Ask a Manager

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

1. My boss announced layoffs while wearing sunglasses (yes, it’s Anna Wintour)

You may have seen the reports last week that Anna Wintour wore sunglasses throughout the indoor, in-office Zoom meeting in which she announced corporate consolidation and immediate layoffs of many of those in attendance. I was in this Zoom meeting and as a regular blog reader, I’m curious to know your thoughts. This is not done, right? Right??

In my opinion, the way in which this news was announced (midweek, as gossip with no official statement, while wearing sunglasses) has only propelled a raft of well-deserved unflattering press coverage. Probably not coincidentally, I’m told a number of comms staffers were laid off last month.

You are correct: laying off people while wearing sunglasses is rude and bad management. It sends the message, “I don’t take this seriously, even though it’s very serious to you, and I’m definitely not invested enough to pay you the respect of looking you in the eye.”

As someone whose whole career is built on understanding the messages clothes and accessories send, Anna Wintour knows this.

2. I suspect our writing job candidates are using AI to write their applications

I was recently involved in recruiting a new copywriter and editor for my team. As part of the application process, we asked applicants to answer a few short written questions. We use this to find out about how their experience meets the essential criteria for the role, as well as seeing their writing style and grammar skills.

We got applications from some brilliant candidates, but there were a couple that gave me pause. The first thing I noticed was a lot of American-English spelling in their answers (think ‘prioritize’ rather than the British ‘prioritise’; we’re based in the UK). There could be several reasons for this, but it did set off a couple of alarm bells for me, as I know most AI generators use American-English. I also just got a bit of an odd feeling from their answers — they felt very stilted, impersonal and “buzzwordy” in a way that just felt strange compared to other applications.

On a hunch, I copied and pasted a few answers into an online AI detector, which said that AI content was likely present. (I also copied some other candidates’ answers into the program and those came up as “no AI content detected.”)

I mentioned my suspicion to the hiring manager, who said she’d take a look. In the end, we didn’t bring these applicants forward as we had lots of candidates with far more relevant experience and knowledge. We sent out our standard email rejection to them, just like the other candidates we didn’t move forward.

But how would you handle this if the candidate was a possible frontrunner? I had no concrete proof that they’d used AI for their answers but it did look like a real possibility. Is this just the way things are going these days? Would you have mentioned the possible AI use in your rejection or just left it? I don’t know if I’d have felt differently if the job wasn’t so writing-focused.

There’s no reason to mention your AI suspicions in the rejection letter (which most of the time don’t contain specific reasons for the rejection, especially when the person wasn’t even interviewed).

I think the question about how to handle it if the candidate was a frontrunner is a bit of a contradiction — because you were assessing these candidates’ writing skills and the thing that tipped you off was that their writing was bad/weird/stilted, so by definition they already weren’t frontrunners for jobs where writing is a central focus. But if you had a candidate whose writing was good but something was still screaming AI to you and the person was otherwise strong, a good next step would be to give a writing test during an interview, so you could see their writing skills in real time.

(Of course, unless the interview was in-person, they could still use AI. But at some point, it’s reasonable to conclude they’re either a good writer or they’re good at using AI to generate good writing. You’d need to decide if it matters for your context if it’s the latter. If it does — like if they won’t be able to use AI once on the job for legal/proprietary reasons — you’d want to make that very clear and ideally invest in assessment processes that rule it out, like in-person testing.)

3. Employer is blowing up my phone after firing me for “misconduct”

My small, family-owned employer of four years let me go in early November. I had had a disagreement with the owner and, having seen them fire many employees out of the blue, I suspected I’d be let go at the next opportunity. They opposed my unemployment claim on the basis of “misconduct,” stating I’d made “too many mistakes and had been warned.” In my opinion, I made a normal number of mistakes (two, in the entire year), and had never been warned, in writing or verbally, nor put on any PIP. In fact, I’d always received excellent performance reviews and had been told I’d be receiving a performance bonus the following week and my metrics were up.

Naturally, I appealed the unemployment decision, and the day after I received notice of my hearing date, my former employer began blowing up my phone (three to five times a day, every business day since then). They never leave a message and it’s causing me considerable anxiety. How do you suggest I handle it? Ignore it? Document it for the hearing? Email them to please let me know, in writing, what they need?

You’re under no obligation to talk to them; feel free to block their number if you want to. Personally, I’d answer one of the calls because I’d be curious to see what they wanted and they have no power over you anymore — but if you’d be happier blocking and ignoring, that’s a fine way to go. It would also be fine to email them, say you’ve seen them calling you repeatedly, and email will be the best way to reach you.

Really, any of these options are fine so do the one that will bring you the most peace of mind. (You can document the calls too if you want, although they’re unlikely to come up at the unemployment hearing, which is going to be tightly focused on what led to your termination.)

4. I retired a year ago and my old coworker still calls for help

I retired a year ago. Before leaving, I thoroughly trained the two employees who would be picking up my duties, which included thorough documentation of processes, logins, and passwords.

However, one of those employees apparently lost the instructions on how to terminate a company-paid cell phone account so my work phone account could be terminated. Ultimately, this person (not a manager) made a decision to just keep paying my wireless account and hope their manager didn’t notice. Over the last year, this person has called me once or twice a month to ask questions about other processes or for advice on handling a situation. I have helped as best I can, feeling that since they were paying for my cell phone, the least I could do was help if I could.

But finally in November, they figured out how to transfer the account billing responsibility back to me, and I said basically, “Okay, so now you aren’t paying my phone bill any longer, please don’t call me for work help any more. I trained you and Jane and it’s been almost a year; you should understand those processes by now.”

Now that person is calling me again, asking for help, and I refused. This is causing some hurt feelings. For example, they used to invite me to birthday lunches at local restaurants, but they’ve stopped since I refused to keep helping. It’s a tradition that retirees are also invited to the annual holiday potluck, but I wasn’t invited. When I said “no more calls,” their behavior in the moment was odd, like with a betrayed note in their voice. This person has a long history of avoiding learning how to do tasks that they don’t want to be responsible for.

Other retirees apparently continued to provide help long after leaving and I don’t want my good reputation/relationships to suffer, but there is no compensation possible, and I want my working life to be OVER. Do you have any advice?

It’s not normal to be expected to answer work questions a year after you retired! In certain circumstances, you might be willing to be consulted extremely occasionally on something very important — but not frequently, and not on basic processes the person was already trained on. Frankly, you could have declined to help even while they were paying your phone bill; you didn’t ask them to do that, and it was their decision to continue it. Their paying it didn’t create any obligation that you needed to repay.

As for what to do now … do you care about going to the birthday lunches and the annual potluck? Because if you don’t, this is easy: you’ve already handled it, and now you can ignore this person’s calls (block the number if you want!) and go about enjoying retirement. If you do want to attend those events, coordinate that with a different person in the office so you’re not dependent on the embittered guy for your invitations. (But also, don’t underestimate the value in making a clean break and letting those events stay in the past now that you don’t work there anymore.)

Either way, you’ve made it clear that you’re no longer available, and you can ignore the calls or say “sorry, I’m retired — I’m no longer a resource for this stuff” without any guilt at all. (If you really want to shut it down, you could ask that person’s manager to ensure the calls stop, which would be very reasonable to do at this point.)

5. Commuting reimbursement in a one-car family

My spouse and I have one car. I mainly use it, because I work out of the house and while my job is technically accessible by public transit, the commute would be four times as long and I have some chronic pain conditions which make that difficult.

My spouse mostly works from home, but infrequently has to travel. He does not usually use our car for work. His boss has mentioned him going to a site that is about 2.5 hours away by car.

If they ask him to drive there, would it be appropriate to either ask to rent a car or if they could cover my Uber to/from work? It would probably be in the $60 range roundtrip. I am not sure if this is an appropriate request, or how to word it.

It’s really unlikely that they’d cover your Uber to and from work, since you’re not their employee, but it would be normal for them to pay for his transportation since he is. He shouldn’t frame this as “I have a car but my spouse uses it” (since that’s too likely to raise “can’t you work out a way to use it on these days?”) but rather as “I don’t have a car” or “I don’t have a car available to me during the day.” They almost surely have other employees without cars, and it’s normal to expect them to cover non-car-owning employees’ transportation to other sites when necessary for the work. He just needs to explain he’ll need that.

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

1. Managers don’t know we can all read their private Slack channel

I work for a small fully remote marketing agency. Our C-suite consists of three people with a Slack channel that they think is private but is not. In that channel, they often talk poorly about others in the company, including my former manager who has recently left. Recently, one of them posted my department’s salaries and raises and wrote some awful things about why some people got bigger raises than others — I was the only one in my department who got a smaller raise. We don’t have an HR department and I currently have no manager.

My question is how or even if I address the comments made about me in the Slack channel, and how do I do that without tipping off to them that the whole company knows about their open slack channel?

You can’t address the comments without tipping them off that their “private” channel is open to the whole company. So you’d need to decide whether or not that’s something you want to do. There’s an advantage to not tipping them off, in that you and others will continue to see their unvarnished thoughts about the rest of you — which gives you a very clear lens into the type of people you’re working for and how they view you.

Aside from this, are you happy there? Do you feel like being there is helping you professionally? Do you get useful feedback, interesting work, opportunities to advance your skills? How’s your quality of life? What kind of pay and benefits do you get? I’m asking all that because this seems like a real shit show — and unless the answers to those questions are glowing, the Slack channel is a sign to think about getting out, rather than anything you need to act on.

2. Wife’s coworker is trampling our boundaries

My wife, 39F, recently started a new job. She has been there three weeks and loves it. There is one coworker, Lisa (57F), who immediately tried to make my wife her friend. Last weekend, Lisa was constantly texting my wife asking her what her plans were for the weekend. She invited herself and actually came to our son’s basketball game, and tried also invite herself to our church. My wife said Lisa is fine at work but outside of work she seems to be obsessive. My wife has tried to set boundaries and they seem to continue to get broken. She doesn’t want to take her concern to HR but is beginning to feel that might be the only option. Do you have any advice for this situation? I’m beginning to stress out over this as well.

Update: I just reread all the text messages. I guess there haven’t been any real boundaries set. There will have to be some set real soon though!

That update came in response to me asking what kind of boundaries your wife had set so far, and your answer is exactly why I asked! So often in these situations, the person whose boundaries are being violated hasn’t really tried to assert any any yet. Often it’s because they feel they shouldn’t have to; since the other person’s behavior is outside of the social norm, it feels reasonable to expect they should just know they’re crossing lines. But clearly, they don’t — so yeah, your wife has to speak up. For example:

Lisa: I’d love to go to that basketball game with you — what time is it?
Wife: Weekends are family time for me, but I’ll see you at work on Monday!
Lisa: I live pretty close to you though; I could just pop by.
Wife: No, thank you. It’s important to me to keep work separate from the rest of my life. I will see you at the office.

I’d bet money that your wife feels holding firm like that would be a little rude, and that’s why she hasn’t said anything similar. That’s one of the ways boundaries get trampled: people worry that the language they’d need to use would feel rude. But it feels rude mostly because we don’t have to say things like that very frequently; when people mostly respect your boundaries, it’s not often that you have to be this direct. But it’s actually kinder to Lisa in the long run if your wife is clear about what is and isn’t welcome behavior, so that Lisa doesn’t spend weeks/months inadvertently pissing off your wife. (And totally aside from kindness to Lisa, your wife has the standing to set whatever limits she wants on her off-hours.)

If your wife is hesitant to do this, remind her that if she skips this step and goes straight to HR, the first thing they’re going to ask is whether she’s done that yet — and if she hasn’t, they’re going to suggest that as the first step.

Your wife might enjoy this:
my needy boss wants me to “adopt” her (and the update)

3. How to answer “describe a time when you disagreed with your boss”

I am gearing up to interview at a company, and a number of my friends there have given me a heads-up that I will be asked a number of behavioral interview questions. One I’m racking my brains on how to answer is, “Describe a time when you disagreed with your manager.” Honestly, I can think of many times when I’ve had a difference of opinion with my boss; but most of them boil down to, “I wanted to do this thing that made sense to me in my position, they said no, so I complied” or “My manager told me to do this thing I knew wouldn’t make sense, but they are my boss, so I did it.” The thing is, this is a small, insular industry, so chances are good that whatever I say will be passed along to my current (hopefully former before long) supervisor.

What is the proper way to respond to this query? What kind of answers does one give that don’t make your current boss look bad or paint the speaker in a poor light?

The key is to leave the judgment out of it. For instance: “My boss wanted to do X, but I was concerned it had downsides we weren’t considering. I figured my job was to explain the downsides I was concerned about and the reasons I thought Y could be better, and then leave it to her to make the final call. She heard me out about my concerns but ultimately ended up choosing X, so that’s what I implemented. I thought the two important pieces for me were making sure she had all the information and then moving forward with the option she chose.”

4. Dream job cancelled after interviews and technical projects

I’m a software engineer and I was interviewing at my “dream company.” I know that concept is kind of BS, but this is truly a company I admire greatly.

Their interview process is known to be a bit involved: since I’m in a fullstack role, I had to do a project for frontend and backend. Each project took about two hours. Then, I had to do two rounds of live coding for 90 minutes each. I also had one behavioral interview. So overall, I sank about eight hours into the process over two weeks. I had no problem investing all this time in such a great company, but I just got an email that the job posting has been cancelled due to budget cuts!

It just seems shocking to me that a well-regarded company would open a position in mid-December, have hundreds of people apply, put people through all those interviews, and then close the posting just like that. It honestly makes me lose a lot of respect.

Is there something I’m missing? Should I write off this company in the future, or should I forgive them and still apply if I see their postings? I’ve been trying to get into this company for years, and I always used to apply to every job I saw from them.

It’s a pretty normal thing to happen. It’s unlikely that they went through all that hiring work for the hell of it — more likely, they had every reason to think they’d be hiring and then something changed (funding unexpectedly lost, project cancelled, strategy needs to shift, key person on team lost and replacing them is a higher priority, etc.). It sucks when you’re caught up in it, but it’s not a shocking occurrence.

That said, that’s a lot of project work to ask from candidates, even if they had ended up hiring someone for the job. Maybe that’s a typical amount in software engineering, I don’t know — but from outside the field it looks excessive.

5. Office-appropriate hats

I’ve been rocking the shaved head look for a while, but I’ve decided to grow my hair out and I can’t figure out how to look less….scruffy. I work in a pretty casual office, so I generally throw on a neutral beanie and call it a day, but are there any other options? I’m assuming a baseball cap is totally out, and I would feel silly wearing a fedora. I’m so close to shaving my head again and suffering through the negative temperature. Any ideas? (I’m a man.)

I am admittedly not up on hats so maybe there’s something I’m missing (hat-savvy readers are welcome to weigh in!) but I think you’ve exhausted the office-appropriate choices. One thing you could try is talking to a hair stylist about ways to look less scruffy while your hair is growing in; they’re often good about figuring out how to do that.

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

1. Employee “works” after playing video games most of the night

My remote employee struggles with attention to detail. He stays up late many nights but has told me he can’t help it and he would prefer to work a later schedule (think log in after 10 am, log off at 5 pm, then log in later). He wasn’t doing very well with those hours and that was getting inconvenient for me, so I asked him to start working more common hours and log in by 8:30 (most people log in between 8 and 8:15 in our small department so he used to really stick out). Our day is officially 8-5 with an hour lunch and most people stick to that pretty closely; being remote, you don’t have varying commutes to deal with. He complied pretty well after I reminded him a couple times.

However, his work has not improved a lot. It’s improved a little. I get the feeling his work suffers because he still routinely stays up until 1 am. (He mentions drinking a lot of coffee and playing video games, which would be my first thought as to what’s keeping him up late.) I have made comments that he needs to review his work more to catch issues, and that if I had his schedule my work product would suffer, but I’m not sure if it’s my business to say directly that he might need to get more sleep if he wants to be effective at his job.

Recently, he mentioned he stayed up until 4 or 5 am for a video game event that lasted really late. Can I tell him that he should be just using a vacation day, or vacation half day, if he finds himself up at 4 am? I am fine with him sending me a note at 4 am that he is taking off that morning. It’s better than him pretending to work and either doing not much or doing something that has very low quality. I plan to tell him so (probably in kinder words) but do you have any advice?

I think you’re focusing on the wrong thing. If his work quality isn’t as good as it needs to be, that’s the issue, not his sleep schedule. After all, if he were going to bed at 9 pm and getting a solid 10 hours of sleep every night but his work quality was exactly the same as it is now, it would still be an issue, right? So keep the focus on the problems in his work; be explicit about the bar his work needs to meet, where the gap is, and what needs to change.

In doing that, it’s fine to say something like, “You’re in charge of your own sleeping hours, but when you talk about staying up so late that you’re not getting much sleep and I see your work quality suffering, I hope you’ll look at whether lack of sleep is part of the problem. But whatever you decide there, I do need to see XYZ changes in your work.” You shouldn’t need to spell that out for an adult, but you can note it as a possible contributor if he doesn’t seem to be putting it together himself.

It’s also fine to say, “If you’re up until 4 or 5 am, it’s going to be hard to work at the level we need a few hours later. If you’re up that late, I’d rather you take the morning off and not start work until you’re reasonably rested. Obviously that can’t happen routinely — I need you reliably working the hours we agreed on — but if it’s only occasional, that’s how I’d prefer you handle it. When you start work, the expectation is that you’re rested enough to work at a high level.”

As you talk about this, be open to the idea that this could be rooted in a medical thing that he could end up needing accommodations for; if he does, he needs to raise that, but keep it in your head as something that could be in play. I know it doesn’t sound like that (he’s drinking coffee and playing video games! no wonder he’s not sleeping) but he wouldn’t be the first person to do that because he has a sleep disorder, rather than the other way around. Right now, though, your job is to be very up-front about what needs to change in his work output.

2. Should I drop out of a books-and-wine club now that I manage someone in it?

Two years ago, I started a position at a higher ed institution. I love my job because we’re a pretty casual bunch and we all get along well!

A coworker from a different unit on campus with whom we have very little overlap invited me and someone else in my unit, “Kara,” to a special-interest book club last year. No one else in the book club works at our institution. At meetings, we usually drink wine, chat about our lives and the book, and generally enjoy each other’s company. Some people smoke weed, which is technically illegal where we live. I don’t smoke with them, and nor does Kara (she’s allergic; I don’t want to be high around people I work with). Kara sometimes gets tipsy to mildly drunk, and I usually drive her home. I’m not close enough to anyone in the book club that I’d invite them over outside of this context, but I like our monthly meetings.

A few months ago, I got promoted (yay!), and I’m now Kara’s direct supervisor. Because of this, and because we sometimes discuss things that aren’t usually things I’d talk to a coworker about, should I bow out of book club? I don’t want Kara to feel like I disapprove of her or am uncomfortable with her, but maybe she’d be more comfortable if I wasn’t there? I also don’t want the other person I supervise to feel like Kara and I are closer because we hang out once a month outside of work. This is my first management position and I’m in the dark!

You should bow out. Socializing with one employee but not the other can cause all sorts of problems (even if just the appearance of bias/extra access without the actuality of it), and that’s before we throw in that she’s often tipsy. I’d advise that even if you were a more experienced manager, but trying to navigate it on top of all the challenges of being a new manager is a particularly bad idea.

Ideally you’d develop a scheduling conflict or something like that, but if there’s no plausible excuse available, it’s fine to be up-front with Kara about it: “It’s fairer to you to be able to relax without your boss around, and I don’t want it to be weird for SecondEmployee.”

3. What does mileage cover?

This situation happened a few years ago, but once in a while I remember it and feel bugged. I was on the road with a few colleagues to a work conference, and one of my staff members was driving. Another staff member offered her money for gas (which prompted others in the car to open their wallets), but I asked if the driver was submitting her mileage form. She said she was. The colleague who had first offered money said, “Well, that doesn’t cover gas.” Our company’s mileage rate at that time was 55 cents per mile. She went on to say something like how 55 cents wouldn’t even come close to covering $3.50 per gallon (or whatever gas prices were at that time). I was pretty confused and didn’t want to argue, so I said no more and gave the driver some cash, but I thought that was the point of mileage — to cover gas, plus a bit for wear and tear on a vehicle. Was I off-base?

No, mileage reimbursement is supposed to cover gas and wear and tear on your car, and it typically does. For 55 cents/mile not to cover gas prices of $3.50/gallon, a car would need to get truly terrible mileage (that would mean the car was getting less than seven miles per gallon — and I can’t find a single car with gas mileage that low; the average seems to be 21 miles per gallon).

4. Letting people know of a terminal illness

I’m terminally ill. I don’t know how long I’ve got left, but likely months if I’m lucky rather than years.

I haven’t been working since before Covid, nothing other than I was taking some time off, intention was to travel but Covid came. My question is, I have a fairly wide circle of people who I have worked with in the past. They’re not local to where I live and I wondered if I should update my LinkedIn and what should I say. Occasionally people will reach out and it seems rude to leave them hanging.

I think you get to do whatever you’re comfortable with in a situation like this! That said, if you have other options, LinkedIn isn’t the ideal forum for this sort of announcement; a group email (or individual messages, if you’re up for it) would be better if you have a way to do it. Another option is to deputize someone from each circle (like one person from each job) and ask them to share the news with others in that circle, so that less of the work is on you.

I talked to my terminally ill mom about this because she has done an excellent job of keeping people informed since her diagnosis. She keeps stressing that because she’s been so open with people about what’s going on (she has an enormous email list that she regularly sends candid updates to), she has a ton of support from people from all eras of her life, including from some quarters that I think surprised her. She says most people’s tendency is not to share enough when it’s happening to them, and as a result they don’t get the full benefit of that support. So I am passing that along from her ❤️