coworker accidentally linked her nudes to our team account, asking for extra pay for overnight events, and more

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

1. My coworker accidentally linked her nudes to our team Photoshop account

My coworker was using our team’s Photoshop account for a personal project (which our manager is aware of and okay with) and somehow she accidentally linked her phone camera roll to the account so all of her personal photos were visible on the team account. This might have been a nonissue, but my coworker has numerous sexually explicit photos on her phone that were then linked to Photoshop without her knowledge. The way she found out about this was our manager calling her after hours and letting her know she needed to unlink her phone photos immediately. Manager did not mention anything about the content of the photos.

Clearly, my coworker is now embarrassed and freaking out about what this means for her job. Could she be fired over this?

It’s possible, but it’s far more likely that her manager will just have a serious conversation with her about being more careful in the future — or might assume the embarrassment has already handled teaching her the lesson (which it probably has). Your coworker could help things along by thanking for the manager for calling her right away and saying that she’s mortified and it will never happen again.

2. Not telling an intern the real reason she was fired

I am in middle management at a company that takes on a fair number of interns every year. At a recent meeting (just middle managers and our boss), my coworker mentioned some very inappropriate behavior from an intern. Apparently, Coworker and Intern were working with a client and Intern started talking about marijuana use at length — how it’s so helpful for her, how much fun it is, but sometimes the way she acts while high is scary to her — while Client laughed along and encouraged the conversation. We all agreed that the internship needed to be ended early, both because of this and because Intern is late more often than not.

Coworker asked us not to tell Intern that we knew about the inappropriate conversation. Boss said that was fine, and that he’d tell Intern she was being fired for arriving late too many times. I suggested it might be a good idea for Intern to know that what she said in front of the client was not okay, for her professional growth if nothing else. Coworker never discussed it with her, so she wouldn’t know. Nevertheless, she was fired for “tardiness.”

Do you think this was the right way to handle it? I understand Boss wanting to respect Coworker’s request not to tell Intern that he knew what Intern said, but at the same time, I feel like Intern deserves to know. What do you think?

I’m with you. Part of the point of an internship is to learn about how work works, and it’s a disservice to the intern not to tell her that that conversation was firing-level inappropriate. It’s far better for her to learn that lesson as an intern than at a regular job where the stakes will be higher. In asking your boss not to share the info, the coworker was prioritizing her own (extremely mild) issues of comfort over what’s actually best for the intern, and it’s too bad that your boss agreed to handle it that way.

3. How do we ask for extra pay for overnight events when we’re working for a friend?

I work part-time as an assistant event planner. The company is owned by one main planner, Jane, who does this full-time and brings in three assistants to help on the day of events. The three of us all have separate full-time 9–5 jobs during the week, so this is side work for us. Event days are long, physical, and often outside in hot weather, but we all genuinely enjoy working together and have become good friends.

As the business has grown, Jane has started taking on more events that are farther away, which often means overnight travel. We’re paid hourly for the event work itself and reimbursed for expenses while on the road, but the travel adds a lot of extra logistical work for us — arranging time off or remote days from less-than-ideal locations for our regular jobs, managing childcare and pet care, packing for several days, etc. It’s starting to feel like we should be getting some additional compensation for that extra burden, maybe a flat bonus for overnight events or something similar.

The tricky part is: I don’t think Jane realizes how much of an extra ask these overnights are. She’s a workhorse who will happily go from 5 a.m. to midnight, and when she’s in the zone she can get tunnel vision about what the event needs, without realizing that not everyone can or wants to operate that way or that we have other responsibilities outside her business.

Jane genuinely enjoys these trips and I think sees them as friend time as much as work time. To be fair, we do too! We don’t want to damage the good vibe we have, but we also want to feel fairly compensated for the extra effort that goes into supporting her growing business. How can we raise this without hurting the relationship?

Be straightforward and explain that the overnight trips require more from you than the local ones do, and ask to revisit the payment rate in light of that. For example: “Can we revisit the payment rate for overnight trips? Our current payment rate was arranged when all the events were local, but overnight events require a lot more, like time off from our regular jobs or arranging remote work and managing child care and pet care. Could we figure out a different rate for overnight trips that takes those factors into account?”

If she resists that, it’s completely fair and reasonable to say that you can only do local events. And since there’s a friendship element here that you’re worried about too, you can acknowledge that by saying something like, “I do have a great time on the trips and like doing them, but realistically it’s not something I can make work with my regular job at the current rate. So I will sit those out, but if you ever change the way they pay, I’d be interested in doing them again.”

4. Who should really be in the “to” field vs. the “cc” field?

The VP at my work requests that we copy his assistant when emailing him to make sure he responds. Often, if I am scheduling a meeting with him, his assistant will be the right person to respond. I feel weird CC’ing her and addressing the email to VP when the assistant is going to respond.

I have been addressing the emails to both of them and talking about the VP in third person when scheduling meetings. The VP needs information on the topic of the meeting, and the assistant is the one that works out the scheduling. I feel like I should actually be emailing the assistant and CC’ing the VP, but that may not be appropriate given his position either. What are your thoughts?

Either one is fine, and different offices do it differently — and in most cases, no one is really analyzing the to/cc fields that closely (there are some exceptions to that, but they’re rare) and you’re probably putting too much worry into it.

In this case, since the VP has specifically asked that you copy his assistant, you should do it that way. And it’s very, very normal to do it that way! The idea is that you’re emailing the VP about the need, but his assistant is copied in so she can handle the set-up. But most likely, they don’t really care which way you do it as long as you’re sending the info to both of them.

5. I’m on leave and just saw my company advertising my job

I work in middle management at a mid-sized office. There have been a lot of money troubles and management drama here in the past year, and I recently went on FMLA to address health issues I’ve been ignoring. The stress of the job was definitely a contributing factor to my declining health.

I will return to work this winter and have communicated my expected return-to-work date to HR, but I was scrolling a job board and noticed that my employer posted an opening for my job. It has a different title than mine but is exactly what I do in my day-to-day. I’m trying to not freak out and tell myself that maybe management has realized how overworked I was previously, so they’re hiring help for me. But I can’t help but think that they are trying to blatantly replace me. Management is known to hold grudges toward people who go on leave. I know that technically my employer can move me to the “same or equivalent position” when I return from FMLA, but I also know there is quite literally no money or space to hire a Second Me for the office.

Is there any way to interpret this non-maliciously? My current thought is to continue with my current return-to-work plan and see what happens, but the uncertainty is killing me.

It’s possible that they can’t leave the work undone and so they’re hiring for it now, with the plan of moving you to an equivalent role when you return or of having there be two people doing the work or at least of having overlap. Or it’s possible that they’re planning to flagrantly violate federal law and push you out for taking FMLA.

One option, if you want to, is to email your manager and say you saw the job posting and ask if they’re adding a second role or envisioning you returning to a different one. But it also wouldn’t be a bad idea to make sure you have a lawyer to contact if they do indeed try to push you out.

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