まるさんの場所にみりあり。Miri’s in Maru’s place.
Nov. 12th, 2025 11:00 pmthe fake charity, the Photoshop predator, and other times AI got it wrong
Nov. 12th, 2025 06:59 pmWe recently talked about times AI got it really wrong, and here are 20 of the most ridiculous stories you shared.
1. The fake initiative
Our execs usually send out a hype email right before the annual employee morale survey, emphasizing wins from the past year, basically trying to put people in a positive frame of mind.
Last year’s included the announcement of a major new program we knew employees really wanted. But it was a bit surprising, because it fell in an area my team was responsible for, and we were out of the loop, despite advocating strenuously for this over the years. So I went to the exec to a) convey enthusiasm for his newfound dedication to launching this program and b) ask what support he needed from my team/get us involved again. It turned out the program wasn’t launching at all; he had just asked AI to edit the email to make it sound more exciting and appealing, and it had done so by … launching my initiative.
2. The predator
Sometimes at work my colleague uses AI in Photoshop to extend a background in a photo or clean up the background. We had a photo of a senior staff member outside: the background shows a building to the left of him and some trees and a road to the right, but it was portrait and we needed landscape. He asked Photoshop to extend the background on the right.
It generated a scary looking woman creeping up behind the staff member.
3. The nickname
I was on a Zoom call with AI notetaking software and was referring to a colleague named Bridget–but on the transcription, every time I specifically mentioned her name, it appeared as “Piglet.” This did not happen when others on the call said “Bridget”! It looked like that was just my nickname for her. I was so embarrassed.
4. The fake charity
My company hired an account manager who insisted he was a phenomenal writer and asked if he could contribute to our blog. The first pieces were just AI slop so I politely thanked him and said we had plenty of posts already.
So he posts a third “article” on his own LinkedIn account in which the AI described how our company collaborated with the CDC on researching a certain disease and publishing a groundbreaking study. Then we apparently went into underserved communities and funded a bunch of clinics and immunizations. NONE of this happened. It was hours before I saw it and forced him to take it down, and there were many surprised comments and shares. Months later, we were nominated for an award on our commitment to caring for vulnerable populations.
5. The transcript
I forgot the meeting was being transcribed and was talking to my cat while waiting for others to show up. “Baby, let me put it in” was at the top of the transcript to my absolute horror.
I was talking about his ear mite drops.
6. The grievance meetings
At my former workplace, the HR director did not know that her AI notes tool was recording her classified grievance meetings with the union representatives and sending a full recap after each one to all parties invited on the calendar invite, even if they weren’t in attendance. We got an email after a bit saying no one was allowed to use AI note takers any longer.
7. The “verifiable information”
Me: I’m doing a competitor analysis on [product type] for [customer segment]. Please give me an overview of all the [product type] products offered by banks in [my country] for this type of customer.
AI: (gushes) Sure! What a fantastic question, you’re a genius! (paraphrasing). Here is the overview.
Me: (searching for one of the product names listed … cannot find it anywhere) I can’t find this product anywhere. Did you make it up?
AI: Ooooh … did you mean actual products? Sorry! In future I’ll only reference verifiable information.
Me: (eye roll, crying into coffee mug, closes AI window)
(It continued to manufacture content.)
8. The job description
My mother is on the board of a wildlife habitat nonprofit. They work with wetland preservation and with both bats and owls. They were looking for a new director, so someone on the search committee decided to have AI make up the job listing. It included several useful traits (a reasonable amount of education, experience with fundraising, etc.) – but it also said the position required “five years’ experience teaching birds to fly.”
They rewrote the job listing.
9. The performance review
I had an employee request to use an AI to take notes during her performance review. The summary was one line: “No meaningful conversation took place”. I was glad I decided to take pen and paper notes because it was a very productive conversation indeed. Apparently the AI disagreed!
10. The baby announcement
At the end of a meeting, a colleague asked their boss to stay on the line for a couple of minutes. The colleague then confidentially shared the great news that they were expecting a baby, and they and their boss talked about a few next steps to plan for parental leave. The AI notetaker then sent out notes to everyone who had attended the meeting with the headline, “Colleague Is Having a Baby.”
11. “Dazzling you”
I’ve been involved in beta-testing and quality-controlling AI translation output because my employer wants to see if has utility in professional use cases. Here are some highlights:
– In an AI translation of a report about elder abuse, it randomly inserted the word “child” in front of the word “abuse” in various places. The concept of “child” did not appear in the source text at all.
– Every single abbreviation in the text was incorrect in a different way every single time. There was not a single correct abbreviation, and not a single abbreviation was translated the same way twice.
– The word “negro” was randomly inserted into a sentence for no apparent reason. This was early in my exposure to AI translation and I had no idea it could mess up that badly, so I spent ages trying to figure out if there was some stealth hidden racist dogwhistles in the source text. A colleague of mine also had a recurring problem of the word “bitch” randomly being inserted into sentences.
– Random misnegating – for example, the statement “more work is being done” is translated as “no more work is being done,”
– It translated the standard “Dear Sir or Madam” opening of a letter as “Dazzling you.”
– Rewording the source text in the source language rather than translating it. Yes, all the settings were configured correctly.
12. The Powerpoint
I asked Copilot to create a table comparing two things. It did an okay job. Then Copilot asked me if I wanted a Powerpoint slide of the table. I said sure, since I was going to put it into Powerpoint anyway. Copilot created the ugliest Powerpoint I have ever seen. Three slides (I only needed one) with a color scheme of lavender, salmon pink, and orange. The background of each slide had kind of a plaid pattern a coworker said reminded her of her grandmother’s couch. A random picture in a cartoon cloud shape.
However, that is better than our company’s internal AI. It doesn’t have the ability to output content into powerpoint, excel, etc, but it thinks it does. It’ll offer to create one for you and then do nothing. Coworkers have spent ages trying to figure out where AI is saving their non-existent files.
13. The comp titles
I work in publishing and I wanted to do some research on competing titles for a potential book we had in the pipeline. Asked AI for the bestselling current books on the topic, and it came up with a list that had some really interesting titles on it – great, I thought, I’ve never heard of half of these so we definitely need to check them out. Yep – turns out the AI had just completely made them up.
14. The editable document
Me: Copilot, can you turn this scanned PDF into an editable word document?
Copilot: Sure thing, Another Kristin, here you go!
Me (after opening the file): Copilot, this file is completely blank.
Copilot: Sorry, I made a mistake, here it is!
Me: (opens second file, sees that it is also blank, closes AI window and puts in request for OCR software)
15. The attack
A friend of mine showed me an AI summary of a meeting where the AI notetaker decided to attack someone for no reason– in the middle of the notes about what everyone was saying, it inserted, “Jane contributes nothing to the conversation.” I guess it was accurate because the coworker had been quiet since that part of the meeting wasn’t relevant to her projects … But why did it do that???
16. The scam
We work with a lot of small businesses just starting up, and as a result are asked to recommend professional services often. Knowing this, a client passed on a discreet warning about the bookkeeping firm we’d recommended to them. They had issues with their accounting software, Quickbooks, and called for help. It was right when Google started providing AI summaries for everything, and apparently their account rep pulled the phone number for Quickbooks’ support out of the AI summary, rather than off the website.
You can probably guess where this is going. The number wasn’t legit, but instead put him in contact with a scammer who’d managed to astroturf their way into the AI summary. The account rep gave the scammer full access to our client’s accounting software before he realized his error. Our client didn’t share a lot of details about the damages — I got the sense that they were saying very little because they were planning legal action — but they wanted to let us know so we wouldn’t recommend them again.
17. The transcript, part 2
A woman I work with introduced herself before an online presentation. Her last name is Buckman. The AI transcriber recorded her introduction as “Hi, I’m Amelia. F*ck, man, it’s nice to see you all today.”
18. The transcript, part 3
Two people stayed on the call after the rest of the team had left and complained about others on the project. Not only did the transcription record this, it tagged the individuals being discussed in the summary as an action item: “@Jane needs to stop dragging her feet and get her sh*t together”
19. The equipment
I recently saw a ~$50,000 piece of industrial equipment damaged and taken out of commission for about a month because Google AI search told a worker that the tightening torque of a screw was 50 ft*lb instead of 50 in*lb.
This resulted in them over-tightening the screw by a factor of 12, which unfortunately didn’t strip the threaded hole (which would have been a smaller problem) but instead warped a bearing assembly that required a full rebuild at considerable difficulty and expense.
The kicker is that the correct torque value was clearly printed in the service manual that is stored in the machine.
20. The privacy expert
We once had a IT person come into a meeting to talk about the importance of data privacy and security who didn’t realize he had an AI notetaker signed in until someone pointed it out.
The post the fake charity, the Photoshop predator, and other times AI got it wrong appeared first on Ask a Manager.
what to do if ICE agents come to your workplace
Nov. 12th, 2025 05:29 pmWith aggressive ICE raids expanding to an increasing number of cities, I’m sharing the following guidance from a community organizer in Chicago about what to do if ICE shows up at your workplace.
I’m in Chicago, which has been targeted aggressively by ICE and Border Patrol for the last two months. ICE actions are expanding into many other cities, and I wanted to share some resources and tips from our city’s experiences with your readers.
Inc. has a solid article on the rights of business owners when ICE shows up. It’s important to know what your rights are, especially about private areas and documentation. However, ICE frequently and blatantly disregards legal limitations, and when confronted with armed, masked strangers, it may be difficult for individuals to physically intervene to stop them from going into off-limits areas. Owners and managers should provide information to employees about their rights, as immigrants and as citizens. Be prepared to document ICE when they’re at your business; you may need evidence of their actions if they violate your rights or abduct any workers. (The latter is critical to help families find out what happened if someone is taken.)
As an employee, you may be more limited, especially if management isn’t supportive. Many places, especially large corporations, are adopting a neutral position towards ICE’s activities, which effectively means letting them operate unchecked. Employees can leave Know Your Rights (KYR) info in staff areas for people to take. Try to get in touch with your local ICE Watch or immigrant rights groups as well. Many of them are sending out alerts when ICE is active in a particular area, so you can be aware if they’re near your place of business.
Some other, more hands-on tips:
- Landscapers, construction workers, and other contractors are extremely vulnerable. Despite claims that they’re arresting “the worst criminals,” ICE literally drives around and abducts brown people working outdoors. If your business employs any of these services, work with them to develop a safety plan if ICE shows up. For example, letting them come inside and go into an employee-only space until it’s all clear.
- Share information and resources, but do not make risk assessments for other people. Don’t tell Latino coworkers to work from home because it’s safer for them, for instance. Instead, if you’re in a position to do so, allow for more flexible WFH as a choice for anyone who might need it.
- If you’re a manager, try to offer compassion and flexibility. Vulnerable employees are going to be extremely stressed with the constant, unpredictable fear of friends, family, or even themselves being abducted. You may also have employees who are volunteering with ICE Watch organizations, which can be emotionally and mentally draining as well.
- In Chicago, raids have been extremely unpredictable day-to-day. We don’t know when or where they’re going to hit. You unfortunately have to assume that ICE could show up at any time. This is why it’s critical to have plans and education as soon as possible.
- Do NOT post about what you’re doing on social media or non-secure servers — which often includes workplace communications. Use a secure app like Signal or have conversations in person. This goes double if you record a raid. Don’t post it online, save it for the lawyers and immigration advocates.
Above all else, the best thing that you can do in your community is to connect with local ICE Watch and immigrant rights orgs. They have information, resources, and contacts that will help you and your neighbors. Get info, coordinate with your coworkers, and build a community to protect each other.
I’m updating this post to add these additional resources shared by a reader:
- The ACLU has a webpage with free, downloadable KYR social media graphics, including phone backgrounds so folks can see their rights without unlocking their phones in the presence of law enforcement.
- If you want to help people share KYR information at work, the ACLU also sells 10 packs of KYR wallet cards in multiple languages that outline your rights if you interact with ICE agents at work.
- For a free version of this, ILRC has a free, downloadable “red card” that you can download in multiple languages and then print and cut up at home.
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how should I manage someone who uses the Gen Z stare?
Nov. 12th, 2025 03:59 pmA reader writes:
I have been managing a corporate team for a little under a year, and I’ve gotten to know them all over the last few months. One employee, Sally, is smart, quiet, and a hard worker. However, when I talk to her, I started noticing that I was getting a lot of silence and a glazed look back. I tried a few different ways to ask questions and have a conversation over the months, but nothing has led to a change in her demeanor. At one point, I was wondering if she was high at work, since she seemed to me to be so checked out during conversation.
Then a few months ago, I learned about the Gen Z stare – and I think that’s what I’ve been encountering! Sally is Gen Z, and the uncomfortable silence and blank stare fit what I’ve been seeing. It’s definitely frustrating and awkward to be on the receiving end of it.
I’ve been thinking about it ever since! I’m a Millennial, and I know that I have Millennial generational quirks that probably drive others at work crazy. It doesn’t feel right to bring a critique to someone that is generational, but at the same time, would it be doing her a service to tell her how this could be perceived in a professional setting? I’d love to get your thoughts on this as workplace norms change over time, and as a manager, how do you respond?
For people who haven’t heard the term, the “Gen Z stare” has been getting a bunch of media coverage. It’s the idea that some Gen Z employees, when spoken to by a colleague or a client, will just respond with a blank, disengaged expression. People older than them tend to read it as rude indifference or even hostility.
I’ve heard it explained as Gen Z being cynical about work, feeling disconnected, and not into performing fake enthusiasm. But the issue with the “stare” at work isn’t the lack of enthusiasm; it’s the lack of anything — no response indicating that they heard what was said, and no information offered in return. Some people say the stare also has an element of “this is stupid; why would I respond?” — which is something they can certainly think privately but which isn’t okay to convey at work. The other explanation getting offered is that this generation came of age with fewer face-to-face interactions and more screens (particularly because of the pandemic) and so they genuinely don’t know what the expectations are around non-digital communication. I think that theory is pushing it, but who knows.
In any case, you’re right that it’s going to affect how your employee is perceived, and it would be a kindness to spell out what appropriate responses at work do look like. The easiest way is to be clear about what you want from her when you see it happening. So for example, if you say something that you’d expect a response to and she looks at you blankly, you could say:
* “What are your thoughts on that?”
* “Does that all make sense to you or do you want me to clarify anything?”
* “I’m having trouble reading your response to that. Can you tell me what you think about the client’s feedback?”
* “I’d like to hear your perspective on that.”
If you do that every time, there’s a decent chance she’ll start learning she’s expected to respond and will start doing it without being prompted every time.
But if not, you could address it more big-picture. For example: “I’ve noticed that when I share feedback or plans for a project or pass along info for our work, you often don’t say anything in response, which makes it hard for me to tell what’s going on on your end of our conversation — whether you’re still thinking about it, or confused, or disagree, or even if you’re just thinking about something else entirely. In a work context, the expectation is usually that you’ll respond out loud in some way when someone’s talking to you one-on-one. If you need a minute to think, it’s okay to say, ‘Give me a minute to think about that.’ But I need you to stay something in response so that we can have a real conversation.”
You should also address it if you see her doing it with a client or a colleague: “When Jane said X, you just looked at her and didn’t respond. In a situation like that, you need to (fill in with examples of appropriate responses).”
Say all of this neutrally, rather than sounding frustrated or irritated. Start from the assumption that she genuinely doesn’t know how it’s landing, and coach her on it just like you’d coach her on how to run a meeting, or how to pitch a client, or how to write better copy. And really, it’s at least as much as a service to her as coaching on any of those topics would be.
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It’s five answers to five questions. Here we go…
1. My husband says it’s inappropriate to dine or carpool with my boss
I have a great relationship with my boss. He is incredibly supportive of my professional growth and is a good mentor. We work well together on projects and complement each other’s skills. We’ve built a great team and are very intentional about culture. Relationships are incredibly important in our field. Some context: He is a man, I am a woman, and he’s about 10 years older than me.
My husband hates my boss, and he’s not shy about it. He says my boss doesn’t look him in the eye or shake his hand when they run into each other at work functions. He always has something nasty to say about him. I don’t get it.
From time to time, my boss invites me to grab dinner after work events or carpool to things together. This sends my husband through the roof. He says it’s great that we work well together but there is no need to socialize outside of work. He’s convinced my boss is being inappropriate. I enjoy carpooling or grabbing dinner with my boss from time to time! It’s fun to unwind and socialize. We talk about work and non-work topics. I NEVER feel like my boss is being inappropriate or flirtatious. The relationship genuinely feels friendly. His wife is awesome, I like socializing with her too from time to time at work functions!
I know you’re going to ask how my marriage is. It’s okay. We’ve been married a while now, there have been bumps that we’ve tried to move past. I genuinely think he’s projecting his issues onto this situation.
But my question is about work. Is it inappropriate to get dinner with your boss and socialize? We’re not in an industry like sales where dinners or social outings are the norm. Our jobs are stressful and it’s just fun to unwind together.
It is absolutely not inappropriate. It’s a normal thing to do when you work with someone. You have a good rapport and good will toward each other, and you have a shared frame of reference (you know the same people, projects, industry, obstacles, etc.). When you’re leaving a work event together, it makes perfect sense that you might decide to grab a meal or a drink before heading home.
Your husband doesn’t even want you carpooling with your boss? I could almost excuse him feeling weird about the after-work socializing (although that would still be way too controlling of him), but objecting to driving together to work events takes this into a different territory of problematic.
Something is going on with your husband / your marriage. It’s not about your job.
2. Should I bow out of our holiday cooking competition?
For about a year, I have worked at an office job where I very consistently bring in baked goods or shareable food items. But I am not pressured to or criticized when I don’t.
My question is related to an upcoming holiday potluck where there is also a cooking contest. I won last year and got a gift card, which was great, but I’m debating if I should even enter this year. Mostly, I’m not sure that’s fair, because I have to imagine consistently bringing in items biased the judges in my favor. (It was anonymous, but I am of a cultural identity that is unique amongst my coworkers, so the flavor profile probably gave me away. Also, small office.) And there are other excellent bakers and home cooks as well, irrespective of whether I’ve brought more items in total and engendered good will that way.
But I don’t even know if I’d win again, so maybe it’s arrogant to assume I need to bow out? As you can tell, I’m overthinking this. But people are asking if I know what I’ll be making, and I’d like to have either an answer or a good excuse soon enough.
You don’t need to bow out! I don’t think you have an unfair advantage just because you bring in food more than your coworkers do; the judges presumably aren’t judging based on the entirety of your contributions over the whole year, but rather on the specific dish you enter into the contest. Moreover, if you do bow out because you feel it’s unfair to participate, there’s a risk of coming off as patronizing to your coworkers — as if you assume they couldn’t compete with you.
I do think that if you start winning the contest every year, it would be gracious to occasionally bow out and cite holiday baking fatigue or similar. But no need so far.
3. Employee says they think the feedback is unfounded … but then makes changes anyway
I have an employee who has been struggling with soft skills in their role — managing relationships with partners, navigating differences of opinion, openness to changing approaches, etc. These are non-negotiable skills for the role given our business model. They’ve been coached on this repeatedly, and we’ve seen some up and down improvement in the past year but it hasn’t been sustained. In their latest performance review, they were told they were not meeting expectations and a plan for correction has been introduced.
In conversations since then, their response has been to dispute the feedback, including things like saying the skills named aren’t requirements for the role (they are), hinting that this is just a matter of opinion and trying to ascertain whether “others” feel this way, and making comments that suggest the feedback isn’t “fair.” When I’ve said that this response is making me concerned about whether they’re taking this seriously — after all, how can you internalize and act on feedback you don’t think is valid? — they’ve said they can find the lesson in anything and they’re committed to working on it. They do seem to have taken the feedback seriously and made changes, but historically that has then been followed by regressions. Given that they’re disputing the feedback but at the same time acting on it, what do you recommend I do?
They can think the feedback is unfair, but if they’re making the changes you want, that’s ultimately the most important thing. Care more about what they do and less about what they think (unless/until what they think starts coming out in disruptive ways). It’s not that the fact that they disagree doesn’t matter — it does, partly because it suggests lack of alignment between the two of you about the fundamentals of the job, and that’s likely to play out in other ways too — but ultimately what matters is what they do.
If they regress again like they have historically, you’d address that at that point (and really at that point should probably conclude that they’re not well matched with the job). Ideally the formal performance plan would have been explicit that the changes need to be sustained over the long term and you won’t start the process again from scratch if they backslide. If it didn’t, then at whatever point the plan is completed, you can remind the employee of that (while also recognizing that they’ve done a good job in building the skills you asked for, assuming that’s the case).
4. I feel guilty about getting my coworker’s job after they were let go
I was offered my coworker’s job the day after they were let go, and I don’t know how to feel about it. I feel guilty but I also really wanted this promotion. I don’t know how I feel about my boss firing him and hiring me in the span of about 12 hours.
Do you have any advice?
It can be weird to feel like you’re benefiting by someone else’s misfortune, but that’s not the right way to look at it! Your coworker presumably was going to be let go regardless and there are all kinds of things that could have been happening behind the scenes, including your coworker simply not being suited for the work after having been given opportunities to improve. You’re not required to turn down a promotion on principle or out of solidarity with someone else.
Realistically, you might not be able to logic your way out of feeling weird about it for a while because that’s how minds work, but if it helps, you’re not wrong to accept the promotion, regardless of the reasons it was available. (I would have a different answer if you, like, set them up unfairly in some way, but I’m assuming that didn’t happen.)
5. We can’t request accommodations until after planned surgeries are over
A few years ago, I had orthopedic surgery. It was scheduled a few weeks in advance and I knew after the surgery I’d be in a brace for a period of weeks, with requirements to ice frequently and physical therapy exercises multiple times per day. I was given restrictions on how far I could walk and what I could lift. I stayed with my parents during this time because I needed a lot of help as I rebuilt the muscle. In advance of the surgery, I requested a temporary accommodation under the ADA to work remotely the entire time I was in the brace. I received a letter from HR saying my request did not fall under the ADA as it was temporary, but nevertheless they supported allowing me to work from home, and my request was granted for the specified date range. My letter was very specific that if anything changed, I had to submit new paperwork and go through a new approval process.
A work friend of mine is now having a similar procedure and asked me how to submit the paperwork to work remotely as she recovers; she said she already talked to her boss, who was fully supportive and just asked her to make the accommodation official. Turns out, our HR department has now changed the policy so that an accommodation can’t even be requested until after surgery because “how can your doctor know what you will need?” and “you won’t need the accommodation until after the surgery.” Both of our procedures were relatively predictable (e.g. you’ll be in a brace for 4-6 weeks and physical therapy will likely last X months) and my friend isn’t requesting the accommodation start until the day of her surgery. HR has also told her they need to decide if her post-surgical medications preclude her working. Again, the post-surgical protocol across these procedures are pretty standard and no one is on very heavy painkillers and certainly not more than a week or so. Our work involves typical office computer work, and public-facing work is pretty minimal and scheduled in advance.
My guess is this new policy falls into the category of “crappy but legal” to make someone worry about submitting paperwork for an accommodation as they try to recover from surgery. But I’m very curious to get your reaction to this.
This is ridiculous, and it’s probably legal. Ideally she can get all the paperwork together and ready to go before her surgery and have her boss file it for her the day of, but there’s no reason it should need to be done that way, and they’re just creating more headaches and stress for employees at the exact moment they’re least equipped to deal with it. Any chance your managers want to band together and push back?
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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.
The post my coworkers have a crush on my boss … and are taking it out on me appeared first on Ask a Manager.
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.
The post I made a gift guide for each employee on your team appeared first on Ask a Manager.
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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