is it rude to send emails late at night, should I tell my boss I’m job hunting, and more

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

1. Is it rude to send emails late at night?

I am currently still in college and involved in a number of clubs that require me to email administrators, deans, and other official people at my university. I have a tendency to be up late (think 2-3 am) doing homework and answering emails from people, and sometimes that means I email these deans and administrators during the wee hours of the morning.

I have no expectation that they are reading my emails or responding at these hours and just assume they will answer when it is convenient for them, just as I email when it is convenient for me. However, I have been told by some people that I should only email these people during regular business hours and that my emailing late is disrespectful of their time. But I am not usually writing emails during regular business hours because I am in class, working, or in a meeting of some sort. While I don’t mind scheduling the emails to go out the next day, I’ve heard mixed reviews on whether or not it is really rude to email after 5 pm.

To summarize, am I really being rude to send emails this late and should I just stick to sending emails during the workweek from 9-5 regardless of my schedule? I’ve heard no complaints from the people I have emailed late but want to be sure I am not coming across as unprofessional!

It’s not rude to send late-night emails. The whole point of email is that you can send it when it’s convenient for you and people can respond when it’s convenient for them. It’s not disrespectful of their time because if they don’t want to deal with email at 2 am, they won’t be in their email then. It’s not like you’re calling them.

There are some cases where the optics of late-night emailing matter, like if you’re a manager emailing your team (because they may conclude you expect early-morning responses or that you expect them to work similar hours), or if you’re emailing job applicants (because they might take that as a bad signal about your work culture). But you’re a college student, not a manager. You’re fine.

2. My coworker answers the questions I’m trying to ask our manager

From day one, a coworker has answered the questions I ask of the trainer/manager. It is very annoying and degrading. How do I politely tell him I didn’t ask him? He is a really nice guy and is friends with my nephew. Also, recently I asked a question of our boss, who replied but didn’t understand what I was asking so this coworker explained what I meant. I said “I can talk” and he got a surprised/horrified look on his face.

I want to apologize for saying “I can talk” if it came off rudely, but I don’t want to give him the power to continue. I can’t think of a way to be nice about it.

Actually, the fact that you recently snapped at him gives you an easy opening. You can sit down with him and say, “I realize I snapped at you the other day when you jumped in to explain what I was saying to Jane. I shouldn’t have snapped at you, but you have a habit of answering the questions I ask her and jumping in when I’m speaking to her. When I ask her a question, I’m asking her, and I’d appreciate if you’d let her answer.”

3. Should I tell my boss I’m job hunting?

A couple of months ago, my boss told me the company was considering outsourcing my function (for efficiency and cost, no reflection on me). If they go ahead, the plan is that I’ll facilitate the transfer to the other company, then they’ll find me another job internally.

The thing is, I realized that I really miss working in my previous unrelated industry, and when my boss told me about the possible transfer I’d already been looking for a job in that industry for a while. I currently have one active application, but it might be months before I actually get a job.

Every time he gives me an update, he always asks if I’m happy and often says that I’m really well thought of and that they want me to stay. If I don’t get another job, I’m happy to stay and not worried about the changes, but if the right job came up I wouldn’t think twice about leaving.

I’m starting to feel really awkward about this. I know you normally advise against telling your boss that you’re looking elsewhere, but I’m worried about his reaction if I were to leave after having reassured him so many times that I’m fine. Should I say something?

No. There’s too much chance that if you tell him you’re actively working on leaving, they’ll drop their plans to find you another internal role, which then could leave you with no outside job and no internal job.

If at some point you take another job and are ready to tell him you’re leaving, you can use the always-convenient “it fell in my lap and was too good to pass up.” (Although really, if they tell you they’re outsourcing your function, it’s not shocking that you might start job searching, and if your boss has any savviness, he’ll know that.) You can also say, “I really appreciate how supportive you’ve been. It meant a lot to me.”

4. My coworker wants me to stay with her while her boyfriend is away

My coworker just texted me and said her boyfriend will be away from Thursday to Sunday. She said she hates staying alone that long and asked me if I could stay with her Thursday and Friday. We already have a weird relationship at work and some days we don’t even talk to each other. Also, she doesn’t have many friends and I feel bad for her, but I need help saying no in the nicest way possible.

That’s a pretty big request from a coworker who you’re not extremely close to!

The easiest way to do it is to have other plans those days that would get in the way. But you risk her asking again another time (or even trying to “solve” the conflict, like by suggesting you come over when you’re done with your other plans). So you’re probably better off just saying you can’t without getting into why — for example, “I can’t, but maybe you can binge-watch shows he doesn’t like or otherwise find a fun way to spend the time!” (If she asks why you can’t — which would be rude but some people do it — you can say something vague about other plans or just needing to be home those days.)

5. How to recommend someone when my last recommendation went wrong

I’m a long time freelancer and one of my clients hires a lot of people in my field. About a year ago, he was looking for more people so I reached out to someone I know (Jane) to ask if she would be interested since she’d recently told me she was seeking freelance work. She said yes so I connected them by email, with my own recommendations of her skills. My client said he’d like to see her resume. She replied saying he could check out her LinkedIn profile. He did not respond to that email, but sent me a message that said, “I don’t ask for much, but I like a resume.” I emailed Jane and told her she needed to send a proper resume, but Jane said resumes don’t matter anymore, it’s all about LinkedIn.

Suffice to say, she was not hired.

This episode didn’t affect my relationship with my client. But now I know someone else I’d like to recommend and I’m hesitant — not because I don’t think she’s a good candidate, but because I worry this freelance client won’t take it seriously because of how my other recommendation went. I worry that any recommendation I make now will be tainted by Jane not taking the opportunity seriously. What’s your take?

Did you talk to your client about the Jane situation at the time and say anything to indicate you agreed she was being weird — i.e., anything to distance yourself from the behavior? If so, I think you’re fine here. Your client knows you’re professional and reasonable from working with you, and having one candidate recommendation turn strange isn’t a big deal.

Even if you didn’t say anything about it at the time, you’re still probably fine here (because, again, it was just one time) — assuming, of course, that you know this person and her work well enough to truly vouch for her. But you could even make a joking reference to it when you email him, like “I promise this one will send you a resume.” (And you could verify that with the person you’re referring ahead of time if you have any doubt.)

is it rude to send emails late at night, should I tell my boss I’m job hunting, and more was originally published by Alison Green on Ask a Manager.



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