my coworker has a crush on our boss and is mad that I asked her to stop talking about him

A reader writes:

I work for a small company. We are an office of about 10 people and most of my colleagues have worked with each other for several years. My position was newly created to take some of the clerical burden off the others, and I’m definitely the new kid on the block, so to speak. Ive been there about four months now.

The problem I’m running into is our chatty office manager, Jan, who I work most closely with. Although Jan is a great technical worker, personally she driving me nuts. Through many conversations with her, it’s clear she has a crush on on our boss, Keith (10 years younger than her, 10 years older than me). Keith is a retired fire fighter and the textbook tall, dark, and handsome. He’s charismatic but professional. For context, Jan’s husband passed away suddenly about a year and a half before I started working there. I think the loneliness of being a widow is setting in and that’s why she had eyes for our boss, simply because he pays attention to her.

It has gotten to the point that whenever I’m alone with Jan, the conversation quickly turns to an unrelated conversation about Keith. Most of the time, I just ignore her or redirect the conversation to the original topic. This seemed to be working up until recently. Over lunch the other day, Jan and I were talking about a time-consuming project the office was working on for a client. Keith seemed irritated about possibly not meeting our deadline. Jan said, “I wonder what his wife does to make him relax at home, I know what I would do. Oh, who am I kidding, you would have a better chance with him since you’re younger.” I finally stopped her and said I didn’t feel comfortable talking about Keith in that manner with her, and frankly the continued conversations about him were getting annoying. Her response was, “Oh, it’s just a little girl talk. There’s no harm in that.” I countered with, “I’d rather talk about something else” and then changed the subject. I could tell I embarrassed her. We awkwardly finished our lunch and she was very curt and stand-off ish the rest of the day.

For the last week, if the conversation happens to drift towards Keith she’ll say, “Oh, that’s right, we can’t talk about about him” or if I have my office door shut (to avoid her!) she’ll proclaim to the office that I’m not being social today.

I’m not sure how to approach Jan going forward. Do I confront her and call out her immature behavior? Since we are such a small office and I’m fairly new, I really don’t feel like I have anyone I can confide in. Do I just keep ignoring her so she doesn’t get a reaction? I also don’t feel comfortable going to Keith just yet because I feel like it will just be an awkward she said-she said conversation. I feel like she’ll just gaslight me to make me look crazy to stay in his good graces.

First things first: You have the right not to be exposed to sexual comments at work, and you have the right not to be hassled when you express that sexual comments are unwelcome. If you want to escalate this, you can.

I’m guessing in such a small company you don’t have HR or even pseudo-HR, which makes this harder. But if Keith is the person you’d need to report it to, you can do that! You mentioned you’re worried it’ll be a she said/she said situation … but that’s true of most reports of sexual inappropriateness at work, and it’s still worth doing if you’re feeling harassed. It doesn’t sound like you’re necessarily at the point where you want to take that option, but it’s there if that changes.

If you don’t want to go that route, my advice is to keep ignoring Jan for a few weeks and then reassess.

If she says you’re not being social because you have your door closed, just ignore that or calmly say, “Yep, just trying to focus.” I’m not sure exactly what she’s trying to get out of you, but my best guess is that she wants you to walk back what you said so that she feels better about it. You don’t need to.

And when she says, “Oh, that’s right, we can’t talk about Keith,” you should take that as a win. She’s right, she can’t talk about Keith. If you want, you could respond very sincerely with, “Thanks, I appreciate you respecting that” … or you can just ignore her. She’s likely to get tired of making those comments eventually. Or someone will overhear and ask why she can’t talk about Keith, and the answer she’s likely to give will reflect poorly on her, not you.

If she’s still doing this a couple of weeks from now, or if she starts escalating how obnoxious she’s being, at that point it might be worth trying to clear the air by saying something like, “I think I embarrassed you when I asked you not to talk about Keith that way. That wasn’t my intention. I’m not comfortable hearing anyone we work with spoken about in a sexual way, even if you’re just joking around. I hope you understand.”

But if that doesn’t solve it, then you’ve got to decide how much she’s bothering you and weigh that against your desire not to bring Keith into it. To help overcome your discomfort about involving him: If a man you managed were talking about you this way and then freezing out someone who objected, wouldn’t you want to know? I’m not always a fan of flipping the genders as a thought experiment unless you can also reverse thousands of years of history and systemic sexism, but in this case it might help you feel more comfortable letting him know.

But let’s hope that after a few weeks of not getting a rise from you with her comments, Jan will pull herself together and move on.

job applicant keeps asking for another chance

A reader writes:

How would you respond to a candidate who continues to ask for an opportunity after you’ve rejected them? This candidate was screened out and we sent them a message about finding a strong group of candidates and moving in a different direction, and we did tell them that we’d keep their resume on file.

This candidate is now badgering me on social media, asking me to give them a chance and asking how they can persuade me to give them a chance. Is there a kind way to say that “We have moved on, so should you?”

I answer this question — and three 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:

  • HR director cried while laying someone off
  • Should I let a new employee work holidays in exchange for other time off?
  • Should I tell my employee to stop addressing people by their first names?

a DNA test revealed the CEO is my half brother … and he’s freaking out

A reader writes:

My dad gave the whole family DNA ancestry kits for the holidays, and it turns out the CEO of the company I work for is my half-brother.

Dad’s not the kind of guy to gift everyone DNA kits as a way of telling us he had a secret love child, so I don’t think he knew he had another kid. We’re all grown-ups and know where babies come from and that things aren’t always what we expect, so I have a feeling this is a shock to everyone. The CEO’s company bio says he’s a “proud Texan, born and raised.” Dad was stationed in Texas ten years before he met and married my mother. The timeline all fits and so do the genes, I guess.

None of my siblings have initiated contact and neither has Dad.

I’ve met the CEO a few times but he works out of the corporate headquarters across the country from the smaller division where I work. About a week after I got my results, an email went out from the head of HR stating that all staff had to take a refresher training on nepotism. The training also included a new clause that said something like “staff are not entitled to privileges personal or professional if familial relation by genes or marriage to executive or management staff is known or unknown or discovered during employment.” Other than being clunky verbiage, I felt like it was aimed at me. I found out no other branch had to retake the nepotism training and the email only came to our office. My manager later pulled me in personally to ask if I had any questions about the policy. She was vague and uncomfortable, and I said I wanted to know why nobody else was brought in 1:1 to talk about the policy and why no other branch had to do the training. She just kind of ignored the question and said she was just following instructions, so now I think this was aimed at me.

I’m happy to drop the whole thing. I’m sure he feels as uncomfortable as I do about this, but to weaponize HR and make my coworkers waste a whole day on mandatory training just to put up a boundary seems messed up. A simple personal email of “Hey, I saw this. I don’t know what to make of it. Please give me space and don’t bring it to work” would have sufficed. Even ignoring it would have been fine by me too since I wasn’t sure I wanted to be the one to initiate a conversation about this without having talked to my dad first. Dad has gotten his results back, obviously, and he’s avoiding the conversation. This is a big elephant in the room made a little harder by the fact that I work for this guy.

What bothers me the most is that weaponizing HR with the intent to make sure I know not to ask for perks feels messed up. I’ve been with the company for five years and have a great reputation. At least I did. What do I do?

I wrote back to this letter-writer and asked, “To make sure I understand, would the CEO have been alerted to these results too, and been able to see your name and connected it to you? Is the company small enough that he’d even make that connection?

Yeah, the company is about 200 full-time employees mostly in our two states. He follows a lot of employees on LinkedIn and I’m in a marketing role so my team is in touch with corporate a lot. I’ve only met him in person a few times, but some projects bring me in close proximity to him and his direct staff. The DNA test has an app, and you get notifications regularly via email and I think push notifications on your phone if you opt-in. I have no way of knowing what he opted into, so I assumed he didn’t know until the weird training.

He has now blocked me on LinkedIn and all social media, and has blocked all my siblings and my parents. I think the jig is up. How do I make sure my job is secure?

Oh no. What a situation.

And what a reaction from the CEO! I mean, yes, this is awkward, but to handle it via a nepotism training targeting only your office and pointedly remind you that you’re not entitled to any special privileges (including “if a familial relation … is discovered during employment”?!) and then having your manager do that weird one-on-one meeting with you to make sure you didn’t have questions?

As if you were about to start demanding a raise and a promotion and your own private bathroom because you share a father. Without even talking to you first.

I don’t want to come down too hard on him because he’s obviously freaking out (and who knows, he might be reeling from learning someone he thought was his father is not his father and maybe he sees you as the walking embodiment of that) … but this is a bit bananas.

I think you’ve got two options. The first is to ignore it. Demonstrate through your very pointed lack of response and lack of requests for special treatment that nothing has changed on your side at work. Figure that maybe his frenzy of self-protective activity will die down in the next few weeks as he adjusts to the news.

The other option is to send him a note that says something like, “I want you to know this isn’t something I plan to follow up on in any way and as far as I’m concerned, it’s your private business. Please don’t worry about it coming up at work.”

The tricky thing, of course, is that a note could make things worse — now you’re confirming you got the news too and you are speaking of it, which can upset people who are working hard to forge boundaries against ever discussing a thing. Or it could make things better — if he’s been worried that you’re going to show up in his office wanting to bond as siblings or that you’ll gossip about the situation at the office, here’s assurance that you’re not. It could set him at ease. There’s no knowing.

The flip side of that is that if you ignore the whole thing, there’s no guarantee that will set him at ease either. He could remain horribly uncomfortable and look for opportunities to push you out, or might hold you back professionally. (Like if you’re up for a promotion that would have you working more closely with him, will he squash that? Will he subtly discourage others from working with you? Reveal a discomfort when your name comes up which makes other people assume there’s something unsavory about you?)

He seems so freaked out right now that personally I’d go the note route; I’d just feel better having said something. But that’s not necessarily the right course of action.

In theory, a third option could be to talk to HR and tell them you’re worried about repercussions to the CEO’s discovery. Interestingly, there’s a law that could be in play here — the Genetic Information Nondiscrimination Act (GINA), which prohibits employers from discriminating on the basis of genetic information, including info about an employee’s genetic tests or the genetic test of a family member. GINA would make it illegal for the CEO to fire you based on what he’s learned. HR would presumably care about that. In reality, though, if the CEO wants you gone for personal reasons, it’s probably going to happen at some point — and even if it doesn’t, there are still ways for his discomfort to harm your career, even if he doesn’t intend it to (see examples above).

Honestly, and I’m sorry to say it, I’d start putting out feelers at other companies. I’m not saying to quit tomorrow — you can give this some time and see how it plays out — but you’ve been there five years, it’s not an unreasonable time to start looking around anyway, and it wouldn’t hurt to have already done some groundwork if you do realize at some point that you’re better off moving on.

boss said Pride shirts violate the dress code, how much notice should I get for work travel, and more

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

1. Boss said Pride shirts violate the dress code

My partner, A (he/him), recently received a call from his grandboss that A.’s shirt during an all-hands Zoom meeting was “unprofessional” and he can no longer wear it to work. The shirt in question is a standard T-shirt, navy in color, clean with no holes, and says PRIDE in rainbow letters across the front. The meeting was totally internal and the team works variously in the office, which is not public, or on job sites. (Think outdoor construction projects where workers occasionally interface with clients. A wears clothing appropriate for weather and safety on job sites.) The meeting occurred on a Friday morning, and the call about it wasn’t made until the next Monday. A publicly identifies as queer and has been open about the fact that he is in a relationship with me, a nonbinary trans person (they/them).

Grandboss cited the company’s dress code, which states: “Appearance must be neat, clean, and professional. Any casual apparel such as shorts, tight-fitting, or revealing clothing is highly discouraged. Any apparel with offensive or inappropriate graphics, verbiage, or competitor’s logos is strictly prohibited.” When A pointed out that other employees in the office also wear graphic T-shirts and other casual attire, Grandboss said, “I’d make the same call if it was MAGA, BLM, left, or right.”

A’s company is headquartered in a very LGBTQ-unfriendly state, but we live and work in an extremely LGBTQ-friendly state with explicit legal protections against discrimination on the grounds of sexual orientation and gender identity. A works in an extremely small, specialized industry, and it would be very difficult for him to find a new job unless he were willing to change careers (or relocate to a different state, but that’s not really on the table for a lot of reasons, including the groundswell of anti-trans state legislation and the fact that I would lose access to a nice pension).

Is there any way A can reasonably push back on this, as he really wants to, or is he better off just biting his tongue? I appreciate any insight you can give; the situation is really frustrating and upsetting.

Wow. A’s grandboss is trying to say the shirt is political … but it’s a shirt promoting inclusion and protection of other humans. (Same for BLM.) In citing the dress code’s prohibition on “offensive and inappropriate” verbiage, is he saying that protecting LGBTQ people is … offensive or inappropriate? What a disgusting edict.

Whether to push back comes down to A’s sense of how that will go over in this particular company (headquartered in an LGBTQ-unfriendly state), his own capital there, and how much he wants to push back. I’d love to tell him that yes, he absolutely should escalate it but — especially given that he wants/needs to stay at this job if at all possible — he has the best sense of what will be safest for him there. If he thinks it’s likely to end in the company backing up the boss (probably by arguing the shirt is “political”) and tension with his chain of command, it might make sense to simply file this away as a damning fact about his grandboss — and his company — but not act. On the other hand, if he thinks someone in HR (and certainly his DEI team if they have one) would be receptive, it could take less capital than you’d think. (Any chance the company has a LGBTQ resource group? If so, they’d be helpful, both in figuring out whether to speak up and in deciding how.)

To be clear, not acting wouldn’t mean what the grandboss did is okay; it would just be about A prioritizing his safety within the company as long as he needs to stay there.

2. How much notice should I get for work travel?

I am in a position that does not currently require travel, but was asked to fly out to my company’s HQ location for a couple of days for an in-person meeting (it would take 10 hours to drive there). Unfortunately I can’t go because I’m out of office that week, but they only gave me 10 days (six business days) of notice before asking if I could travel to this meeting. Is that amount of time reasonable for a role where I am not normally expected to travel, and if not, how many days advance typically would be reasonable? My sister thinks anything less than three weeks would be unreasonable, but since this would be my first ever business trip after almost six years with my company, I wanted to see if we’re both off-base.

You’re both off-base. It’s not strange to be given 10 days of notice for a trip, even in a job that doesn’t normally require travel. Sometimes things come up without a ton of notice.

Typically it’s reasonable to expect at least a few days notice (unless you’re in a job that’s travel-heavy), but even then something could come up faster and you might be asked to travel. If you can’t do it because of the short notice (for example, if that wasn’t enough time to arrange overnight child care or so forth), you’d explain that — but it’s not inherently unreasonable for an employer to ask.

3. I want a new job but I don’t want to screw over my team

I’d like to get a new job, potentially within my company or potentially somewhere entirely new. I’m fortunately in a position where I can walk rather than run away; as long as I’m somewhere else before the end of the year I’ll be a happy camper.

However, I like everyone on my current team and I don’t want to leave them in a difficult spot if I can help it. And if I left now, they would be in a tricky spot indeed. Two of our most senior team members left within the past months, and several other teammates (including the one that would have to assume my responsibilities should I leave) have been dealing with very unfortunate personal issues which caused them to have to take several weeks off previously.

I know I should prioritize my needs over making everyone else’s lives easier, but I do have the flexibility to stay for at least a few more months before I start to get antsy. I’ve cleaned up my resume and cover letter, but have not applied anywhere yet since I worry I might get a great offer that I would want to take ASAP.

Do you have any advice on how to best navigate this? How much of a grace should I give before I start applying to other places? Will I be burning a bridge by leaving to early? Am I totally off base and should just start applying places now?

Leave on the timeline that works for you; if you want to start applying now, start applying now. Having people leave, even at inconvenient times — even at very inconvenient times — is a normal part of doing business, and your organization will figure it out. You will not burn a bridge unless the place is wildly dysfunctional (and if that’s the case, all sorts of other normal stuff you do could burn a bridge too, and you can’t cater to irrationality).

Keep in mind that if you wait, other things could happen that could make it even more inconvenient for you to leave a few months from now! Someone else could leave. You could be assigned a huge project that they’re counting on you for. Your boss could get sick. There’s no guarantee that waiting will make things better, and it could make them worse. Go when it’s convenient for you.

4. Asking for a clothing allowance

I work for a nonprofit. 90% of my work is wholly unglamorous work-from-home stuff. Increasingly, though, I’m called upon to be a spokesperson for our organization on TV. I’m happy to do it because it is great for our organization, but it’s not at all what I was hired to do (we didn’t even do TV when I started).

Here’s the thing: I’m naturally kind of scruffy, don’t wear makeup, buy all my clothes secondhand. TV standards for women’s appearances are so high! Is it okay to ask my boss for a small annual stipend for me to buy smart clothes and makeup for TV? The only other employee who acts as a spokesperson is male so always wears the same suit and no makeup and no one cares either way.

This is such an interesting question, because the way you’ve framed it, it is a business expense but different managers will see it different ways. Some managers will think, “You have to buy clothes for work and sometimes those clothes need to be professional, and that’s not an expense your employer will cover for you” … but others would be open to it if you pitch it the right way. It’ll depend on your manager, but it wouldn’t be unreasonable to say something like, “With the increased amount of TV I’m doing, I think it’s important that I look the part by wearing clothes and appropriate makeup that represent us well. I would literally never buy anything like this and doing TV for Org is the only time I’ll use it, so would you be willing to consider that a business expense?” She may or may not agree, but it’s not an outrageous thing to inquire about.

Just as a point of interest — although it’s not the same situation — my brother-in-law, who is a TV news reporter, has been reimbursed for (some) clothing, makeup, and at one point haircuts. He notes that it’s been cut back on in recent years though.

5. VP missed our call for a complaint I’m trying to escalate

I’m trying to escalate an issue, and my VP offered to meet. She gave me a particular time for a phone call, but then she didn’t reach out and I was left hanging. I went to her because the two levels between me and her aren’t listening. There’s no official route for issues like these except for an ethics complaint line, and this isn’t an ethics issue. What do I do?

Follow up with her! Send an email saying, “I’m guessing you ended up with a conflict for our 2 pm phone call yesterday. Is there a time we could reschedule for? I’d like to talk with you if at all possible.” (Also, if you can, arrange it so that this time you’re calling her rather than the reverse.)

weekend open thread – Jan. 28-29, 2023

This comment section is open for any non-work-related discussion you’d like to have with other readers, by popular demand.

Here are the rules for the weekend posts.

Book recommendation of the week: L.A. Weather, by María Amparo Escandón. A Mexican-Jewish family in Los Angeles tries to navigate secrets, divorce, money, and guilt.

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

it’s your Friday good news

It’s your Friday good news!

1.  “I am very excited to share my Friday good news — you can count me as one of those that thought ‘this will never happen to me!’

I got fed up with my job this summer when they denied me to work from home one additional day (to make my schedule 2 days in office and 3 at home) and then got further fed up after promotions were announced. I got nothing – nor did anyone in my entire department – and I realized there was no path for me to move up or make more money beyond the 1-2% COLA for a few years. I resolved to start looking in November, after my 401k had vested another 20%.

Well, I didn’t even make it that long – after one frustrating day in September, I decided to just go ahead and apply to a bunch of remote jobs I saw online that were well suited to my skills and interests. From this batch I had three interviews. One ghosted me afterward, another I made it to the final round but passed on because the salary was too low, and the third I started last week!

I got a 30% salary bump in a fully remote position with truly amazing benefits at a company whose work aligns with my values. I keep pinching myself because I keep thinking someone is pranking me. But after a week of onboarding I am believing it is true. And the silver lining is – it turns out I became 100% vested in my previous 401k since I had turned 55 this year. On a side note, I had also been nervous about applying for jobs with gray hair for the first time…but apparently that didn’t matter.

So keep the faith, AAM readers — your next and better job may be just around the corner! Here’s to a wonderful 2023 to all. ”

2.  “I know you hear this all the time but I never thought I’d be writing to you. I work in a company that has very little room for growth or upward mobility. In July my boss quit her job very suddenly. After 6 years in my position I applied for the job only to have them hire an external candidate who used to work for the company 4 years ago and with whom I had some history of conflict when we worked together previously. I was bitterly disappointed and began job searching in earnest. I got several interviews but no one would hire me. I resigned myself to working for this person and to just keep my head down and handle it with as much grace as possible.

Fast forward two months and the person they hired hates the job and quit and the promotion was offered to me! At first I was still a little resentful but I remembered your oft-stated advice that being second choice for a job is not a bad thing and often works out. I gladly accepted the position and will be getting almost a 30% raise, and a job that I can really grow into! Thank you so much for your advice.”

3.  “I’ve been reading your blog for a few years, and I wanted to share good news!

I was working in a non-profit organization for the past decade, and while I truly loved my work, I struggled to cope with a very toxic manager and a dysfunctional leadership team. When I was promoted to a manager myself a few years ago, I started reading your blog to learn more about how to support my team, and it helped me realize just how toxic the situation had become. But I loved the work so much I just continued to tolerate it. Over the past six months, it got so much worse, and with support from your amazing readers and lots of late nights reading past questions, I started a job search. Last month, I was hired into the exact position I had been hoping for, with the bonus of being fully remote!

Every meeting I’ve been in so far has been professional and productive. My new supervisor actively solicits my input on projects, and I’m already realizing how underutilized my skills were in my prior position. I’m actually looking forward to our busy season and to new challenges, and my mental health is improving by the day!”

open thread – January 27-28, 2023

It’s the Friday open thread!

The comment section on this post is open for discussion with other readers on any work-related questions 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 take your questions 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.

I’m fully remote but my boss wants me to come in once a week, how much personal printing is OK at work, and more

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

1. My company made me fully remote — and my boss still wants me to come in once a week

Recently, my company made me fully remote. I signed a contract stating that I am 100% remote. After signing the contract, I had a meeting with my manager and she said that she would still want me to come in at least once a week because everyone has to come into the office. She stated that it is unfair that I am remote while the team has to come. They only made me remote to be “competitive.”

Could they do this? How do I talk to my manager and say I don’t want to come that much? I can consider coming in once in a while but not every week. How to professionally say it’s not right that I am expected to come in when remote only to make other employees feel better?

So she’s openly admitting that they only offered you a benefit to get you to stay but they had no intention of honoring it? Wow — that does happen, but companies don’t usually admit it immediately afterwards.

Whether or not they can do this depends on the contract. Was this an actual document signed by both of you with wording that doesn’t give them any wiggle room? The thing that can be tricky about work agreements in the U.S. (where worker contracts are rare) is that even when they’re written down, they’re often written to preserve the at-will nature of employment … meaning “we agree to X for now, but we can change this at any time.” So you’d need to look at exactly what the wording is. You should also talk to whoever coordinated this contract — probably HR. They might explain to your boss that what she’s asking is the opposite of what the company just committed to.

If neither the contract wording nor HR resolves it, then the framing you want for your boss is: “We just negotiated this and signed a contract stating that I would be 100% remote. I accepted that in good faith and assumed the company was operating in good faith as well. I can of course come in for major events when necessary, but coming in once a week is the opposite of what we just both signed in our agreement.”

2. How much personal printing is acceptable at work?

Is there a general cutoff for when personal printing/copying on the office machine goes from acceptable to unacceptable?

In the past I’ve used my office printer for personal items (printing out a copy of my tax return, for example). These were never more than a couple pages long.

I’m moving soon and am required to print flyers and leave them under the windshield of cars on my block letting them know the space outside my apartment will be reserved for a moving van. I estimate this will require maybe 50 flyers or so. I’m planning on just going to a copy shop, as this feels different than my previous personal printings. Is it, though? In the grand scheme of things, it really wouldn’t occupy the copier for more than a couple minutes, and wouldn’t use that much ink/toner. I realize there’s no hard and fast rule, but what is the dividing line?

I don’t think there’s an exact dividing line! I agree that a few pages is fine in most offices and 50 pages is too many. I’d say the line is maybe around 15-20 pages, but it’s not like the addition of one more page to make it 21 would make it instantly unacceptable. And to further complicate things, it can depend on what you’re printing. In a lot of offices, printing out a 20-page dull government form would read differently (better) than printing out 20 flyers for your band. And in other offices, an even higher number of band flyers would be a non-issue. (In reality, though, most people printing out band flyers would do it early in the morning or late in the day when fewer people were likely to around and probably no one would ever know.) So it’s a judgment call, depending on the norms of your office and what you’re printing … so not a very satisfying answer.

Probably the best litmus test is, “How would I feel if my boss were standing right by the printer when these came out?” That accounts for variations among bosses, offices, and content.

3. How do I choose who to lay off?

I am in an unfortunate position that I think a lot of managers might also find themselves in in the coming months — our company is likely to have layoffs this year, and I have been asked to choose who on my team would be let go. I appreciate that I am being allowed to make the decision because I think I have more insight into the strengths and weaknesses of my team members than the higher-level managers do. But the other managers and I were given no guidance about how to make the choice — we were just told the number of people who would have to go, and to submit the names by the end of the month. Do you have any guidance on how I should be approaching this, and what sorts of things I should be thinking about?

This sucks, I’m sorry.

From a strictly business point of view, you want to think about the makeup of the team that you’ll have remaining after the layoffs are over — what skills and experience will be needed, whether any projects are being added or cut (for example, you might have a really talented llama groomer, but if you’re scaling way back on the llama grooming program, you’ve got to factor that in), and how the people who remain will work together to achieve what needs to be done. Who will be the most crucial people to have on that team?

That might be obvious, but sometimes managers approach these decisions strictly by seniority (which doesn’t always correlate well with these factors) or strictly by performance (which should matter a lot, but can also be more nuanced — like with that llama groomer example).

4. When should I disclose my imminent maternity leave in a job search?

Like many, I was laid off in the fall, and have been job-searching ever since. In December, I had a final interview with a company, who has enthusiastically pursued me throughout their interview process. They told me they’d be in touch again after the new year.

When the new year rolled around, I heard from the hiring manager – and it was mixed news. They do want to offer me the position I interviewed for (hooray!), but unfortunately, their company is under a hiring freeze at least until February.

Here’s where it gets complicated – I am pregnant, and am due at the end of February. So far, I have not disclosed my pregnancy in the interview process, so as not to introduce potential bias into the company’s decision making. And when it was possible that I could have been offered the job in January, I could have worked for 6-8 weeks before having to go on parental leave. Now, however, that window is looking smaller and smaller because of this hiring freeze, and I am getting nervous about *when* to disclose my pregnancy. I don’t officially have a job offer yet, and don’t want to jeopardize the offer either way.

Here are what I see as my options: (1) Wait to disclose until I get an official offer, knowing this may mean that either the employer decides not to make the offer (which would suck), or best-case, I work for a week (or less?) before the baby arrives. (2) Knowing that the company is experiencing a hiring freeze, use a flexible start date as incentive to still hire me, and disclose now … before I have an official offer. My message to the hiring manager would be something like, “I know Company is under a hiring freeze for a while; I need parental leave ‘til at least April – does this help at all?” Worst case, again, the employer decides not to make an offer; best case, I have the job starting at a date that works for me.

Is there a third way of moving forward here that I’m not thinking of, or is one of these two options best? I don’t want the employer to feel deceived, but nor do I want my pregnancy to cause me to lose an amazing opportunity.

The thing about hiring freezes is that there’s no knowing when they’ll be lifted — and they probably can’t hire you right now for a start date in April (or later) because of the freeze. So most likely, option 2 wouldn’t help you.

Given that, go with option 1 and if they do come back to you with an offer, you’d disclose at that point. They can’t legally pull the offer because of your pregnancy, unless it’s truly that the timing of your leave means it won’t work — but that would be the case whenever you disclose. There’s also a good chance their next contact won’t be right at the start of February — it could be later in the month, or March, or even later, depending on when they lift the freeze and how much they’re prioritizing this job against other vacancies at that point. So at whatever point they make an offer, you’d just say, “I had a baby in (month) and am on maternity leave until (month) — would (date) work as a start date?”

how do I give notice to my boss if they’re on vacation?

A reader writes:

I am planning to go back to school a month from now, to up-skill and ultimately career switch. Originally, I intended to provide my boss 2.5 weeks of notice before starting my program. However, I just found out this morning that my boss will be on a month-long vacation starting mid next week, which happens to coincide with my entire notice period. Now my original plans to resign are at significant risk as I do not want to burn bridges with my current team and employer. Here are the issues:

1. How do I give notice to my boss if they are on vacation?
2. Even if my boss finds out that I will be leaving while they’re on vacation, they cannot do anything to plan for the transition during their time off.
3. Unlike finding a new job, I cannot simply negotiate a later start date with the educational institution I plan to go back to school for. Start dates for classes are far less flexible than new jobs.
4. I may be blindsiding my boss if I announce my resignation. As we do not have a close relationship (we get along but on a very transactional level), I am not comfortable with informing them about my educational plans until I plan to provide my notice. The reason is that I’m afraid I will be pushed out or added to the dreaded layoff list once they learn that I’m no longer interested in my current position. I still need a paycheck until I resign.

What I plan to do is to talk to my program advisor for the school I plan to enroll into to see if I can be transferred to a later cohort, which is two months after the original one I enrolled in. This way, I can give notice after my boss returns. Although this isn’t the optimal choice for me, I am prepared to change my plans if the risks of my current situation are too big. Please advise on how I can navigate this sticky situation.

Don’t change your plans! You can still resign at the time you planned to.

If your boss is on vacation, you can give your resignation to their boss, or to HR if you have it. It’s true that your boss won’t be able to do anything to plan for the transition while they’re out, but that’s just how it goes sometimes. It’s inconvenient, but it’s definitely not something you should change your school enrollment over.

Side note: Some managers would prefer to hear the news while they’re out. (I used to be one of those, and I now realize how very unhealthy that was.) You don’t need to decide if this is the case for your boss. The person who you give your resignation to in their absence can make that call if they want to.

When you resign, you can say, “I realize this timing is really bad with Alex out. I’ll make sure to leave thorough documentation on where all my projects stand, and given the circumstances I can be available for a call or two once Alex is back if there are things they need to wrap up with me directly.” You don’t have offer that last bit, but if you generally have good will toward them, it can be a good thing to offer.

In a different set of circumstances — where you didn’t worry you’d be pushed out earlier than you want to leave — it might make sense to give your notice now, before your boss leaves for vacation. But you’re not required to risk losing several weeks of income just to make things easier for your employer (and if they want people to do that, they need to build a culture where people know it’s safe to).

updates: the lying director, the apology muffins, and more

Here are three updates from past letter-writers.

1. Dealing with a horrible, lying director and management that won’t act

Several years later, wanted to thank you, acknowledge how right you were, and give an update.

I stayed for 3 more years after the post. Funny enough, Lying Director quit, Terrible Executive Director tried to claim credit for it by claiming they fired the Lying Director, and I decided to stick around for a little bit longer because suddenly the organization was on track to do something really exciting that I and the other Good Directors had been trying to make happen for a while. We made history (international front page news and mentioned in books in multiple languages!), and my department was widely acknowledged to be at the center of much of the wins. My resume is fantastic because of staying the extra few years.

And all throughout, you were totally right that the real problem was the Lord of the Flies style executive director. Terrible ED actually got worse (which I did not think was possible), and got even more toxic when the pandemic started. Commenters were right that working at a place where the person at the top is the biggest obstacle to success just won’t work. A mass exodus did happen around the time I left, it didn’t wake up the Board and nobody asked why the ED couldn’t keep a good team together.

After we made history, I found another job, took a huge 30% paycut, which was totally worth it because now I do NOT have weekly nightmares about work AND I’m working only about 40 hours per week instead of the 60 – 70 I used to work so it’s probably actually not even a paycut if I think about it hourly AND my dentist has said that I’m not grinding my teeth as much!

2. My coworkers had to work late when I messed up — should I bring in muffins?

I’m glad that I listened to you and the commenters and did not bring in any baked goods. Honestly, the implications that you and the commenters suggested — i.e. seeming a little overly apologetic, unintentionally leaning into gender roles, etc. — had not occurred to me, so I’m glad I asked you first. For what it’s worth, I have brought in donuts before as a way of making up for an accident (years ago, I used something that belonged to a fellow intern, thinking it was common property), which worked then, but you’re right that doing the same would have been excessive in this situation.

It ended up that that project I wrote to you about wasn’t, as one commenter suggested, an overestimation of my abilities — rather, it was an ordeal that would’ve been made much easier with more time and more support from my boss. In fact, he liked the work I did on that first one and let me do two more — on topics of my own choosing! — later in the year, with more support (and more time, when possible.) It made a huge difference!

Thanks to everyone for their help!

3. Can I ask my coworkers to keep masking around me and not come to work sick?

I am the writer who asked about how to ask for accommodations at my work in March while going through chemotherapy, and whether I could really ask my coworkers to mask more for me.

I am very happy to report that I not only kicked cancer’s butt and went into full remission, but my coworkers could not have been more conscientious or accommodating. I wore an N95 mask religiously, took my breaks/meals in either my car or an empty office, and I was able to remove myself from any situations where I would have had more than passing contact with sick individuals. My manager absolutely went to bat for me, and while we couldn’t really REQUIRE people to stay home while sick, people were amazing about wearing masks and hand washing and sanitizing surfaces. I was lucky that my immune system only really tanked once or twice, and I managed to not get sick a single time. I also handled chemo symptoms way better than expected, and my coworkers and manager went above and beyond to be flexible for me. It’s really situations like this that let you know how much your coworkers care about you, if you’re lucky enough to have them! Thank you to you and all of your readers for the kind responses and helpful advice!