weekend open thread – October 31-November 1, 2020

Here are the rules for the weekend posts.

Book recommendation of the week: The Smart One, by Jennifer Close. A tale of two sisters who both find themselves living back at home, their lives not working out as they’d planned.

* I make a commission if you use that Amazon link.

a Halloween round-up

Halloween 2020 is not a normal Halloween, so here’s a round-up of Halloween posts from years past.

should I wear a Halloween costume my first week at a new job?

my office’s “kid-friendly” Halloween party was terrifying

my boss goes overboard for Halloween

I live where I work, and now there’s a haunted house next to me

our office may be haunted — how do I keep it from distracting from our work?

my employee sent a memo to management about ghosts in the building

I’m in trouble for being too tired to work the day after Halloween

my employee got fired for wearing a Halloween costume to work … and trick-or-treating in an important meeting

my piece for Slate on Halloween do’s and don’ts

a special Halloween episode of the Ask a Manager podcast (from 2018 — with stories of people’s spooky experiences at work, including voices when no one is there, a creepily laughing doll, a fired guy’s ghostly revenge, and more)

And if you still need more, here’s last year’s post where people shared spooky things that have happened to them at work.

it’s your Friday good news

It’s your Friday good news, with more accounts of success even in this weird time.

1. About a year ago, I took a new stretch role at my current company in a different department. This job came with significantly more responsibility (both managerial and otherwise), a nice step up in pay, and work that sounded like an interesting way to expand my skills. For reasons that are too numerous to get into here, almost right away I started to sense taking this new role was a mistake. But I promised myself I’d give it a fair shot and at least stick it out long enough to get over the initial learning curve, work to change things, and then reassess.

Despite my best efforts to improve the situation by managing up and across (and of course down, though that wasn’t the source of my concern), the situation only grew worse and the job developed into a significant source of stress in my life. I stuck it out longer than I otherwise might have due to general Covid uncertainty, but as I felt myself recently becoming disengaged in and discouraged about the work I am doing, I decided enough was enough. I brushed up my resume and wrote targeted cover letters explaining my desired career shift (using your advice of course!) and applied to a few openings that needed my technical skills over managerial. I accepted that I’d likely have to take less money for more enjoyable work.

This week, I accepted an offer for a technical/individual contributor role at another company! I haven’t been able to give notice yet as I’m still waiting on the offer contingencies to clear, but I already feel a huge sense of relief and excitement about the new role! On paper it looks like the new job is a step down from my current one, but I’m certain it’s the right choice for me at this time in my life. The icing on the cake is that I’ll actually make more than what I do now, and they’re even throwing in a sign on bonus! I had set myself up for a false choice between money and enjoyable work- but it turns out I can have both.

My advice to anyone else in a similar spot- prioritize yourself and choose what makes you happy, even if it’s not a conventional choice. I’m a Type A “fixer” by nature and I had more loyalty to my current company than was good for me. I was also a bit hesitant to step off the fast track I’ve been on, even though I knew in my heart it was making me miserable. But in hindsight I should have done this so much sooner. It’s ok to try something that doesn’t work. It’s ok to opt out and move on. Be kind to yourself.

2. Thanks to advice from your blog, I jumped from the public to private sector in a significant career jump, negotiated pay, time off between jobs, and increased vacation days. That’s not something I’ve ever had to do in the public sphere and I would have caved with the minor pushback I initially received had I not been as well equipped thanks to you.

But more than that, reading Ask a Manager for so long has helped me understand how interviewing is a two way street and that I really need to suss out what the culture and management style of an organization. I’ve struggled a lot with feeling like I have to warp myself too much to fit into company culture, but I made a concentrated effort to toss that mindset aside. The honesty and forthrightness helped me land the job and feel excited about starting it.

3. Long time reader writing to say thank you for all the advice and entertainment I’ve gotten from your site over the years. I have accepted an offer for a new job with a 50% pay increase! I was determined this was going to be the salary I negotiated on but they came straight in at the top of their advertised range. I don’t think this would have been possible if I had anchored the negotiations to my current salary and your language for declining to disclose this was immensely helpful.

So, thank you to you and the commenters for all their advice. I’ll definitely keep checking daily, but first I’m going to enjoy a nice break between positions to do a whole lot of nothing.

4. The pandemic has not been easy for my husband and I. I found out I was pregnant right when the pandemic hit, and the pandemic has made my job very difficult and probably emotionally unsustainable. My husband was laid off from his in July, making matters worse, and he has a kind of niche set of skills and unusual background and the job market where we live is very competitive, so has endured multiple long and grueling job searches in the recent past already. He wasn’t happy where he was, but with a baby on the way and my job feeling tenuous we needed stability. We set ourselves up physiologically for another long and demoralizing search on top of pandemic and new-parent anxiety, but he has perused a lot of your advice before, so he was at least ready this time, and after just three months he landed a job interview at a great local company with great benefits and culture, and a lot of opportunity for growth. It was the kind of interview he’d never landed before, almost too good to be true. Well, he heard back that he got the job this week! And since, as irony would have it, of *course* they wanted him to start right around my due date, he used your advice to negotiate a flexible start date two weeks after whenever the baby is born (which could be any time now.)

5. I wanted to write in to share a little good news of my own since these weekly posts have been really lovely to read. But first of all, I want to say thank you for all the extremely helpful advice you’ve given your readers over the years! I’ve been reading for a long time, and your website has really helped me navigate things in my work life. A few years ago, I decided to switch careers – I pursued a niche performing arts degree, decided not to pursue it professionally, then felt extremely lost and took a job I didn’t like until I figured out what I wanted to do, which turned out to take a few more years than I expected. I eventually realized I really didn’t want to be doing what I was doing, so I decided to re-train and enroll in a part-time program to learn a new skill. I eventually left the job I hated to finish up some classes and start freelancing full-time last year. It’s been rewarding but very, very hard.

I learned that freelancing is not great for me, but there are very few full-time positions in my new field so I thought I didn’t really have a choice. However, a great full-time opportunity recently came up, so I applied even though I never thought I would get the job. But I did! I just started my new position, and I’ve now successfully transitioned into a full-time job in my new field! I’m thrilled, and it feels pretty surreal. Ask a Manager has been so helpful throughout this journey, and I can’t thank you enough.

open thread – October 30-31, 2020

It’s the Friday open thread! The comment section on this post is open for discussion with other readers on anything work-related that you want to talk about (that includes school). If you want an answer from me, emailing me is still your best bet*, but this is a chance to talk to other readers.

* If you submitted a question to me recently, please do not repost it here, as it may be in my queue to answer.

giving people a heads-up before a coworker is fired, telling your boss he’s unapproachable, and more

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

1. Is it okay to give people a heads-up before a colleague is fired?

I am working with HR to let someone go. The person is directly involved in a number of active cross-functional projects.

Typically terminations in our organization are communicated post-event, but I feel a bit like I will be blindsiding several team members. The termination shouldn’t be a major surprise as this individual has had performance issues, including interpersonal issues.

Would you ever recommend giving select team members — potentially managers and project managers — a heads-up that this event is coming so they can somewhat prepare? I thought about communicating it vaguely, e.g. “change is coming that may affect this project,” but that would just create more confusion and paranoia. Or, do I just sit tight and deal with the teams after the deed is done?

As long as you trust the people you’re talking with to be discreet and not share what you tell them with others, you should be able to give a confidential heads-up to managers and project managers when there’s a real need to know. I’d try to avoid sharing it with peers of the person but sometimes it’s unavoidable, depending on the details of the situation — but keep the number of people you discuss it with to a minimum and on a truly need-to-know basis. And ideally this heads-up would be within days of the firing happening — you don’t want colleagues knowing for weeks when that person doesn’t know themselves. (And really, once you know for sure you’ll be letting someone go, you should do it quickly anyway, not let it drag out.)

2. Telling your boss he’s unapproachable

Due to COVID, our company had to lay off some people, and re-org those remaining. I was on a team that got re-orged; as a result, another teammate and I were split from our really great manager, Tom, and given to a totally new one who is the polar opposite personality-wise, Brad. While Tom was very warm, supportive, and easy to talk with, Brad has an overall demeanor that is best described as very serious/intense bordering on cold. He’s not a malicious person, but he’s not someone you ever feel comfortable around. I’m always relieved when our one-on-ones are over.

I have occasional skip-level meetings with his boss and indicated that I found Brad to be rather unapproachable. Next thing I knew, in my next one-on-one with Brad, he asked me point-blank if I found him unapproachable or difficult to bring issues to (the answers being “yes” and “yes”). I was so uncomfortable and basically stuttered for a bit until he moved on. I’m also irritated that his boss clearly told Brad I’d said this. I never specifically said it should be confidential but I guess I assumed that was common sense to at least anonymize the feedback or something.

I’m struggling with how to approach this. I am usually a fairly forthcoming employee overall, and am comfortable giving more concrete feedback like “When you changed that deadline to X, it made it harder for me to do Y” or whatever. But this feels more personal, like attacking the person instead of the work. How do you give actionable feedback on soft skills? Also, is this even my job to deliver it?

Nah, it’s not your job to tell an unapproachable manager that you find them unapproachable. It’s useful if you can, but it’s also the kind of feedback that his own manager should be delivering, and without pinning it on specific people. So his boss messed this up.

Now that it’s out there, though, it might be useful to revisit it in a future one-on-one and say something like, “You asked me earlier about whether I found you hard to bring issues to. I was caught off-guard when you asked, but having had some time to think it over, I do find it difficult to raise some things with you because ____. I feel awkward giving that feedback, but I also didn’t want to ignore the question since you’d asked about it.” Obviously, temper this advice with what you know of Brad; if you think he’d react badly, skip it. But there can be value in having this kind of open discussion if you’re up for it and don’t think you’ll be penalized in some way. And some managers who fit Brad’s description genuinely don’t know they’re putting people off and can become better managers from hearing it. But again, it’s not your job if you’d rather not take it on.

3. In which I am stumped

I’m a newly-promoted manager (yay!), and AAM has been a great resource for me during the last couple months of learning to manage. Lately, I often find myself thinking up resolutions to various scenarios so I can try to be prepared in unexpected or outlandish situations. I’m interested in your take on how to professionally handle something that’s stumped me.

A few jobs ago, I had a coworker with severe priapism (persistent erections not caused by sexual stimulation). He always carried a doctor’s note with him and was extremely open about his condition; usually whenever we had a new hire, he’d take that person aside and explain that if they ever noticed anything, it wasn’t personal. It was a very small company, and since he was a genuinely nice guy, there was never any trouble there.

But it got me thinking on how to navigate something like that if someone with this condition wanted to keep their health private (as would be their right), and a coworker complained of sexual harassment. What could be done then?

Wow, I have no idea! You’ve stumped me. If I were the employer in this situation, I’d consult with a lawyer. But I’d imagine it’s easier to handle it internally within an office; it would be much harder more difficult if the person had a job that required him to deal with various members of the public on a regular basis.

4. Application systems that won’t accept a cover letter

I know the importance of cover letters from your blog, and also because for me in particular, I have a wide variety of experience and it helps me explain which aspects are aligned with the job I’m applying for. However, I recently applied for a job at a major media organization, and the online application system didn’t seem to have a way to attach a cover letter. There was only space for one file (resume), and I kept thinking throughout the process that there might be a place at the end to attach more documents, but of course, you don’t know that for sure until you’ve completed the entire application process. I even paged back through to see if I missed something – I didn’t.

Is this some kind of new normal? If so, and sometimes you don’t get to submit a cover letter (but you don’t actually know that you won’t be submitting one until you’ve completed the process), how do I explain how my experience aligns with the particular job I’m applying for? I thought about PDFing the cover letter and resume together and attaching that as my file, but the system parses your resume into individual jobs. Also, if you later apply for a different job at the same organization, the cover letter would be wrong since it would be for the first job you applied for.

It’s not really a new normal; there have always been employers who just don’t care about cover letters and don’t set up their systems to invite them.

Sometimes when this happens, you can just include a cover letter in the same PDF as your resume, and that’s the best way to handle it. But when there’s no way to do that, that’s a clear sign that this employer doesn’t want cover letters — and if that’s the case, you’ve just got to work with that. It does mean you won’t be able to explain the things a cover letter would let you elaborate on, but that’s the weird choice those employers are making. (I say weird, but certainly some managers simply don’t care about cover letters. I think that’s a mistake for most jobs, but they’re out there.)

5. Can I tell interviewers I’m leaving my job because of how they’ve handled Covid?

Part of the reason I’m job searching is that my management team is getting very antsy about getting us all back in the office. Our CEO is old school and hated the idea of letting us work from home to begin with.

In the event a hiring manager asks my reason for leaving, is this a bad answer? In general, I try to avoid badmouthing any of my previous employers in response to this question. Is there a good way to answer the question to this effect? I imagine discussion of precautions going into a new job is inevitable, but I’m concerned about framing that conversation coming from this angle.

I wouldn’t get into all the details (like that the CEO is old school or hated remote work — ultimately that stuff isn’t the point) but it’s fine to say something like, “My office is reopening faster than I think is safe for our area, and I’m looking at employers that are taking a different approach to the pandemic.” Of course, that will likely screen out employers that are doing the same thing as your current one — but you presumably want to do that anyway.

how to negotiate remote work once you get a job offer

A reader writes:

I completed final interviews for a fantastic job and I believe I have a good chance of getting an offer soon.

My conundrum has to do with remote work: when people return to the office post-COVID, my commute would be more than an hour each way. This is not possible for me to do very often.

During the final interview, I casually asked the hiring manager about their remote work culture in non-COVID times. She replied, “Work from home is fine sometimes, but not all the time.” I didn’t want to press at that stage, so I didn’t find out what “sometimes” means to her.

This is an individual contributor role, the work can easily be done remotely, and another of this manager’s direct reports works remotely full-time from another state. Also, presumably I’d spend the first six months or so working remotely due to COVID, so I’d have that time to prove myself as a remote worker. And I have worked remotely full time in all of my past jobs and have been continuously praised for my work quality, speed, responsiveness, and dependability.

If I do get an offer, I’d like to focus my negotiation not on salary or vacation time, but on the ability to work from home most of the time. Can you give me an idea of what language to use when I ask? How much of the above context should I include to back up my request? Also, would it help to include options, such as “I’d be open to either working in the office one day a week, or one week a month — whichever you prefer”?

This is the language I’m considering: “I’m really interested in the work, but the commute is giving me some hesitation. Would you be open to allowing me to work remotely, post-COVID? I’d love to come into the office once a week, or one week a month — whichever you prefer. I have worked remotely full time in all of my past jobs and have been continuously praised for my work quality, speed, responsiveness, and dependability. I would agree to make any long-term work-from-home arrangement contingent on my performance as a remote worker during my first six months in the role. If you’re able to allow a remote work arrangement, I’d be thrilled to take the job.”

If I can’t convince them to agree, I’ll have to walk away from the offer, so getting this right is very important to me.

Your proposed language is good!

It’s smart, too, that you’re addressing this head-on, not hoping it’ll somehow work itself out after you’re hired. With so many positions having become temporarily remote, I’ve heard from a lot of people who are considering taking a remote-for-now job without disclosing that they’d want to remain remote long-term and instead are just hoping/assuming it’ll be allowed once the office reopens. In some cases, that might work! But in others it won’t, and it’s dangerous to count on it. Plenty of employers will bring people back at some point, and while we probably won’t see quite as much opposition to remote work as we saw in the past, there will still be managers who want people in-person. (And sometimes that’s legitimate! You can’t always tell before you start a job how challenging it really might be to do the role fully from home.)

When working from home is a nice-to-have perk but you’d still take the job without it, sometimes it can make sense to just see how things go — demonstrate that you work well remotely and then try to negotiate continued remote work later on. But when it’s a deal-breaker for you — as it is in your case — it’s smart to address it directly during the offer negotiation and try to come to a clear agreement.

Your proposed language is good because it covers these bases:
– You explain why you’d like to stay remote (the commute).
– You offer to come in sometimes, and you’re specific about what that could mean.
– You’re clear that you’ve done it successfully in the past.
– You offer to make the arrangement contingent on performance (which it likely would be anyway, but spelling it out signals you’re comfortable with explicitly linking the two, and that you’re likely someone who at least strives to be conscientious).
– You make it clear that if they say yes to this, you’ll accept the job — they don’t need to worry that you’re going to try to negotiate for a bunch of other things they don’t know about yet.

Do be aware that, assuming you don’t have a contract (most U.S. workers don’t), whatever is agreed to won’t necessarily be binding. The employer can change their minds in the future or a new manager can come in who doesn’t like remote work or so forth. But having a written agreement significantly strengthens the likelihood of an employer sticking to it; if nothing else, it avoids mistakes and misunderstandings and people forgetting conversations a year later.

Good luck!

where are you now? (a call for updates)

At the end of each year, I publish a slew of “where are they now” updates from people whose questions I answered here in the past. In past years we’ve had several hundred each December and it was amazing (and has let me take most of the month off, so thank you).

If you’ve had your question answered here in the past, please email me an update and let us know how your situation turned out. Did you take the advice? Did you not take the advice? What happened? How’s your situation now?  (Don’t post your updates here though; email them to me.)

Note: Your update doesn’t have to be positive or big to be worth submitting. We want to hear them all, even if you don’t think yours is that interesting.

And if there’s anyone you especially want to hear an update from, mention it here and I’ll reach out to those people directly.

what’s the most Machiavellian thing you’ve seen or done at work?

We need a distraction, preferably one full of intrigue and drama. So let’s talk about the most Machiavellian thing you’ve ever seen done at work — self-serving schemes or manipulation that you watched being carried out (or carried out yourself!). We’re looking for stories of underhanded machinations, double-dealing, and conniving.

Share in the comments!

taking work calls on my honeymoon, traveling after graduating, and more

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

1. Do I really need to take calls from work on my honeymoon?

I’m getting married this weekend! Yay! I’m taking two weeks off for the honeymoon. The original plan was to go to Hawaii, but due to the times, we are staying put. I thought about cancelling or shortening the time off, but I decided that I had few enough opportunities to celebrate so I needed to take advantage of the one thing this year that is an absolute good in my life.

However, some big changes are looming at my company that’s all very hush hush right now. I only know because of my position. I wear a lot of hats at work (small company) — IT, budgets, office management, contracts, vendor management, marketing, etc. I am very involved in this hush hush big change, and I know that things can’t just be put on hold because I’m not there.

I’ve done everything I can to prepare for the two weeks: given account access to other senior people, written up detailed documentation, talked through items that might occur until I’m blue in the face, etc. But my boss is not satisfied. She wants me to promise I would be available if “something came up.”

I’m going to be on my HONEYMOON! I have had this time off planned and approved since January! I have been struggling this whole year (started working with a therapist and was prescribed antidepressants because my mental health was deteriorating), and I really want to unplug and recharge. But with everything going on with the business, I don’t know how hard of a line I can draw. All information that would be needed is filed so those with access can see it, so I am not needed to actually access any info, but I am likely to know more easily and quickly what that info is or where it’s located or which vendor to reach out to.

Do I tell her that if it’s an emergency they can text, and I’ll get back when I can? Do I say I won’t be available at all? If I were going to Hawaii as planned, I really would be more out of touch, but it’s harder to convince people when you’re staying home.

You’re going on your honeymoon and the time off has been approved since January. Say you won’t be available at all. If it helps it go down easier, say you and your fiancé have promised each other for months that you’ll turn off all devices and be unavailable during this time. (You shouldn’t have to say that, but sometimes that kind of thing can help.) You can also say if it were anything other than your honeymoon you’d find a way to be flexible but it’s not possible for this.

If you anticipate a lot of pushback, it might be more effective to be vaguer: “I can’t promise anything, we’ll probably have our phones off most of the time…” and then keep yourself unavailable. Change your outgoing voicemail message to say, “I’m on my honeymoon and unavailable until (date) and will get back to you then.” And then just don’t respond.

This doesn’t sound like a situation where you’re the only one who could help in an emergency; it sounds like it would just save them some time and energy, and that doesn’t meet the bar for making you work on your honeymoon.

2. Traveling after graduating

I am a third year college student and I’ve been reading your blog for years. It’s helped me avoid bad resume advice and feel a lot less anxious about the world after I finish school. Right now I have a more long-term question. I am very disappointed that I will be unable to study abroad due to the pandemic. I had been looking forward to it for years. However, now I have the opportunity to graduate a semester early. I am considering using the savings I had set aside to study abroad to travel instead for a few months after I graduate (assuming it’s safe by then). My parents are concerned that having any period of time between when I graduate and when I start working will be a blemish on my resume that I will have to explain for the rest of my life. I understand that if I waited to travel until after I had been working for a few years that wouldn’t look great to employers, but do you agree that I need to start work immediately after I graduate? Is it really going to be that harmful in the long run to wait a couple of months before applying for jobs?

Here’s the advice I would have given you before Covid: Nah, you’re probably fine. There are a handful of industries that hire graduating seniors on a fairly strict schedule — like they’ll have a class of new hires who graduated in the spring, and if you miss that it can be hard to get in the door with them as an entry-level hire. But they’re the exception; most employers don’t hire that way. Traveling for a few months before you start your job search isn’t likely to be a big deal.

Here’s the advice I have to give now: I don’t know! None of us really know how the job market is going to shake out right now, but one thing that’s clear is that there’s a lot more competition than normal because so many people have lost their jobs this year. New grads will be competing against people with more experience who are wiling to work for less money than they used to be, so I’d be more cautious than usual about doing anything else that would put you at a disadvantage. Traveling for a few months after graduation probably won’t do that, but look at the state of the job market your senior year before you decide anything for sure. (And to be clear, that’s not about employers caring that you took a few months off to travel — they won’t — it’s about how long your job search might end up being. Your degree is just as fresh in August as it is in May … but if you don’t start searching until August and then your search takes months because the job market is bad, at some point it is going to seem more stale, and employers interested in new grads will be focusing on the class after you.)

3. How can I explain declining to recommend a former friend?

Someone I was very close to in college, but have since drifted apart from, has had a career change and is entering my industry. We used to be nearly best friends for our early years as this person was very charismatic, but I stopped contact after I realized they were actually quite manipulative and vindictive. Perhaps somewhat relevant, I saw them working at their on campus job regularly, and they were not a reliable employee.

We have not spoken in about three years since graduating, aside from the occasional birthday wishes. They’ve since requested a referral to an open role at my company. I’ve reviewed their portfolio, and even if we were on good terms, I don’t feel like it’s up to the standards my team would expect. It covers skills we are looking for, but there were multiple errors that I noticed immediately.

To be honest, I don’t even want to give them advice on why their portfolio is lacking, and there’s no way I’d actually refer them to my company. Still, we share a lot of mutual connections from college (again, they’re very charismatic and still fairly popular in our circles), and I’m concerned about burning bridges. Is there an elegant way out that won’t give them much reason to go scorched earth and badmouth me to our mutual connections? Am I being too harsh on someone whose work ethic may have changed in the past few years?

You’re not being too harsh. Of what you know of this person, they’re unreliable, manipulative, and vindictive — each of which on its own is a reason not to recommend someone. And yes, it’s possible they’ve changed in the last three years, but you also know they have errors in their current work. You don’t owe anyone a recommendation or referral; in fact, you owe it to your company to not vouch for someone who you have a negative opinion of.

One option is to say something like, “For this role, I know we’re really looking for X but I’d be glad to tell you if that changes,” where X is something they don’t have (a strong background in Y, more years of experience, or so forth). But if there’s no plausible way to do that, another option is to just be vague — “Let me see what I can do!” or similar, without any promise to take a specific action.

4. Our bad manager is driving away all our staff

I work for a small company of about 25 employees and no HR. We’ve got two managers and a semi-retired owner. Since the pandemic started, one of our managers basically forced the other out of his position and now he’s a regular employee, allowing her to unilaterally make decisions. Unfortunately her handling has been extremely reactive, and she works from home a lot, meaning she is very out of touch with her employees’ experience living with her decisions — reopening without consulting staff to figure out their comfort levels, abruptly changing schedules and job descriptions, and more. Recently we lost three long-time staffers due to her — two to extreme abuse at the hands of customers that could have been prevented had a manager been there instead of at home, and a third to overwork. The third is a sad case of our manager stomping on her boundaries and repeatedly calling her on her days off to cover shifts and answer emails, even though she was told to stop by that employee. We’ve got another staffer about to quit for that same reason.

How do I tell her that she needs to back off a bit before we lose the rest of our staff? The rest of us are afraid to say anything because she has a habit of ignoring unpleasant truths, especially since she was explicitly told why those people quit and she changed nothing.

If she has a habit of ignoring unpleasant truths and she’s already been told why the other people quit, do you have any reason to think speaking up will change anything? Unless you have particularly strong influence with her, it doesn’t sound like it’s likely to make much difference — especially because it’s not one lone thing she’s doing (potentially easier to stop) but rather is a pattern of bad judgment and poor management skills (much harder to fix). If you’re going to talk to anyone, it sounds like it needs to be the owner, who may not realize that the three recent resignations were due to this manager (with a fourth on the way).

5. How do I figure out work-from-home expenses?

Our small office shut down due to Covid in March. I now go in once a week to do work I can only do in the office but work from home the rest of the week. At home I use my personal laptop and home printer. Although I took home a ream of paper for my printer, I’m beginning to realize that much of my printing is work-related and I’m replacing my ink cartridges more frequently. And I haven’t been keeping track of whether or not I’ve used more than a ream of paper so far. (Most likely, I have.) Also, I’m using my computer much more each day due to work. Recently, its charge time has gone down by half and I’ll need to replace its battery. When I first started working from home, my boss tried to load the Windows Office Suite on my laptop. It didn’t load and my personal version of the Word Suite disappeared. To get it back, I’ll need to buy a new copy. We think it was because she tried to load a PC version on my Mac but we’re not sure what went wrong. Since I can use the Apple versions (Pages, Numbers, etc.) instead, we haven’t really addressed this.

My productivity is much higher higher at home since I have so many fewer interruptions. So, my boss agrees that working from home can continue until the pandemic is over and possibly longer. She’s talked about budgeting for a laptop to replace my office desktop computer which I could also use at home. Although that would solve my computer costs, I’m much more comfortable with my Mac—I’d just like a Mac version of Windows Office loaded on my laptop. Or is that a bad idea? (I don’t save anything work related onto my computer, only on USB sticks to keep work and home files separate. And I use Chrome only for work and other servers for my personal use.) And what about the other expenses—battery life, printer ink and printer wear and tear, etc.? How do I determine what I should be asking for in terms of home office expenses? Or should I be itemizing home office expenses on my taxes instead? (Although I don’t pay that much in taxes right now so I wonder if I’d really recover the expenses in the first place.)

The basic principles are that doing your job shouldn’t cost you money and your employer should cover its own costs of doing business. That means they pay for your paper, ink cartridges (if you use them for personal stuff too, figure out a rough percentage for work use), computer, and whatever else you need to do your job. I’d avoid using your personal laptop if given the choice; even if you prefer working on a Mac. Using your own computer as your main work machine blurs the lines too much, and it’s hard to figure out (much less get) appropriate compensation for wear and tear. Until/unless that happens, they should cover the cost of your new battery since if you don’t get it, you can’t do your job. They also should reimburse you for the app your manager deleted if indeed you need to buy a new copy (but make sure you really do; normally you’d be able to just re-download it unless you had a very old version).

Don’t rely on itemizing home office expenses on your tax return; that deduction went away for almost everyone but the self-employed last year.

my frustrated employee is unlikely to advance

A reader writes:

I have a direct report, Jill, who has been on my team for a few years now. When I started out as manager for the team, we had an initial one-on-one partially to get a sense of where she saw her career going. (We had worked in the same department before, but different working groups.) She expressed that she was frustrated with her lack of upward mobility and felt like she was one of the best workers on the team but was not given any “good” projects or moving up.

Once I started working with her, I understood why she was having this issue. She is super challenging to work with. Any time she is given instructions, it almost seems like she is purposefully interpreting it wrong. As a hypothetical example, if I were to tell the team that the CEO is walking through the office tomorrow and we should all dress up a bit and throw out the example of wearing a blazer (a step up from out normal office wear), Jill would show up to work in PJs and an blazer, and then act like anyone could have gotten confused over what was said the previous day. It is like this any time she is asked to take on anything or do anything out of our typical day to day, and the result is I find I cannot trust her in meetings or project work outside our group.

The core focus of our department is a job that is very repetitive and straightforward. Jill does exceedingly well with this work. The issues only crop up when she is working on a higher level project or with people outside our working group. I have told her bluntly multiple times that this behavior is holding her back from advancing. (There is no opportunity for advancement with the basic task that is the bulk of out work.) While she still claims an interest in promotion, she has not taken me up on any offer of help or coaching on these issues.

From my point of view, while I would ideally like to see Jill meet her personal goals, I am totally fine with her continuing to do really good work in her current (entry-level) position. From time to time, she will tell me that if she does not get promoted or moved onto other projects soon, she will leave the company. When this happens, I always explain the behavior that is holding her back and tell her that I am happy to work with her on it but I understand if she decides that a different role elsewhere would be a better fit. So far she has not left, and this just seems to be a cycle of having this conversation every once in a while. Which to me is fine, because at the end of the day I have a team member who continues to do good work at the job she is currently employed in.

My previous boss seemed to think this status quo was fine, but I now have a new boss who is worried this is going to become an issue. He has cited just a general concern that it’s not really fair to know that someone is unfulfilled in their job and considering leaving and not either fire them or see them move into a new position. From my end, I guess I am not really sure what I should be doing beyond what I am. I don’t see the point of firing someone who is good at their job (we have a large enough team that there’s not a issue of needing to make room for someone who might reasonably advance, or being overloaded with work if someone quits). And I am not going to promote someone just because they have longevity or would like to advance. My new boss is really pushing me to put Jill on a PIP and get moving in one direction or the other.

At the end of the day, he is my boss so I will go along with his call on this, but I was hoping for some insight on if I am totally off-base with thinking our status quo is fine, and maybe there are some pitfalls I am not thinking off or if it might be worth pushing back a bit more on his thinking on this one. For what it’s worth, he seems generally reasonable and this is the one area so far where we cannot seem to get on the same page.

You don’t put someone on a performance improvement plan or fire them just because they aspire to a promotion that you don’t think they’re suited for. If that’s really what your boss is arguing, that’s strange and it’s worth pushing back.

But I wonder if there’s more to it. In particular, I’m curious about how often Jill’s problems with understanding instructions come up. If most of her work is routine and she’s not misunderstanding things on the reg, then fine. But if she’s regularly doing the equivalent of your PJs-and-a-blazer example, I’d come down much more heavily on the side of “we’ve either got fix this or we all move on.” (What qualifies as “regularly” depends in part on the severity of the misunderstandings. If they’re minor, maybe it’s not a big deal if happens a few times a month. If they’re major, a few times a quarter could be a huge problem and a deal-breaker.)

Ultimately, you can’t keep someone on your team who you can’t rely on to understand basic instructions and if that’s happening frequently, that might be where your new boss is coming from. But then the performance management, and potential firing, would be about that — not about the fact that Jill would like to advance.

So it’s worth pushing with your boss to clarify exactly where he’s coming from. Is he mostly concerned about Jill’s unmeetable aspirations or is it more about what sound like real issues with judgment and critical thinking? If it’s the former, I’d tell him that you don’t feel comfortable firing someone because they want a different job than the one they have, that you worry about the message that would send to the rest of your staff (who’s going to feel comfortable sharing their professional goals with you if they’ve seen a coworker fired for doing that?), and that your strong preference is to keep Jill in her job as long as she continues to do it well, while continuing to be transparent with her that she won’t advance without real changes. You could also point out that everyone will leave for a new job eventually and it’s not weird that you know Jill wants to move on at some point. That’s true for any job, but especially for an entry-level job.

It also might be worth having another serious conversation with Jill about what is and isn’t possible for her at your company. I know you’ve done that already — but you’re also dealing with someone who doesn’t comprehend information in the expected way, and that might be happening here too. In the past, you’ve told her what she’d need to do to be promoted, and she’s seemingly ignored you and then asked again later on. Maybe it’s time to stop focusing on “you’d need to do X to make that happen” and instead level with her that it’s probably just not going to happen. (Because based on what you’ve written here, it really sounds like it won’t, and probably shouldn’t.) It might be a kindness to tell her, “I know you’re interested in moving up. I want to be up-front with you that I don’t think that will happen here. If that means that you decide to leave for another job, I understand and fully support you in that. But I want you to have that info so you can make good decisions for yourself.”