I don’t want to chip in for a birthday gift for our boss, apologizing to a former coworker, and more

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

1. I don’t want to chip in for a birthday gift for our boss

My boss’s admin assistant preselects gifts for our collective boss on his birthday. My boss has at least 15 direct reports, and we are being asked to pitch in $20-$30 each for a large item for his birthday – totaling over $300. It is being framed as mandatory — in fact, the gift has been preselected and prepaid for (without consulting any employees who are expected to chip), and now we are all expected to pay for it.

I am about $30K in student debt. I can kind of afford it, but don’t want to incur additional expenses.

While I could just give the money and suck it up, it strikes me as incredibly inappropriate to preselect a gift and then demand an amount from employees, and I don’t want to do it out of principle. I barely ever interact with my boss or his admin assistant. My birthday came and went recently, with no recognition in any form from my boss or admin assistant. Which is fine — a “happy birthday” is more than enough.

Am I rocking the boat unnecessarily by saying something along the lines of “finances are tight right now, so I can’t contribute” (which is awkward because it’s already been purchased) or “next time, can you please run this type of purchase by me before expecting me to contribute”?

It should be completely fine to use either of those responses, or “It’s not in my budget, sorry!” or anything else along those lines. Your boss’s assistant shouldn’t be doing this at all; it’s incredibly rude to spend people’s money for them without their proactive consent, and employees shouldn’t be gifting upwards at work anyway. Any reasonably functioning office should accept that response without any additional pressure. But if the assistant does continue to pressure you, at that point she’d be so over the line that ideally you’d escalate it to your boss or HR to intervene.

2. Can I apologize to my former coworker for how my company treated her — when I was involved in what happened?

I work in management and typically do not become friends with anyone at work. A few years ago, we hired a director who I instantly connected with on a personal level. We exchanged gifts for each other’s kids, grabbed lunch when they came into town, and worked on a coupled high-level corporate projects together. Recently they were selected in a random corporate audit that did not go well. I was not involved in the investigation, but I was brought in to the confrontation with them due to my job. Corporate asked for an explanation and rebuttal from this person and evidence against wrongdoing. They were unable to provide evidence in time due to IT issues and ended up resigning due to frustration. Corporate did not accept the two-week notice and made it effective immediately. I had to be the one to tell them. I was also told if they had not resigned, they more than likely would have been fired due to the nature of the findings. When I saw the report, while they were grossly negligent, I would have recommended a final warning and reimbursement back to the company. It read to me like serious disorganization more than anything. I really feel like the company was in the wrong with how this was handled, regardless of my personal feelings towards my colleague.

A few weeks later, I noticed I was no longer connected with them on LinkedIn, and it really hurt my heart. A mutual friend liked one of their posts, and I in turn liked it. The next day, I saw I was blocked and it crushed me. I want to apologize to them for how they were treated in this situation. I honestly don’t believe anything had been done maliciously by my colleague, and I don’t think they had been given a fair shake to defend themselves. Since I had to be the one to deliver all the bad news, of course I am “one of them” and did not help someone when they needed me the most. What should I do? Should I reach out and talk to them? Would that also be career suicide? My heart is crushed at losing this person in my life, but I also don’t want to compromise my job. I am high ranking in my company as well.

If you could go back and redo things, I’d suggest seeing if you could recuse yourself from the situation due to the personal relationship.

Unfortunately, contacting this person now and telling them you don’t agree with your company’s decision or how they were treated carries some not-insignificant risk because you’d be a high-ranking representative of your employer (the one who delivered the decision, no less) undermining the company’s decision, which could impact your company legally and otherwise. For example, if your coworker decided they had grounds to sue, they could end up citing your statements to them as evidence that they were mistreated. Your company would likely see that as a pretty serious misstep on your part (and a breach of your duty to them), which could affect your job. That doesn’t mean you can’t do it, especially if you truly believe your company was wrong, but be aware of that risk.

That said … if I’m reading between the lines correctly, it sounds like this person misappropriated  company funds for personal use? If so, that’s very serious and your company’s response doesn’t sound like an overreaction.

3. My employee puts herself down

I manage a number of project managers, including Jane. Jane has been in the role about one year, and is very good at her job — hard-working, detail-oriented, and conscientious. However, her manner of speaking is very self-deprecating. She prefaces all of her (valid and useful) questions with “This is a silly question” and asks for clarification by saying things like, “I’m probably being a ninny, but could you tell me more about X? This happens in one-to-ones, in meetings with other project managers, and in wider meetings with stakeholders.

I find these phrases mildly irritating — she is not a ninny! — but I recognize that they are pretty harmless. My concern is that I think they make Jane come across as unsure of herself and more junior than she is and may impede her ability to lead projects now and progress in future. I get the sense that these phrases stem from Jane’s worries about work; when a project went significantly over schedule (through no fault of hers), she was anxious about how it would impact her reputation with me and my manager, despite my reassurances that she was handling it appropriately. That said, no other colleagues have mentioned this way of speaking, and I have only received positive feedback about her work.

Is this manner of speaking is actually a problem and/or something I should raise with Jane for development? I don’t want to be seen to be policing how women speak in the workplace, nor exacerbating her already present worries about how she’s coming across. For context, we work in a female-dominated industry/organization which is known for being cosy and friendly. I am only a few years older than Jane (early 30s vs late 20s) and have myself done work on my communication style and work anxiety in the past, so I might be reading into this more than is necessary.

You’d be doing Jane a favor if you talked to her about this! She’s undermining herself and almost definitely affecting the way she’s perceived, and she’s also probably reinforcing her own self-doubts when she speaks that way. You could say something like, “Jane, you’re talented and you do great work, and I’m so glad to have you on my team. I want to mention something that I’m worried could impact the way others perceive you: You tend to preface questions with ’this is a silly question’ or ‘I’m probably being a ninny.’ Your questions aren’t silly and you’re not a ninny. I’m worried you’re undermining yourself with those comments, and I want to make sure nothing detracts from people seeing you as skilled and competent.”

Since it sounds like you’ve worked on similar issues yourself in the past, don’t be afraid to allude to that too (and what helped you) if you get the sense it would be useful.

4. Everyone wants to complain to me about my boss

I recently got a job working for a performing arts nonprofit. I was originally hired as events help but with the way things are they didn’t have hours for me. I was approached by the finance team and they offered me hours with them. Finance isn’t my favorite but I’m doing okay over there.

The problem is my friends (and some superiors) in other departments stop by to say hi and end up complaining to me about my boss, the head of finance, Jane. It starts out with “how’s working for finance” and ends with “this is everything I hate about Jane.” Jane is widely disliked. She has a reputation for making things more difficult than they need to be, micromanaging, and seizing control of other departments. I don’t personally have a problem with her. She’s very exacting but I do well with specific instructions so her “micromanaging” is somewhat helpful to me, though there is a lot I find stressful. How do I get people to stop complaining about her to me, while still maintaining my relationships with other departments? Should I just get out of finance and seek hours elsewhere?

You shouldn’t need to switch departments over this! Just set boundaries with people. When someone starts complaining about Jane, interject with, “She’s my boss now so I don’t feel right complaining about her. Thanks for understanding!” If you want, you can add, “I actually haven’t had a problem working with her,” although that risks drawing out the conversation further when you’re just looking to shut it down.

5. My boss doesn’t want me to take a late lunch break

What’s your stance on your employer telling you within what periods to take a lunch break? My manager seems to be annoyed I don’t take a lunch break between 12-2 pm every day. For example, yesterday I ended my lunch at about 2:40, and he seemed dissatisfied with my explanation that I didn’t get around to it earlier as I was working on something.

Personally I don’t even eat lunch on my break. I’m a late luncher, so I’ll go out for a walk and eat in the afternoon, but his demands about the time I take a break (whether or not I’m even ready to) seem quite … demanding. Just wanted to know your thoughts.

It depends. In some jobs, the way you time your lunch can affect other people or their workflow — for example, if your manager normally counts on being able to find you for time-sensitive work in the afternoon, it can hold things up to discover you’re not there. In jobs where work often needs to be dealt with in real time, it can be easier to have a standing expectation that everyone will be done with lunch and back to work by 2 (or whenever). But there are other jobs where it doesn’t really matter at all. Even then, though, unless you’re particularly senior, it doesn’t strike me as outrageous to ask people to generally strive to take their lunch within a two-hour window in the middle of the day.

6. Company won’t let us see the org chart

I work at a corporation with several hundred employees spread out among numerous offices and departments worldwide. Especially since we don’t see many of our colleagues regularly (even in non-pandemic times), it would be very helpful to have a standard org chart that shows who is in which department, and who reports to whom. But our leadership has refused to circulate an org chart, on the grounds that such a document would reveal confidential information that cannot be shared, even internally. (We do get a bare-bones employee directory, broken down by department and office, which lists names and phone numbers, but not titles or reporting structure.)

This seems nuts to me. While, like every corporation, we deal with some confidential information, there’s nothing especially secret about what we do, and an org chart would merely include people’s titles and reporting structure, none of which seems proprietary. Of course an org chart wouldn’t include any substantive information about business plans or strategies, and employees’ public LinkedIn profiles typically give much more detailed information about what they do, and, as far as I’m aware, no one has ever complained about that.

Is this normal? I used to work at a very large corporation with many thousands of employees, and we had a detailed org chart available on our intranet for every single employee from janitor to CEO, which showed his/her picture, contact info, and reporting structure. It was very helpful.

This is indeed odd. Org charts are very normal and not typically considered a closely guarded secret from an organization’s own employees.