t change my own time off request, she will report me for misusing a sick day. That’s false. She saw me in the grocery store while I was picking up a prescription on a sick day. I can get a note from my doctor that I was seen that day if you need me to. I think it’s hugely problematic that she’s trying to blackmail me to change my days off, so I want to make sure you’re in the loop that that’s happening. She also is refusing to do (specific work tasks) because she’s upset with me. Obviously, I rely on her to do XYZ to be able to do my own job. Can you intervene, so that her harassment stops and I can do my work?”
If your boss won’t intervene, then he’s passive to the point of negligence and you should say the above to HR as well. This is the kind of BS that managers should handle on their own but which HR will usually step in on if you need them to.
Meanwhile, with Jane, tell her this: “I’m not going to discuss my time off with you any further. If you want to report seeing me in the store picking up a prescription, feel free to. I can get documentation from my doctor if I need to, and I’ll happily let (manager) know the situation myself. But I’m not going to discuss this anymore.” If she continues to push, say, “You need to talk to (manager) about this. It’s not up for discussion between us anymore.”
But if your boss is at all decent, he’ll shut this down once you explain what’s been happening.
If the outcome is that he gives Jane the days off she wants and so you’re both gone on the same dates, let people know ahead of time that you will be on your honeymoon and 100% not reachable. Tell them you won’t be responding to calls or texts, and then stick to that. In fact, block everyone from your office during that time away so you don’t even see it if they’re trying to contact you. If you feel weird about doing that, then tell your boss in advance what you’re worried about, and reiterate that you will be 100% inaccessible. People do this! You’re allowed to take a freakin’ honeymoon without work calls.
But stop fearing Jane. What she’s doing is super messed up in a way no decent manager would condone, you have the power to expose that, and you should use it.
The update to this letter is essential reading! Do not miss it.
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I’m off today. Here are some past letters that I’m making new again, rather than leaving them to wilt in the archives.
1. Should you hire employees to babysit?
I help supervise a group of about 20 student workers at a college. Most of them know I have a one-year-old and some of them really love babies (I sometimes bring him by during my non-work hours briefly to make their day). I’ve had at least two workers tell me they’d love to babysit. They’re good responsible workers, but I’ve been uncertain as to the advisability of that and haven’t followed up on their offers. This is likely to come up again as new students come in and learn I have a child. My gut says that babysitting (while paid) is more personal than a typical employment relationship and could blur professional boundaries or lead to an appearance of favoritism, so I should just kindly thank them for the offer and say we’re all set in that department. Is that the right call or am I overthinking this?
People sometimes do this and it’s fine, but if it goes wrong, it can be disastrous. For example, if you hire one of them and there are problems with their care of your child (say you find out they’ve been negligent or cruel), would you be able to keep that from affecting things at work? What if you have a dispute over pay? Are you comfortable leaving them unattended in your home? And you’ve also got to consider the power dynamics; even though they’re volunteering, there’s a risk they’d still feel obligated to say yes when you ask (or that they’ll be happy to do it once or twice but feel pressured after that). It can also make other workers wonder if you favor or give special access to the people who sit for you.
Some people do this and make it work, but if you want to play it safe, it’s wiser not to cross the streams.
– 2020
2. Locker room etiquette when your gym is full of coworkers
My office recently added some cool new perks on top of our employee benefits. My favorite? They’re now offering anyone who wants it a free membership to the gym right across the street from our office. It’s been hard for me to work out previously because of my commute, so I’ve been taking full advantage of this perk since it took effect a couple months ago. Lots of my other coworkers have jumped on this perk as well, and I’ll run into them at the gym frequently. Overall, it’s been positive, but there’s one thing I don’t know how to handle — the locker rooms.
I’m pretty comfortable in my body, and I’m not that awkward about changing in your standard locker room full of strangers. But the prospect of a coworker — or worse, my boss — walking in on me changing has me feeling incredibly awkward. So far, I haven’t been seen by my coworkers while changing and haven’t walked in on anyone else from my office, but I know it’s only a matter of time. This is a situation I’ve never encountered before — I didn’t know anyone who worked out at my previous gyms. What should I do if I run into a coworker in the locker room while one or both of us are in various states of undress? Should I just change in the toilet stalls to avoid anyone seeing me? I might be making a bigger deal of this in my head than it actually is, but it has me feeling really uncomfortable.
It’s pretty much the same locker room code as always: There’s a collective agreement to ignore everyone else’s nudity.
The last time this came up, a commenter offered this, which I really liked:
“I think there’s a big difference between functional nudity and casual nudity at the gym. Functional = in order to change, I have to take off my clothes. I am no longer 12 and trying to hide my body at all costs, so if someone glances over at me while I am changing, they will see me naked. Casual nudity = I am wandering around naked, blow drying my hair naked, etc. This is fine generally in a locker room, but is best to avoid at a work gym. Though I would totally blow dry my hair wearing a bra and not a shirt to avoid getting hot/sweaty.”
In other words, make any nudity fairly quick. Don’t linger.
But it’s also completely fine to decide you’re just not comfortable with locker room nudity around coworkers at all and change in a stall. There’s no shame in that; you’re not being weirdly prudish if you got that route.
– 2019
3. Is it unprofessional to brush my hair in common areas of my workplace?
I am an assistant manager, and today something weird happened. I did not get to finish my normal routine this morning as I had to go to the UPS store (for work) so I showed up to work with my hairbrush. I work at a preschool and typically, by the time I arrive to work, there are no parents here as they have all dropped off their kids and left. I walked around to say good morning to the teachers and collect breakfast dishes as normal, but I brought my hair brush along and brushed my hair as I was walking between the classrooms.
The manager above me made a point to rush up to me and tell me I need to do my beauty stuff in the bathroom. I was confused by this as I thought she meant the makeup in my purse but no, she explained that me brushing my hair was unprofessional. I am young, so maybe this is just a rule on professionalism I have never heard before. I am just confused. This was pretty much a one-time thing, and not a habit I have. Is it really all that unprofessional in this otherwise rather relaxed atmosphere for a work setting?
Yeah, there’s an etiquette rule about not doing personal grooming in public. Some workplaces might not have thought it was a big deal, and it’s not the biggest deal in the world, but it’s also not outlandish for your manager to ask you not to do it. (It’s also the kind of thing that can be frowned upon without anyone telling you, so it’s good that she did. She might have done that because you’re young and she figured that you’re still learning professional norms.)
– 2019
4. I accidentally sent a highly personal medical email to someone who reports to me
I am currently on maternity leave and will return to work in a couple of months. While I’ve been out, I’ve emailed my team at work a few times with baby updates and replied to anyone personally saying hello, all from my personal email as I no longer have access to my work email.
Yesterday, I sent an unrelated and angry email about a very personal medical matter to a person on my team by accident. This person reports to me. The first three letters of her name in her email are the same three letters of the person I was trying to email instead, so you can see how I sent this by accident and this worker’s email was saved because of the above previous correspondence while I’ve been off.
It was only caught because the worker emailed me back acknowledging this wasn’t meant for her. I’m mortified. How can I save face? All I’ve done so far is email her back thanking her, apologizing, and stating that I trust her to keep this between us because of the personal nature. Is this all I can do and never speak of it again?
Yes! You handled it well. If she’s at all a decent person, she’ll understand that this kind of mistake happens and will keep it to herself. We’ve all been there with a misdirected email at some point or another, and most people are sympathetic when it happens.
You don’t need to take any further action; anything more would be belaboring the point and focusing her on it more. Assume you’ll both wipe it from your minds and never speak of it again.
– 2019
5. How to bring up experience at an interview that I forgot to mention on my resume
I’m returning to work after doing a postgraduate degree. I’ve got an interview coming up, and in the course of prepping for it I realized that one of the projects from the job I had before going back to study is in a really closely related area to the role I’m interviewing for. The problem is that I hadn’t mentioned that project in either my cover letter or my CV when applying. Obviously I want to bring up this relevant experience in the interview, but what’s the best way to frame it in a way that is more “this candidate has useful experience” and less “this candidate didn’t fully think through their application”?
Just be matter-of-fact about it! “I realized one of the projects I did at Job X might be relevant here. It’s not on my resume, but (details about the project).” No reasonable interviewer is going to think not including it originally means you’re flighty or thoughtless. Interviewers know lots of people use the same basic resume for all the jobs they apply for, and they also know humans will not always instantly realize precisely how relevant something might be to a job they’re not terribly familiar with yet.
I’ve interviewed many candidates where I thought, “Oh! That’s really relevant — I’m glad you mentioned it.” Sometimes I’ve even thought, “Oooh, you should include that on your resume! It’ll help you!” But I’ve never thought, “What kind of doofus didn’t write this down originally?”
– 2020
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秋晴れの庭。The garden with clear autumn weather.
Nov. 10th, 2025 11:00 pmI got an abusive message from an email subscriber — should I let his employer know?
Nov. 10th, 2025 06:59 pmA reader writes:
I run outbound marketing for a tech startup serving founders and salespeople. We often send promotional/announcement emails from my email address to subscribers who have opted in to receive our updates.
We recently sent a very harmless and innocuous announcement message, to which I received the following reply: “Why the FUCK am I getting this email”
The message was from a personal Gmail account and included the sender’s cell phone number. A quick LinkedIn search revealed that the sender is employed at a major financial services firm as a personal wealth advisor (investment manager) for high net worth individuals.
What he doesn’t know is, I’m a client of his firm. While he is not my investment advisor, one of his colleagues is, and his unreasonable reply — in response to a message he opted in to receive — honestly makes me reconsider my business relationship with the firm. If they employ someone who casually exhibits this degree of unprofessionalism, especially when it took more time to send an abusive reply than it would have to just … delete the email and never think of it again (even deleting and unsubscribing would have taken less time!), it undermines my trust in their ability to manage my money.
So my question is, should I make someone at the firm aware of his behavior? I could let my own investment manager know, but I’m not sure what he would do about it, other than directing me to someone higher up in the organization. Blasting this guy publicly on LinkedIn isn’t really my style, but a world in which someone can be disproportionately abusive in response to a low-stakes “problem” like a marketing email is not one I want to live in, let alone support by giving them my business. I also understand the logic of letting it go, especially given that the reply came from his personal email address, but it’s really made me mad and I don’t want his conduct to go unacknowledged because acting like it’s okay when it clearly isn’t feels like a tacit endorsement. Should I let his employer know?
Nah, let it go. They won’t care.
I’d argue you shouldn’t really care either. A ton of people forget they’ve subscribed to email lists and then send rude responses when they’re annoyed to receive what they think is spam, not realizing they opted in. Is it rude and, frankly, fruitless? Yes, absolutely. Is it something his employer will care about? Probably not. Will it look extremely strange to contact them about it? Yes.
I don’t want to imply that we should accept casual rudeness as the norm. We shouldn’t! But you’re also kind of overreacting to it in this case. He thought it was spam, he was annoyed and, yes, his response was over the top, but your response to it is also pretty disproportionate.
If this guy were your investment manager, I could see caring a little more — like who is this hothead I have managing my money and how else does he behave when he thinks he’s anonymous? But you’re far enough removed from him that you should just delete his reply and not give it any additional thought. (Or at most, you could reply to say, “You received this message because you opted into our mailing list. I’ll remove you.” But nothing beyond that.)
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