Ask a Manager

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

1. I can’t afford to buy breakfast for my team every month

At my job, we have weekly meetings where my whole team gets together in the morning. At these meetings, one to three people present what they’ve been working on for the past month. We are an academic research lab in a university, and 15 members of the team attend these meetings. At these meetings, my boss requires that one person presenting bring breakfast of some kind for the whole team. This means most people bring breakfast about once every one to two months.

This has been irking me for a few reasons. I am the lowest paid member of our team (think sub-poverty level for our area) because I am still a student and I am expected to pay for breakfast for all the higher members of our team once a month (my boss makes, literally, 10 times what I make). Additionally, not everyone on our team performs a research role (i.e., support staff/admin staff) so some people are never required to bring breakfast (since they never present), despite also eating it every week. And finally, I rarely eat because I’m still Covid-conscious in small rooms and prefer to keep my mask on, so it’s not like I’m saving money on getting myself breakfast during these meetings (oftentimes I don’t even end up getting to eat any of what I brought).

I know it’s something my boss is really married to, and he has done this for many years if not decades. Financially, I can make it happen since it’s not terribly often, but with rising food prices and inflation, my budget gets tighter and tighter every month. Should I just grit and bear it to keep the peace? I know many people in our group look forward to eating during this meeting every week.

No, you should speak up. And really, they should have been exempting you all along. While I don’t love this kind of system for anyone, you’re a student! You should never have been asked to buy breakfast, not even once.

Say this: “As a student, I’m not in a position to buy breakfast for the team — I really can’t afford it. So I need to exempt myself from the rotation. If that means I should opt out of eating, I will.”

Don’t get into how some people are never required to bring breakfast; that’s not really the point. The point is that you can’t afford to do it, so you won’t be. Period. And notice that with this language, you’re not asking for the favor of being let off the hook; you are telling them you cannot afford it and thus cannot do it.

You could say this privately to your boss, although on some teams, it would be more effective if said in front of the whole team (you could raise it as a sort of housekeeping measure at the end of one of these meetings). Which will work better depends on your boss and your team.

But whenever you say it, say it forthrightly! Don’t be shy about it, or embarrassed. You’re a student, for F’s sake. They’ve all been there and they should all get it.

2. Should you always ask about a gap on someone’s resume?

Should you always ask about a gap on someone’s resume?

Not all gaps, no. People have gaps on their resumes for all sorts of unremarkable reasons — took some time out of the workforce after having a baby, dealing with a health issue, taking a few months off in between jobs, travel, and on and on. The existence of a gap on someone’s resume shouldn’t be a big deal in and of itself.

Ask about a gap if you’re genuinely trying to figure out someone’s career trajectory and there’s a glaring hole that’s genuinely getting in the way of that. Generally that should mean that gaps of only a few months won’t be relevant and gaps from years ago shouldn’t matter at all. (And gaps from during the pandemic shouldn’t surprise anyone.) Personally, I only ask if the gap is a current one (“what have you been doing since leaving X?” — and that’s not a gotcha, it’s genuine interest in knowing because there could be info that’s relevant professionally — like a job they left off not realizing it would be relevant or, for some positions, whether they’d done anything to keep their skills up-to-date during that time if the gap is a long one) or if there’s a pattern of multiple gaps (and then I want to understand what keeps driving them to leave jobs with nothing else lined up — not because that’s an inherently bad thing, but because it can be a bad thing depending on the reasons — like if they’re constantly getting fired, always walking off in a fit of rage, etc.).

3. Invitations to a retirement party that’s much bigger than anyone else’s

Our CEO’s admin assistant asked me to design retirement party invitations for one beloved coworker, who is liked by many any our organization and has been a big part of being involved in many company activities, as well as philanthropic work in her 30 years at the company.

Our company normally only hosts cake/punch in a large conference room, no matter how many years a person has worked here. However, this particular employee is having a big dinner party planned by the company at an off-site event venue with drink tickets, etc.

The admin asked me to somehow word the invitation so that it doesn’t insult others who don’t get this kind of retirement send off. How would you word an invitation in this circumstance?

That’s an impossible task, because of course others are going to notice the difference and be hurt or demoralized. It’s likely to be a major messaging issue, and asking you to come up with the messaging yourself without any direction is ridiculous.

You could try going back to the assistant and saying, “I’m struggling with how to word this in a way that doesn’t raise questions about why Jane’s event is so much more elaborate than other retirement parties have been. Can you explain to me what the messaging is supposed to be so I have something to work with?” My guess is the assistant may not know either and it probably wasn’t her call, but since she’s the one asking you to do it, you’ve got to point out that you can’t do it without more information.

4. My coworker refuses to reply-all when she needs to

I have a coworker who works at an off-site location who I need to email frequently with questions. I often include her team lead and our manager in the emails so they are in the loop and can also see her replies with information I’m trying to find out.

The problem is, she is terrible at the reply-all function and always ends up only replying to me. At times this is fine, but many times there are instances where she is having problems or issues I can’t help her with, and instead of replying-all so her team lead also reads it, the message only ends up with me.

I know the usual problem is more commonly with too many people hitting reply-all when it’s not necessary, but this is a reoccurring instance where I really need her to reply-all. I’ve even pointed it out to her for the more serious issues, letting her know that she should be looping in her managers to draw attention to specific problems. Is there another way to deal with this? I find it constantly frustrating and not sure if there’s anything I can do.

Ask her one time very clearly and explain why (“can you please reply-all when I’ve cc’d Jane and/or Cecil since they need to see the answer too?”). If she continues not to, you can try one more reminder … but after that, you probably need to accept that for whatever reason she’s not doing it and you can’t make her. In that case, you can just forward her replies to Jane and Cecil with “FYI” or “You were left off the cc, but looks like Ophelia needs help with this” or so forth.

Some people will just never manage their email the way you want them to. It’s reasonable to ask once or twice, but after that you’ve just got to work around it. (There are exceptions to this, of course, like if you happen to be their boss or if they’re causing havoc with customers by not doing it.)

5. Do I have to reveal my arrest on job applications if my record was expunged?

I was arrested years ago. Later the case was dismissed and all records of it were expunged.

When applying for jobs, sometimes they ask if you’ve ever been arrested. I answer yes because I have. However, I’ve been told that since my record was expunged and if you look it up there’s no evidence of it, I should say no. But I feel like that’s lying. I don’t mind telling anyone the story because they would be able to see that I didn’t do anything wrong. But I worry about people just seeing “arrested” and having a negative opinion about me. What are your thoughts?

You can answer “no” to that question. That’s what expungement is — legally speaking, it never happened and you’re permitted to say no. You might feel better about it if you reword the question in your head to, “Do you have any legal record of arrests?”

Caveat 1: Certain government jobs or jobs working with vulnerable populations (like children) may still require you to disclose expunged records for relevant charges, so make sure to closely read what you’re answering. (You could also check with the lawyer who handled your expungement to be sure.)

Caveat 2: Order a copy of your own criminal history to make sure your record was actually expunged correctly. I recently had an old arrest from a political protest sealed (it was a bad arrest; I was there to bail out other activists but they arrested all of us, and having it on my record annoyed me on principle) and when I double checked my report months later to be sure, it was still there, despite the judge’s order to seal it. It’s fixed now, but if I hadn’t checked I wouldn’t have known they’d messed it up. My lawyer told me the same thing happened to another one of his clients, who didn’t find out until a prospective employer ran his background check — and his offer was pulled over it. So definitely check.

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

1. I don’t want to eat lunch with my boss so frequently

I have a good manager. He is friendly, supportive, and very flexible with letting me leave early to pick up my young daughters. We have a good working relationship, and I enjoy my job. Roles in my area of expertise are somewhat rare, so I plan to stay in my job long-term.

My manager often asks (maybe one out of 3-4 days) if I want to go out to lunch with him. Alison, I do not. But I accept some of the time because he lives alone and seems to crave social interaction, and it seems like a decent human thing to do, especially when he’s so good to me. But I’m an introvert, and I really value having an hour to myself where I can take a walk, run an errand, etc., without my kids in tow. Not to mention, his favorite topics of conversation are Kids These Days and The Way Things Were. Obviously, I can’t bring my true self to these conversations, so I do a lot of “mm hmm” and “oh yeah”s.

Recently, he sent me an email telling me to block out the lunch hour for us to have lunch together on an upcoming day, which rubbed me the wrong way because I want to be able to decide how to spend my lunch hour (at our company, lunch is an hour long and people actually take it) and he wasn’t even inviting me, just sort of … ordering me. On the other hand, I’m already getting so much flexibility, so maybe this is a small price to pay?

Should I just see these lunches as part of my job? We generally go to places I wouldn’t choose but the cost of lunch is similar to what I’d pay anyway (we each pay for ourselves). I am his only direct report and he doesn’t go out to lunch with anyone else.

You don’t need to go every time he invites you! The easiest way to get out of it is to say you already have plans for that time — errands you need to run, a book club you need to get caught up on, calls you need to make, walks you promised your doctor you’d start taking at lunch. (Conveniently, it sounds like you do want to take walks and run errands, so it should be easy to say that’s what you’re doing.)

It’s worth accepting his invitations occasionally as an investment in the relationship, especially considering how much you like the job and generally like working with him. But that means once every two to three weeks at most, not every three days. Since this will be a shift from what you’ve been doing, it makes sense to explicitly name that for him — i.e., “I’ve resolved to start walking at lunch most days so I won’t be able to eat with you as frequently” or whatever excuse you’re using. And then if he invites you anyway: “I’m going to walk today/catch up on my book club/run some errands, so go ahead without me.”

Alternately, if you think he’d be open to hearing it, you could just be straightforward: “I’ve found having the hour by myself in the middle of the day helps me to recharge for the second half of the day. So I’m going to do more walking/errands/reading. Please don’t take it personally if I don’t join you!”

2. My manager told me that my coworker’s sexism is something I should work out with him on my own

I’m a woman in a managerial role. I have found a male coworker who started a year ago to be condescending and dismissive, not only to me but to many female coworkers in ways that I have not seen him act with men. It’s not nasty or overtly offensive, just a general feeling that he thinks our suggestions, concerns, and questions are irrelevant or based on misunderstandings (they’re not). He also explains extremely basic concepts to us in ways that imply we don’t already know them. Think things like “work weeks” or the subject matter of my own job. I have heard similar things from other women about him.

He was particularly dismissive in a recent one-on-one meeting, which I had asked for because he had ignored my and our mutual boss’s request that he include me in a planning process. I emailed our boss that while I got the information I needed, the meeting was frustrating. I explained the pattern I was seeing with him with women and expressed concern that it may be causing friction on a committee that he chairs. I said I was providing this feedback as she’s his manager and I’d be happy to talk more about it but I’m trusting her to handle it in whatever way she sees fit.

A few days later, she said she would like me to follow up directly with him to work it out. I took a few days to sort out my thoughts, and then I explained that I would not be doing that and that it’s inappropriate to ask someone in the targeted group of discrimination to “work it out” with someone with a bias. I reiterated that I provided the info to her because she has a wider view on his work and could do something (or not) as she thinks is appropriate. She said she thinks managers should talk to each other when they have problems, and maybe he “didn’t mean it that way” or could explain why his behavior wasn’t gender-based. I said I am not going to call a meeting to tell someone I think they have problems with women, and that asking people to work out interpersonal issues on their own as a first step is absolutely appropriate but this is not an interpersonal issue, it’s a systemic-bias issue.

She’s not going to force me to meet with him, but she was so confused about why I wouldn’t that I’m wondering if I’m off-base. It seems like I’d be making myself vulnerable to someone who’s already shown a pattern of dismissing me, in a manner that’s unlikely to yield any benefits to anyone — other than maybe to him, so that he can explain away his behavior!

You are not off-base. When someone reports discriminatory behavior, the answer is not “work it out with them yourself.” You reported this to your manager so she could look at the pattern and decide if she needed to address it. “Work it out with him yourself” is a blow-off, it’s dismissive of your concerns, and no decent company wants managers responding to discrimination complaints that way. (This may or may not rise to the level of a legal concern for your company, but it certainly has the potential to in the future, depending on what else this guy does.)

If you want to, this is something you could take to HR — particularly your manager’s total abdication of any responsibility for addressing it, which they should be interested in.

Read an update to this letter. 

3. Should I let my employee buy my crocheted toys?

In my current role, I’ve recently started managing people for the first time. It’s been a great experience so far, and I’m learning a lot! I’ve come up against a low-stakes situation I’m not sure how to handle, though. I have a little side business crocheting toys and other things. It’s nothing official, and orders are placed by sending me a message through my page on social media and money is dealt with separately (rather than placing an order through a website with a checkout page). One of my direct reports recently saw some of the things I make, but she doesn’t know about my little side business. She’s mentioned that if I ever went “official” that she’d love to order something for her son.

Normally, I’d just let her know that I take orders and work something out from there. But since she’s my direct report, I feel weird taking her money, even if it’s in exchange for something she wants. But I also don’t want to offer to make it for free just because she reports to me, since she may feel like she “owes” me something. And I also feel strange not mentioning it at all, since that feels unfair for her!

Is there a good way to handle this? Am I overthinking things? If it helps, I generally charge less than $40 for the things she’s interested in, so we’re not talking huge gobs of money, though I don’t know if that matters.

I’d leave the interaction exactly where it stands now — she complimented your work, you said thank you, and that can be the end of it.

If you offered to sell her something, most likely it would be fine. But it opens the door to potential weirdnesses that you’re better off avoiding as her manager. For example, someone on your team could hear she’s buying things from you and wonder if that makes you see her more favorably (even if it doesn’t) or wonder if they should buy something themselves just to be in your good graces. (Or, less likely but still possible: What if she’s unhappy with the product but feels she can’t say anything since you’re her boss? Or she does express dissatisfaction, and you disagree?) Whether or not you think any of that’s likely to happen, as a manager you shouldn’t take the risk. Err on the side of caution.

I wouldn’t worry about it being unfair to deny her the option, since it’s not as if you’re denying her something key to her life that she can’t obtain anywhere else. And if she ever does hear about it, you can just explain you keep your side business separate from your day job.

Read an update to this letter. 

4. Can I file a complaint about my spouse’s manager?

I just found out that my spouse’s general manager has been driving up our street. We live at the top of a big hill that is a dead end. They have been videoing the drive up our hill and back down and showing it to other managers when my spouse had called out sick on the same day we had an ice storm and could barely get out of our driveway due to our driveway’s incline.

I am wanting to file a complaint with my spouse’s company but I know this general manager will retaliate against them as he has done this to my spouse in the past. Several other employees have filed complaints against this manager with nothing being done, due to him talking his way out of it every time. This same manager has had several HR investigations in just this past year but all were dismissed when the GM confessed that he, a married man, had been sleeping with the HR investigator.

I’ve asked my spouse several times to make a complaint to their GM’s supervisor or higher up until something is done. But my spouse, who has been with this company for over 10 years, is afraid of being fired as they are close to being able to retire with the company. Would it be wrong if I contacted my spouse’s company and filed a complaint myself?

Yes, you would be wrong to do that. You’d be undermining your spouse and destroying their ability to manage their own career in the way they judge best. And not that it would change the advice either way, but because you’re not an employee of this company, you don’t have any standing to file a complaint with them about an internal issue … so most likely your complaint would be ignored, or would cause drama and then achieve nothing. (Frankly, even if your spouse filed a complaint, it doesn’t sound like there’s reason to believe it would change anything.)

You cannot make your spouse manage their professional life the way you want them to. You can talk with them about how their decisions are affecting you, and you can set your own boundaries on what you will and won’t stick around for (although to be clear, this doesn’t sound like it rises to that level). But you cannot cross the line of complaining to their employer yourself. This is your spouse’s workplace, your spouse’s professional risks, and your spouse’s call to make.

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

1. I feel stuck working for my father

I’m in my second or third career now, if I ever had one. My father is the president of a small company and has been trying to get me to work with him my entire life. I worked for him in high school, between summers in college, and even as an “internship” right out of college. I had a brief career in IT consulting, after which burnout caused me to hop around for a few years to decompress, doing mostly warehouse and retail. The frustration is that I feel like I’ve never been able to craft a vision for a career. Every attempt to put something together was rebuffed by my parents (I’m 30 now). There wasn’t any support for things of interest, even if they were realistic, because the expectation is that inevitably I would go back to work for my father.

Every time I do go back to work for him, I become the every-man project manager with projects that vastly outweigh what I’m compensated for – things like acting as Safety and Inventory Manager for $16/hour. He’s been trying to get me to do financial analysis as well (I do not have a finance/accounting background). Each time I leave for another opportunity, my father become pseudo-hostile, saying he “can’t understand why I would try to leave.”

I’ve recently started my third stint working for him – whatever sense of independent self-esteem I had has since eroded, and I almost feel resigned to stay here until he retires. I am tired of the nepotism and unrealistic expectations. Am I unreasonable in wanting a separate and fulfilling form of work away from my father?

No. You’re only being unreasonable in continuing to return to work for your dad when you want to separate from him professionally. The way to solve this is to stop working for him! I know that’s easier said than done — family has weird claims on us and you clearly grew up in a family that exerted a lot of pressure on you to do what they want — but it’s the only path out.

You don’t need your parents to approve of your career choices. They can rebuff your preferences as much as they want; you are the only one with the power or the standing to decide how you will spend your work life. But that requires you to believe that, and it sounds like on some level you don’t. What’s keeping you tethered to your father’s company right now is how susceptible you are to your parents’ pressure. Because you’re having trouble resisting it — and especially because your sense of independence feels shaky — therapy could probably really help you start to untie those binds.

Read an update to this letter.

2. My boss disclosed my pregnancy

I am writing to you as a very scared eight-week pregnant woman. Today I had some scary complications relating to my pregnancy, so I decided to fill my boss in before I left for the hospital. On my way to the hospital I got a call from our HR department checking in on me because apparently my boss told her. I didn’t think too much of it since that is HR. I later texted my boss to fill her in on what was going on and asked her to please not tell anyone else. She responded that she already told my coworker what was going on. I’m extremely upset because (1) I am an extremely private person when it comes to medical issues and (2) I really dislike this coworker and I do not want to discuss my pregnancy nor its complications with her.

Was this disclosure of my pregnancy without my permission legal? This isn’t the first time my private medical information has been leaked around the office. I had a miscarriage a few years ago that apparently went around the office despite me only informing my boss about it. I’m an extremely passive, anxious individual. How do I keep this from happening again in the future?

I’m so sorry — that’s the last thing you need to be dealing with at an already stressful time.

Your boss probably didn’t violate the law when she mentioned the situation to your coworker. There are some laws protecting your medical privacy in the workplace; for example, if you share medical information in connection with a request made under the ADA or FMLA, your employer can’t share that other than with people who have a legitimate work-related need to know. But assuming neither of those was in play in this situation, the legal angle isn’t the one you want. Rather, the privacy angle is — because regardless of the law, it’s still entirely reasonable to expect your medical info won’t be shared at work without your permission.

I suggest doing two things. First, talk to your boss and say, “I was upset to learn you had shared my pregnancy with Jane. I want to ask that in the future you keep my medical information confidential; I’m very private about it and would never want it shared in the office.” Second, talk to HR and say that on multiple occasions now, your private medical information has been shared with coworkers. Explain you’ve already spoken with your boss about this, but you’re looking for their assurances that your privacy will be protected as well, and ask them to consider reminding managers to keep employees’ medical info confidential. (They’re likely to want to do that, because in many other cases the ADA or FMLA’s protections would be in play.) You mention that you’re very passive so I realize you might not want to have either of these conversations, but they’re the best way to protect yourself in the future.

Also, it’s important to remember is that you rarely need to share medical specifics with your boss in the first place. It’s generally enough to just say you won’t be in because of illness or a medical emergency — you don’t need to give any details if you don’t want to. And if for some reason you do, you can stress your desire for privacy along with it (“please don’t share this; I want to keep it private”).

Read an update to this letter.

3. Is a good employee harder to manage than a bad employee?

I work at a very young, progressive, healthcare tech company in a kind of call-centery position. It is a very touchy-feely place and the office is extremely casual. The company was a very successful start-up that got bought by a much larger company.

I was having issues with my manager and skipped a level and organized a meeting with her manager. I’m a high performer and I was freaking out because my manager would cry nearly every time she spoke to me. She would ask me for management advice on how to treat my coworkers, and then tell me that by performing so well I was making the rest of the team look bad. I had a super awkward one-on-one where she openly sobbed at me for an hour … because in my quarterly review feedback, I wrote that I needed her to be my boss, not my therapist. My grandboss then explained to me that since my manager was new, I needed to have low expectations and her interview was so good that she’d eventually impress me. Her final comment really surprised me: she said a good employee is always harder to manage than a bad one.

I’ve since been moved to a new team with a new manager who has not yet cried at me, but that statement is still really odd to me. What do you think? I’ve never been in a management role but I would imagine that a low-performing employee would take way more work to manage than someone doing well.

Yeah, that’s a weird and inaccurate statement. All employees take time and effort to manage well, but good ones certainly aren’t harder than bad ones. Low-performing employees generally take quite a bit more time — you need to supervise their work much more closely (and judging how closely to do that can be a whole project unto itself), give more feedback, work to bring their skills up to par, have potentially uncomfortable conversations, and do some really serious evaluations to figure out if they’re going to be able to reach the bar you need or not (and if not, there’s all the work of dealing with next steps from there). Great employees can have their own special needs too — for example, figuring out how to keep them challenged and engaged, making sure their work is recognized in ways that are meaningful to them, etc. — but it’s less work, and it’s far less emotionally draining. And good employees make good managers’ lives easier, not harder.

The only explanation I can think of for why someone might find good employees harder to manage than bad ones is if they struggle with management in general. In that case, they might find it hard to keep a smart, driven employee engaged, or might handle it badly when a strong employee points out errors or weaknesses in systems, or could even feel threatened by them.

But frankly, your grandboss sounds like she was so invested in defending your manager (telling you to have low expectations?!) that her comment might not really reflect what she’d conclude if she thought more deeply about it. Otherwise, though, she’s telling you something pretty damning about her own management abilities.

4. Coworker tries to figure out people’s zodiac signs

Here’s an absolutely low-stakes issue! I recently joined a new team at work and one of the members of that team likes to guess people’s zodiac signs after a couple weeks of interaction. In a team meeting, while trying to guess somebody else’s sign, she said multiple disparaging things about a zodiac sign. Of course, she was saying bad things about my sign.

I’m much more amused than offended, but the more I think about it, the more this strikes me like something that’s actually a potential problem for my company. However, I kept my concerns to myself. I’m trying not to be such a Leo about it.

Yeah, if you were her manager, you should tell her to cut it out — explaining that she’s insulting various people on the team (regardless of whether anyone believes in astrology or not) and that not everyone would appreciate being publicly analyzed in that way. But since you’re not her manager, simply being amused is the best response.

5. I was asked to interview for a lower-level job than the one I applied for

I’ve recently been applying for management positions in my field. After eight years of experience in my job, I believe I’m ready for the next step, and I know I can’t find it at my current organization.

I recently had a second interview at a company I would love to work for, with a manager who I clicked really well with. I was so pleased to receive an email asking to schedule a final interview … for a lower position. I was confused, and emailed the recruiter back to clarify. He confirmed that I was being asked to interview for the lower role, but didn’t say why. I can only surmise that the manager liked me, but someone else was more qualified for the management position than I am, so she figured she could fill the lower role with me.

I know nothing about this lower role — not the responsibilities, not the salary — and I suppose it seems unfair to me that they expect me to do a final interview for this role in this situation. The lower role is the same as the role I have now, and I’m not interested in making a lateral move. I want to be considered for the role I applied for. Is this a common practice? Is this a red flag? What should I do?

It’s not unusual for a hiring manager to decide that she’d rather consider you for a different job. She might think you’re a much stronger fit for that one, or she has stronger candidates for the first one, or she’s on the verge of hiring someone for the first one, or you have some specific skill that would be a plus for the second job. But she and/or the recruiter should be explicit about why they’re moving you on to that track and should give you enough information that you can decide if you’re interested in being considered for it or not, not just assume that you’ll happily show up for an interview for anything they come up with. However, in fairness to this hiring manager, it’s entirely possible that she assumed the recruiter would take care of those things and he dropped the ball (that happens a lot). So I wouldn’t say it’s a red flag.

You can ask if you can still be considered for the original role, but usually when this happens the subtext is “no for job #1 but let’s talk about job #2.” If you’d be willing to at least hear about the other job, don’t be shy about saying, “Could you send the job description and salary so I can get more information about it before we schedule a meeting?”