how can I move out of working in retail?

It’s the Thursday “ask the readers” question. A reader writes:

I graduated with an MFA in fine arts several years ago and worked briefly as an adjunct after finishing school. The work was low-paying for the effort I put in and so unstable that I found myself abandoning the thought of pursuing a career in academia. I eventually got a job as a salesperson with a fashion retailer with a reputation for treating its employees well. I initially never had any plans in staying with this company, but I was encouraged to pursue a promotion and got it! After two assistant manager positions, I eventually landed a department manager position in 2018. I am grateful for everything I’ve learned during my time with this retailer and am currently working under a lovely store manager and alongside good people.

The problem is I can’t stand being in a customer-facing retail position. As an introvert, it’s the worst, most stressful part of my job. In the last two years alone, I’ve had to kick customers out for having sex in the fitting rooms or using the fitting room as their personal bathroom (eww). I’ve had to deal with entitled customers abusing salespeople or attempting to commit fraud. I’ve had to deal with a customer spouting homophobic nonsense at one of my salespeople and have been the victim of harassment a time or two myself. It’s to the point where every time I get a call for a customer issue, my heart starts pounding and I get that horrible sinking feeling in my stomach.

I’ve tried pursuing non-customer facing opportunities inside and outside of the company with no luck. Even with a resume focusing on my accomplishments and a tailored cover letter, I’ve never been invited to an interview outside of my company.

This past winter, I went to a career counselor who confirmed that retail wasn’t for me. I have many skills that I feel are transferable to other work and she guided me towards academic recruitment (combining my sales and academic experience) or executive assistant type positions. With her help I revamped my resume and made sure my cover letters explicitly linked my skills from my current position to what each job description is looking for.

And then the pandemic hit… The northeast metropolitan area I live in went from having a good job market to a terrible job market overnight, and the positions I’m applying for sometimes have over 300 applicants. I’m glad I didn’t lose my job through all of this, but dang do I feel pretty discouraged. I’m terrified that I’ll be pigeon-holed in customer service positions forever. The burn-out I’m feeling right now is affecting me in my personal life and is finally starting to seep in at work as well, despite how much of a happy façade I have.

Do you or any of your readers have any advice on escaping retail? Am I going about this the wrong way? Am I going to have to wait out the pandemic to have any sort of chance?

Readers who have successfully moved out of retail or seen others do it, what’s your advice for this letter-writer?

trainer says I need to shadow her for a year, charged vacation days during a natural disaster, and more

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

1. My trainer says I need to shadow her for a year before I can do my job

I was lucky enough to recently land a new job in an organization I’ve long wanted to work for. While a lot of the position is new to me, I have related experience that I think helped me land the job. The job is split between two departments, but with similar duties.

It’s been seven weeks now on the job. Training went really well with the first department, and I’m now doing that work independently. I know I don’t know everything, but I’m 90% comfortable in the position and I know who I can ask if I have questions. But I’m having troubles with June, the woman training me in the other department. I’m supposed to take over the position from her, while she remains in the department.

It feels more like a job shadowing than a training. June will have me watch her do certain tasks and has told me a lot of general information; she says it will take a year of this before I can take over the job. I still don’t have access to many things (budget, network drives, etc.) that I will need. She insists that I cannot go to meetings without her. She is still the email contact person for everything, so I am not even in the loop on most things happening.

I am going crazy! I feel like I am an intern, rather than a woman with over a decade of professional experience who is successfully doing the job in another department. I have tried a few times to tell her that I’d like to work independently and I’d like to move towards taking over the position, but she shuts that down and insists it will take a full year of training before I am ready. The weird thing is that she asked for a new hire because she didn’t have time to do this job. I think she doesn’t want to put the initial work in to adequately train someone and figures it is just easier to have me watch her. But I don’t want to move this slowly, and I don’t think my boss will have a high opinion of me this way either.

How do I approach this with her? I’ve thought about going behind her back to start getting the access I need, but I don’t like being underhanded. Or is this the sort of thing I should raise with my boss who just seems to care that the work is being done and doesn’t care if it’s me or June doing it? June is nice and I don’t want to burn a bridge with someone I will continue to work with; I like this job and this organization very much, but I can’t be her shadow for a year.

Some people get very, very possessive of their jobs and have a hard time relinquishing the work to someone else, even if they asked for the help.

You should talk to your boss about it! It might seem like she doesn’t care as long as the work gets done, but it’s very unlikely that she intended to hire someone who wouldn’t take over the job for a year. And if she’s a decent boss, she’ll care about it because of the impact on your morale as well.

I’d say this: “I’m done with training for Department A, and I’m doing that work independently now, which is going great. But with the B work, June has told me I’ll need to simply watch her do the work for a full year before I do the job myself. That wasn’t my understanding when I was hired, and shadowing her for a year doesn’t sound like what you had in mind when we talked earlier. Is there a way for me to move more fully into the role more quickly?”

If she seems shocked (which she should) and says she’ll talk to June (which she should), at that point you could say, “I want to make sure that raising this with you doesn’t damage my relationship with June — is there a way to navigate this that won’t cause tension with her?”

Another option if you’re worried about June’s reaction would be to skip the above and instead ask for a meeting with your boss to talk about how things are going, then let her uncover this herself during that conversation so it’s not like you went straight to her to report it … but going straight to her is also fine. This is the kind of thing managers want to know!

You also could talk with June about it first, although it sounds like you’ve tried and she’s been unreceptive. If you want, you could say, “I want to give you a heads-up that I’m going to talk to Valentina about the transition timeline since I think her intention was that I’d take on more of this work more quickly” … but you don’t need to do that, and frankly there’s a chance that a heads-up would just let her lay some kind of groundwork for arguing that this is needed.

2. Being charged vacation days during a natural disaster

I work for a mid-sized company at their office in Texas. We have been working remotely for most of the last 12 months. Last week, many of us were stuck in freezing homes with no electricity, no heat, no cellular data, and eventually no water. Today, HR advised us to use our vacation time for any days we were unable to work.

Honestly, I’m appalled. I was already planning on mentioning how disappointed I was in the response when we stayed open. Even when I did have power, I had neighbors in homes that had been unheated for more than two days and the entire state was under advisement to conserve energy. None of us should have been working those days, using power instead of conserving it.

Is there a way to approach HR about this? Should I look for a new job? This has totally reframed how I think of my work and the workplace culture.

It’s actually not terribly uncommon for companies to have people use vacation days when weather keeps them from coming to work.

But this wasn’t just bad weather. This was a massive crisis that caused widespread suffering. And this is not how you treat employees during a crisis. It’s the opposite of how an employer signals that it cares about its employees.

I wouldn’t look for a new job over it unless it’s part of a pattern of callous behavior. But I’d try pushing back with a group of coworkers to see if you can get it changed, pointing out that docking people’s already limited time off for days spent dealing with a crisis that affected so many people sends a terrible message about the company’s support for employees.

3. My boss over-praises me to higher-ups

Why does my supervisor keep over-praising me to the bigwigs? This has happened on at least two occasions. The first time was during my annual review. He praised my efforts, and, while I don’t mind him letting our bosses know how much I do, he definitely over-sells it (especially when raises and bonuses are on the line). He actually does this to his own detriment because he literally tells them that I do everything multiple times.

The first time, our big boss looked at him and said, “Well what do YOU actually do?” and I had to swoop in and give a mini speech about how we’re a team, and I couldn’t do my job without him, he’s the best supervisor I’ve ever had, yadda, yadda.

The second time was more recent. We were meeting with a different big boss, mostly to analyze how my supervisor and I have been operating our department during COVID. Throughout the meeting, he kept praising me and everything I do. I was baffled because it had nothing to do with the meeting, and I actually started feeling a little uncomfortable. The other big boss literally said, “You’re digging yourself into a hole” to him. I swooped in again and said we’re a team, I couldn’t do anything without him or his guidance, and so on.

I’m so confused as to why he does this. I don’t want to make it seem like I’m asking him to up sell me to the bosses for whatever reason. I do do a lot of work and I appreciate the recognition, but I don’t want him to throw himself under the bus for my sake.

It’s hard to say for sure! He could be worried about protecting you/his team from potential cuts (and he could have reason to be worrying about that, or he might have just decided it on his own). He could know in a general sense that managers should advocate for their people and make sure their work is visible to higher-ups and is trying to implement that without enough skill. He could just be bad at reading a room/judging what and how much is appropriate and when.

I wouldn’t worry about his bosses think that you’ve requested this; if it reflects weirdly on anyone, it’ll reflect on him, not you (because if you’d requested it, presumably he’d run that through his own filter of what’s appropriate).

4. Letting staff know they can still take mental health days during Covid

I manage a team of workers. Our organization has taken strong measures as it relates to COVID-19, which means anyone who experiences any of the various symptoms must be out of the office for a minimum of five days after they stop having symptoms and in some cases need a negative test result. We work in an industry where taking a significant amount of time off (especially unexpected time off) means a lot of catch-up when you get back in the office, so I am not worried about my staff abusing the “free vacation” or anything like that. My question is actually about the exact opposite: I know that many of us have taken a sick day in our careers when we weren’t physically sick but just needed a mental health day for whatever reason, and generally in those cases people fabricate symptoms (or just say “sick”). I am wondering how I can let my staff know that if they just need a day to reset, I’m okay with that and they don’t have to be worried that by telling me they have a headache/upset stomach/etc. they’ll be home for a week.

They’ll probably figure out wording to use that won’t trigger a one-week quarantine (“under the weather, nothing resembling Covid” would do the trick), but if you want to spell it out you could say, “I know sometimes we all just need a day off here and there to preserve our mental health. Please don’t feel you need to get into specifics in order to avoid an unnecessary quarantine — it’s fine to simply say you’re under the weather but it’s nothing on the Covid symptom list, and that’s enough for me.” You could add, “Please do make sure that it’s definitely not anything on the list though — our individual judgment about what it is or isn’t should not override the guidance from the CDC.”

5. How do I get a former client to stop contacting me for more help?

A few years ago, I did some logo work for a friend of a professional contact. Every few months since then, this guy has asked for tweaks to the design. Sometimes I charge him and sometimes, if the tweak is small, I do it quickly and send it along. However, it has been about three years since I did this work for him, and I’ve moved on from doing graphic design work and no longer have access to Photoshop or design software and have no desire to continue to do design work. I sent him all the files I had, including the Photoshop files, so he can have them and potentially hire someone else. I explained that I no longer have Photoshop.

But he continues to reach out to me. Today he said he can pay for a monthly PhotoShop subscription for me to work. I’m not sure if he means instead of paying me, as he didn’t say anything about payment for me. I’m tired of this client and want him to move on, so I can move on with my profession and my actual 9-5 career.

On a different note, but still related, he gave his sister my information to help her with a logo. She insulted my work and refused to pay for it, which soured me on the two of them a little bit, even though that was the sister, not him. It reaffirmed my decision that not working with them anymore was the right decision. However, how do I respond to his message that he wants some more color changes and is willing to pay for Photoshop? I don’t want to be rude, but also want to tell him I’m done working for him and he needs to find someone else. Help!

It’s not rude to explain you’re not longer doing that kind of work! Just like it’s not rude to explain you’re unavailable, booked up, retired, on a year-long vacation, going on the lam, or anything else that makes you not available for someone’s project. I mean, if you tried to send work to your old accountant and she told you she was actually working as a dentist now, would you think it was rude that she wouldn’t do your taxes anyway? You would not.

You can keep it very simple: “I’m not doing design work at all anymore, but there are lots of great designers out there who should be able to handle it. Sorry I can’t help, and good luck with it!” (Normally I’d suggest referring him to someone specific, but I don’t think you should do that to your contacts in this case.)

If he pushes after that: “I’m really not doing this work at all anymore. I’m focused on other commitments.”

And if he pushes after that (which would make him basically as rude as his sister), feel free to simply ignore him. You’re not tethered to this person for life just because he’s obnoxiously pushy!

my coworker doesn’t quarantine after flying all over the country

A reader writes:

My office split 60/40 working in the office versus working remotely. Due to my husband’s job in healthcare and my office’s looser adherence to health rules, I’ve continued to work from home.

One of my coworkers, who is in his early 30s, has resumed traveling for fun. A lot. He’s taken 10 trips since October, which have included long-haul flights to higher risk parts of the country and staying over at other people’s homes. He’s stated that he misses seeing people, is in generally good health, and wants to take advantage of discounted flights while there are fewer travelers. Our official office policy is to adhere to state guidelines and quarantine after trips, but that hasn’t been happening, from what I can see over Zoom. The leadership team is back in the office, at least part-time, so they must have at least some awareness of this employee’s weekend activities.

So far, I haven’t said anything when his travel plans come up in conversation. My rationale is that I’m not in the office, but seeing this person share an office (unmasked) with another coworker is a strong deterrent for me to come back. It has also made for some awkward phone calls with clients who aren’t back to “normal” when it comes to travel hearing that this employee “just got back from their neck of the woods.” Thoughts on how to best handle this?

Agh, your coworker. He wants to take advantage of discounted flights while there are fewer travelers. What a delightful member of society he is.

Here’s the good news (maybe): Your office has a policy requiring quarantining after trips. He is not following that policy. You should raise that with someone in authority.

I know you’re thinking that since the leadership team is back part-time, they must know what he’s doing … and if they’re not enforcing the quarantine rules, that must indicate they don’t care. And maybe that’s true. But very often, a rule just isn’t getting enforced because no one has pointed out the problem. Maybe they’re not paying enough attention to know if he’s quarantining or not. Maybe they assume his manager is on it. Maybe they’re thinking, “Ugh, Cecil has always been such an ass” without connecting that to “and I have the power and the obligation to do something about it.” Who knows.

But you should speak up. Talk to your manager, talk to HR, talk to whoever is best positioned in your office to act on it (which is some combination of authority and willingness and Taking Covid Seriously). Say this: “I know our policy requires quarantining at home after out-of-state trips, in line with public health advice. I’m concerned that it’s not happening — for example, Cecil was back in the office right after his recent trips to X and Y, both of which are hotspots for Covid. What can be done to ensure that policy gets followed so we don’t have an outbreak at work?”

If you feel you lack standing to say this because you’re not in the office yourself, I’d argue you do have standing. It affects you if your office has unsafe working conditions and people get sick and/or die. And you could say, “In thinking about when and how I could return to the office, this is very much on my mind.”

As for clients: If a client expresses surprise or concern about Cecil traveling, that’s something you should pass on to your manager too: “Jane at Oatmeal Emporium seemed shocked that Cecil was doing recreational travel during the pandemic, which I guess he mentioned while he was taking her order for groats this morning. How do you want me to handle that?”

It’s possible your office won’t care about any of this. You mentioned their “looser adherence to health rules” and some unmasked colleagues, so maybe they just don’t care. There’s a weird number of companies that don’t. But some do act when pressed (even ones you don’t expect to), so it’s worth raising it and finding out for sure. If it turns out they’re fine with the state of things, it’ll at least be confirmation that you need to continue to work from home.

a drunken cowboy, gingerbread house chaos, and other office contests that went badly

Last week, I asked you to share your stories of workplace contests gone awry. Here are 10 of my favorites.

1. The chili cook-off winner

Not my story but my dad’s, and it makes me laugh every time. His workplace hosts an annual chili cookoff and everyone would bring in a crockpot of their chili, put it in the kitchen, and then judging and mass chili consumption would happen at lunch.

One year, one of his coworkers brought in an empty crockpot in the morning, took a bowl of chili from every other crockpot and dumped it in his crockpot while people were working, stirred it up and called it his own chili. He ended up WINNING that year for his “depth of flavor”, and confessed after he got asked for the recipe and had no answer. Everyone wanted to riot!

2. The run-down gingerbread house

My work did a gingerbread house contest a couple years back. All the employees could vote for their favourites. Most teams spent hours on it and made really beautiful things but mine was basic and fell apart before I was done. I put a sign on it that said “for rent: $2000 per month” since the COL in my city is super high and I figured at least people would laugh even though I obviously wouldn’t win.

I was wrong because I won in a landslide despite putting in less than 30 minutes of work. Most people were good sports but some people were definitely bitter!

3. The free day off

We did Office Olympics with events like rubber band archery and seated trashcan basketball. Beer, wine, and snacks were provided, but we got into trouble with a VP pulled out some whiskey. At the end of the event, I grabbed the mic to thank the organizers and participants, and yadda, yadda, yadda… I announced that everyone would be receiving a free PTO day, which I had absolutely zero authority to give. Thankfully management made sure we all got home safe and followed through with the PTO day like it had been planned and approved.

4. The drunken cowboy

Long ago, my company had an annual Halloween parade and contest. And then there was the year that someone came in as a drunken cowboy. Problem came when a vice president who was acting as judge grabbed the bottle of Jim Beam and took a swig and found out it was real. I’m still not sure how the cowboy kept his job…but it was 15 years before we had another costume contest.

5. The steps contest

Our work has a terrible “who can walk the most steps” contest. It’s framed as a fitness thing, but it’s pretty ableist and frankly comes off not great when all of us are working from our homes, are pressured to work more hours, and a lot of folks (particularly at more junior levels) find it hard to find the time for regular exercise.

So, sorry not sorry, I attached my activity tracker to my siberian husky’s collar and am KILLING it. I’ve made my views known and no one listened, so if the doggo wins the prize will go straight to the furloughed employees assistance fund.

6. The hot sauce contest

The full story of the hot sauce eating contest, in all its horrifying glory.

On year as part of our Oktoberfest party the party organizer (Brad) decided that we would have a hot sauce eating contest. I don’t do spice, so I sat the whole thing out. The prize (singular) was an Amazon gift card.

The contest starts with maybe 20 people, a good mix of folks from all the departments in the building, sitting panel-style at the front of the big conference room. They start with some mild hot sauce served straight on a spoon, and they’re off to the races. And people start dropping out left and right as the sauces keep getting hotter and hotter, until we comes to the last two people, and the hottest sauce. This sauce is so hot that it comes with a large warning label. Brad dons a pair of nitrile gloves before even opening the box the bottle comes in. This sauce is so hot that rather than a drop on a spoon, it is presented as a tiny drop on a toothpick. (It’s called The Source.)

Both people eat it. Neither bows out. So Brad sort of stares at them and gets two more toothpicks.

Again they eat, and again neither bows out. Neither is even sweating, unlike Brad, who is looking very concerned. See, the bottle says not to ingest more than 2 drops in a day, for the sake of your esophagus.

At this point half the audience is shouting “tie tie!” in an effort to get them to stop before someone gets hurt. But then one of the bosses (who had tapped out 5 sauces earlier) shouts that there is only one prize, and to keep going. So Brad gets out the bottle again. Now the audience is in a complete uproar, with some demanding that the contestants keep going, while others insist that they stop. While the toothpicks are prepared someone shouts “I’ve got five bucks if you stop!” which starts the passing of the hat to scrounge up enough cash to balance the Amazon card.

Eventually a tie is declared and the hot sauce eating stops. One contestant threw up in the bushes on the way to his bus, and the other missed work the next day because she was up all night with GI distress.

And that was the last eating contest.

7. The IT contest

Some people shouldn’t try to manage IT departments. Case in point:

Our boss back then had a “really fun great contest” in mind to increase team morale across the various local IT departments. There were about 6 different teams he directly managed.

His plan? “The team that identifies AND fixes the most system errors in a month gets several days paid leave! And an award of whatever food they like.”

Anyone with any experience in IT or software engineering knows what happened next: the most colossal amount of service failure calls logged EVER. Heck, wander into the LAN room, disconnect a random cable and you could get 20 calls logged before you put the cable back in. Edit permissions in Active Directory!

There was 2 days of this before the boss sent round a single line email: “This was a f**king stupid idea eh?”

8. The voting cheat

My ex company (which was pretty huge at around 500 people) regularly held inter-department competitions – charity bake sales (most popular stall), staff walking count (total number of steps collated on a fitbit). As one of the smallest and least known departments, we always ranked the lowest… until one day, a colleague of mine realised the most popular stall voting sticker looked exactly the standard yellow circle sticker you can find in any stationary store. Several votes were added to our count, and for the first time in YEARS, our department won something.

(If it’s any comfort, you don’t get a prize other than a mention in the next company news letter)

9. The unfamiliar foods

At a staff picnic, we had a contest where blindfolded contestants were given various foods to guess and finish. Unfamiliar stuff like pickled eggs, sardines, huge Castelvetrano olives, caviar (the cheap stuff, not the good stuff), pickled mushrooms, etc. The staff team responsible went out of their way to serve items that our contestants would probably be unfamiliar with — that was the point. I got a whole HEAD of garlic in oil. I did not win the contest; I did not even complete the contest. I’ve often thought later how lucky they were not to serve something that would have triggered a food allergy.

10. The gingerbread chaos

One of my lovely former colleagues always had great ideas for fun contests and she outdid herself at one holiday party. The teams in this contest had 15 minutes to assemble and decorate a gingerbread house from a kit. Not too difficult, you may think. But everyone assembling and decorating had to do it wearing a blindfold. Each team was allowed one non-blindfolded member, who was allowed only to shout out instructions.

Well, I’m glad they put down a tarp first and made the participants wear plastic aprons, because I’ve never seen so many gumdrops go flying and so much icing get squirted everywhere. It was total chaos and hilarious to watch. And if you’re wondering how difficult it was, the winning house had two walls standing, one of which fell over right after the contest ended.

my employee is level 10 drama all the time

A reader writes:

I’m the assistant director for a very small company that provides vocational training. Our classes are heavily regulated by the state, and there are a number of additional rules in place due to Covid. We are doing the best we can overall, and thus far it looks like we may be able to survive the pandemic and come out on the other side.

My issue is one of my direct reports. She is intelligent and has good skills but is rapidly spiraling out of control. I’ve known her for years, before she came onboard, and she has always been melodramatic. Everything is TEN ALL THE TIME and she must always be the center of attention.

In the 18 months that she’s worked here, every cold has been cancer, every personal setback has been sabotage. She pushes back against every rule. Every safety step we take is a personal affront to her (the Lysol smells bad! the mask is stuffy!) There have been multiple times where her parent was at death’s door or her kid ran away from home or she got evicted or her car broke down or someone stole all her money (so she says) and she just … emotes all over the place, to anyone within earshot. It’s exhausting and I am losing what little remaining patience that I have, especially because these issues are really hard to believe when it’s every day.

I really try hard to be understanding and accommodating of my staff, especially in these uncertain times, but … it’s so much. And on top of that, I’m not able to give her feedback because she is holding me (and everyone else) emotionally hostage. Anything I point out, any mistake or correction, is met with tears and drama. Yesterday, when I was telling her something that needs to be fixed, she told me she might as well “just kill herself.” It seemed like a blatant guilt-trip, and I told her point-blank that I was concerned about her and want her to see her doctor because she’s very obviously not well, that we want her to be well, but we need to be able to discuss work things and work issues without worrying it’s going to send her off the deep end.

It’s a shitty feeling. I know I wasn’t as compassionate as I should have been, but (and this sounds so callous) there aren’t enough staff to do all the things we need to do when one is so completely out of touch with reality. What can I do?


It’s hard to say “have less drama in your life” to someone like this because they tend to believe the drama is all external and that they can’t help the string of Very Hair-Raising Events that happen to them … not realizing that much of it is about the way they respond to events and how much chaos they create around them (not all of it, of course— there are surely real emergencies too). And you don’t want to come across like you’re saying “have fewer bad things happen to you.”

Given that, I would focus on the pieces of this that directly affect your employee’s work. There are two obvious ones in the letter: her response to workplace rules and her response to feedback.

The next time she complains about a safety step, it’s absolutely reasonable to talk to her in private and say, “I don’t know if you realize that you frequently complain about safety steps, like X and Y. Not everything that’s required at work will be exactly to your tastes, but I need you to roll with it anyway because complaining so often creates an unpleasant environment for other people. Certainly if something is causing you a genuine problem that you need us to accommodate, come and speak with me or HR. But otherwise, I need you to just move forward with whatever the procedure is without negativity.”

And if it continues after that, the next conversation would be, “We talked about this before, but it’s still happening. It’s important to me that other people not have a regular stream of negativity or complaints in their work environment and if it continues, over time people will be reluctant to work with you. Is this something you’re up for working on?”

Her response to feedback is an even bigger problem, and one you need to address with urgency. You have to be able to give her regular, timely feedback, and she needs to be able to hear it — that’s a basic requirement for staying on your team. You can’t have someone work for you who refuses to talk about mistakes or things you’d like her to do better; it’s not an option. So, step #1 is that you have to continue giving her feedback despite her reaction to it. If she cries, you can say “Would you like me to give you a minute?” or “Would you rather resume this conversation later this afternoon?” — but you need to give the feedback and you need her to engage with it.

If you think it will help, you can try addressing the pattern itself — saying something like, “I’ve noticed that when I give you feedback on a project, you often become upset — you’ve cried and even told me you should harm yourself because I asked you to correct something. I will always need to give you feedback, and I need you to be able to engage constructively in those conversations. If you need a minute to compose yourself, that’s fine. If there’s a way I could handle those conversations differently that would be helpful for you, I’m glad to try to work with you on that. But in order for you to stay in this job, I need to be able to give you feedback on your work and have you receive it professionally.”

You might feel awkward having this conversation, but there’s no avoiding it, just like you’d also have to talk with her if she were, I don’t know, coming to work drunk. Plus, it’s actually kinder to address it directly than to avoid it, because what she’s doing will seriously hold her back in her career. It will harm her reputation and her relationships with coworkers, prevent her from moving up to higher-level positions, and make people not want to work with her. It might feel compassionate to endlessly accommodate it, but it’s kinder to be honest what she needs to change to meet some pretty basic professional expectations.

And if she continues to refuse to take feedback after that, that is a serious performance issue and you have an obligation as a manager to address it as one, just like if she were chronically missing deadlines or making repetitive errors.

The stuff about her personal life is harder to raise in a work context — but you can change the way you respond to it. If she has a new personal crisis every day, there’s a point where it’s reasonable to simply say, “That sounds rough, I’m sorry you’re dealing with it. I’ve got to jump on a call, but I hope things go well” and end the conversation. You don’t need to let her emote endlessly to you. If that sounds heartless … I don’t think it is! You’ve tried hard to be emotionally generous with her, but there are limits to what you can do that’s actually useful, and you’ve got to be able to focus on your job (and so does she).

The steps above won’t fully solve the problem but they should improve the most egregious aspects of it (and the part about feedback has to change or you can’t keep her on) and should get you to a better place than where you are now — or if they don’t, it’ll be clear that you have to take more serious steps to deal with it.

Ultimately you’re not asking her to change her personality, but you’re setting limits on what behavior is and isn’t okay at work.

my mother-in-law got a job at my company, my new coworker is someone I talked to on a dating app, and more

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

1. My pushy mother-in-law got a job at my company

Over the summer, I took a job at a new company. Last week my mother-in-law called to announce that she had also gotten a new job … at the same company. We’ll be reporting to the same grandboss, though thankfully not to the same boss.

How on earth do I handle this? I don’t think this would be ideal even under the best circumstances, but my mother-in-law can be very pushy. She really likes big events in her adult children’s lives (graduations, weddings, relocations, new babies) to be conducted according to her preferences. She struggles with boundaries, and I prefer to be as vague as possible with her about the details of my life because she can be very critical. If she had been working at this company before I started, I would not have applied for the job, but now that I’ve had it for a few months, I really don’t want to restart a job search during a pandemic. I had no idea that she was even looking, let alone that she was applying to my current employer.

Also, I’m newly pregnant! My husband and I hadn’t planned on telling either her or our employers about my pregnancy until the second trimester. I was already dreading the increase of pushiness/criticism I have seen with her other grandchildren … and now I have to work with her every day. Do you have any advice? Am I crazy for being annoyed that she applied for a job at my work without even a heads-up?

Fortunately, I will be working from home for the foreseeable future. Even before the pandemic, many of my coworkers had negotiated remote work arrangements, and I was told that my role was considered compatible with remote work once in-person people return.

Updated to add: It turns out she’s going to be working more with HR and with my direct manager than I previously anticipated. I’m not super thrilled about her potentially having access to my performance reviews and this makes me even more wary.

Yeah, this isn’t great. But the saving grace — and it’s a big one — is that you won’t be working with her in-person, because that would open the door for a lot more potential weirdness, especially after you announce your pregnancy.

And yes, it’s odd that she applied there without telling you. Maybe she applied before you announced your job there, who knows — but once it was clear you were working there, it’s surprising that she didn’t tell you. (That said, if it’s a big company and she assumed you wouldn’t have much overlap in your work, it’s less weird.)

Have you talked with your boss about your concerns? A lot of employers would take steps to ensure her work won’t overlap with yours simply because of the family connection, especially where anything HR-related is concerned. And if you explain it’s important to you to keep as much of a firewall as you realistically can, a good boss will try to help you with that or at least will be straight with you if it’s not going to be possible. (Keep in mind, too, that working with HR doesn’t necessarily mean she’ll have access to your performance reviews; it’ll depend on the specific work she’s doing.)

It could be worth talking with your mother-in-law as well. Obviously it depends on how you think that conversation would go, but in a lot of cases you could talk with a family member about keeping work and family separate, wearing work hats while you’re at work, and being conscious of not crossing boundaries despite being colleagues.

But a lot of this might be about waiting to see how it goes, and being prepared to shut down anything inappropriate when it first happens so that you’re very clear from the start. For example, if she sends you work IMs about the pregnancy, you can say, “Oh, I don’t really talk about it at work. Got to jump on a call right now, have a good day!” Breezy refusals to engage might be surprisingly effective, since when you’re remote she can’t hijack your focus in the way people can when they’re right in front of you.

2. My new coworker is someone I was talking to on a dating app last year

I am a recent college grad working my first professional job. I was hired in May, and since March the company has been working remotely with no immediate plans to return to the office. I have one specific coworker who works with me on different facets of the same projects.

Here’s my problem: this coworker and I knew each other before I started working here. A few months before I started working here, I matched with “Josh” on a dating app. We got along really well, exchanged numbers, and made plans to meet up. We texted every day for several weeks, but the day before we were supposed to get together, I called off the date. I was still getting over a bad break-up, and I was home from college at the time, so I knew I would have to go back in the next few weeks anyway. He was very understanding and kind about it, and we haven’t texted since.

When I was hired, I recalled that Josh worked for the company, but there are hundreds of employees, and I didn’t immediately see his name anywhere, so I figured he must have found another job in the meantime. Little did I know, he goes by a different, more phonetic spelling of his name at work so as not to confuse clients. So when his position changed and he joined my team last month, I was initially unaware it was him Our company-provided computers do not have cameras, so I rarely ever see my coworkers’ faces. It wasn’t until he added a profile picture to our chat software that I realized who he was.

When we communicated over the phone before I realized this, we had such a good camaraderie, but now I’m insecure about my job performance or anything I might say to him. He has not given any indication that we knew each other before, so I am wondering if he even remembers me, and I am unsure how to address the situation. I wouldn’t even bring it up, but I am still interested in him romantically. Our workplace is very young (almost everyone on my team, my supervisor included, are in their 20’s or early 30’s), and I know that workplace dating is so common that it’s a bit of an inside joke in company culture, so that part wouldn’t be taboo.

We have occasionally talked about our personal lives on work calls, but I would really like to rebuild the budding relationship we might have had. However, we do still have to work in direct contact with each other, and I am worried he no longer feels the same way about me as he did a year ago. I still have his cell phone number, but I’m too nervous to actually text him again. How can I stop feeling awkward about this? Do I bring up the fact that we’ve talked before? Do I attempt more overtly romantic overtures? Or do I just leave everything as is and hope he brings it up, or even forget about these feelings entirely?

Well, if I can give some unsolicited dating advice: I would not recommend thinking of yourself as having romantic feelings for someone you texted with for a few weeks a year ago but never met in person. Certainly some people do carry on long-term relationships before they ever meet, but when you’re talking about a few weeks of texting, it’s easy for your mind to fill in the blanks about what the person is really like and you can end up invested in an idea of someone that doesn’t match the reality. (This was in fact the cardinal rule of online dating from the dating advice blog I used to run years and years ago in my youth.)

Of course, you do know him better now from your work calls! All I’m saying is, don’t put too much weight on the texting from last year.

Anyway. Back to this blog. Don’t attempt an overly romantic gesture with a coworker. Work just isn’t the place for that. But you could say something like, “I just realized we texted each other for a few weeks about a year ago, before I working here, and didn’t meet up because I was about to go back to college. If you ever want to have that drink, let me know! But just continuing to discuss the Jones account is good too, of course.” I wouldn’t say this on one of your calls since that puts him on the spot and requires an immediate answer; an asynchronous method like email or text would be better. And of course, you’ve got to be prepared for a no (which could be because he doesn’t want to pursue anything with a colleague/isn’t dating right now/has a partner/lost interest) so don’t say it unless you trust yourself not to make things tense or weird if that happens, especially since you’ll have to keep having contact with him.

3. I’m bombarded with requests for my time, despite having created a bunch of resources to answer questions

I’m a very well-known entrepreneur in a very popular field in my area. As it prospered during the COVID era, there are more and more people wishing to switch into this field every day. I consider this a great thing, and I have made myself very helpful and approachable – I have created informative brochures, Facebook groups, held lectures to college students interested in this field, etc., etc.

But lately, it’s getting SO exhausting. People are constantly emailing me with questions that could easily be found in absolutely any of the free materials that I have created; they are asking for “quick” phone calls to get information, and it’s even spreading and it’s really starting to take a toll on my time and mental health.

I don’t know how to stop. I very much value my work and my approachability and it has so far resulted in some great business opportunities, but it is not possible to continue this way. Still, I feel very, very rude for saying no or pointing to a brochure. Any advice on how to stop without feeling awful?

It’s absolutely okay — and often necessary — to put limits on how you spend your time, which for well-known and/or busy people often means saying no to requests. It’s not rude to do that! I mean, it’s possible to do it in a rude way, of course, but you don’t sound like you’re at risk of that.

What many people do is have a kind of form letter response that they can copy and paste,  modifying as needed to fit the situation. For example: “I’m really encouraged to see the growing interest in the X field! My schedule means that I can’t say yes to every meeting request I receive or I would never get to see my family, but because I get a lot of queries like this I’ve created materials that answer the most common questions I hear. (Link to resources.) I hope that helps, and good luck!”

More here and here.

4. We’re hiring someone else with my job title — what does it mean for me?

This week my boss announced they would be hiring someone with the same job title as me. They didn’t use descriptive words like “additional” or “replacement” so I don’t know what this means for me. I’ve been struggling lately and I guess I was shocked by this announcement since I had not heard anything about it, despite being very honest with my challenges. Do you think this is a bad sign or just an oversight and I should be thankful?

You can ask! I’d say it this way: “I wanted to ask about the search for another rice sculptor. When this person is hired, will that change anything about my role?”

It’s possible this is an additional person to take on some of the work, or it’s possible they’ll have totally different projects than you. It’s also possible they’re looking for a replacement in case you don’t work out, since you’ve been struggling. A decent organization wouldn’t do it this way, without talking to you about it, but it’s not impossible. Asking about how the role will intersect with yours will get you more info. (If they’re seeing this person as a possible replacement for you and they’re shady, they won’t necessarily tell you that — but you’ll still get some insight from raising the question.

5. Mentioning personal adversity in a cover letter

I’m a recent grad on the job hunt so I’ve been writing tons of cover letters. Some of the organizations I’m applying for are nonprofits that deal with poverty and surrounding issues. One of the reasons I’m interested in the work they do is due to family history — specifically growing up in an immigrant family that experienced poverty (fortunately, that time in our lives has now passed). In a few cover letters, I have mentioned this personal experience as part of explaining why I’m interested in the work. I’m wondering what your take is on this, in terms of if it’s appropriate to spend time in a cover letter discussing personal adversity as it is related to the organization’s work, or if that’s seen as too personal or something? This kind of thing totally flies in college applications, but I’ m not as sure for job applications.

For nonprofits, it’s really common for cover letters to say something personal about why the person connects to the organization’s mission. Don’t spend a ton of time on it — most of your letter should still be about why you’d do a great job in the role — but one to three sentences, absolutely.

Even outside of nonprofits, there can be room for it if you’re applying to do work that is in some way connected to a social mission or working with a specific population or so forth.

how can I convince my employee not to work until 2 AM?

A reader writes:

I am a manager who has a great team and several high-performing employees. We are all working from home these days due to COVID. One of my employees in particular will often stay up late into the night working on assignments I have given her. I know this because she will send me emails at 1 or 2 in the morning with updates on her work. (We are all exempt and on salary so overtime pay is not an issue here.)

She is producing high-quality work and I have no issues with her work performance. Because she works so hard on projects, they often come in well before deadlines as well. My sense is that she does this because she finds the work interesting and engaging and doesn’t want to stop. But I worry that she is going to get burned out by working such late hours, and also that other employees on my team will see her working so late and wonder if they are expected to do so as well. (I have tried to address this directly with my other employees and told them that it’s not what I expect.)

I’ve tried to tell her many times in our one-on-one meetings that she doesn’t need to work that late and that I don’t expect her to do so, but it doesn’t seem to stop her. I really don’t want to make this into a formal performance issue either. Do you have any suggestions on how to “convince” her not to work so hard?

Well, you can talk to her about the importance of pacing herself so she doesn’t burn out — it’s a marathon, not a sprint, etc. etc. Explain you care about her being able to do the work well long-term, not just doing a lot of it in the short-term.

But given everyone’s situation right now with pandemic stress and being trapped at home … I wouldn’t press too hard. This might be how she’s coping. You don’t want to push her to stop doing something that might feel like a lifeline right now.

It’s also possible that she’s working late at night because she’s working less during the daytime — either because her current life necessitates that (like if she has to oversee her kids’ online schooling during the day) or because she simply prefers it. If that’s the case, you shouldn’t force her back into a more traditional schedule if this one works just fine.

But you’re right to worry about the message her late-night emails could send to colleagues. It was wise to tell your other staff members directly that you don’t expect that … but I’d also think about suggesting that she hold her emails until the next work day. She can write them at 2 a.m. if she wants, but schedule them to go out the following morning (or just save them as drafts until then if her email program doesn’t let her schedule them). I know it feels a little odd to be like “disguise how hard you are working” but that wouldn’t be the message. You’d frame it as, “You and I both know you’re working these hours because they work well for you, but when people see others doing this, it can make them feel like they’re expected to be checking email at all hours.” If she manages people, you definitely need to say this — but either way, you can frame it as being thoughtful about what signals she might otherwise inadvertently send.

I do think there’s a weird thing going on right now where many people suddenly have a lot more flexibility in the hours they work. For some people that sucks — it’s because school and child care is still in such disarray that working odd hours is their only option, or boundaries between work and home have been blurred so much that it feels like work never ends. But other people have found a real freedom in being able to manage their own schedules in ways that weren’t as common pre-pandemic. Obviously that’s not happening in all jobs, but there’s more of it going on than there used to be. It’ll be interesting to see if it becomes a lasting change. (If it does, it’ll almost certainly be both good and bad — good because more freedom is generally good, but bad because it’ll undoubtedly add to the already mounting pressure some people face to be available all the time.)

I got promoted, but I can’t get a fair salary

A reader writes:

I was hired as an entry-level, salaried employee five years ago. After less than a year, a new position was created for me – not a promotion or lateral move, but an entirely new position, one with a different expertise. The salary for my original position was average, and my salary adjustment when I was moved to the new position (one I wanted and helped create!) was a 22% increase. Had they paid me the average salary for the position, it would have been closer to a 100% increase.

When I questioned the rationale behind the new salary and explained that the average for this position is significantly higher, I was told I had received “a significant raise” and could not be given a larger one.

If they had hired for the position from the outside rather than promoting me into it, there’s no way they would have offered the salary I was given for it. It’s a highly-paid field and I’m making peanuts, comparatively. (That said, I have no interest in leaving my workplace; I intend to stay there for a very long time and while the money isn’t everything, it is still something.)

I was later approached by a recruiter to take the same job at a competitor where I would have been paid above the average for this kind of work. I turned it down because it was a toxic workplace, but I did use their offer to eke another 20% out of my employer. But, still: I’m severely underpaid compared to what I could be paid anywhere else.

It seems that I’m being penalized, unintentional as it may be, because they hired from within, and they’re looking at the position shift I made as a step up the ladder of that role, but my previous position would never lead to the one I’m now in; they’re completely unrelated positions! Any advice on how to navigate this in a way that doesn’t make me look like I’m ungrateful or making an absurd request to push my salary significantly higher? I just want to be paid fairly!

You can read my answer to this letter at New York Magazine today. Head over there to read it.

our staff aren’t underpaid but think they are

A reader writes:

I work at a nonprofit with about 200 staff. Staff constantly bring up how underpaid they are and ask for bonuses, cost-of-living increases, better benefits, everything. They take up a lot of meeting time talking about it, send all-staff emails, badger the board, send nasty emails to any committee that has anything to do with money, and get angry at the person who cuts the paychecks. It’s not everybody, but might border on 50% of staff who are adamant that we are underpaid.

But our staff is very well-paid by market comparators. Our HR department commissioned a report from the most capable local compensation consultants, and they found that our staff are among the highest-paid employees in their job categories in our region (and, I should point out, these are professional jobs that are decently-paid to begin with). They literally would take a pay cut if they went and did this job at any other organization, whether private sector, government, or nonprofit. Employee response? The report was rigged.

W are given regular increases, every year there is a bump to pay scales, there are benefit improvements all the time, and our leadership has been fantastic during COVID. None of this seems to satisfy a vocal group of staff. Another factor is that because we are nonprofit, we cannot have salaries that are too high or we risk being de-incorporated by the government (the government in our region has shown that they will do this). Staff know this, but the griping continues, constant and mean. It is poisoning our entire workplace.

Because of some weird things about our structure and the overall culture of our organization (if you try to get people to stop using all-staff email, for example, there will be an outcry about quashing dissent), I think the only tool we have here is communication. I think our leaders need to convince people that we are well-paid and the regular increases are enough to keep us that way. Looking at facts and figures doesn’t seem to be doing anything. How do we convince people that they’ve got a pretty sweet deal?

I don’t know that you should spend a lot of time trying to convince them, on top of the time and effort you’ve already invested. You’ve given them the info. They don’t believe you. And they’re poisoning your culture. You’re probably better off being really clear about what will and won’t happen and encouraging people to make their employment decisions accordingly.

Before I go any further, I need to give a caveat: I’m taking you at your word that your staff are paid well. It’s not necessarily the case that they’re paid well just because they would earn less everywhere else, because there are jobs that are systemically underpaid everywhere. But for the purpose of this answer, I’m going to assume they’re earning at least a living wage and presumably above that.

Okay. So what is going on here? What you describe is so unusual — “constant and mean griping,” along with hassling people who have no power over their pay, and a set of beliefs so fully at odds with what the facts seem to be — that I’ve got to think something else is going on. There are some hints in your letter of other culture problems, and I’d bet money that your organization has some serious work to do on its culture in general.

It’s good to have a culture where people feel comfortable raising issues, but what you’re describing — the “constant and mean griping,” the nasty emails, the anger and badgering — is not a functioning, healthy organization. Dissent is good! People feeling comfortable pushing back is good! Ongoing meanness is not.

So I don’t think you can solve this without taking a bigger look at whatever’s going on with your culture. And because of that, I’m hesitant to offer advice on addressing just the pay piece of things, because I don’t think that on its own will address whatever is really going on.

That said, you can certainly lay out everything you’ve done to assess your organization’s pay and how you’ve reached the conclusions you’ve reached. You can say that if anyone wants to bring you additional research that tells a different story, you’ll be happy to take a look at it (and mean that).

And from there, you can set limits on what behavior is and isn’t okay. You can’t just say “stop talking about pay” — that’s terrible from a PR, morale, and management standpoint, and it’s also likely to violate the National Labor Relations Act (depending on the specifics of how you implement it). But you can put your foot down about spending significant meeting time on it, badgering the board, sending nasty emails, or being rude to the person who cuts the paychecks.

You also can say that you want to be really clear about what the organization can and can’t offer for salaries and what will and won’t be happening in the future, so that people can make the right decisions for themselves. And you can say that you fully support people who are unhappy with their pay in leaving for better opportunites. When you say that, it shouldn’t sound like “there’s the door” but rather a genuinely supportive, “We’ve considered this from many angles and want to be transparent that our salary structures will not change. Please give some thought to whether that will work for you, and if it doesn’t, we understand and we’ll do whatever we can to support you in finding another position at a different organization. But we can’t continue discussing it over and over. It’s become a distraction to our work, so we need you to decide if this will work for you or not.” And then you enforce that the same way you enforce any other work standard; you have to mean it and you have to be willing to follow through if the behavior continues.

But something else is going on there.

what are you wearing on work Zoom calls these days?

This post is sponsored by thredUP.

So, what are you wearing on Zoom calls for work these days?

For a very short time at the beginning of the pandemic, a lot of people on video calls were mirroring what they’d wear in the office – at least from the waist up. And then a lot of people went way in the other direction for a while – sweats, hoodies, even pajamas. Now at least some of us have swung back to somewhere in the middle – comfortable clothes that still roughly qualify as business casual, at least through a camera.

I was interested to see what a personal shopper might suggest for work video calls these days, so I asked the lovely people at thredUP to put together some clothes for Zoom calls for me.

If you don’t know them already, thredUP is the largest online thrift store that buys and sells high-quality clothing for women and kids. You can shop on-trend, like-new fashion from top name brands and designers for up to 90% off estimated retail. (That’s not a typo – it’s 90%, which is an enormous discount.) They have a massive selection, with brands like Anthropologie, Ann Taylor, Banana Republic, Theory, J.Crew, and more.

In addition to offering regular shopping, thredUP also offers Goody Boxes, which is a personalized shopping service. You explain what you’re looking for and fill out a style quiz that asks you questions like what colors you do and don’t like, how you prefer items to fit (fitted, looser, etc.), how you feel about things like animal print and ruffles, and lots more. You pay a $10 deposit which goes toward anything you decide to keep, and they send you a personalized box of 10 thrifted items picked by their stylists to match your size, style, and budget. You only pay for what you keep and return the rest (with no charge for return shipping). And it’s not a subscription so you’re not locked in; you can just do it one time if you want.

It’s pretty nice to just explain what I want and then sit back and let someone else dress me! If you’d like to try it yourself, click here to order your first Goody Box today!

When I ordered my box, I said I was looking for items with some visual interest that were still work appropriate. I asked for blues, greens, and other darker colors, and said I wanted to avoid orange, yellow, black, and white (limited colors is the redhead curse), and no animal prints, logos, or ruffles. They stuck to that! I’m keeping most of what was in my box, including a very cute Boden dress that I will wear on calls when I need to disguise myself as more professional than I actually am. (Returning the rest is easy with their free shipping label.)

Here’s some of what I’m keeping.

If you’d like to try it out yourself, click here to order your first Goody Box today!

Disclosure: This post is sponsored by thredUP. All thoughts and opinions are my own.