coworker photographs our cubicles when we work from home, new manager might join my hobby team, and more

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

1. Coworker photographs our empty cubicles when we work from home

My company established a three-days-a-week-in-office rule beginning in April 2024. Over the last two years, and with a new CEO who is very vocal about being pro-flexibility, the three days has become more lax. Plus, we are encouraged to work from home if we have appointments, are sick, have childcare responsibilities, etc., on days we would normally be in office.

I recently found out there is an employee who is keeping track of whether or not I am in office, going as far as taking pictures of my and a coworker’s empty cubicles if we are working from home. One of my coworkers who sits in our cubicle “square” saw him, and said he comes in and loudly says things like, “Oh, look who isn’t here again!?” And I’ve personally seen him poking around in other cubicles of people were working from home that day.

This employee is not our boss, not on our team, and does not even sit on our floor. We do not know what he is doing with these pictures, but we assume he sends them to our boss, whom he is allegedly friends with. I have seen him going into and looking around other people’s empty cubicles as well (mostly women). There is also history of this person tattling on people’s comings and goings. He seems to be specifically targeting female employees, and now I am one of them. I am so bothered by his behavior, I removed pictures of my family in my cubicle because I do not want pictures of my children on his phone. The friendship between him and my boss makes me question if I say something to my boss. Do I approach the perpetrator directly or go to HR?

You could say something directly to this coworker if you want to! The next time you see him poking around in other people’s cubicles, say, “Are you looking for someone?” or “Are you looking for Jane? She’s remote today.” And then if necessary, “Is there something specific you need? I don’t think people want you poking around in their workspaces while they’re not in the office.”

But you don’t need to address it directly with him if you don’t want to, and instead could go straight to HR. Be sure to include that he seems to be targeting women (which takes it from annoying/obnoxious to creepy and potentially a lot more pressing to HR).

For what it’s worth, whatever he thinks he’s “documenting” sounds like it’s not going to get anyone in trouble, but it’s obnoxious nonetheless.

2. My new manager might join my time-intensive hobby team

I work in a small office (about 50 people), and we have a new director starting in about a month. The majority of my role is project management and admin support for the director so I’ve had some contact with him already, and I’m excited to work with him, with one major reservation: we share the same team-based, time-intensive, athletic hobby. (Think team triathlons or similar. One person’s performance has the potential to make things great or awful for everyone.) There’s only one place in my area that does this, and I know he’s looked into it, so I’m sure we’ll be on the same team shortly after he moves here.

While I love this hobby and I wish more people did it, I have some concerns about how it’s going to impact our working relationship and on my enjoyment of the hobby. It’s time-intensive (often eight hours a week plus occasional weekend travel), so between this and working very closely together, he and I are about to spend a lot of time together. How do I get off to a good start maintaining boundaries and not having my work life and hobby bleed together? The last thing I want is to have a bad day a work turn into a bad practice, or vice versa.

It’s also going to be obvious to other people in our organization that the new director and I spend a lot of time together outside of work. Are there ways for me to make that less of an issue in the office? I do worry people will think there’s favoritism going on. For what it’s worth, some people in the office know about my hobby, so it’s not going to seem like I started it to suck up to the new director.

If you haven’t already, find a way to mention to him early on that you’re an active member of that team because he really should recuse himself from joining it once he realizes you’re on it too. It does create the potential for issues — from awkwardness in his relationship with you, to both of you being unable to escape work dynamics, to perceptions from others on the team that you have special access to him. But that’s all his to manage, both as your manager and as the person coming in who isn’t already on the team.

3. Can my boss “unofficially” cut off certain employees from receiving new clients?

I work in the office of a small business. For the sake of anonymity, let’s say we groom llamas. We’ve got three office staff, about two dozen groomers, and one owner. A large part of my job is setting up new clients with a groomer. I and the other office staff have a lot of flexibility over who we set up with who — if a client wants their llama groomed every Wednesday at 3, I usually have between one and four groomers with availability and I’m the one who sets up the appointments. Some clients stay with the same groomer for years. The groomers are all independent contractors who set their own schedules but only get paid when they’re working. If they have big gaps in their schedule, they don’t get paid for those.

The owner is lovely and well-liked, but she can be extremely petty too. My issue is that she will “unofficially” direct us to stop giving clients to Groomer X because they’re too busy or too flaky or she suspects they might be planning to leave soon. That’s understandable from a not-jerking-clients-around standpoint, but it feels unfair, especially when Groomer X ends up with a schedule that’s more holes than clients and functionally gets a pay cut, often leading to them eventually leaving. If she would just say “this is what I’ve decided,” I could deal with it as boss’s orders, but usually it’s roundabout by way of office gossip. If I do still give Groomer X new clients — even when they’re the only one who still had availability at the time the client requested — I get significant pushback from the owner and other office staff complaining that I’ve just made more work for them, didn’t you know Groomer X was supposed to have a freeze on new clients, etc. The more work part usually turns out to be true, too, when Groomer X leaves and we have to shuffle their clients into other groomers’ schedules.

Is this legal? Is it just a conflict-averse way to fire certain groomers without actually having to fire them? I feel guilty because some of the groomers who are being cut off are nice people and I feel like if they are truly allowed to set their own schedules (as independent contractors are supposed to be able to do), we should be accommodating that even if we think they’re overbooked or might be planning to leave soon. Can I legally get fired for scheduling llamas with someone who has only unofficially been closed to new clients? I do love the rest of my job and most of the people I work with, but this one thing feels ethically icky and I sympathize with the groomers who get stuck in an untenable situation.

Yes, it’s legal for the owner to do this, and it would be legal to fire you for not complying. But your boss is a bad manager — if she wants groomers to operate differently, she needs to tell them that with her words, not just stop scheduling them. Some of the groomers, if not all, would probably be happy to adjust what they’re doing if they knew she wanted them to — or if they couldn’t, they could have an actual conversation with her about whether their availability still aligns with the business’s needs — so it’s bizarre that she’s being so avoidant.

Do you have the kind of relationship with the owner where you could say, “If you feel like Jane isn’t opening up enough of her schedule (or fill in with whatever the owner’s objection is), could we tell her that and see if she can adjust it? She probably doesn’t know you’re concerned about it and might be able to fix it.”

4. When your example of a conflict involves one of your interviewers

The question you answered recently about providing examples of how you deal with conflict in an interview made me think of a question.

When you’re applying for internal jobs and have a good example to share involving one of the interviewers (i.e., one of your current colleagues), how would you advise dealing with that? Especially where you might want to say something not entirely complimentary about the interviewer’s own behavior.

I’m not thinking of launching into a rant or being excessively critical, just giving examples in a measured, balanced way that might involve some level of saying “in this situation, you did X or said Y, which I found less than ideal and here’s how I responded effectively and positively to that.”

You’d nearly always be better off finding a different example. The exception would be something where there could be absolutely no implied criticism of the interviewer’s behavior — something like, “I know when you and I were working on X, we came to it with different perspectives on Y, and my approach was ___, which I think was helpful to both of us and the final project, by accomplishing Z.”

But if there’s any hint that your assessment of the colleague was less than complimentary, pick a different example. You’re trying to get the interviewer to feel warmly toward you, not feel defensive.

5. Insurance stopped covering my ADHD meds

This month, the insurance my job provides decided it would no longer cover the medication that I take for my ADHD. Problem is, switching could be an arduous process. I don’t tolerate stimulants well, and there’s only one other drug of the class that I take covered. At best, I am going to have potentially up to two weeks where I’m anywhere from “not at my best” to “only barely functioning.” At worst, I’m going to have to probably stop medication entirely for a while (the other non-stimulant meds have side effects that are a bad idea for me).

I’ve seen your advice on explaining medication issues, but what do you do when you genuinely don’t know if you’ll return to a functional baseline in a few weeks?

Say this: “I’m dealing with a medical situation that is making it hard to be at 100% right now. I’m working with my doctor to resolve it and we’re hopeful I’ll be back to normal soon, but I wanted to mention it in case you notice me seeming off.”

Or: “Our insurance stopped covering a medication that I take and so I’m working with my doctor to find a new one that will work, but we don’t know yet how long that will take. Meanwhile, I may seem off so I wanted to let you know what’s going on and that we’re working on it.”

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