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

1. My boss keeps giving me food I can’t eat

Is there a tactful way to ask my boss to stop giving me food-based tokens of appreciation? My boss occasionally gives donuts, cookies, candy bars, or buys pizza for our small work group to show her appreciation. While I know it is the thought that counts, I cannot eat gluten. My boss is aware of this dietary restriction, yet continues to give me the “gift” of gluten-containing items. She is a wonderful manager in many other ways, and but these small tokens leave me feeling annoyed instead of appreciated.

“Would you take me off the list for food items? I can’t eat them so they go to waste.”

Then if she forgets and gives you food anyway, hand it back to her in the moment: “Oh, remember I can’t have this, let me give it back to you for someone else.”

Also, with the pizza for the group, is there something else she could order for you at the same time (ideally from the same place but if not, then from somewhere else)? If so: “I can’t eat pizza, but I’d love it if you included me by getting X on the side so I can participate with everyone else.” If she doesn’t want to do that, so be it, but if she actually wants you to feel included and appreciated rather than excluded and annoyed, you’ll be giving her clear info about how to do that.

2. Employee gave lots of notice, but now we have someone who could replace him

I’m writing this question on behalf of my boss, who owns the company (I’m his EA). One of his employees (Gary) gave notice that he’s moving out of state, likely three to four months from now. My boss has cultivated a workplace where long notice periods are common, because he is known as someone who isn’t going to push someone out early or punish them for giving notice.

However, my boss just learned that a different person (Lance) is interested in working here full-time. My boss has wanted to hire Lance in the past and Lance comes highly recommended. The position is hard to fill as it takes very specific expertise.

In a perfect world, my boss would hire Lance and let Gary just work until he leaves. Unfortunately, we don’t have the budget to have both of them at once. My boss is trying to find solutions to make sure he does right by Gary, while also finding a replacement for him in his hard-to-fill position.

His main solution right now is to have a conversation with Gary to see if he can get a firmer timeline of his departure, especially because he suspects Gary might leave sooner than he originally said. It feels like an imperfect solution, though. Do you have any ideas of how he can navigate this?

Your boss should go back to Gary and be honest: “I appreciate the amount of notice you gave me and I don’t want you to regret doing that. That said, now that I know, it would really help if I can get a better idea of your timeline because I have someone in mind for your role who won’t be available indefinitely, and I want to figure out if he’s even a possibility or not.”

Your boss just needs to be careful not to push Gary out earlier than he wants to leave; if he starts feeling tempted to do that, he should remember that the only reason he even has this potential opportunity to hire Lance is because Gary generously shared his plans early — and that if he’d stuck with a more typical two weeks, this wouldn’t even be coming up. Plus, if other employees get any whiff that Gary got pushed out early, your boss is much less likely to get that kind of early notice from other people in the future.

Related:
what to do when an employee announces she’s resigning … at some point but not now

3. Turning down a lateral move at a lower salary

A couple of months ago, I got very close in the interview process for a more senior position at a different division within my company, at a slightly higher salary. I was told that I was a strong candidate and it was a difficult decision, but they ultimately hired another candidate. It became clear that they already had someone from their department in mind for the role, and were surprised to find another strong candidate in me. The department head encouraged me to apply for the role that the candidate they hired would be leaving, which would be a lateral move with the same title as the one I currently have. There are reasons why I’d be interested in this change, including a bad personality fit with my current boss.

I applied and when they reached out for an interview, I asked the recruiter to check that my current salary would be met in the new role. I was surprised to learn that while they could get close (higher than the starting salary listed on the job post), it would be a small pay cut from my current salary, rolling me back to the salary I had one cost-of-living-increase ago. I agreed to an interview to assess if the role would be a better fit for me, but was asked to let them know if I wasn’t interested after the meeting so they can move on in their search. It went well and I think there would benefits, including a more experienced manager and more room for career growth. After the interview, I felt good about the prospect and told the recruiter I’d accept the position if offered it. But after thinking about it over the weekend, I can’t get over that it might come at a small but real material loss to my income.

Do I have any leverage here to negotiate a salary match if given a job offer? How is this complicated by me wanting to leave my current role? It seems doubly painful since I know I’m qualified for a more senior position. But on the other hand, they have shown themselves to have a preference for hiring people from within their department — but then again, is it fair of them to ask me what that’s worth to me? Help me wrap my head around this!

Sure, it’s fair for them to ask that. They’ve already agreed to increase the salary but their budget is their budget, and if it won’t work for you, it’s reasonable for them not to want to waste anyone’s time.

If you wouldn’t take the job at the salary they’re offering, tell them that now. They asked you explicitly to let them know and you told them you’d accept, so if you’ve changed your mind about that, you need to tell them. If you go through their whole process and then try to negotiate more money at the end — after they were up-front and asked you if they should be focusing on other candidates — it’s likely to reflect poorly on you. Right now it’s early enough in the process that you can simply say, “After thinking about it more, I’m very interested but couldn’t take a pay cut from where I am now.”

4. A company asked me to keep checking in for updates … how often should I contact them?

I’m currently job hunting, and I recently interviewed with a company that wasn’t hiring immediately. They were very transparent that they didn’t have a position open immediately and that it could be months before a something became available. The interview went really well, with the interviewer encouraging me to check in often for updates.

That was two weeks ago, and I sent a follow up today asking for updates. They responded that the interview went well, but there wasn’t anything new on their end.

How often should I be following up? After that initial follow up, I was thinking monthly.

Should I respond to the email to say thanks? And should I do that with each of their updates? I don’t want them to think I’m rude for not saying thanks, but it feels excessive (I’d imagine most updates are going to be a short “Sorry, no updates”) and I don’t want to clutter their inbox.

Checking in monthly would be way too often. Every two to three months is the absolute most frequently you could do it without seeming annoying (and don’t do every two months like clockwork; vary it). If they have an open position that you’re a strong candidate for, they’re going to remember the person who’s been in touch within the last few weeks without you reminding them so frequently that you exist.

And sure, it’s fine to respond to their emails to say thanks, now and in the future.

5. Applying to two different jobs at the same company

I’ve worked in IT customer support my whole career, but I enjoy and am much better at the customer support side of things than I am dealing with IT systems.

Last week I saw that a local company had just posted a role for an IT department manager. Parts of the role seemed appealing to me and fit my profile quite well, so I figured I’d throw my hat in the ring to see what happens. I wrote a nice cover letter that I’m hoping will get me at least a phone conversation with the hiring manager and later got a response explaining how the company doesn’t use automated processes to review applications and that a real human would soon get back to me. However, the very next day, a customer service manager role was posted, and now I’m absolutely kicking myself because I know I’m a much better fit for this role and I would have definitely applied for it over the IT manager one if they were both presented to me.

My partner thinks I should sit tight and wait to hear from someone on the IT role, but a friend said I should apply for the customer service role as well, so now I’m torn. What should I do?

Apply for the second one. Just make sure you write a letter that speaks very specifically to the second role and isn’t generic. If it’s a small company, you should also explicitly address that you applied for the IT manager job, but you’re also throwing your hat in for this one because (reasons). If it’s a large company, you likely don’t need to do that but at a smaller one, the same people may be reading your application for both and you’ll be better off explaining it head-on. (It shouldn’t be lengthy or defensive, just a sentence or two that explains why you’re applying for two seemingly very different jobs.)

Don’t take your partner’s advice to wait until you’ve heard back on the IT job, because you risk the window closing on the one you want more.

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

1. My boss keeps pulling on my ponytail

I started a new part-time job at a restaurant a few months ago. I like it, for the most part, and I like the managers. But one of them, Phil, has a rather odd habit. He semi-regularly tugs (hard!) on my ponytail, which I am required to wear by policy and sanitation standards. The context of when he does it comes across as playful/friendly, for example when saying hello upon first seeing me that day or while laughing after I made a joke. I was extremely shocked the first time it happened and thought I’d gotten my hair caught on something before Phil made a comment (it was a “hi, nice to see you” hair tug as while I was passing through the kitchen).

This has happened six times since I started in March, which now that I write that down seems excessive for my short tenure and part-time status. I don’t know how to go back and reset this completely bananas boundary without it making things awkward. I suspect he doesn’t realize how hard he’s pulling and would at least be more gentle if I asked him to be, but I also think he’d be offended if I asked him to stop all together. I’ve definitely heard him complain about other staff members behind their backs, although usually for justifiable work reasons that I’ve seen firsthand, so maybe he’d take it in stride and I’m just catastrophizing. The power dynamics and gender roles make it feel so daunting to bring up. Do you have any suggestions?

Hopefully you’re just catastrophizing, because someone who takes offense to being asked to stop causing someone else physical pain … would be a serious problem as a human, let alone as your boss. Right now, though, there’s no reason to think Phil will take offense to a perfectly reasonable request. The fact that he complains about other employees’ work means he’s indiscreet (and maybe sucks at managing people), but not that he’s a bully who will ignore a direct request to stop pulling your hair.

(Of course, one could argue that the fact that he’s pulling your hair at all means he’s a problem — that’s not okay behavior — but if I’m reading your letter correctly, he thinks it’s playful and being well-received. Which is bad judgment, but not inherently the sign of a bully.)

So, the next time he does it: “Ouch! That really hurts — please stop.”

That’s the soft version. If Phil is a decent person, he’ll be mortified that he hurt you and will stop.

If the soft version isn’t enough to stop the hair-tugging, move to “Stop touching me.” Say it in a serious tone and don’t soften it with a smile. You need to remove any ability for him to read it as playful jesting in return; make it clear you mean it.

Assume that will take care of it. If it doesn’t, there’s a bigger problem with Phil — but so far, we have every reason to assume that simply telling him to stop will take care of it.

I do want to flag that there might be a bigger issue playing out on your side: you’re concerned you might offend someone if you ask them to stop causing you physical pain. Any chance you tend to be overly deferential to people with power, or to men, or to some other dynamic in play here? Because that’s not something you should ever need to worry about without the person giving you a specific reason to fear it.

2. My boss hates babies, and I’m pregnant

I have a good relationship with my boss and we work closely together. They are very staunchly child-free, which I have no issue with, but they have shared some very anti-baby/anti-mother sentiments that have made me worried about how they will react to my news. As a specific example, when another member of our department said they will never have kids, my boss responded “oh good, I hate kids!” My boss has also made comments about how pregnant people are always making excuses and are lazy.

I’m early in my first trimester and am not telling anyone yet, but when I eventually have to say something, I’m worried about how my boss will react. I have tried to lay the groundwork over the past year of mentioning that my husband and I will “eventually” have a child so the announcement won’t be a huge shock. Do you have any advice on how to break the news? No one in my department has kids, so I don’t have anyone to turn to for advice. To clarify, I don’t think my boss would become retaliatory, I’m more worried about making things awkward around the office if I approach this wrong.

You shouldn’t need to walk on eggshells around your pregnancy announcement! So first and foremost, your boss has seriously messed up by creating an environment where people working for them dread announcing a pregnancy. (Particularly those comments about how “how pregnant people are always making excuses and are lazy.” First, WTF? Second, great way to create a legal liability for the company if someone happens to bring a pregnancy discrimination claim down the road. Third, WTF?)

Anyway. Sometimes the best way to share news that you think the other person will react to inappropriately is by just proceeding as if of course they will have a normal and reasonable reaction because you trust them to be a normal and reasonable person (even when you don’t). Sometimes that sends cues to the other person about how they need to respond if they wish to be seen as normal and reasonable. Your boss may not be in that group, but it’s a reasonable place to start. So: when you’re ready to announce, don’t tiptoe around it; be matter-of-fact, direct, and cheerful. “I have news I’m excited about. I’m pregnant and due in December. We can talk about my plans for leave closer to that time, but I want to let you and the team know.”

If your boss says anything inappropriate in response, feel free to let your face convey “that was wildly out of line.” Out loud say, “I’m going to pretend you didn’t just say that. Moving on…” Or even, “For the sake of HR and legal, I’m going to pretend you didn’t say that.” But if there’s anything inappropriate from them after that, talk to HR. It’s illegal for your boss to create a hostile workplace based on your pregnancy, and any decent company would be grateful for the chance to know one of their managers is this out of line so they can shut it down.

3. How do I accept praise when I don’t think it’s warranted?

I started consulting after only a couple of years in the workforce once I realised my autism and severe ADHD makes it impossible to hold down a permanent job. This has worked out really well. I specialize in project work and short-term contracts (if it were up to me, I’d never take a role longer than eight weeks). This means I’m not usually anywhere long enough to get really bored and it doesn’t matter that I don’t fit into the office culture.

The last couple of years there have been fewer of these very short-term jobs and less project work available, meaning I’ve been in jobs four or five months at a time. This is definitely long enough to get bored. Once the interest of learning a new job wears off, I stop trying hard at work. I always get things done, but I don’t put any extra effort in.

But my clients keep praising me. Even though the work is easy and I’m not trying very hard. I hate getting praised, especially in front of other people, double-especially when I haven’t done anything to deserve it.

I’m finishing my current contract soon, which will mean a morning tea and the GM talking about how great it’s been to have me. This GM has been so lavish in his praise I’m wondering if I actually have done well; it feels more like the patronizing “Oh well done, aren’t you clever” that adults trotted out when I was 10 and had gotten my coat on without help. But assuming he does mean it, how should I respond? I know I shouldn’t say “It was easy for me” or “But that’s just what you hired me for.” So far, I’ve just said “Thanks” and sat there like a potato. Is that enough? What do the neurotypicals want from me in this situation?

Some options:

• “It was my pleasure.”
• “I’m glad it was helpful!”
• “You’re very welcome.”
• “I was happy to help.”

Any of those will be appropriate and received well.

Also, keep in mind that clients aren’t necessarily thanking you because they think the work was incredibly hard. They’re thanking you because it was very helpful to have you do it.

Related:
I don’t know how to accept compliments graciously

4. I met a candidate’s counteroffer and they asked for even more

I’ve made an offer to a job candidate who is a compromise candidate — not the best in the list of finalists, but the one who makes the most people happy. I’m not fully comfortable with this, but I’m trying to think of the long-term buy-in by my team. All the finalists were deemed acceptable, but the team had strongly conflicting preferences, and this is the person that checks the most boxes for the most people involved in the search and on the team.

My question, though, is about negotiations. I offered a competitive salary. The candidate came back asking for a modest increase. I was able to secure this increase and change the offer to the exact amount they asked for. Instead of accepting the revised offer, the candidate is coming back now asking for more. (I’m fudging the details a bit to keep this anonymous, but they gave a personal reason, along the lines of “my kid is going to college in the fall and I need to make a deposit on their housing fees this summer.” This strikes me as a good reason to want more money, but maybe not the best argument for why someone deserves a higher salary.)

How long is it prudent to continue to negotiate with a lowest-common-denominator candidate that I feel lukewarm about? If someone asks for more, gets it, and then asks for more beyond that, should I continue to entertain these incremental salary request increases? When does a job candidate’s request for a better offer become tantamount to declining an offer?

I wouldn’t continue to negotiate at all. You made an offer, they asked for more money, you came up to the exact amount they asked for. That should be it. Their request for even more makes them look flaky and like they weren’t negotiating in good faith the first time. I’d be hesitant to continue at this point even if they were a great candidate, but for someone you’re already lukewarm about? The only reasonable answer is, “We’re not able to go up any further. If the offer doesn’t work for you, I of course understand.”

Also, if you’ll be the person managing this hire, you should make the final decision on who you think will perform best in the role. Absolutely take other people’s input into account, but if you’re the one ultimately responsible for their success, you’re the one who should make the call you think is right.

5. Interview identity flub

I was recently in a second (and final) round interview on Zoom for a team lead position at the parent organization for my field, and when the interviewer put a long, multi-part question in the chat I saw that there was another candidate’s name listed in the title of the Zoom meeting!

I am in a very small and tight-knit field (there are about a thousand of us total in the U.S. and Canada), so I’m familiar with this other candidate (who has a unique not Jane Smith-y name).

Because it happened mid-interview, I feel like a floundered a bit on my next answer, sort of waiting to see if anyone else in the interview (three interviewers) was going to acknowledge what was there. They never did, and I re-centered eventually and moved on.

Should I have said something in the moment when it was throwing me for a loop? Or after the fact? Or is this one of those things that it’s most polite to just pretend isn’t happening? I have no doubt it was just a copy/paste error when creating the calendar invite for my interview, but I keep second-guessing myself about my decision to just ignore it. (And, if this context matters at all, this is a very relationship-oriented field with high expectations around collegial behavior and interaction.)

Is there any chance they had a scheduling mix-up and thought you were actually the other candidate? You probably know if this is or isn’t the case — if they called you by your correct name, referenced things that wouldn’t be on the other person’s resume, etc., then they know you are you and not the other person. And in that case, it’s just a clerical error, like that someone copied over the info from the other candidate’s interview when setting up yours and forgot to change it. That’s no big deal and doesn’t require you saying anything.

On the other hand, if looking back you realize that absolutely nothing was said that couldn’t have been said to Morgana Bumbleberry too, then ideally you would have confirmed in the moment — “I just want to make sure you know I’m Nicolina Warbleworth, despite the name on the screen.”