asking to meet in person when you’re remote, asking for tuition reimbursement for a degree I already finished, and more

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

1. Asking to meet in person when you’re normally remote

I hope you can give me an outsider’s position on the current dispute that my husband and I are having. He recently started a new job at a well-known tech company less than two months ago. It appeared to be a fantastic move and was a great bump in salary, and he would be working with a few former coworkers who he loved working with in the past, including one who would be his new manager. Well, his new manager/former coworker was suddenly put on leave, and then let go. (He was let go due to a very complicated crazy series of events that ended with him being accused of stealing trade secrets from one company and bringing it to the new company. There’s a lot more to it than that, but that’s the gist. My husband was not involved in what was happening and wasn’t aware of any of this until after his manager was let go two weeks ago.) Now my husband is a lot less enthusiastic about this new role and has major concerns about his future in the company.

So here’s the question: My husband’s job is 100% remote and we live three hours away from his office headquarters. He reached out to his new manager (who was his manager’s manager until two weeks ago) and asked for an in-person meeting. His manager was fine with this, but I asked my husband why he would spend six hours in the car to meet with his manager for an hour or so when there is such a thing as a telephone or Zoom. He said he wanted his manager’s full attention because he wanted to discuss his future at the company and believes you do not have anyone’s full attention when you are talking through a screen. He feels this is a good use of his (and the company’s) time and resources. I understand the seriousness of this conversation, but it seems tone-deaf to me and may make his manager question how my husband prioritizes things, especially since his job is considered fully remote, and we’re so far away. If you were his manager, would you feel this request was really odd? What would be your concerns if he was your employee and did this? Would you feel differently if we lived closer to the office? Or am I wrong and this is a perfectly fine request due to the crazy circumstances that lead up to this meeting request?

If he were driving six hours for routine meetings, I’d question that for the reasons you mention (and would be concerned that he wasn’t a great fit for remote work). But I definitely understand him wanting to do it for very important meetings, like an annual performance review — and I’d put “some highly alarming stuff went down right after I started, my manager is gone, and I now have serious questions about my future here” in that category! It’s not that he has to drive in for it, but it’s reasonable that he wants to. Some people feel they connect better in-person, or just feel more comfortable having important conversations in person, especially when the stakes are as high as this one sounds. I don’t agree that it’s the only way to have someone’s full attention, but showing up for an in-person meeting when you’re normally remote does change the vibe, and it sounds like he wants that. I rule in his favor!

2. Can I ask for tuition reimbursement for a degree I finished before starting my job?

I’ve been offered a job, and I think they are at the top of their salary range. They do offer $2,400 tuition reimbursement every year. Since I already have my degree (and I need the degree to do this job), would it be inappropriate of me to ask for this as a student loan payment instead?

It’s an interesting proposal that would benefit a ton of people, but I’ve never known a company where it would fly. That doesn’t mean they don’t exist, but typically companies offer tuition reimbursement at least in part because they believe they’ll benefit if you get more education than you started with… and aside from that, the benefit is usually written to clearly cover current classes but not ones you took before coming to the company. Also, if word got out they offered that retroactively, it would end up costing a lot more than it costs them right now because a ton of people would want it (which further lowers your odds).

You could have more luck trying to negotiate additional vacation time or a one-time bonus.

3. I feel guilty about how much I’m charging my former company for freelance work

I quit my job and then decided to offer to stay part-time, which they were eager to accept. I threw out a much higher hourly rate than what I was previously getting, and they accepted. Now I feel guilty. I feel like I asked too much, feel like I don’t deserve that much hourly, feel greedy, and feel like other coworkers deserve more than me. Should I go back and lower my rate even though they signed off on it? Why do I feel like this?

Good lord, no. If they didn’t think paying you that rate was in their best interests, they wouldn’t have agreed to. They’re not offering you charity, after all; they negotiated a business deal with terms they felt were acceptable. And you noted they were eager to accept — that’s not a company with concerns about what you’re charging.

Also, I don’t know how the new rate compares to what you were earning there previously, but it’s typical for freelancers to double the hourly rate they were earning as an employee because you’ll be responsible for your own payroll taxes (which are significant), won’t get benefits like health care or paid time off, and won’t have the protections of a regular job. Very often people who agree to freelance for a company they’ve just quit undercut themselves by asking for their former hourly rate or something close to it — because they figure “hey, this is what I’ve been earning” — and then lose money on the deal because of the factors above.

4. Should I warn my boss against promoting my colleague?

I recently resigned from my company to take a new position. After my grandboss sent a note to the larger team letting them know, someone I work with from another department reached out asking questions about what my role involves.

Having worked with this person over the years, I know they would be terrible in the role. I and my other colleagues have expressed concern to our manager in the past about this person’s performance, so they are aware to some extent of our team’s issues with them. However, our manager is very hands-off and doesn’t fully understand just how bad this person is.

I’m on the fence about whether I should share my concerns with my manager before I leave. I worry about coming across as unprofessional and also I know they’re not pleased that I’m leaving.

For the sake of your coworkers if not your manager, please do tell your manager! It’s not unprofessional as long as you frame it objectively and from the perspective of what’s best for the team, rather than about a personal dislike. For example: “Jane told me she’s interested in applying for my role. Candidly, I’ve worked closely with her over the last few years and I’d have serious concerns about her ability to do the work because of XYZ.” If your manager seems unconvinced, you could add, “If you do interview her, I’d recommend probing into X and Y, which are my two biggest areas of concern.”

5. Taking vacation at the end of my notice period

My company has a four-week notice policy. I can get my unused PTO paid out up to a certain amount. PTO accumulates every week and I am over the amount I can get paid out, so I want to take some time off to get the benefit.

How do I word my letter and timing of my resignation letter so I give four weeks AND take another week or two of PTO? Is this what I should say? “My last day will be Friday, September 30. I have accumulated PTO and will be using time the weeks of September 19 and 26, so effectively my last working day will be Friday, September 16.”

There’s a good chance they won’t let you do this, unfortunately, and instead will just tell you that your last day will be September 16. A lot of companies have policies against using PTO during your notice period (check your handbook) and even those that don’t might figure this plan is a violation of the “we only pay out up to X days of accrued time” policy. You can try it because they might let you, but it would be safer to take the time off before you give notice if you can.

my boss says I’m not ready for a promotion, but is giving me work above my pay grade

A reader writes:

I am a Junior X, which is an entry-level employee in higher education. In my specific industry within higher ed, people in my role stick around for two to three years before they get promoted or leave. I am approaching that three-year mark in a few months. I talked to my manager several months ago about getting promoted to a Senior X, which she said was a possibility, and began giving me the job duties and workload of a Senior X for my career growth.

Several months later when I brought up the topic of being promoted again, she said that I wasn’t ready but gave me helpful feedback that I have put into action. I’ve improved so much within the past several months that my successful projects have gotten attention from people in other departments, and I have received nothing but praise from my manager and her boss on these projects. In other departments, these are all projects a Senior X would have taken on and I went far beyond expectations on these projects.

Recently, I talked to my manager again about my career growth and she said indicated that I’m still not ready to get promoted. I am getting frustrated that I am doing the workload of a Senior X (successfully enough that it’s gathered attention from our peers!) without the pay or the title. How do I continue the conversation on revisiting my pay and title given these circumstances? (Also, for what it’s worth, when I was hired I was told that there was career growth within my organization and I know for a fact that lack of funds is not an issue at my organization.)

Since your manager is saying you’re not ready to be promoted, ask her specifically what you need to demonstrate in order to be promoted.

Be careful, though, that she’s not moving the goalposts — telling you to do X and Y, and then when you do that telling you that you also need to do Z. That’s not always a sign that a manager is intentionally not being straight with you — it could be that she’s not thoroughly thinking through everything she wants to see from you, or that she’s spotting weaknesses she hadn’t seen before as she watches you do higher level work — but if it happens more than once, you should name it and ask what’s going on. (“We’ve talked several times about what I’d need to do to get promoted and you agree that I’ve now done those things successfully. Is there something else standing in the way of my being promoted?”)

In general, you should be wary of doing the duties of a Senior X at the pay of a Junior X for very long. In some orgs, you’ve got to do that to get promoted — but it should be for a limited period of time, not indefinitely, so it’s also reasonable to ask about that. (“My understanding is that projects like X and Y would normally go to a Senior X but I’ve done them successfully for four months now and I’m concerned about continuing to do Senior X projects at Junior X pay.”) That said, be aware that this can be more nuanced than it looks; sometimes you’re doing an abbreviated version of what a Senior X would do or not doing it with the same skill, and your manager is using it to get you ready to work at Senior X levels even though you’re not quite there yet. But other times, they’re just getting Senior X work from you for cheaper. It’s worth a conversation about exactly what’s going on, so you have a better sense of which of those possibilities it is.

If none of that gets you closer to a promotion, the rest of the answer may be in this part of your letter: “people in my role stick around for two to three years before they get promoted or leave.” If they’re not making real moves toward promoting you, at that point it’s likely time to look at promoting yourself by leaving the organization.

my employee keeps joking about getting fired

A reader writes:

One of my top executives has been regularly joking about being replaced in her position within the company. As the owner, I asked her why she was doing this, questioning if it stemmed from a place of insecurity or from unhappiness in her position. She said insecurity — that she was not performing well in her role. This team member has been shown appreciation, respect, and admiration for her stellar performance thus far. I reassured her she was ideal for the position. But the uncomfortable jokes have still continued regularly, even after further discussions and boundaries have been addressed. I’m not sure how to handle this situation. Advice please!

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

Other questions I’m answering there today include:

  • How to set boundaries with clients on my days off
  • Getting gender right when we’ve never met in person

can I ignore my coworker’s calls and only communicate by email?

A reader writes:

I work for a state corrections/law enforcement agency. We have state-issued laptops and cell phones. Our schedule is very flexible and self-directed: we work in the field, from home, and in the office. Our hours are set, but where we are working and what tasks we may be doing vary. I prefer to communicate by email or text with my clients, coworkers, and community partners whenever possible for multiple reasons: 1) I am often unavailable by phone due to working in the field in high-risk situations (think: police-related activity, warrants, arrests, searches), 2) I prefer to have correspondence in writing to refer to in the future and to avoid miscommunication, 3) I dislike talking on the phone. I worked in a call center previously for over a decade and that experience created much disdain for taking calls. I am neurodivergent (ADHD) and struggle to stay on task throughout the day. One unnecessary phone call can disrupt my work process for an hour or more.

I don’t flat refuse to answer the phone, and I realize sometimes it is necessary. However, in a situation where it is not, I am wondering if my approach is inappropriate or unprofessional.

I have a colleague in the same agency with a more specialized position that requires that I consult with him occasionally. The process to ask him questions is to be done in a specific referral format, via email. He then is to complete the request, update the system, and respond advising he’s done it. He can email any questions or clarification. I am thorough with my requests and respond quickly if clarification is needed. Inevitably, every time I submit a request, he calls me. I might be able to tolerate this, but this individual is extremely condescending and difficult. He over-explains things (once, he explained to me how C-section births work), and has a very short-sighted/hard-lined approach to his work. I find his calls exhausting, unnecessary, and unpleasant. I have begun ignoring his calls and responding by email. I feel as though his behavior is intrusive and presumptuous. I have discussed with my immediate supervisor who is already aware, and my coworkers have the same experience with him. Since the odds of having a productive conversation with him are low, is it inappropriate for me to not take his calls unless absolutely necessary?

From a purely logic-based standpoint, absolutely. Your logic is sound. The call are unhelpful, unnecessary, and unpleasant to boot. Email makes sense.

But from a political or relationship-based standpoint … maybe not. I can’t say whether it’s true with this guy or not, but in many cases there are benefits to occasionally getting on the phone with someone like this. Not every time, but occasionally. He’s obviously a phone person, and letting him have some of the communications on his terms (rather than only on your terms 100% of the time) can be an investment in the relationship.

You might figure you don’t care about the relationship, but sometimes investing even just a little in relationships at work can pay off in ways you don’t expect — things like the person being willing to prioritize an important request from you even though they don’t strictly need to, or being willing to stay late to get you something you need, or including some extra detail that helps you do your job better.

In other cases, the need is political. If the person is higher up than you are and clearly prefers the phone, that might just be the way it needs to go; their position gives them the prerogative of doing it their way. Sometimes that’s for good reason, like that it’s faster for them and their time matters more in real dollars to the organization. Sometimes it’s not for any good reason, but the hierarchy means you’re going to have to do it that way anyway.

It’s also worth considering that to people who love email, it’s easy to feel like obviously email is the superior method and everyone should be using it in these situations, end of story. It’s useful to remember that to people who prefer the phone, they often feel the exact same way about the phone. To them, the phone is more efficient and it’s faster for them to get what they need. So insisting on email every single time — even if it’s because you’re sure it’s the better method — can be too strong of a stance. You’re basically saying you’re going to prioritize your communication preferences over theirs every single time … and that can make you look difficult, prima donna-ish, or just out of touch with how business still gets done in many offices. (You might not care if he thinks that, but it can look that way to outside observers who you do care about too.)

To be clear, I am not saying that your solution isn’t the right one for this particular coworker. You might weigh all of the above and still decide that his behavior on the phone is enough of a problem that he belongs in permanent email jail, regardless. If your boss is fine with that, so be it. But sometimes investing in an occasional phone call with these people — again, not every time, not even half the time, just occasionally — will pay off.

employee walks off the job to cry every day, getting more info before an interview, and more

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

1. My employee walks off the job to cry … every day

I manage a very busy retail pharmacy. I have a young employee who does well at her job but has trouble controlling her emotions. Almost daily she finds something to be upset about and cries daily. It could be an imagined slight from a coworker, a text she receives from family or friends, an interaction with a customer, or sometimes just her own anxiety. When one of these incidents occurs, she walks off the job and sobs in the back of the store. This leaves my other employees to pick up the slack and customers waiting for prescriptions to have increased wait times which they are very vocal about, causing stress for everyone. I have tried to be empathetic but my patience is wearing thin.

Yesterday she left her post to cry in the back and called her boyfriend in on his day off (he is also an employee) just to console her. Turns out she had received mean texts from a high school ex (she’s a college senior) and two former high school friends. The boyfriend/employee asked me to go back and talk to her. After finding out the problem, I told her my solution was for her to stop looking at personal texts at work and then she couldn’t be bothered by them. I told her that I had a business to run and walked away. The boyfriend later told me he couldn’t believe that I would say that to her when she was so upset. I have tried to comfort her in the past but the situation has gotten ridiculous. Looking for advice on how to handle this ongoing.

I can see why that came across as callous to her boyfriend, but it’s not surprising that you’re fed up considering that this has been happening daily and you’ve tried to be empathetic up until now! You do have a business to run, and you can’t have someone constantly walking off the job and sobbing in the back while you have customers waiting to be served. It’s not fair to your other employees either.

That said, this wasn’t the way to handle it — and I suspect that you handled it that way because of pent-up frustration from putting up with it longer than you should have until now. (That’s a reason to always address problems before your frustration gets to the point where you’re blowing up!)

I’d say this to her: “I apologize for snapping at you the other day. I shouldn’t have done that. However, I cannot allow you to continue walking off the job when you’re upset. It’s disruptive to customers and the rest of the staff, and it’s unfair to other employees who have to cover for you. I understand that you’re having a hard time. I can give you some time off if you need it. But while you’re here, I need you focused on work, not distracted by other things, and I need you to maintain a calm and professional demeanor with coworkers and customers. Is that something you can do?”

If she says yes but she continues being disruptive, I think you’d need to seriously reconsider whether you can keep her on. It’s reasonable to treat “calm and professional demeanor” as a job requirement like any other.

2. Why can’t we get more information before an interview?

As has been noted before, video interviews are a bit more involved than phone screenings. Piggybacking off of this, as well as the fact that many jobs do not list salaries, I often wish preliminary/first-round phone interviews were more substantive and commonly used. Sometimes phone screenings seem so short and more “I am just making sure you can speak in a cogent manner and seem sane.”

As an applicant, it seems that questions or compatibility (organization’s needs, salary, or questions about remote, hybrid, etc.) could be just as easily discussed in a phone conversation before I invest in an intensive video interview process. Sometimes job descriptions can be vague or so boilerplate that I often want to have a better idea of the job, organization, and salary before a lengthy video interview. Is there a way to broach this with an organization? Is it reasonable for me to want clarity prior to a video interview that may run at least an hour? I do not want to seem demanding to an organization or video-averse but video interviews require a lot more planning, time, energy, and logistics I have to work through. Am I being unreasonable or am I alone in these desires?

You’re not being unreasonable. And you can indeed say, “Before we both set aside time for a video interview, could you share the salary range with me, as well as whether the job is remote, on-site, or hybrid?” More and more candidates are doing that now. (However, a warning: if you’re not a strong candidate, you risk not hearing back after that. If the organization has plenty of strong candidates and you throw up obstacles to setting up an interview, they might just move on with the others. So you’ve got to proceed with that in mind.)

But questions about the job, the organization, their needs, etc. are better held for the interview, because those require real conversation (or at least the person you’re asking is likely to think they do, because of interview conventions if nothing else). The exception is if you have a very simple, straightforward question that could easily be answered in a sentence or two, like “are you looking for people with experience in X or in Y?”

I fully agree with you, though, on the usefulness of substantive phone interviews for the first round, and I’m sad to see them so often getting replaced by video.

3. My Spanish-speaking coworker shouldn’t have to be my translator

I started working for a new company about four months ago. We work with the public both in person and over our website chat function. As the main person who manages the chat on the website, I typically have to respond to the questions we get. Recently I’ve gotten a few questions submitted in Spanish so I went to my coworker who I know speaks Spanish and asked if she could help translate and form a response. She said she would help but commented after the fact about how it’s annoying that she’s expected to help because she speaks the language and doesn’t get any extra compensation for it. I totally agree with her and quickly apologized for even asking for her assistance, but now my question is what should I do moving forward?

I don’t want to keep exploiting her skills but I also need assistance when these questions come up. How should I bring this up to management? My first thought is to screenshot the chat question and send it to our operations manager and ask how she would try and answer the question, but I’m worried she will tell me to ask my coworker. I just want to do the right thing.

Handle it the way you would if you didn’t have a coworker who speaks Spanish — so presumably by asking your manager what to do, and ideally suggesting that the company locate a professional translator to contract with for these questions. But if she tells you to ask your coworker for help, then you could say to your coworker, “Jane asked me to ask you to help with this, but I know you have concerns about being asked to do this on top of your normal job. Would you like me to handle it a different way with Jane?” Ultimately it’s really up to your coworker to address this with your company (especially since you’re new) — whether it’s by refusing to do it, or negotiating for a pay bump, or whatever solution she wants — but you can help by not going to her as your default for assistance or by making it clear it’s your manager’s directive if you’re told to (and again, suggesting the professional translator route).

4. How much to share with clients when I’m unexpectedly out

I have a minor question about email etiquette that has, unfortunately, become relevant to me the past month. I had to take unexpected time off for a family funeral followed by sick days when I got Covid. By their nature, neither of these absences were things I could plan in advance for, and because they came back to back I ended up missing way more work than I expected at the outset.

Now that I’m back at work and catching up on old emails, I’m wondering if it makes sense to explain my absence when emailing clients. There weren’t any urgent needs left waiting, but there are a number of non-urgent emails that I left sitting for longer than usual (think three days to a week+ response time, rather than my usual less-than-24-hour response time). Does it make sense to mention I was out for a family emergency/out sick when following up with these emails now, so clients know why it took longer than normal to get back to them, or is that unnecessary/too personal?

It’s up to you and depends to some extent on the relationships you have with clients. It’s fine to just say “I was out for several days” but it’s also fine to say “I was out for a family emergency” or “I was out sick.” I don’t think you need to get into it being a family emergency and being out sick — ultimately the details don’t really matter that much to clients — although it wouldn’t be a big deal if you did. It only gets too personal if you start sharing more personal details (“stomach bug I could not shake,” “a lot of family drama around the funeral,” etc.).

5. Showing title advancement on your resume

I have a question about something you wrote in this post, “do job titles matter?” You wrote: “By keeping you title-free, there’s no way to formalize a promotion. You keep taking on more and more responsibility, but you’re still just ‘business development’ (or whatever). Being able to show advancement matters for your resume, and it matters for raises too.”

When you say that being able to show advancement matters for your resume, do you mean advancement within the same company? Like, should we be showing on our resumes that we started out as data entry, then promoted to admin, then promoted to project manager? I usually just put the highest position I held at the company on my resume, like if I started out at a loan place as a cashier and left as the manager, I would put manager down as my job title on the resume. Is this hurting me?

Definitely don’t do that! First and foremost, it’s not accurate — if you’re saying that your job title was manager for the whole four years you worked somewhere but you were really only a manager for two of those years, you’re misrepresenting the depth of your experience! Plus, if a prospective employer calls your old company to verify your employment, the info you provided isn’t going to match up with the info your old employer gives out — and it will look like you tried to misrepresent your work experience there. You need to include all the titles you had there, and ideally the time periods you held them.

That also helps with the thing you’re asking about: showing career progression. It reflects well on you that you were promoted from X to Y to Z. You want that to be evident! It shows that someone looked at your work multiple times and thought, “She’s capable of doing more.” That’s a good thing.

my employee delivered a status update … in song

I’m off today. This was originally published in 2015.

A reader writes:

I am a newly promoted manager and am stumped on how to handle something bizarre that happened in a meeting today, primarily because my sense of humor is getting in the way. I asked one of my employees to explain the progress he’s made in the assignment he’s been working on, and he said, “I would love to tell you…in song.” He proceeded to pull out a harmonica and “find his note,” before erupting into a musical ditty explaining everything in detail. It was so weird…that I did not know how to respond in the moment. Making it worse is that I find this hysterical, and I could not stop smirking the rest of the meeting. Whenever I think about the occurrence, I start to laugh again.

However, that doesn’t mean I find it acceptable, and intend to have a serious discussion with him tomorrow. But I’m curious to know how you would address it, particularly since my potential laughter and smiling will not convey how unacceptable I find his behavior. I do not want this to seem like a suggestion. Am I immature in not being able to hide these emotions? Am I making too big a deal about the situation? I never thought I would have to deal with this as a manager.

I actually think this is hilarious. Is there a reason you find it unacceptable and want to address it with him? I mean, obviously you don’t want all status updates being delivered in song, but unless it becomes a pattern, I’d just assume it was an amusing one-off from someone having a good time (which is not a terrible thing if it doesn’t impede people’s work) and leave it at that.

I’m not saying this is necessarily happening with you, but some managers — especially newer managers — have a tendency to feel like they have to establish capital-A Authority and sometimes see casual behavior or things that deviate from the norm as Things That Must Be Stamped Out. But if you’re having that impulse, it’s important to ask yourself why. Does the behavior in question really have an impact on the work? Is it something where you’ll do more harm than good by coming down on someone for a one-time occurrence? Is it really a significant problem?

If there’s more to this — like you didn’t get important information you needed or you think he has a habit of not taking work as seriously as you need him to — you should address that. But if it’s just a single song? Let yourself laugh (with him, not at him), appreciate his musical talent, and move on. It’s okay to have a little silliness at work.

I’ve been overworked for months and my manager won’t help

A reader writes:

I have been covering for a coworker who is the lead for our shared role for the past two months. Covering her for a few days would normally have been no problem, but due to our clinic being short-staffed and an increase in clientele, this is starting to take its toll on my productivity and mental health. Conversations with my managers haven’t been productive — they say a bunch of stuff but nothing happens, no help gets hired in, and I’ve had no increase in pay.

I’m over two months behind on my paperwork because I’m balancing doing four people’s jobs some days. The job I originally was hired to do has become my last priority most days. I feel like a failure because I’m crying every day, I’m not being paid enough to even function (my car is literally on its last leg), and I’m being overworked so much that I can’t look or interview anywhere else. I get in at 7 am to try to get a head start and usually skip my lunch and I don’t leave until 5:30 or 6 some days. I even tried for a promotion to escape from the work and they thought I wasn’t qualified … even though I’m nearly single-handedly running a clinic in less than nine months since I started.

I can’t just decide to go back to working eight hours a day because of the number of clients who are now being scheduled. I don’t have the option of electing to see only half of the people who are scheduled with us. I then have to enter in all the data from those visits or else it goes unprocessed and leaves an even bigger mess for me to crawl my way out of. Plus, if our paperwork isn’t done in a timely fashion, it could affect our future funding. So I feel stuck working all these hours, and my managers won’t help. How do I escape this situation?

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

how do I ask the CEO if I can “borrow” his assistant for my projects?

I’m off today. This was originally published in 2012.

A reader writes:

I am eight days into a new job. It is a rather large corporation. When I was hired, I inquired about an assistant to answer my calls, emails, etc., because I had one at my previous job. My boss, the CEO, mentioned they would look into this after a month or so of me working to evaluate whether I would need the help.

His assistant is great. I noticed that because she is so quick and precise with her projects that she sometimes helps out other departments when she has some free time during the work day. I figured this might be because she doesn’t have enough assignments of her own. I asked her to help me on something a few days ago, but she said she was unable to help me on finance-related projects without expressed permission from her boss. She did let me know that there were other assistants in the finance department that might be able to help me, but they were all busy at the time.

He was out for the day, and she didn’t feel like it was appropriate to disturb him to ask him about this issue. I understand this and appreciate it, but I don’t think the project is what she thought it was. I am actually pretty sure she could have helped without the CEO having an issue with it.

I would like to approach the CEO about borrowing his assistant when she has free time to act as my assistant until the company appoints me one, but I am unsure of how to phrase my request in a way where it won’t undermine his position and what he told me about an assistant when I was hired. I don’t want to come off as sounding that I am entitled to an assistant, but his assistant is bright and quick, and seems to have a great grip on the industry. I am new to the industry and would like to make the most of my new situation. I also think that sharing an assistant with my CEO would give a chance to make a impression and prove myself at this job. I would love for him to mentor me since I am new to the industry and the work world in general.

I should note that I am a supervisor and have one other employee under me who is a designer and doesn’t have any assisting responsibilities. I would ask the designer to stand in for one, but it would seriously cut into their other work duties.

How do I go about asking the CEO this? How do I sell it as a benefit for him? Am I out of line in asking?

What?!  Dear god, no.

Do not ask him.

Do not ask his assistant for help again.

Do not under any circumstances ask anyone else to be your assistant either.

Do not, do not, do not.

When you asked about an assistant originally, the CEO was skeptical. He then said they’d consider it after you’d been working a month. If you ask to start borrowing his assistant after eight days, you will look like you’re ignoring what he said earlier.

And, actually, I think you probably are ignoring what he said earlier. For instance, you wrote, “until the company appoints me one.” But there’s no “until” here, because it’s not a given that it will happen — the CEO said they’ll assess in 30 days whether you need one. That means it might not happen, ever. (It probably also means that he really doubts you’ll need one. And it’s pretty unlikely that he’s going to create a whole new position unless you can really demonstrate it’s needed.)

Most jobs don’t come with assistants — for anything, but especially not to answer calls and emails. In most offices, you’re going to be pretty high up before you have a dedicated assistant (if ever), and it’s especially unusual to have someone else handling your emails and calls. If other people at your level don’t have that in this office, you need to accept that that’s just part of the deal with this job and this particular culture.

Pushing for an assistant in a culture that doesn’t operate that way is a really good way to signal “this is not a good fit.” So proceed with caution.

And holy crap, do not try to get your designer to act as your assistant. Not only would it cut into her other work, as you noted, but that’s not the job she signed up for. You will alienate her, and probably piss off your CEO too (who, again, explicitly told you the company isn’t prepared to pay someone to assist you). If your job doesn’t come with an assistant, do not try to co-opt someone else’s job to fix that for you. That is not nice, and it’s not playing by the rules you were hired under.

You can read an update to this post here.

will it hurt me to stay in a job where my boss doesn’t like me, cheating in the office bake-off, and more

I’m off today for family stuff. Here are some past letters that I’m making new again, rather than leaving them to wilt in the archives.

1. Will it hurt me to stay in a job where my managers don’t like me?

I’ve come to accept that my supervisors (my manager and VP) and I mutually dislike one another on a personal level. Part of it is a function of differing pesonalities and different approaches to project management. But part of it is an entrenched dysfunctional culture at my department and organization and how my supervisors have managed to operate within it for a combined 20 years in the organization and how I have been reacting to the culture in my two years.

Despite the personality clashes, the manager and VP pretty much leave me alone to do my work. As long as am productive, I am generally left me to my own devices. So in a lot of ways I’ve been able to thrive in my performance and results despite the dysfunction. But the formal reviews I’ve gotten have been tepid at best (despite a lot of raves and positive feedback from coworkers up and down the org ladder outside my department). Also, my supervisors don’t seem to put a lot of thought and care to making their performance reviews. I get the impression from their comments on my last review that they took all of 15 minutes each to gloss over what I wrote, scrawled some comments in a hurry and that was it. There is no opportunity given to program staff like me to put in a review about our superiors.

Will it be harmful for my career in the long run to stay in a comfortable but dysfunctional workplace, knowing my supervisors don’t like me on a personal level? I like my work, the hours are humane, the commute is pretty good, and the pay is above average. But the passive-aggressiveness, petty sarcastic remarks, demeaning tone that they talk to me in, and general lack of clear communication pretty much leave me demoralized on a regular basis. I’ve gone to EAP counseling, and I’ve sought your advice many times on specific incidents. I’ve been job-hunting also, but so far no luck in a year and a half of effort.

I am curious if you think I am doing more harm to my career and mental health by staying in a dysfunctional situation where my bosses just plain do not like me and the feeling is mutual. I can make the job work day to day, and in a lot of ways I have excelled. But I know I’ll never get official recognition or respect from them.

Ugh, sorry you’re dealing with this. Yes, I do think it’s harmful to stay in a job where your managers don’t like you. It might be low-grade harm, but it is harmful:

  • You’re less likely to get raises, promotions, good projects, training opportunities, and other benefits that often accompany a good relationship with managers.
  • You’ll forego the reputation-building that a manager who likes you can do for you — speaking well of you to others and introducing you to people who can become part of your network / help you professionally / hire you in the future.
  • You won’t get useful feedback to help you develop professionally. Your peers can give you positive feedback, but it usually takes an invested manager to show you where you could be doing things better or differently.
  • It can endanger your job. You can end up first on a layoffs list, or not get the benefit of the doubt in a he said/she said situation, and so forth.
  • And most of all, the situation will almost definitely impact your head in bad ways — eating away at your self-image, instilling in you a defeatist attitude in regard to praise and recognition, and generally making you feel miserable.

So keep actively looking at other jobs. Tolerate this place in the meantime, but try to get out.

Read an update to this letter here.


2. Cheating in the office bake-off competition

This is more lighthearted but I am bothered by it. We’re having a departmental baking competition. There are about 70 people in the department and at least 10 are entering. One of my colleagues, Candice, is very talented and clearly the person to beat. Another colleague, Stuart, has been saying that he’ll get his nephew to bake his entry as his nephew is a semi-professional cake decorator. Stuart has mentioned it openly to a couple of people now, who have both jokingly said that’s cheating, but he seems quite set on the idea. He’s filling in the entry form right now.

If he does enter with a cake he didn’t make, should I mention it to the organizer? Only if he wins? How do I tell the organizer without sounding weird and petty? I would prefer not to create a bad atmosphere and be dramatic, but this really isn’t fair for the people who make their own cakes!

Why not just mention it to the organizer now and let her decide how to deal with it? You could just say, “Hey, if you only want people to enter with cakes they baked themselves, you should let people know that. Stuart is talking about entering with a cake made by his nephew, who decorates cakes professionally.”

I wouldn’t wait to see if he wins before speaking up — that’s likely to cause much more drama. The easiest thing would be for the organizer to head this off now.


3. A coworker wants to take over my job (and may have thrown away my mug)

I’m the front desk person at our office. When I started, I joined a team of four other admins, plus our boss (who’s just the best). Flash forward half a year and two of the original admins have left. “Susan” was one of the new hires. Unfortunately, she’s not the kindest person. She just talks down to me like I’m very young (I’m 28, she’s a few years older). She slips in comments aimed at taking me down a peg. She tends to complain a lot. But worst of all, she has a habit of seeking validation when she’s speaking to you. She will repeat herself over, and over, and won’t end a conversation until you validate her in some way (agree with her point, give her a compliment, etc.). Still, I try to keep everything professional, light, and polite. And I understand why she feels she can talk down to me, I look very young, I’m a front desk person, and she’s a step up on the admin chain. It’s not nice, but it’s not a big deal. I get along great with everyone else in the office, and work is great otherwise.

Because of my degree and previous experience, I am our office’s creative project person. I make posters and pamphlets and all that fun stuff. When Susan started, she volunteered for the next creative project. She told us that she was the creative person at her last job. That was fine, but we found out Susan does not have the skills I do. Her results weren’t professional, and she didn’t take our boss’s suggestions or feedback well. So projects went back to being assigned to me.

Susan didn’t take it gracefully. She tried to get me to agree that her project was good and our boss was wrong, and also said I need to teach her how to use the creative programs. I was pretty evasive for that conversation. I didn’t say no, but I also didn’t put anything on the calendar. I don’t want to teach her to do the work I love doing when she clearly has it out for me, wants to replace me in that role, and doesn’t take instruction well. Is that unfair of me? Am I being too sensitive?

Also, this week I found my very distinctive-looking coffee mug in my trash can. It was a fluke I found it, because it was buried under papers and tissues. If I hadn’t gone looking for a Post-It note, it would have been thrown out overnight. I tried to recreate how it could have fallen in, but it does not seem possible it’s an accident. Since I’m on really good terms with everyone, I feel like Susan might have done it. I know I can’t tell anyone about that suspicion, and it’s such an odd, childish revenge that maybe I’m wrong. I’ve hidden the mug for now, and I’m sort of waiting to see if she asks me about it.

Nope, it’s not unfair of you not to want to teach Susan to do your work for you — in general, and especially given the way she treats you. If she asks you again to train you to use design programs, tell her that it took you a lot of practice to master them and it’s not something you can quickly teach to someone else. If she pushes, you could say, “I’d suggest doing a formal course if you’re interested.” (Not because that’s what it will necessarily take, but because you want to emphasize that you’re not going to be the person training her.)

I’d also talk to your boss and say something like, “Susan has been asking me to train her in how to use design programs so that she can do our design work. I’ve told her that it takes a lot of practice to master and there’s no way I can impart a degree in graphic design and a couple of years worth of experience to her. But I wanted to talk to you about it too, because I really enjoy doing our design work and would like to hold on to it. I get the sense that Susan would like to take it over, so I wanted to ask you if we can officially keep it as part of my job — and if so, if you can let her know that?”

As for the mug … I don’t think there’s much to be done there other than to take it as additional evidence that Susan is a jerk. If more things like that happen, at that point you’d need to talk to your boss, but for now I’d wait and see how this plays out.

Read an update to this letter here.


4. Is referring to an orgy in my cover letter going to hurt me?

I was applying to jobs in advertising and I put the following paragraph in my cover letter. I haven’t been contacted by a single agency and, after reviewing my cover letter, I am concerned that putting the word “orgy” in the letter might have been inappropriate:

“Although I enjoy my current role in sales, I am looking for a position that allows me to better utilize my problem solving skills and that both inspires and applauds creativity. (As you can imagine, bringing creativity to a financial software company is like bringing the Pope to an orgy… not so much appreciated by the operations manager or the software developer.) Having performed quite a bit of research on your agency, I feel that I could make a significant contribution as well as learn quite a bit from your organization and would like to explore whether there might be a position that would match a person with my experience and skill set.”

Do you think I may get a response, or have I ruined my chances? Should I call and speak to the hiring manager and apologize for the offensive language?

Yeah, it’s inappropriate. There are some people who wouldn’t care at all (and some who may even like it because they’ll think that it shows personality), but enough who would care that it’s not worth the risk. There are other ways to convey what you were trying to say there, even ones that could show personality without turning anyone off.

In general, avoid sexual and religious references in job applications. (And definitely avoid combining them!)

I would not call to apologize, however. That’s just going to compound the weirdness. At this point, what’s done is done. Just don’t do it again!

Also, as a side note, I’d avoid the type of negativity that you had in that sentence, aside from the orgy reference. Claiming that your last company didn’t appreciate your creativity — or worse, that a whole industry doesn’t — feels a little off and raises the question of whether you might be quick to feel unappreciated, slow to realize that there may have been other reasons it didn’t go over well there, etc. Those aren’t good things. Keep it positive.


5. How thankful should I be to my employer for doing something they’re obligated to do?

Just how thankful should I be to my employer?

It seems like my employer expects me to be a lot more thankful to him / the organization than I am. Here’s an example: last winter the furnace went out at my house. I live in employer-provided housing for the convenience of my employer (it’s normal in this industry), so it was my employer’s responsibility to replace the 25-year-old furnace. They did so promptly, and I was glad to have the heat back on!

A few days after the repair was completed, my employer put a copy of the bill in my box at the office with a “FYI” written at the top. Over the next few weeks, my boss brought up the cost of the repairs repeatedly. The unspoken but very clear expectation was that I should be exceedingly grateful that the organization chose to repair my furnace and to do so promptly. I seriously think my boss expected a handwritten thank-you note and a box of cookies.

I just … don’t feel that way! Of course I’m glad to live in a house with adequate heating, but my thankfulness for that is directed more towards God and the factors in my life that lead me to be employable than to my specific employer. I’m not surprised or overwhelmed with gratitude that my employer fulfilled his contractual obligation to provide me with livable housing, and it felt crass that he gave me a copy of the bill and repeatedly brought up the cost as if I owed him fawning adoration. Alison, am I off base here? Should I be more thankful to my employer, or is he the one being weird?

He’s being not just weird but fairly crass and rude as well. This would be like if your boss were constantly telling you that his profits were lower this year because he had to pay you your wages. To which you’d presumably be thinking, “No shit.”

Certainly a quick “hey, thanks for getting the furnace taken care of so quickly” makes sense to do, because that kind of thing is good for the relationship. But it doesn’t require you to install a plaque honoring your boss above the furnace or anything like that.


is it still OK to wear a mask to a job interview?

A reader writes:

I am a new grad from an MLIS degree and I am also high-risk for Covid. I am now starting the job searching process, and I just got an email asking me to come for an interview. I am still masking everywhere in my life, which is non-negotiable for me, but I’m worried about the optics of wearing a mask at the interview when the vast majority of people where I live aren’t wearing masks anywhere now.

I’m hoping for some advice about how to address this or if I even should. Should I mention it via email that I’ll be masked, as a heads up, or should I just wear it without mention? I’m comfortable just saying I’m high-risk in the interview if it comes up, but is there a better way of handling that? I also don’t want them to worry about my high risk status re: my ability to work. I’m worried it may hurt my chances, but also I will be wearing it while working anyway so I know there’s an element of screening them out if they cause a fuss. I just don’t really know how to handle this professionally!

First, I’m glad you’re not asking if it’s okay to wear the mask — because I’m getting those letters too. It is okay to wear a mask to a job interview! We are in a pandemic. And while many people have decided to lower their personal risk assessments, many people have not. It is absolutely fine to wear a mask to a job interview — whether it’s because you’re high risk, or live with people who are high-risk, or want to protect other people around you, or simply don’t want to risk getting Covid or long Covid.

It’s not something you need to give an employer an advance heads-up about. You can just show up wearing a mask. If no one else is wearing one, then at the start of the interview, you could say, “I hope you don’t mind that I’m keeping my mask on — I’m higher risk and being careful.” (Or “I live with someone high-risk” or “my mom is high-risk” or “I’m still being cautious.”)

If you go with “I’m still being cautious,” there are some people who will judge that. They aren’t the majority and they aren’t reasonable but, as we all know, they’re out there. If an employer is going to judge you for not wanting to get a deadly disease during a public health emergency, I’d argue that you’re far better off finding that out now than after you’re working for them.

Because the thing is, this is very much a screening tool for you. First, you’re planning to wear a mask every day on the job, so it makes sense to find out now if that’s going to be an issue. Second, an employer who doesn’t hire you because you’re wearing a mask is an employer who you do not want to work for. Throughout 2020 and 2021, my inbox was full of panicked letters from people whose employers weren’t taking safety precautions seriously and who felt forced to risk possibly dying or killing their loved ones in order to pay their rent. The pandemic is in a different place now, but that kind of callous disregard from an employer carries over to all sorts of things that affect what it will be like to work there. So if the mask does screen out a small number of employers, that’s a good thing. Make it part of your own assessment of them.