Ask a Manager

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 ❤️

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

1. Nude drawing as a work social event

We have a group of people in our office responsible for planning work social events. They need to seek approval prior to booking any events due to previously breaking activity guidelines.

Recently they have asked for approval to hold an event doing a life drawing class. My immediate reaction is that this would be inappropriate as a work event, in the office or even outside of it, but am I just being a prude? I know there is nothing inherently sexual about life drawing, but something about nudity at a company-funded event sits uncomfortably with me.

There is nothing in our activity guidelines about this kind of activity, just that events should promote our firm’s culture, be inclusive, and not push people outside of their comfort zones.

Assuming we’re talking about an unclothed model, you’re right that it’s inappropriate! “Company events shouldn’t include nudity” is a reasonable and useful line to draw. You should want everyone to remain clothed at company events, including non-employees.

I’m curious about the history with this group since you mentioned they’re already getting more supervision because of previous problems! Without knowing more it’s hard to say, but I wonder if there needs to be more of a shake-up there. (But either way, I’m very interested in hearing what else they’ve suggested!)

2. My team member wants to use the Myers-Briggs test to understand each other

I’ve got a new person seconded into my team. She’s great, really pleased to have her on board. This week she asked me something that threw me. We’re on a deadline presenting to have the opportunity to move wooden dollars around the organization and I can see she’s getting very stressed by my boss and I basically winging it, so I had a chat with her, apologized for it being so up in the air and not the way that she likes to work, and promised to take a different approach with her the next time this needs to happen and said we’ll work to make the rest of the day work well for her. But then she asked me what my Myers-Briggs type is, as she had talked to my boss about his and she can see how they fit and work together.

I’ve got quite negative opinions on MBTI-type things, especially in a context where you use it with more seriousness than a magazine quiz. I have never (to my memory) done one, and I want to be careful about not using this sort of persona shorthand in my team as a norm, but I also don’t want to undermine someone who has had a bad day and is getting used to a new team. What’s a good way to not “well actually” her?

“I don’t know my Myers-Briggs type; I’ve never taken the test.” If she suggests that you do: “It’s not my cup of tea, but I’m glad you found it useful.”

If she pushes for the whole team to do it or otherwise to use it more officially: “I’m glad it’s been useful to you. That type of test can be controversial and enough people aren’t comfortable doing it in a work context that it’s not something I’d want to make a team activity. But if there are things you want me to know about how you work and communicate, or that you want to know about how I do, that’s absolutely a conversation we can have.”

3. My coworker announced she’s quitting and now is upset that she wasn’t invited to a conference

I work on a small team with a manager, two leads, and five other employees. I’m a lead and I have some say in what our team does but ultimately most decisions come from our manager.

One employee, Helga, announced that her boyfriend was finally assigned his final posting for his military stint and she was moving there to be with him. Of course we’re all thrilled for them both — it’s been a long journey for him and she’s been in limbo while he jumps through all the hoops of his specialized training. She’s very excited for this next step and constantly talking about it — where will they live, what kinds of jobs are there, what kinds of parks and activities can they do, etc.

Our team also has a big work conference coming up where our boss plus two other employees will go and present some of our work. Our supervisor sent out an email to everyone except Helga asking who’d like to go. His thinking was that while she’ll still be employed with us, she’ll be departing soon after and it would be a waste. In the end, our boss picked the other lead and one of her peers out of eight of us. Now she’s upset that she wasn’t even invited and is doubting her life announcement to the group. Who is in the right? Our boss, who is being strategic, or Helga, who right deserved to be invited even if she was planning on leaving several months afterwards? I guess this also touches on how close should you keep your personal life out of your work life.

Helga is in the wrong. Conferences are a mix of networking and professional development, and it’s reasonable not to make that investment in an employee who’s about to leave — particularly when it would mean someone else wouldn’t get the opportunity to go. Helga is being unrealistic in thinking your company should continue investing in her to the same degree when she’s about to leave.

That said, your manager could have avoided the whole thing by just sending the email asking who was interested to the whole team and not making it so obvious that he wouldn’t consider Helga.

4. Employee worked unauthorized overtime

I work on HR. A report of mine from one of our satellite offices is very close to the business, to the point that she often acts on requests without reflection.

The last example happened two weeks ago when the business needed background checks run on six people. She volunteered to work eight hours on a Saturday to make that happen quickly, due to an audit that would happen the following Tuesday. She asked me for approval via email and I refused to approve the extra hours, as working on a Saturday would make no difference to the actual end result (the vendor running the background checks would only start working on them on Monday anyway). Additionally, these are processes that take at least two weeks, so results would not be ready in time for the audit. She worked on that Saturday regardless and now she’s asking for compensation hours, claiming someone from the business approved them.

How would you manage the conversation? I appreciate her willingness and at the same time I can’t afford her to put hours on every single demand from the business, specially if there isn’t a strong business case to justify it.

Since she’s saying someone approved the extra hours after you explicitly told her no, you’ve got to find out who she says that was, and why she sought approval from them after you’d already told her no. Either she’s lying about someone else approving it (which would be a very big deal) or she went around you after you’d already told her no (which is also a big deal, although not as bad as the lie would be).

But beyond that, the conversation is: “I need to be very clear: you cannot work extra hours without my explicit permission. I appreciate that you’re coming from a place of wanting to get work done, but your eagerness is costing us money that there’s not a business case to spend. Going forward, you cannot work extra hours without my written approval. If I am unavailable, I will deputize a specific person to give you approval in my absence. No one else is authorized to okay it. Can you confirm that you understand that policy and will follow it?”

Aside from the unauthorized overtime, it sounds like this employee also needs some coaching around judgment, prioritizing, and smart decision-making. To tackle that, start by naming the areas you want her to improve in, give some recent examples of things she should have handled differently, and explicitly say you want to work with her to build those skills. Often in situations like this, the employee sees the behavior as a strength (“I act on everything immediately!”) and it can be eye-opening to realize that their manager doesn’t see it that way.

5. My former manager keeps contacting me after I changed jobs

I left a toxic work environment right before the holidays. I work at a university and started a new job in a different department right after the new year. My former manager, who I don’t hold in high regard, has been emailing me asking me to confirm whether I completed certain tasks before I left. I gave her updates on everything in process multiple times leading up to my departure, created a detailed spreadsheet about the task she is most concerned about, and completed everything I could before I left.

Because I still work at the university, do I have any obligation to answer her emails? I obviously don’t want to burn any bridges, so I have been directing people who write to me regarding my former job to the proper contacts, but I really don’t wish to speak to my former manager. It feels a little like she is attempting to continue to exert control over me. One of my biggest gripes about the manager is her extremely overbearing and micromanaging style. While superficially I left on good terms, there had long been tension and issues I brought up that were never resolved.

If you didn’t still work in the same organization, you’d have zero obligation to respond and could simply ignore the emails. (I’d still recommend one or two polite responses making it clear you were unable to help, just for bridge-preserving purposes, but if she continued after that, you’d be free to ignore it). It’s tricker when you’re still in the same organization. Depending on internal politics, you still might be able to ignore the messages, but generally in that situation you do have to finesse it a bit more.

First and foremost, though, don’t answer right away. Let a few days go by (so she sees she can’t rely on you for instant answers) and then reply with versions of, “It should all be in the documentation I left” and “I’m so busy with my new role that I’m not in a position to be of much help, but I left really extensive documentation on the X drive and you should find everything you need there.” If it continues after that, let your new boss know what’s going on and see if you’d have her support to draw a firmer boundary.

Related:
how long after resigning should you still answer questions?