my employee assumes I’ll always pay for her food, no answer to a time-off request from new job, and more

This post was written by Alison Green and published on Ask a Manager .
It’s five answers to five questions. Here we go…
1. My employee assumes I’ll always pay for her food
This is more of an “am I the asshole?” type question. My husband and I run a small business and have one full-time employee, Jane. During tax season, it’s really stressful and one day we decided to take a break and take our employee down the street to a nice restaurant and treat for a big lunch as sort of a morale booster. We made it clear that we were treating, and the lunch was for our convenience during one of the 12-hour days. We put it on the company credit card, and it was a business expense on the books.
The next week was stressful but the weather was nice. Jane suggests we take an ice cream break. Great idea, let’s drive down and grab some. All three of us get in my car, I place the order and get out my personal credit card, and when it is time to pay, Jane doesn’t even offer. She just stands there and lets me pay.
This week, there is a calendar entry that neither my husband nor I made that says “Taco Tuesday.” Jane made it. She thought it would be a good idea to take a therapeutic break to go grab lunch again. I agreed, so we all go out to lunch and when the bill arrived she jumped up from the table and went to the restroom. I sorted out my husband’s and my share plus tip and laid cash in the folder, and when Jane came back she said, “Thanks for lunch.” I said, “I didn’t think this was a business lunch!” like I was surprised. She was embarrassed and grabbed her card and paid for her share, and then hid from me for the rest of the work day. Should I have discussed beforehand that we weren’t going to eternally pay for lunches and ice cream? I think I handled it fine, but I’m not a professional manager/HR person.
It can be tricky in these situation to know who’s paying for what, because it’s so common for managers to always cover the bill when they’re out with employees. If you had been the one to suggest the tacos or the ice cream, Jane wouldn’t have been wrong to assume you were paying … unless you said something ahead of time like “not our treat this time” or “can’t expense it, but want to go grab X with us?” (as the boss, you should always make that clear before someone accepts the invitation so they know the terms). But even with Jane being the one to initiate the plans, a lot of bosses still would have picked up the bill; it’s just a common thing that happens because of the power dynamics. Jane shouldn’t have assumed you would, though, since she was the one to propose the plans.
In any case, because the power dynamics make the “who pays?” question less clear than it would be if you were all peers, ideally you would have addressed it up-front before solidifying plans. For example: “We can’t do it as a business lunch — we don’t budget for a lot of those — but if we’re all paying our own way, sure!” Or, “I saw you put Taco Tuesday on the calendar! It’s not something the business would pick up the tab for, but I’m always up for sharing the bill on tacos if you want to.” Or just addressing the pattern head-on: “We’ve covered some treats lately but we can’t do that as a regular thing. If it’s an event we initiate, we’ll always cover the tab, but otherwise I wouldn’t want you to assume that.”
Also, if it’s just a time or two, it’s worth it to have the business pick up the bill as a small investment in morale, even if you hadn’t originally planned to! But it does seem like a pattern was developing that you needed to clarify.
2. Should I tell a community partner’s boss that he was unprofessional?
I’m a program manager for a school board. My staff work in schools providing education around mental health. I am new to this role (this is my third month) and prior to this I was in the same position as my now staff.
Part of my staff’s role is to make connections with community partners and bring them into schools for presentations. The idea is that if the students meet these people in a safe environment, they are more likely to seek them out outside of school. We have worked with one organization for a long time. Today one of my employees came to me with a concern about one of this organization’s staff, John.
John was booked to come into a class and do a series of presentations on topics like financial literacy, career planning, and conflict management. My staff had told me earlier that he had been hard to get organized. He wouldn’t answer emails and missed several deadlines in confirming dates and sending us information on his topics that we could pass along to the teachers. He also just didn’t show up for one of the sessions. When that happened, I emailed his supervisor to make sure he was okay. Apparently his schedule had changed and he said he sent an email that must not have gone through (we did receive an email from him about 10 minutes after his supervisor replied, saying he wouldn’t be coming that day, but by that point it was three hours after the scheduled session).
Today my employee told me that the teacher told her they don’t want John to come back. Apparently he was not very professional in how he spoke to the students, talked about how he never finished high school and was doing great, made jokes about high school not being important, didn’t manage his time so didn’t get through all the content, and acted, in her words, “like a bro, not a professional trying to educate students.”
I’m wondering if I should say anything to John’s supervisor. We could very easily just not invite him back, but if we want to work with this organization again, John is their go-to person for youth presentations. It would be near impossible to not have him assigned to the job if we asked for more presentations. And it seems weird to ask for someone else without giving a reason. I know if my employee behaved like that, I would want to know so I could coach them to improve.
This is my first time in a management role. Previously if I had a situation like this, I would tell my manager and let them deal with it. But now I’m the manager! I’m also an anxious person who hates conflict, so this is extra challenging for me.
Yes, contact John’s manager. Those are serious issues for someone who’s presenting to students, and it doesn’t make sense to invite the organization back without addressing it. It’s very reasonable to explain what happened and ask if they can send someone else in the future. (What they do with that information in regard to addressing it with John is then up to them.)
3. Can’t get an answer to a time-off request from new job
At the end of March, my partner accepted a new job with a start date of May 15. In the offer conversation, he brought up two somewhat-long vacations that we have planned for the summer (one for two weeks and one for four weeks). The organization said that they would try to accommodate him and would let him know as soon as possible. We understand that these lengthy amounts of time off may not be approved, but would like to know either way so that we can plan. The two-week trip is to Alaska at the end of June, and plane tickets just keep getting more and more expensive with each week that they don’t provide an answer.
My partner continues to follow up each week, and multiple times now the answer has been, “We’ll let you know by next week.” Three weeks later, we still don’t have an answer. We’re beginning to feel pretty frustrated and think that this may be a red flag that this organization doesn’t value employee work/life balance. Is there a reasonable or standard amount of time for getting time off approved before starting a new job? Is this a ridiculous thing to back out of a job over?
It’s possible there’s something going on that genuinely makes it hard for them to answer him yet, but if you need the answer right now you’re safer assuming it’s a no and planning accordingly.
Would your partner have accepted the job if the company had  said no to the vacation time initially ? If so, I don’t think their delay warrants backing out of the offer; it sounds like they’re at least trying to make it work and probably don’t realize they’re making things harder on you. If he might not have accepted the job originally if they’d said no … well, it doesn’t sound like that’s the case, but if it were, he could try one final “I’m sorry to keep asking, but at this point the timing means I really need a clear answer so I can plan” … but if they’re not ready to give a yes, that statement just makes it more likely that they’ll give a no. Which means he likely needs to choose between a clear no right now or a potential yes with a longer wait to get it.
4. If I quit, will I have to pay my org back for the leadership program they’re sponsoring me in?
I work at a nonprofit that has been going through transitions, including a change in the executive director. A year-long program for developing leaders in a sector (that my organization’s work covers) launched in my city at the beginning of the year. I told my organization that we should have someone apply even though the role that would normally lead my organization’s work in that sector has been vacant for almost a year. It was decided I was the best person to apply for the program, and I got in. It also looks like my organization wants to move me up into that vacant role.
I am looking to leave my organization, preferably sooner than later. I would have a little guilt if I left soon after getting promoted, but I can deal with that. The issue is my work paid for my participation in that program. It’s not a super high amount, but it is an amount I would not want to pay my organization back. It feels different from (for example) them paying for me to attend a conference and me leaving, because I assume in those situations the organization eats the cost and the employee won’t still get to go to the conference, etc. I would/could continue participating in the program, so I would still be getting benefits. It also would mean my organization won’t benefit from having a staff person in that program, making connections, learning about best practices, etc., despite paying for someone to go.
I just want to get a gauge of what is normal in this type of situation. Is it a normal “sucks for the organization, they should’ve retained the person they were investing in better” situation? I can’t imagine the right route would have been for me to decline opportunities because I knew I wanted to leave at some point.
Yeah, this is basically the same as with business travel, conference registration, etc. — as long as you’re still working there and don’t have concrete plans to leave (like another job that you’ve accepted, not just “I’m hoping I’ll be leaving soon”), it makes sense to proceed with arrangements the same way you would if you were planning to stay. That’s because there’s no guarantee that you’ll be gone by the time those things roll around, and it doesn’t make sense to put your work and professional development on hold meanwhile. Then if you end up leaving before the thing your employer has paid for has happened, the organization does typically eat that cost . (Sometimes they can transfer the thing they paid for to someone else, but not always. If the leadership program is already underway, this is probably a case where they cannot, and that’s just how this stuff goes.)
Do be prepared, though, that they might expect you not to continue in the program — probably not, but if you’re really there to represent the organization and its interests, it could come up. If it’s more about professional development for you and you’ve already started the program, it’s less likely. But either way, paying them back shouldn’t come up.
5. Are salaries typically listed as pre- or post-tax?
A university I’m hoping to work for lists a range of target salaries with the other details on their job board. These seem to always be specific, not-round numbers (think $4627 monthly). Do you think the sums they list are pre- or post-tax? I assume they’d want to list the pre-tax wages since those will be more and will attract the eye, but they’re such specific numbers I’m not sure. Or maybe in fields other than the one I’m coming from it’s customary to give very precise salary ranges, even pre-tax? In my current field it’s a very standard “$900/week, 60 hours guaranteed” type thing and always pre-tax.
It’s almost certainly pre-tax.
It would be extremely weird if they were listing salaries post-tax because (a) that’s not how this is ever done and (b) they can’t know what tax bracket you’re in so they couldn’t accurately list the post-tax amount regardless.
Universities — like government employment — often list their salaries as very specific, non-round numbers because they are weird bureaucracies.
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