my Gen X coworker is trying to “grandma” the Zoomers and it’s getting weird

A reader writes:

I am writing about a new coworker who has no concept of boundaries.

“Hannah” is in her mid-40’s and is pretty advanced in her career (in a technical position that starts at $100K a year). She sees herself as a “grandma figure” to the Gen Z coworkers in our small office. I’ve noticed that some of these employees are patterning after her behavior and I’m concerned that it’s going to lead to damaging office norms.

Examples include encouraging the engaged women in the office to rethink their weddings — she’s going through an acrimonious divorce — and demanding all early-career coworkers exchange personal phone numbers with her so that “they can text her if they need anything, day or night.” She makes elaborate birthday gifts, demands that the women eat more because she feels they’re too thin, and frequently refers to these employees as her kids or grandkids.

Some of these colleagues have shared in conversation that her overly familiar behavior makes them uncomfortable, but that they don’t want to hurt her feelings by not playing along. Others have started way oversharing because they hear her doing the same and assume it’s normal to discuss very personal situations with casual coworkers.

Her behavior is extra strange to me because she is, at most, 20 years older than these colleagues and nowhere near what most would consider to be the age of a typical grandmother.

Hannah hasn’t done any of this to me since I’m slightly closer to her in age (31) and in a higher level role. I don’t know how to help these early-career employees set boundaries without causing a blowup since it’s clear that this woman would take any attempt at distance as a personal slight. Do I need to mind my own business? If not, how should I navigate this?

It is indeed intriguing and surprising that Hannah landed on “office grandmother” rather than the more typical (and still problematic) “office mom” and I wish we knew more about why.

As for what to do about her …  I don’t think it’s yours to solve and you shouldn’t put that burden on yourself. It would be different if you were her boss or the manager of some of the people she’s being inappropriately parental (grandparental?) to, but assuming you’re not, your role is probably mostly uncomfortable bystander for this one.

However, you don’t need to censor yourself, and you’re allowed to have natural reactions to things she says. For example, if you hear her telling someone to eat more because they’re too thin, you could say, “We shouldn’t comment on people’s diets or bodies at work. It’s not our business.” If you hear her encouraging someone to call off their wedding (!), feel free to say, “Whoa, I’m sure Jane doesn’t need relationship advice from colleagues.” If she’s pushy about demanding people turn over their personal phone numbers to her, you can say, “No one needs to share that if they’d rather not.”

And if coworkers share with you that Hannah is making them uncomfortable, encourage them to push back with her and to maintain their own boundaries; assure them that Hannah is the one acting weird and they’re not weird for disliking it. You can also encourage them to talk to their managers about Hannah’s overstepping if you think it rises to that level.

Sometimes just modeling “no, this isn’t normal; yes, you’re right to think it’s strange” — as well as letting people see someone push back with her in the moment — is enough of a counterweight to keep people grounded in more sensible norms.

But beyond that, you don’t have much control over the situation, and you don’t need to take responsibility for fixing it.

should you require video on during team meetings?

A reader writes:

I manage a team of 15 that holds a Zoom meeting once per week. While they work independently most of the time, there are major projects where everyone has to be on the same page, and we get updates during these meetings.

I’ve noticed that the people who turn their video off (and I know they’re set up for video because it’ll be on at the start of the meeting) often end up reaching out to me to ask questions that we covered in the meeting. Sometimes they reach out hours later, sometimes a few days later. I’m starting to think that the ones with the video off are leaving the area, muting the team, or just totally zoned out. Can I require them to keep the video on? Do you think it would help?

I answer this question — and two others — over at Inc. today, where I’m revisiting letters that have been buried in the archives here from years ago (and sometimes updating/expanding my answers to them). You can read it here.

Other questions I’m answering there today include:

  • Company photoshopped heavy makeup on all the women’s headshots
  • How long do I have to forward emails to my old boss, when I still work for the same company?

my dishonest employee blames technology when he messes up

A reader writes:

How do I deal with an employee, Miles, who is dishonest but gets emotional and doubles down when confronted with technological proof?

For instance, he’ll tell me he submitted a work product when the timestamps on shared documentation (which are visible to both of us) show that the work wasn’t completed by the deadline.

Separately, I’ve suspected that he’s using generative AI to complete work, and multiple AI detectors — which I acknowledge are imperfect — also say large parts of his work are AI generated. (It may be fine to use AI in other circumstances, but it violates our policy prohibiting using AI to write external-facing documents, which he’s responsible for.)

If I confront him, Miles gets defensive, frustrated, and visibly emotional, denying that he missed the deadline or that he uses AI or whatever, and insists he doesn’t know why the timestamps/AI detectors would say that he did. I feel like I’m arguing about reality. Or maybe I am crazy and things like timestamps and multiple AI detectors (and just my own instincts that something is off) are giving me the wrong impression?

I wrote back and asked, “How’s his work aside from this? I’m skeptical you should be keeping him on and wondering what the rest of the picture looks like.”

Honestly, I think he struggles with time/task management. When I set really strict deadlines and help him break down the work into small chunks (outline by this date, draft by this date, etc.), the work is good. My armchair psychologist take is that he gets in a shame/insecurity spiral when he feels like he’s falling behind, leading to shortcuts and dishonesty. But whenever I try to get to the underlying problem, he says the technology is lying, and I’m not sure how to dig deeper. How do I correct a missed deadline if he insists (to the point of getting emotional) that the deadline wasn’t missed?

I think you’re probably going to end up needing to fire this guy, but let’s break it down a little more.

First: is it acceptable for the person in Miles’ position to need that much hand-holding with time management? Is it okay that you have to break work into such small chunks for him, or does the person in this job need to be able to manage their own work more independently? If it’s the latter, it might make sense to just focus there: he needs to manage the work more autonomously, without missing deadlines, period. If he can’t do that, there’s your answer.

But for some jobs, it would be more reasonable to help him with those aspects of the job. If that’s the case here, then let’s look more closely at the defensiveness, denials, and potential lying.

The first thing to do there is to bring in IT. If Miles says that the timestamps on shared documentation are wrong or otherwise claims technology is malfunctioning, then let’s take that very seriously and ask IT to investigate. Most likely they’ll confirm that he’s wrong, but who knows — it’s worth verifying with them, at least. From there, if Miles continues to blame technology, you can hold firm: tell him that IT says he’s wrong, that these supposed tech snafus aren’t happening to anyone else, and you need him to meet deadlines, period.

You should also make a point for a while of checking right when something is due to see if he has submitted it or not — if he hasn’t, you can speak to him about it on the spot and sidestep the technology claims entirely.

With the AI concerns: focus less on whether he’s using AI and more on the qualities of his work that are making you suspect it. There’s something about his work that’s ringing those alarm bells for you — stilted writing, overly buzzwordy, weird leaps in logic, whatever it is. Focus there; those things are work quality problems and they’re easier to address without getting drawn into a debate about whether he did or didn’t use AI. (Although if he is using AI, he’s probably leaving tracks on his company computer that your IT team could find for you, if you want to know for sure.)

It’s possible that by approaching it this way, it will change things for the better — maybe there really have been some tech problems and by getting them fixed, it’ll let you both move forward without that distraction, or maybe by focusing on the specific weaknesses in his writing he’ll be able to use that feedback to improve. I’m guessing not — but the advantage of going into it with an open mind is that you’ll see pretty quickly that either he can do the job at the level you need or not, and you won’t need to get bogged down in the framing he’s currently trying to use (which is “I’m not responsible for any of this”).

boss is always scratching his chest, drinking non-alcoholic beer at work, and more

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

1. Manager is always scratching his chest inside his shirt

I am a recent transfer to my current office, 10 years with my company, and I have an issue with a manager. “Mark” wears his shirt with the top three buttons undone and he is rarely seen without his hand inside the shirt, scratching his chest. Am I wrong to be grossed out by this?

Mark is my direct manager, over my immediate supervisor. I have talked to my supervisor about my feelings and I was told that if I felt like this was a serious concern, I should take it up with HR.

What can I do? Short of reporting this to HR or trying to ignore him, which is hard to do since he will stand right in front of you and scratch his chest while he talks to you.

You’re not wrong to be grossed out; someone regularly having their hand inside their clothes is odd, and three unbuttoned buttons is more skin than you see in most offices.

That said, your supervisor is correct that unless you think it’s a big enough deal to take to HR (and I agree that it’s not), there’s nothing you can do about it. Mark’s scratching his chest; he’s not fondling his man parts or otherwise crossing glaring lines. The behavior is uncouth, but it’s not obscene.

At most, the next time he does it you could say, “Are you okay? You keep scratching yourself” — which could make him realize he’s doing something noticeable enough to be remarked on — but if that doesn’t work, then realistically you probably just need to accept the dude is a bit boorish (or very itchy).

2. Is it OK to drink non-alcoholic beer at work?

In your opinion, would it be okay for an employee to drink non-alcoholic beer in the office? Since it contains no alcohol, they wouldn’t be getting drunk and negatively impacting performance. But maybe it falls under the category of “not work appropriate.”

In most offices it would seem pretty weird. It’s an optics issue, not something strictly logical. Partly it’s that people won’t necessarily know it’s non-alcoholic at first glance; a lot of non-alcoholic beers look exactly like regular beer, and it’s not a great move to look like you’re swigging a beer at your desk, whether or not you actually are. Many people won’t stop to check and will just assume they’ve witnessed you drinking at work. But mainly it’s just going to come across as a weird choice in an office — like you’re trying too hard to be provocative, or not sensible enough to know that it will come across strangely, or just too invested in the choice in some way.

If you want to debate whether it should be okay to drink non-alcoholic beer at work, that’s a different question. But realistically, in most offices the optics are going to be bad.

3. My employee won’t take any time off for an injury

I work for a mid-sized city and was recently promoted to the division manager (leading eight staff overall). Our work group is tight and hardworking, and we are all super passionate about our work. As is often the case in the public sector, there is always more work that can be done.

One of my coworkers, Faye, has always worked long hours. She works late and nearly every weekend, and almost never takes time off. Even when she goes on vacation, she usually works part days throughout. She is extremely smart, dedicated, conscientious, and hardworking. Faye is now my direct report, but we worked for years as colleagues running parallel programs. I consider her a work friend, but she is older than me and we are figuring out what our new work relationship is.

When we were peers, how she took time off was none of my business. Now that I am her supervisor, I’m running into an issue because Faye is dealing with a really bad back injury. We are going into the third week of her working through extreme pain. She has been continuing to work through it from home, since she says it doesn’t make a difference if she’s working or not. She’s been working slightly fewer hours, but mostly just pushing through, working through pain and pain-induced insomnia.

I know it’s not appropriate to manage her time off, but I am starting to be concerned because I strongly believe in taking time away from work, unplugged, to heal and recuperate. I also don’t like the expectation it sets for the rest of the team. We get generous time off, with interchangeable vacation and sick time that rolls over into the next year. Faye has about 10 weeks of time saved up, in addition to access to paid medical leave through our state. Our workplace also has a donated leave program.

What is my role here? Is there anything I could/should do, beyond letting her know we can cover if she needs to take time off? I did encourage her to turn on her out-of-office message so she feels she can step away from email, which she did. And I’m covering any in-person duties (which are pretty minimal).

I agree with your philosophy about real time away, unplugged … but I also believe in letting adults make their own choices in that regard until and unless it’s affecting your team.

Reasons to tell Faye she needs to disconnect would be:
* if you’re seeing signs that other team members feel pressured to mirror her behavior
* if “working through pain and pain-induced insomnia” is affecting her work quality or output (hard to think it wouldn’t, but who knows)
* if you have reason to think she’s burning out
* if you need her at her well-rested best for something more important in the near future
* if her never being away means you have no chance to spot weak points or cross-training needs on your team (or fraud, for that matter — there’s a reason many financial jobs require people to fully disconnect for two weeks each year)
* if your sense is that she’s doing this because she truly feels there are no options to cover important work (in which case you’d need to work to find some)

I suspect at least a few of these are in play. But if they’re not, you can urge her to take real time off and emphasize that things will be covered in her absence, but otherwise should leave it to her to decide.

4. My manager won’t take any responsibility for us dropping a ball

Last week, my boss messaged me, “So, how’s project A going?” and I had no answer because I had done … nothing! This is a project that usually requires over a month of preparation and coordination between multiple teams at the company. However, I never knew it was my responsibility! I replied that I didn’t know it was my responsibility and I thought another team had it handled. He mentioned a meeting we had with the other team a few months ago where we had apparently agreed to handle the entire thing. But it didn’t come up in any documentation, meeting notes, my monthly goals, our yearly goals, and he hadn’t checked in until today, a week before the project was supposed to be completed!

In my work life (eight years) and under this manager (1.5 years), this has never happened to me before, and certainly not on an assignment that requires so much preparation. I have always gotten really good feedback on my ability to juggle multiple projects, prioritize, and communicate effectively, so this really rocked me. I feel like my manager dropped the ball on this, but he refuses to take any responsibility for it.

I did work like crazy to get everything figured out in less than one week so we are still on schedule, but it was one of the worst weeks I have ever had at work. We had a follow-up conversation where I mentioned the lack of communication or documentation, but he seemed completely nonplussed at the situation (and definitely not apologetic). I apologized for any miscommunication and really tried to give him the benefit of the doubt … but I can’t help feeling that I shouldered the entire situation and he has walked away oblivious to how big of a problem it was. How do I get across to him how much this affected me? And how do I prevent this kind of thing in the future?

If he’s normally a good manager who communicates well, one option is to leave it where it is now, since you’ve already had a follow-up conversation where you mentioned your concerns. I see why you’re thrown by his response to that (or lack of response, really) but if it’s not part of a pattern, you could just figure it’s been addressed, you see it differently for whatever reason, and it’s now settled enough — as long as it doesn’t keep happening.

But the other option is to go back and say something like, “I know we talked about it a bit, but I’m pretty rattled that I was unaware of such a major project for so long, and I hoped we could figure out where we miscommunicated so I can make sure it doesn’t happen again. If your sense is that I dropped the ball somewhere, can we dig into what happened so I’m better prepared next time? Or if your sense is that something else caused it, can we figure that out too?” There is a danger here that if your boss feels it’s already been discussed and handled, it could be annoying to reopen it, so you should factor in your sense of that, and also how open he’s historically been to acknowledging when he has messed up. If he’s not one to admit fault, there may be no point in revisiting it — not because he doesn’t necessarily need to hear it, but because in that case his previous non-response is probably as good as it’s going to get.

Also: he mentioned a meeting you were a few months ago where your team agreed to handle the project. Unless you have reason to doubt that’s correct, one takeaway might be that you need to be more proactive about following up with your boss on those types of commitments yourself, rather than assuming he’ll check in with you about them.

5. Submitting a reference from a job not listed on your resume (because you were fired from it)

My partner, Linda, was recently fired without cause after a month at a new job. She was still within her probationary period, the job was not a good fit, and the training was extremely lacking, which is why her performance suffered.

At this job, Linda worked closely with Tracy. Tracy was in a tenured position but not in Linda’s chain of command. Tracy was very pleased with Linda’s performance and was definitely one of her cheerleaders during her time there. Now that Linda is back in job-search mode, Tracy reached out and offered to be a reference.

However, Linda was only at this job for a month and, due to the nature of her departure, she is not including this position on her resume. Is it appropriate for her to list Tracy as a reference? If so, how would she note that Tracy is a reference from a job not listed, and with such a short length of employment? I’m concerned that a hiring manager will see yellow flags at best if Linda includes Tracy as a reference. Linda has other options for references, but they are from a position that ended in June.

I wouldn’t use Tracy as a reference, unfortunately. It’s more likely to cause concerns than it is to strengthen her candidacy (because of the firing, but also because one month of working with someone generally isn’t enough to produce sufficiently strong and nuanced feedback to outweigh the firing, or even to count for all that much on its own).

The exception would be if Tracy is personally connected to someone Linda is applying with; in that case, it could change that calculus (in part because Tracy would be able to talk more candidly about what happened and her assessment of Linda would carry additional weight).

the miniature diorama, the burn book, the gun, and other weird items left behind in desks

Need an amusing distraction today? I do.

Last week we talked about the oddest things you’ve found when cleaning out a desk or workspace, and below are 15 of my favorite stories you shared.

However, what is not my favorite is the knowledge that 30 of you — 30 separate people — thirty — reported finding nail clippings left in a desk you inherited. Why?

And yet, even burdened with that information, we must move onward.

1. The diorama

I found an entire, miniaturized diorama of the office, complete with desks, tables, smoking area outside, and hung up motivational posters. The cherry on top was that each person working there had their own figurine, complete with distinctive accessories.

When I found it, the former employee was posed as having his feet up on his desk, smoking a cigarette and eating a miniature Subway sandwich. He had left the position to open a Subway franchise.

2. The statues

We had an intern who drove the whole office crazy with his elitist behavior. After his time with us had ended, we needed to look for info on the computer he had been using, and we discovered a folder full of dozens of pics of ancient nude male statues. One of my coworkers pointed out that *of course* even his porn would be pretentious…

3. The burn book

I was doing a deep clean of a desk I was assigned and found a note taped to the underside of a drawer. It was basically a burn book of every employee the person who had my desk prior worked with. It ended with, “Whoever reads this, you’re welcome!” I agreed with most of it, honestly.

4. The emails

I just cleaned out my desk and found that my predecessor printed out EVERY email she sent, then highlighted them, made comments and annotations in red pen. These were emails she had sent, not emails she received. My favorite one was one she had sent to the CEO telling her she was an idiot … not long before she was fired.

5. The photo cut-out

My manager was fired. When we cleaned out their cubicle, we found a two foot tall cardboard photo cut-out of her manager’s head.

6. The notes

A few months after one of my coworkers was fired, their desk was cleaned out for a new hire. Under the desk we found at least 50(!) post it notes with varying messages, including comments about women colleagues’ bodies, Bible verses, comments about hating management, and “do not get fired again.” Guess that didn’t work out for them.

7. The condoms

Condoms. Lots and lots, with various *ahem* features. I put them in a clear jar and left it on their new desk with a post-it facing outward “Don’t need – free to good homes.” The person was incompetent, unpleasant, entitled and out of the office for a few days.

8. The Fungus Basement

My current company has … the Fungus Basement. Old laboratory space in a damp basement that became contaminated with fungal growth- it’s hard to sterilize fungus away and it wasn’t worth the risk of contaminating newer lab space, so an entire working lab got locked away in a lightless basement being slowly overgrown by The Fungus™. We just heavily sealed all the doors and vents to keep it in there, and I can’t imagine what a horror movie set it’s turned into.

9. The hair

At my first museum job, straight out of grad school, I was assigned a storage closet for event props, catering equipment, and our beer/ wine/ snacks for donor events. It had clearly not been cleaned in many years, and was so full and disorganized it was impossible to close the door. I went in one weekend, with my mom, to clean it out and spend some time with a parent I had not had a lot of one on one time with due to working and school. Was super excited about the day and very energized to clean up something that was irritating me.

But then we found the gallon-sized ziplock bag of human hair. No explanation, no label, nothing. Somehow someone stacked it above the cans of lighter fluid, which seemed to us at the time the only logical place to store a gallon of human hair.

10. The rubber stamp

A rubber stamp saying, “This article is also available in Esperanto.” To my knowledge, we have never published Esperanto-language works, but this stamp was in our mailroom for years until I finally took it to my desk. The actual stamp part is gone, but I’m keeping it to mystify whoever ultimately cleans out my desk.

11. The cheese

I wasn’t there to witness it, but the woman sitting next to me and the company parted ways. Her desk was always covered in opened crisp packets, half-full bottles of pop and other detritus.

My boss had to clear the little drawer cabinet we each had under our desk. He discovered that departed coworker had been storing cheese in it.

12. The quesadilla

A coworker left, and another coworker and I were the only ones left to clean out her desk. Amongst a melange of personal effects, we found a hard copy of our reporting schedule with a handwritten missive at the top. It read, “I am a quesadilla.” It is now my go-to mantra during inane work situations.

13. The pistachios

Pistachio shells. I moved into a cube in a corner after the previous guy had moved on. He had apparently been snacking on pistachios for years, and instead of using the garbage can ALSO UNDER HIS DESK, he just tossed them under his desk and called it good. It wasn’t visually obvious, but as soon as I tried to sit down my feet encountered a ~2 foot tall mountain of pistachio shells.

14. The gun

Wasn’t a desk but a car. My first job out of college was as a car salesman. I’d just sold a car and since it was a slow day I figured I’d help out the lot attendants and clean out the big stuff from the trade-in. Usually it’s just trash, but sometimes people leave stuff like IDs or important documents in the glove box, or CDs or the like.

In this case it was a .38 revolver. I called the guy and he said, “Oh, THAT’S where I left it! Can you hold on to it for me?” So for a few days underneath some sales forms in my desk drawer was a revolver and a set of bullets.

15. The tiny ducks

About two months ago I lost a team member who left for another job. She was a delight.

Someone had taken on an innocent office prank of hiding very tiny ducks everywhere. They were multicolored “rubber duckie” style ducks that fit on the tip of your finger. They were often on top of bulletin boards, water fountains, mundane places but they usually brought a smile.

She was very reserved but always nice and positive. When I opened her drawer to clean out, I found the entire bag of the ducks. I had to send her a text to let her know she had been outted as the duck prankster.

my employee panics when we spend money

A reader writes:

I have an employee who tries to save every penny of the organization’s money, at the expense of significant amounts of time. I’ve explained sticker price vs time costs multiple times, and yet any amount of money over about $50 sends him into an anxiety spiral where nothing I say makes an impact. I need him to be capable of watching the company spend money on supplies, IT infrastructure, furniture, advertising, etc. without getting panicked and suggesting high-effort, high-salary-cost ways of saving minor amounts of money.

I have discussed with him both why specific expenses are necessary and that this pattern is untenable. He agrees, but the next time an expense pops up, he panics and genuinely thinks we don’t understand that there are cheaper options, even when I remind him our earlier discussions.

He has acknowledged that he struggles with anxiety. When he’s not actively anxious, he’s good at his job. But the spirals are killing it. Barring moving him to a role where he would have no knowledge of our expenses at all, I’m at my wits end. Is there a framing for this that might sink in? I’d rather encourage understanding than just shut him down, but at this point I’ve done everything I can think of.

I answer this question over at Inc. today, where I’m revisiting letters that have been buried in the archives here from years ago (and sometimes updating/expanding my answers to them). You can read it here.

how do I manage petty behavior between two employees who dislike each other?

A reader writes:

Where is the line between what is and is not acceptable when talking about pettiness between coworkers?

I’m dealing with two employees on the same team who simply do not like each other for a variety of reasons. Luckily, these two do not have to actually work together very often but sit in the same suite. They are both big personalities, have strong opinions, and can both come off strong. Apart from counseling them on being aware how they come across when interacting with each other, I’m at a loss for how to address the pettiness they’ve both adopted from the perspective of “you both need to remain professional with each other” — things like saying goodbye to everyone on the team except the other one, ordering dessert for “whoever wants some” with ingredients that the other is allergic to, not holding the door open for the other “without realizing they were there.” I have a hard time figuring out where the line is between “you are not meeting the expectations of appropriate conduct” and “come on, just don’t be a jerk” especially when one claims things like “you can’t prohibit me from ordering the dessert that I want and offering the leftovers to others.”

Their work performance is pretty solid. They’re both passionate about the work they do, execute it well, and are (for better or worse) both sort of “staples” of the team (subject matter experts and likely committed to being at this company for a long time).

The way to approach it is to focus on the outcome you want, which is “no one on the team can tell you don’t like person X.” They can feel however they want to about each other, but if other people pick up on those negative feelings, that’s a problem — because it will make the working environment uncomfortable for everyone.

So yes, of course they can order whatever dessert they want even if the other person happens to be allergic to it, and of course sometimes they might not say goodbye to absolutely everyone when they’re leaving … but rather than getting mired down in those details, focus on the outcome you need from them, which is they can’t make people uncomfortable with their behavior and they need to treat everyone with a baseline level of warmth and pleasantness.

I would frame it this way: “You need to conduct yourself in such a way that you’re not making this a negative work environment for other people. If people can tell you don’t like Jane, you’re not meeting that job requirement. If people perceive you as being petty or vindictive, then you’re failing at that. And I take that very seriously — it is an absolute requirement of being on this team that you treat everyone with respect and that you don’t make the rest of the team uncomfortable. Unless you truly need me to give examples, I’m not going to go through the pettiness I’ve seen instance by instance; I assume you understand what I’m talking about. It needs to change if you want to remain on this team.”

And you should hold firm on that line. Solid work performance or not, you can’t keep people who behave this way. They’re poisoning the environment for the entire team … and at some point the rest of your staff will start to worry about how they’ll be treated if they somehow end up on the wrong side of one of these employees.

helping an awkward new employee, boss asked me to talk to a coworker about her cleavage, and more

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

1. How can I help an awkward new employee connect better with coworkers?

I am a senior team member. Reporting to me are Bill (mid-level — seven years of experience), and three people at the junior level (one to three years of experience). Bill is the newest hire on my team, hired because we really needed someone to take some stuff off my plate and also hopefully act as a resource and mentor to the more junior staff.

Bill’s work is good and I am happy with the hire, but without fail, he says the perfectly wrong thing. It is harmless, socially awkward stuff: trying to join a joke but the delivery is loud and the reference is obscure, or unknowingly suggesting something that is a pain point. Think of Michael Scott’s cringiest social moments and you will have an idea.

This is compounded by the fact that two of my junior level staff applied for this role when I announced we were hiring. I discussed with each of them that the move just was not right, they were too junior for the responsibilities, and they understood, I think … but it for sure makes interacting with Bill extra grating. Bill has noted to me that it is hard to join a new team where there are established relationships so I know he is picking up on it. The two staff members will text and grab coffee together sometimes, though they are certainly cordial to everyone. I have organized a weekly lunch, but it winds up just adding to the awkwardness because Bill kills the conversation with a disconnected statement about a topic we all finished talking about 10 minutes ago.

I think Bill’s attempts to make social strides, especially with everyone but especially with these two is just adding to the pressure and awkwardness of it all. It is painful to watch! Any suggestions of how to coach someone on connecting with coworkers, but to just the right degree? Should I be taking any other action to make everyone like each other more?

It’s not really your role to coach Bill socially. And he may just be an awkward guy, which is okay — people are allowed to be awkward! There are probably some places where you can coach around the edges (“when you made that reference to X, people were confused because X is pretty obscure and most people don’t know what it is”), but I wouldn’t count on it making a significant difference. I’d also lay off the weekly team lunches, or at least do them much less frequently — they don’t sound like they’re working and might be making things worse, and either way that’s a lot of organized togetherness.

What I do think is your role, though, is looking for ways to set up Bill where he can do better. What’s he good at? Can you look for opportunities where it would be logical to pair him with one of your junior people to collaborate, in an area where he has expertise and is comfortable? Can you keep an eye out for times where a junior employee is struggling with something and you can genuinely suggest Bill as a resource? And then set Bill up for success there as much as you can — for example, letting him know that he’s great at X specific nuance of Y and asking him to collaborate with Jane on that specific element of it. You’ll need to keep an eye on how those interactions go — you don’t want to increase everyone’s aggravation if he doesn’t handle those well — but the hope would be that if people have more positive interactions with him, it might change their comfort with him and he might start feeling less awkward too.

The goal should be less about revamping Bill’s personality — some awkwardness and quirkiness is totally okay in most roles — and more about getting everyone more familiar with each other through the work itself and helping the rest of your team see Bill’s value.

2. My boss asked me to talk to a coworker about her cleavage

I am the office coordinator for the school where I work, and my boss asked me to talk to a coworker/friend of mine about showing cleavage at work. My boss has been approached my parents as well as other staff members about this coworker’s clothing. I don’t know how to approach this. She’s an educational assistant and most of the EA’s here are fairly dressed down, as it can be a pretty physical job. She does have a large chest and I know that that can be an issue when buying clothing, as I have the same issue.

I just feel uncomfortable speaking to her. I think the reason my boss asked me to speak to her is because I am friends with her and so that it’s not an “official” reprimand and could be dealt with discreetly.

Her direct supervisor is a man, but the principal (the one who asked me) is a woman. I do have some authority within the school but it’s mostly organizational; I have some administrative responsibilities and have been asked to sit in on these types of meetings in the past with other employees, but I am in no way a supervisor of anyone and I am not in HR.

You should decline to do this. It’s not your job to give dress code feedback, and it sounds like you’re being asked to do it so someone else can avoid an awkward conversation, which is not a good enough reason. And if it’s really true that they want to avoid it being an official reprimand, they can easily accomplish that by … not making it an official reprimand. Managers can give feedback without it being memorialized as formal discipline; it can simply be a conversation/reminder about the dress code.

If your coworker isn’t in compliance with the dress code, that needs to be handled the same way your employer would handle any other dress code problem — which presumably means a reminder by someone with the authority to issue that kind of reminder, not asking a friend to pass along a message.

I’d go back to your boss and say this: “I thought more about your request that I talk to Jane about her clothing, and I don’t feel comfortable doing that. It should come from someone with the authority to discuss the dress code and answer questions if she has any. I think she’d feel very awkward hearing that from a peer, and I’m not comfortable delivering that feedback to a peer.”

Related:
my employee’s clothes accentuate her chest — how do I talk to her about it?

3. Left out of a group chat

I work in an office of eight (one manager, me, and my six coworkers), which is then part of a larger division. For the past week or so, my coworkers have all been discussing different New York Times games. I normally play Wordle myself, so I jump into these conversations too. It’s been a fun thing to chat about in the mornings.

However, my coworkers will also discuss these games in a Teams chat that I’m not a part of. I was out sick one day earlier this month, and I’m thinking that might have been the day they started it. I guess I’m just confused by the fact that I’m part of these regular conversations, and for some reason all six of my coworkers (even the guy who started three weeks ago!) have not thought to add me? My coworkers are all very nice people who treat me well, respect my time, etc. — my point being that I have no reason to think they’re purposely excluding me as some sort of schoolyard bullying tactic.

Do I bring this up to them? Do I bring it up to my manager? Thinking about it, I don’t think I care, but it does seem a little hurtful. I mean, what would my manager even do? Wag his finger and tell them to add me?

It sounds like there’s every reason to believe it was unintentional — it’s likely they did start it on the day you were out and then haven’t thought very deeply about it since. You can just say, “Hey, can I get in on the games chat on Teams?” and that shouldn’t be weird (particularly if they’ve talked about it in front of you) and should take care of it. The only way this would be weird is if your coworkers were a bunch of exclusionary asses and it doesn’t sound like that’s the case.

Note: the New York Times tech union is currently on strike and asking people to honor their picket line by not playing Wordle and other NYT games during the strike.

4. My organization doesn’t post job openings until the old person has already left

My organization seems to have a policy of not posting a staff member’s position until that person has left. Is there any way that this makes sense? I don’t know why they want four weeks notice if they don’t use that time to find the replacement. Hiring is slow anyway, so this routinely means that positions are open for months, which I cynically think maybe they like because they are saving money while everyone scrambles to cover the workload. Anything I’m missing here?

I’m curious whether this is actually their policy, or whether it’s just what happens in practice because they’re slow and/or disorganized. If it’s their policy, it’s a bizarre one! Generally a notice period (even a four-week one) isn’t long enough to hire a replacement and have them start while the departing person is still there to train them, but there’s no reason to squander that time; generally you want to move forward on filling soon-to-be vacancies with some sense of urgency. (There are some exceptions to this, of course, like if questions need to be worked out about the position before you post it, but typically you’d want to begin recruiting pretty quickly.)

By the way, four weeks notice is two weeks longer than the standard in most industries, and you might consider whether you really need to stick to that:

can I give 2 weeks notice when my employer says they “expect” 4 weeks?

5. I’m ready to retire young but don’t want to burn bridges

I’m a mid-career manager of a small team of experienced individual contributors involved with fairly high-profile projects for my organization. The organization consistently struggles to prioritize work and provide the appropriate resources; we often are trying to do too much, all at once, with too little. Despite this, my team is well-respected and gets things done. However, I’m tired and have been vacillating in and out of burnout for years. Vacations offer only a short-term fix. I suspect that I have undiagnosed neurodivergence that makes my set working conditions especially challenging.

My company does not offer sabbaticals. I have been focused on FIRE (Financial Independence, Retire Early) for years and I’m finally at a point where I feel like I’ve accumulated enough that I can take an indefinite break and am planning on resigning within the next six months. I’ve worked for this organization for a long time and, as I’m still relatively young, I’m sure my resignation will come as something of a surprise. I don’t want to leave my small team and my manager in a bind, but for the sake of my own best interests, I’m not comfortable giving more than a couple of weeks notice.

I have not yet determined if my mini-retirement will turn into full-blown retirement and mark the end of my corporate career. How do I frame my resignation and deal with questions from colleagues during my notice period when I’m not leaving for another job? I want to leave on good terms, but I’m not open to being convinced to stay with the organization while they figure things out. I want a clean break on my terms.

You’re overthinking it! You’re allowed to resign any time you want. It’s true that people might be surprised to hear that you’re not going to another job but you can say, “I’m taking some time off before deciding what I want to do next.” That’s true! “What I want to do next” doesn’t need to mean a job, necessarily. Or if you’re up for sharing more, you could say, “I’ve worked for a while to be able to take a long break from work, and now I’m able to do that.”

If you’re pushed to stay longer since you don’t have the deadline of a start date somewhere else, just hold firm: “I do need to stick with X as my last day because I have some immovable plans for right after that.”

This isn’t bridge-burning! You’re not an indentured servant; you get to decide when you’re ready to leave a job. And leaving a job for any reason nearly always creates some inconvenience for the team you’re leaving; that’s just part of the deal with resigning, not a reason not to do it.

how do you stay focused on work during anxiety-inducing world events?

A reader writes:

I wonder if you have any tips/tricks on how to keep focused on work when there is a major event going on? I recall trying to work for several weeks after the 2020 election and January 6 and know my work was not efficient or good quality during that time. I’m so anxious about the election results that I know I will be following all day and probably many more days after since it’s unlikely we’ll get results for some time. Focusing on work during this time seems extremely difficult and pointless.

Things that help me when I need to focus during difficult times:

•  Remember that when a crisis is happening in the world, it’s natural and human to be distracted. As long as your work allows for some ebb and flow, you don’t need to perform at 100% every minute. (Don’t take this advice if you’re performing surgery tomorrow, but otherwise give yourself some grace.)

•  Remind yourself that there’s nothing you can do to change tomorrow’s outcome. Whatever you could have done to help affect the outcome, that time is now behind us. (Unless you still need to go vote, in which case do that immediately, or are going to walk off the job and drive people to polls or make GOTV calls, in which case go for it.)

•  To the extent that you control your work activities on any given day, choose them strategically. Maybe tomorrow is the day that you’ll organize all your files and do other undemanding work, or maybe it’s the day to throw yourself into something intellectually demanding as a distraction. Know yourself and plan accordingly.

•  It’s okay to take breaks to check the news but schedule them so they don’t take over; for example, you might decide you’ll check the news for five minutes every two hours, but nothing so momentous will happen in between that you need to check more than that. The feeling that constant vigilance will somehow help is an illusion to give yourself a sense of control, but it doesn’t actually change anything; all it does is keep you in a state of stress.

And this one isn’t work-specific, but during particularly stressful events it can help to put energy into doing the kind of good in the world that you want to see more of: help others, donate to charity, be extra kind to someone. Time is going to pass this week whether you spend it paralyzed by stress or not; you might as well choose to spend it putting good into the world.

have a question about holidays at work?

I’m doing a column for Slate answering questions about holidays at the office, and I want your questions! Maybe you’re wondering how to get out of buying gifts for all your coworkers, or you want to avoid being shafted in the Secret Santa this year, or you’re terribly afraid your boss is going to hand out nude, gold Barbies. Whatever it is, you can post your question below or email it to me at alison@askamanager.org and you may see it answered in an upcoming column.