Posted by Ask a Manager
https://www.askamanager.org/2025/12/i-saw-my-coworker-buying-a-beer-during-work-hours-my-bosss-wife-messed-up-his-business-travel-and-more.html
https://www.askamanager.org/?p=30582
I’m on vacation. Here are some past letters that I’m making new again, rather than leaving them to wilt in the archives.
1. I saw my coworker buying a beer during work hours
I saw a coworker at the pharmacy near our office this morning (9:45 a.m.) buying a 40-ounce can of beer. I was confused at first and I couldn’t figure out what to make out of it, but then I also remembered that this coworker always falls asleep in meetings.
I wasn’t sure if I should have approached her (I didn’t want her to think I’m being nosy). I do not want to jump to conclusions because I also thought she might have bought the beer for someone else (i.e., a homeless person in NYC or whatever). She got back at her desk around 10:15ish without the bag. I also saw her sleeping at her desk (pen in hand, head down) at noon today.
In terms of her quality of work, my team and I stopped going to her because we never get good answers from her anyway. I also overheard her team members question her ability in doing a project. Is this something that I should report in case she needs help or in case this requires disciplinary action?
The fact that you saw a coworker buying a beer before work is not, in itself, damning. She could have been buying it for after work or, as you say, for someone else. Who knows.
If she’s sleeping on the job or otherwise not performing her work in a way that affects you, or if she’s coming to work smelling like alcohol and/or appearing intoxicated, you should absolutely talk to your manager about those things. But “my coworker sucks at her job” and “I saw that same coworker buying a beer” is not enough of a connection to report someone for being drunk at work — that’s just too much speculation. Focus on the things you know for sure.
– 2018
2. Intern uses “stay gold” as her email sign off
There’s an intern at my office who signs off all her emails with “Stay gold.” For example, an email from her might read, “Thanks for sending me the TPS reports! Stay gold, Jane.” I asked her about it and she confirmed it’s from the quote “Stay gold, Ponyboy” from the book The Outsiders. We work in a pretty casual industry so it’s most likely that people will write it off as a weird quirk, but I’m afraid that if she tried using that sign-off in a more formal industry or office that people would think it’s unprofessional. Should I encourage her to start using a more common sign-off?
First, this is hilarious.
But yeah, that’s going to come across weirdly in many (most?) offices, and as an intern she won’t have the capital built up to make it read “amusing quirk” rather than “inexperienced worker who doesn’t take work seriously / has no sense of professional norms.”
If you’re her manager or oversee any of her work, it would be a kindness to talk to her about professional sign-offs.
– 2020
3. Telling my boss his wife messed up his business travel
I used to work as an executive assistant to a person who did a lot of business travel, but also did a lot of travel for his side-business activities. This was all legit, above board kind of stuff and his main job was aware of it.
As his assistant, I handled all the business stuff: booking flights, doing expense claims, all that jazz. However, his wife handled the side-business travel and I was instructed to liaise with her to coordinate schedules and handle any times when business travel would occur in conjunction with side-gig travel. His spouse was awesome, really organized and a great person to work with, but this was still a little bit awkward. It became more awkward when she made a mistake and booked travel for him at a time he was required to be somewhere else for his main job. I double, triple, and quadruple checked all of our email correspondence and it was for sure something that had gotten mixed up on her end, I am confident in that. So I was between a rock and a hard place: it wasn’t MY mistake but I was probably going to wear it because how am I supposed to present all the evidence to my boss that his spouse, his partner in life for over 20 years, the mother of his children, was the one that made the error that was sort of a costly mistake? He and I had a great working relationship, great communication, he had my back, all in all he was a great person to work for.
I ended up just doing my best to fix it and make everything work out, but it never sat right with me that I had to sort of pretend that it was my fault. I think that if I had tried to present everything to him that it WASN’T my mistake might have just made me look like a jerk or be really self-serving. Did I only have those two choices: screw-up or jerk? Or was there a third option that I just didn’t realize?
You were being way too delicate! It wouldn’t have been a jerky move to tell your boss that his wife mixed something up, because you wouldn’t have said it in a jerky way. You would have just matter-of-factly told him, “Hmmm, it looks like Jane booked you in Atlanta on the 20th when you need to be in San Diego. I’ll let her know.” Your brain was going way overboard with the “partner in life for over 20 years, mother of his children” thing. It’s just a routine business thing, not particularly sensitive information.
If I were your boss and I found out that you were pretending something was your fault because you thought I’d dislike you if you told me my spouse had messed something up … well, I’d actually be really concerned. I’d worry about your judgment, or whether I’d somehow given you the impression that I was too fragile to hear normal business stuff, or whether my spouse had done something to scare the crap out of you. I’d wonder what else you might be sugarcoating, and what else I might want to know that you might not tell me.
It’s worth looking at whether you’re being overly delicate with your current colleagues/manager, because this is a strange instinct! This is just normal business stuff, not anything you needed to dance around or hide.
– 2018
Read an update to this letter here.
4. My amazing new job has a catch: my father
I just started a new job at what appears to be a great company. On my first day, I learned that my new company is owned by the company my father works for. I also learned that interaction between the companies is expected to increase, and while it’s not probable, it’s possible that I could end up working with my father. At least one of the higher-up members in my division even knows him. (Aside: this company definitely has no concerns about relatives working together.)
The problem is that my father and I have not spoken for three years. I might be able to have a very distant professional relationship with him, but, to be frank, almost any interaction at all would make me want to quit.
It’s known that my father works for the parent company, but no one knows that we have had an intense falling out. Should I mention this to my team lead? I’d obviously couch it in professional verbiage, a la “My father works for [parent company], but we do not get along. If at all possible, I’d prefer that any work that might involve him or his team be delegated to someone else.”
This is literally my second day on the job, and I’m worried about coming across as full of drama. I’m also worried that even though it was my father who disowned me, my reporting our soured relationship will make me look bad, but I specifically want them to know that this goes beyond the potential awkwardness of working with family so that they never intentionally put us together. And, finally, I’m so new to the company that I have no metric with which to gauge how reactions to this information would go.
Yes, mention it to your manager. Your wording is good, but I’d tweak it to this: “I hadn’t realized the extent to which [this company] works with [parent company], but now that I do, I feel I should let you know that my father works for [parent company] and we’ve been estranged for several years. I wouldn’t want that to cause any awkwardness in a work context, so I’m hoping that if we ever have work that might involve him or his team, it could be assigned to someone else.”
Companies generally don’t want to invite family drama into their work, and it’s pretty likely that if there’s a way to keep you from having to work with your dad, they’ll try to accommodate that. (There might not be, of course, but it’s a reasonable thing to flag.) You’re not going to come across as full as drama as long as you don’t … come across as full of drama. In other words, if you conduct yourself professionally and maturely (as opposed to, say, complaining about him all the time, sobbing in meetings when his company name is mentioned, etc.), that’s not going to be outweighed by having a difficult family connection.
And remember, lots of people have tough family dynamics. You’re not weird or dramatic for having one too.
– 2019
Read an update to this letter here.
The post I saw my coworker buying a beer during work hours, my boss’s wife messed up his business travel, and more appeared first on Ask a Manager.
https://www.askamanager.org/2025/12/i-saw-my-coworker-buying-a-beer-during-work-hours-my-bosss-wife-messed-up-his-business-travel-and-more.html
https://www.askamanager.org/?p=30582