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

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.)

Read an update to this letter

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.

Read an update to this letter

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.

{ 363 comments… read them below }

  1. nnn*

    #5: Elaborating on Alison’s “because they are weird bureaucracies”:

    The highly specific, non-round numbers are often the result of the established pay scales being subject to specific cost-of-living increases over time. If the workplace is unionized they are negotiated in collective bargaining agreements, and sometimes even non-unionized bureaucratic workplaces standardize their payscales and provide standard increases.

    So years and years of 0.75%+1.3%+1.85% etc. etc. results in non-round numbers for all.

    1. Eric*

      and then throw in the geographical cost of living adjustments that the federal government does …

    2. Kevin Sours*

      It can also be an artifact of converting timescales.
      $70,000/year is $5833.33/month

      1. Madame Arcati*

        In my government job (and all the ones I’ve seen) even the annual salaries (which is how they are advertised over here) aren’t round numbers, nowhere near. It’s the product of so many factors – people, percentages, public perception, politicians and all in all a shed load of sums. There can be no rounding beyond a few pence as that would mean it deviated from what has been carefully calculated and agreed, and there is no negotiation at a lower level (my salary is set by the actual government and in academia I should think it is agreed at the very highest level of the university).
        I just looked to see if my annual gross salary even ends with a whole pound (and zero pence) and was genuinely surprised to see that it does! But of course monthly gross, and monthly net, don’t.

        1. Governmint Condition*

          Where I work, we now have a title whose annual salary grade is exactly $111,111.

        2. Anne of Green Gables*

          This is also frequently the case for other non-salary elements. I am in the second bracket of “years total service” at my (non-union) academic institution, which means I accrue 11 hours and 10 minutes of vacation leave each month, for a total of 16 3/4 days a year.

    3. fanciestcat*

      Yep, and a lot of public employers are required to post their salary ranges online for all positions anyway, so they just pull that for the job ad. I’ve only ever worked in local gov, do private sector employers actually pay people round numbers pre-tax? Proof that you get used to your environment I guess, because for some reason that weirds me out as much as the LW was confused by non-rounded numbers!

      1. Tinkerbell*

        Yeah, when my wife was interviewing for senior programmer positions, almost all of the initial offers ended in multiples of $5K or $10K. I suspect it’s not as big a deal to be precise on this when the company is doing individual raises anyway – if they offer you $90K and they had really meant to budget $88K, you may just get a slightly lower raise next year.

      2. ApollosTorso*

        Yes, all of my salaries have been nice round 28k, 32k, 50k numbers (and I’ve earned those low wage full time office job real numbers in my 20s)

        1. amoeba*

          Huh, interesting! I’ve never had a nice round number as a salary, ever, I think, both in academia and industry. Even in my current industry job, the increases are always done in percent, not absolute numbers and as was said above, that doesn’t normally result in nice numbers. Probably more the norm with highly regulated compensation processes such as in large companies and academia? (For us, it’s pretty much automatically calculated by an algorithm based on our performance rating and our position in the salary band…)

          1. I am Emily's failing memory*

            Yep, in my company we tend to make offers that are an even something-thousand or something-thousand-500, but then as soon as you go through your first annual review period where merit raises, equity adjustments, and COLAs happen, all of those are specific percentages that will crooked up the number going forward. If you ever end up with a round number after your first year it’s sheer coincidence.

          2. ThatGirl*

            My salary at my current job started at a nice round divisble-by-1o number, but after two merit increases it’s now like XX,445.72 … and of course, individual paychecks are never going to come out at a nice round number.

          3. BubbleTea*

            Same, I’ve never seen a round number salary and would actually be suspicious if I saw one advertised because I’d assume it was just approximate.

          4. GammaGirl1908*

            When I’ve had round numbers as salary, they haven’t stayed that way because of percentage increases. That is, even if I started at, say, $45,000, if I got a 4% raise, my next salary would be $46,800. Then another 4% would be $48,672. Maybe some organizations consciously round up to the nearest 100? But then it’s not a 4% raise. One of those numbers would have to bend.

            But now I work for the federal government, where we get things like 4.1% yearly increases and locality payments of 32.49%, so it’s all scrambled eggs. If you come into the government in DC as a GS-7 (which is pretty normal with a bachelor’s degree), you start at $53,105, which is a random number by any standard.

        2. Alice*

          I took a new job offer recently and didn’t like the fact my offer was not a round number (just a weird quirk of mine). I asked them to round it up to the nearest 10k and it worked! I basically negotiated by default

          1. Union Nerd*

            Government jobs wouldn’t be able to round up, in part due to salary bands in collective agreements and also because of equity. There is no negotiation, the starting salary is based on years of experience.

            I know it’s not ideal for all, but it’s a relief for those of us who feel awkward advocating and asking for more. I can do it during my yearly performance evaluations where I talk about the good work that I have done for my group, but I really appreciate the consistency when starting a job.

      3. amoeba*

        Adding to what I said, even though the actual salaries aren’t rounded for us, I think it’s not uncommon to round the range for the ad? (Not sure because unfortunately, in my region and field, they are normally not posted at all…)
        So, even though the actual range would be something like 82,517.53 to 99.124,89, you’d just give “82.500-100.000” or whatever. Those specific numbers for a range would surprise me a bit, indeed.

      4. Hlao-roo*

        In the private sector, I have started with round numbers (usually to the thousands, like $63,000). But after my first raise, the round number goes out the window. Continuing with the example of $63,000, a 2.5% will increase the salary to $64,575. Another 2.5% raise on top of that will increase the salary to $66,189.38.

      5. alienor*

        In my current job I started at a round number because that was what I negotiated, and then as soon as I got my first annual increase, it became non-round because it was a percentage based on my previous salary. But, if I decided to leave and they posted my position, they wouldn’t use the number I’m actually earning, it would be the rounded range for my grade level, because the next person might start lower or higher in that range than I am.

      6. KatEnigma*

        Yes. You probably won’t end on a round number as COLA is added in subsequent years, or even the first year, but the offer is always round numbers.

      7. MCMonkeyBean*

        My starting salaries have always been round, even numbers–then once I start getting raises they are percentages and the salary stops being round.

    4. The Person from the Resume*

      The numbers are just the accurate pre-tax numbers because how does the company know what tax bracket you’re in?

      I get where the LW is coming from because she’s used to round numbers which are a bit easier to talk about, but unless the company is rounding to the nearest dollar, hundred dollar, or thousands dollars each time they give a raise or adjust a salary that inital round number is lost very quickly. Plus companies usually think annual salary when budgetting for the position; if the LW is looking at monthly pay, it’s already been divided by 12 and probably isn’t even really actually an even dollar.

      Also it probably made sense in the pre-computer days to round to make things easier. Making the math easier isn’t necessary with computers doing all the calulations, sharing the data with other computers, and printing the numbers.

      1. Antilles*

        I get where the LW is coming from because she’s used to round numbers which are a bit easier to talk about, but unless the company is rounding to the nearest dollar, hundred dollar, or thousands dollars each time they give a raise or adjust a salary that initial round number is lost very quickly.
        It’s certainly true over time at the same firm. I think here it’s primarily about just seeing something different than expected during the up-front search process.
        OP mentioned they’re doing their first academic job search coming from a different field, so I suspect they’ve previously seen a lot of private industry ads where they tend to round off salaries to “$60k-$65k” or whatever. But now they’ve started this search in university and suddenly seeing pay scales of like $60,127 – $64,718…and huh, that’s a weirdly precise number, what’s up with that?

    5. House On The Rock*

      I work for a large, public university and for postings where salary ranges are listed, they are frequently based on the actual salaries of people in that job title, which of course are not round numbers given the way raises, promotions, and salary adjustments work out.

      Depending on the group and/or HR person doing the posting, they may round up to the nearest $100 increment, but not always.

      Unfortunately, this means that we have ranges for Senior Woolly Headed Nit Picker like $59,282 – $103,245 and hiring managers are forever explaining that most candidates are not starting at the top of the range because that salary is held by an actual person who has been in that job for 30 years.

    6. Recovering Government Worker*

      My last job in government, where nearly all non-appointed positions had pay described in hourly terms (which side note – I’ve since learned is also not common everywhere), I was paid $39.8604 an hour. That’s a period, not a comma. Technically my salary was calculated to the hundredth of a cent.

  2. Gemstones*

    Getting a lot of secondhand embarrassment for Jane…I can’t imagine inviting someone, let alone my boss(es), out repeatedly with the expectation that they pay for me.

    1. Tinkerbell*

      God, yes! The only time I would 100% assume they’re paying for me would be if it’s presented as a gift/celebration (like a company holiday party at a nice restaurant) or if we’re on a business trip together and they’ve already covered all my other meals… and even then, I’d be prepared to cover my portion of the bill just in case!

      1. Radioactive Cyborg Llama*

        No one should have to pay for their own meals on a business trip, though, that to me is a lot different.

        1. The Cosmic Avenger*

          Yes, but even when I traveled for work with a client or supervisor, we all had to pay our own tabs, since we were reimbursed set amounts individually.

          1. Pogo*

            In my industry you are reimbursed for everything you spend, and generally the “most senior” person picks up the tab on their own card and then puts in for reimbursement. I love doing it for the cc points!!

          2. goddessoftransitory*

            Yeah, that’s where the “we all need separate checks/receipts” thing kicks in, to many a server’s consternation.

    2. Captain dddd-cccc-ddWdd*

      It does seem strange! I can only assume she’s worked at larger companies before where “the company” pays for those lunches rather than the individual manager as such, whereas here the individual ‘manager’ is actually the owners who are paying directly out of their own pocket (effectively).

      [It does seem to be quite a common line of thinking (‘oh, “the company” is paying for that’) similar to “government pays for that” not acknowledging that ‘government’ money is just tax contributed by everybody!]

      1. MK*

        Ok, but is it common in these companies for the subordinate to actually “ask” for these lunches? I wouldn’t think it odd if it was the OP suggesting it, or if it was a more spontaneous thing, but I don’t understand how she got from “my boss invited for lunch once” to “work lunches are a weekly thing! I can make suggestions about where to go!”.

        I do thing the OP should have had the “this isn’t a business lunch” conversation when Jane put the taco lunch in the calendar rather than wait for the check.

        1. Snow Globe*

          I can understand that the OP didn’t realize ahead of time that Jane thought the OP would be paying. Jane put the lunch on the calendar!

        2. EPLawyer*

          That was a really weird jump by Jane. Oh they took me out once, let me just start putting lunches on the calendar so they will buy me lunch once a week. That is pretty far outside the professional norm so I don’t blame OP for being confused about who pays.

          1. ferrina*

            I wonder if OP made some off-hand comment like “We should do this more often” and Jane took that as a directive to set up more work lunches. I’ve definitely had embarrassing social cue misreads like this.

            1. EPLawyer*

              I would buy that IF she hadn’t bailed for the restroom right as the check came. Without a word. I can see if you gotta go, you gotta go, but you usually pull out your credit card first or say, I’ll be right back and will add my share then.

              Its the combination of presuming to calendar the lunch AND expecting boss to pay that is just so weird.

              1. Fishsticks*

                Yeah, making sure to be in the bathroom during the time people are paying could just be a coincidence of timing, but it does seem oddly purposeful.

              2. House On The Rock*

                When I read that I actually laughed out loud, because there’s a running joke in my spouse’s family about ways to duck out of the bill, including having an emergency bathroom visit or pretending to not realize it’s on the table.

                My FiL did a whole bit (while my MiL was paying) of looking at every single thing in the restaurant except the check and then having to tie his shoe for an extended period of time.

          2. The Rules are Made Up*

            yeaahh even in my industry, in which it’s custom for the highest paid/most senior person in the group to pay for group dinners on trips (even though we all have company cards and none of it would come out of any of our pockets anyway) the difference is that….. it’s customary. Your manager doing it once doesn’t make it a custom.

      2. Gemstones*

        I mean, I do expect the company/boss/etc. to pick up the tab if it’s a work lunch. Like, we’re all going out to x restaurant as a team, or meeting with clients, etc. I’d never expect to pay in a situation like that. But I can’t imagine asking a boss to go out to lunch or just putting lunch on the calendar and expecting them to go along with footing the bill. It’s the idea of proposing the lunch and then expecting to be paid for. That feels uncomfortable…

        1. madge*

          “I mean, I do expect the company/boss/etc. to pick up the tab if it’s a work lunch. Like, we’re all going out to x restaurant as a team”

          *weeps softly in publicly funded higher ed

          1. Colette*

            I spent most of my career in high tech, and it was normal to pay for your own lunch if the group went out. (Sometimes the company paid, but usually that was for stuff that was brought in, not a team going out with each other.)

            1. Cyborg Llama Horde*

              In my tech jobs it’s always been:
              – If my coworkers and I self-organize lunch, the expectation is that everyone pays their own share, usually on separate tabs, regardless of whether or not the boss is part of the group. (Very rarely, when the company was flush, if the department head came along he would pay on the company card, but we didn’t usually invite him and he paid even more rarely.)
              – If it is a sanctioned Team Event (weekly lunch, celebratory event, occasionally a farewell outing, etc.) it’s paid for by the company, or the extent to which it’s paid for by the company is explicit from the start (“First drink is on EmployerCo”).
              – Meals when we were traveling were always paid for by the company, though how exactly that worked in practice generally depended on whether someone with a company card was present.

          2. Another Anon Fed*

            Same – the math involved at times in making the per diem work is real. I think the biggest plus spouse and I had was at least our managers were always really, explicitly clear what your per diem number for food was.

            1. Another Anon Fed*

              Of course Per Diem is only a thing when either of us is traveling for business. During the day to day normal routine – lunch is going to be on you.

              1. Kuddel Daddeldu*

                True. I’m in Germany, and there are set perdiem rates that dictate how much the company can pay me for food on a business trip before it becomes taxable income, so that’s what I get. I don’t need to collect receipts for food, so that’s a plus.
                The rate is not really generous; more than enough for fast food but just doable for a sandwich for lunch and a simple sit-down dinner.
                I never made more post-tax money (corrected for inflation) than about 25 years ago: I was on a project out of country for 7 months, and we got a perdiem in (literal) cash of $120 per day, IIRC, every day. It never turned up on any tax records that I know of. It was more than my post-tax salary.

        2. Smith Masterson*

          Did they discuss work? If so, the owners should pick up the tab. Also–what if Jane mistakes these lunches as a “thank you for working 12-hour days.” One lunch per week (tacos) is a small ask.

          1. Op*

            I am OP and it was 100% not a working lunch, which made me feel really uncomfortable. She didn’t even clock out, so I was paying her hourly wage plus payroll tax and on top of that I was expected to foot the bill for the lunch. It felt weird because it wasn’t my idea. And we aren’t a big high rolling business, we are new and she has a higher pay than we (the owners) take.

            1. Boof*

              “she has a higher pay than we (the owners) take” oooo, I bet she doesn’t know that. I mean yeah you get some “equity” from owning the business usually if you ever decide to sell it, but you can’t really pay for lunch with equity!
              But it’s best to be very up front in any situation where you’re going out to eat with someone who’s treating / not treating, before you head out.

            2. Sad CPA*

              oof that is tough! If she’s a CPA and you do public accounting I fear that expensing meals during busy season is industry standard and something you will have to budget for, regardless of employee level or seniority.

              1. Oh, please*

                Why? This is a very small business and the employee isn’t working overtime. We all have busy periods (and before you sniff at me about tax season, I’m tech support for hospitals – I fix ventilators as well as computers and networks). I expect food when I’m pulling 12 hour days / 6+ day weeks / travel. Otherwise, it’s work. I can buy my own tacos and so can this employee.

    3. Thistle whistle*

      One free lunch and she assumes you will pay for everything, to the point of starting scheduling meals? That is totally brass neck!

      1. Ladida*

        Yeah it is the scheduling that strikes me the most too. It would be reasonable to expect her bosses to pay when they invite her out to lunch, even if they do not explicitly mention it is a treat. But even if the company had a budget for team lunch or sth it’s would be up to them to set the budget and frequency.

        1. Uranus Wars*

          yeah, this is sort of where I land. If I say “hey, let’s run out and grab coffee (snack, etc.)” I always pay, even if we don’t discuss work…but my reports has never asked me if I want to grab a coffee and ASSUMED I will pay. Over 10 years they ask an average of 1-2 times a year, not once a week.

          No one ever just put a lunch on my calendar – if they request a meeting it’s during regular hours and every once in awhile I’ll reply back with a new time and say “let’s do a lunch meeting instead – my treat” and they either accept or keep original time based on what they are doing for lunch that day.

      2. M2*

        The LW writes about one of the 12- hour days. Anywhere I have ever worked if you worked a 12 hour day the company paid for your dinner. I have family who own their own small business and during a busy period will once a week pay for employees take out lunches from a local restaurant.

        1. CommanderBanana*

          My firm will pay for meals if you have to stay a certain amount of time past the normal end of day. It’s in the handbook.

        2. Helewise*

          That sounds amazing, but I’ve never experienced that myself (and work 12-hour days at least weekly).

          1. Kuddel Daddeldu*

            I work offshore or on ships from time to time; meals are on the client – long days (12 hour shifts, no weekends) are the norm and there is generally no alternative to eating in the mess room anyway. On some cruise ships, where we can dine in guest areas, we may get charged for drinks apart from water/coffee. That’s fine (I don’t have a soda addiction, and alcohol on the job site is frowned upon).

        3. Another CPA*

          In public accounting, it is very common for the company to buy dinner when you work over 10 hrs. Pre-covid, we had catered dinners 3-4 nights a week plus breakfast and lunch on Saturday during Tax Season. Post covid, we have a corporate account with Door Dash that we can order from each night as applicable.

          1. Also CPA*

            Yes, I was going to comment this! In Jane’s defense, free meals are VERY common in public accounting during busy season. Personally, I really frown on this employer for wanting her to work 12 hour days and not providing dinner or anything. I think that’s an important detail most people aren’t catching. It’s not like Jane is working 8 hours and going home with plenty of time to meal prep and grocery shop.

            1. Op*

              I’m OP and I’d like to clarify that I work the 12-14 hour days. Employee does not. Employee works a regular shift 9-5 and we give bonuses, raises and gift cards, flowers and order door dash during tax season to keep the office tension down. I also will mention her pay eclipses both of ours (the owners) because she is essential to staying open and sane. We will eventually catch up our salaries but we haven’t yet.

        4. fhqwhgads*

          True but that was the first time when the OP did invite the employee and intended to pay. It’s not clear to me if these other things the employee put on the calendar were during that time period too, or a more standard schedule time. Either way tho, you don’t invite your boss to lunch so they will pay for it. That’s just…bizarre.

      3. Falling Diphthong*

        Enough that I wonder if one of the owners tossed out some sort of “Oh, this is great, we should totally do this regularly going forward” and the phrasing to them was “This was fun” and to Jane was “You plan it, we’ll make it happen.”

      4. Sick of Workplace Bullshit (she/her)*

        Yep! I thought she was doing this on purpose for sure. Leaving for the washroom when the bill comes? Definitely a planned move, and counting on the awkwardness of OP bringing it up to get out of paying.

        1. Well...*

          Yea, that stuck out to me too. Feels like LW just returned awkwardness to sender in this situation.

          But in hindsight, to avoid awkwardness altogether, maybe it’s best to just address it before going out.

      5. madge*

        Right? I wonder if one of the bosses said something casual along the lines of, “this was great, we should do it again” and Jane just RAN with it.

        I’m mortified on her behalf.

      6. The Person from the Resume*

        Exactly! This only started after the LW invited her out and paid for a lunch during what was going to be a long day. The LW was clear about paying and there was a specific purpose and the LW initiated it.

        I’m not really getting second hand embaressment for Jane because this doesn’t look to me like Jane got confused. With Jane initiating the invites or just scheduling the meals and strategically disappearing when it’s time to pay, she knows what she’s doing. She’s doing this to “get a free lunch.”

        1. EPLawyer*

          THIS. Somehow she decided that once a week as part of her compensation package she is getting a free lunch. Which …. is not really a thing you can just decide for your employer.

      7. Phony Genius*

        I was getting vibes of “If You Give a Mouse a Cookie” while reading this one. It needed to be shut down, but probably before going out to the restaurant.

    4. 2023, You are NOT Nice.*

      I got caught up in something like this when I was about 17. I worked for a small place as receptionist and often went to get lunch for the group (I had to walk to get it). The first time I was asked to go, I had to tell the mgr who was placing the group order I didn’t have any money for lunch, so she paid. I got french fries and tea. After that, it became a thing but only because I still had no money and didn’t know then how to get out of it.

      1. Eldritch Office Worker*

        I did wonder if Jane was younger. This isn’t your case, but younger people can also misunderstand norms if they are encountering them for the first time.

        1. rebelwithmouseyhair*

          And they have less money and they are used to Mum and Dad paying for everything when they go out with family, which is perhaps the only other instance of going out with people older than you.

      2. Smithy*

        Yeah – I will also say, that because work/professional norms can be different and can also include people who you’d never socialize with otherwise – being around “different but within reason” and “different but not within reason” takes time to learn.

        I had one job where a group of us started doing happy hour semi-regularly where most of us had similar job titles/pay bands. In this context, most people paid their own way but if someone very junior joined it wasn’t uncommon to cover them or pay for someone on their birthday. Over time, as frustrations at work increased – the frequency increased as did the number of people who joined which included a few people a little more senior. Most of those more senior people would adapt by paying an outsized share (think double or triple what they owed) and then the rest of us would split the remainder.

        However, one more senior staff member started covering the entire happy hour bill all the time. And while we’d always do the “here’s my card, let’s split it” – she’d pay for everything always. To the point, where if you were ever like “gee….a free meal tonight might be nice, maybe I’ll ask her for happy hour….” wouldn’t be an insane thought to have. How more senior staff should act at happy hours isn’t written in stone, but anyone learning norms from this colleague wasn’t actually learning norms…..

    5. kiki*

      From the headline, I thought I might agree with Jane because if your boss/manager is inviting you out to work lunch/dinners, I really think the boss should pay. But Jane’s inviting people out and then assuming it will be paid for! That’s audacious, for sure

    6. TurnedMeIntoANewt*

      Yeah. “Hey, I feel like getting tacos. Buy them for me.” feels wild. I will say that I’ve always worked in non-profit or government settings, so I’ve never had that stuff paid for to begin with.

      1. Heidi*

        It was more like, “I’m putting an appointment on your calendar for you to buy me tacos.”

        1. Be Gneiss*

          There is a 100% chance I’m going to send my boss an appointment to buy me tacos. This is genius.

      2. General von Klinkerhoffen*

        It seems to be incredibly common on dating apps – but never at work!

    7. LCH*

      i picked up my boss from the train station once (i worked at a remote location) and was like, do you mind if we swing by the drive through coffee before we go to the work site since i usually go there before work. and we did. and then she paid with the company card! it was a nice surprise.

      so just assuming is very cringe.

    8. Sad CPA*

      The company expensing meals is industry standard during tax busy seasons – since individuals are working 12 hour days for 2-3 months it’s seen as a way to keep them in the office, healthy, and (reasonably) happy.

      I can’t speak to other industries, but I would be shocked if a firm didn’t pay for my meals during a busy season given how demanding the work is. (For context, most large firms are paying for meals and coffee every single day for tax professionals in an effort to retain them and to get them into the office

      1. Sad CPA*

        OP I just saw your comment that the employee is only working 40 hour weeks, in which case I wouldn’t expect daily meals (though daily meals are becoming more and more an industry standard regardless of hours worked in public). Weekly free meals are fairly normal – staying clocked in during them is absolutely not though.

    9. goddessoftransitory*

      Right? I read that and was going “but…who expects this repeatedly? And schedules it?”

      I would only think my food was paid for if I was attending a work event that was clearly labeled “lunch” or “bagels meeting” or whatever, or catered. I can’t fathom going We should go to Taco Tuesday and by We I mean You’re Paying, boss!

  3. Elizabeth the Ginger*

    I work in K-12 education and my salary is also a strange non-round number – like not even a round number of dollars. (My contract for next year is for a yearly salary that ends in $0.54!) We have a salary chart based on years of experience and what degree you have, and then those numbers are adjusted every year by some percentage. I assume at one point in time each salary level started as a round number, but the adjustments quickly threw that out of whack.

    1. Irish Teacher.*

      I just posted Ireland’s secondary school salaries below. It’s a link so awaiting moderation. And I have extra pay for certain qualifications on top of that.

    2. Madame Arcati*

      Lol re your last sentence – I expect you are right but with some professions that go back a long way, including teaching, it could be a good couple of centuries since it was a nice round number!
      Extreme example but in the govt dept I once worked for, one of the big bosses in history probably got paid in percentages of duties collected from fleeces and wine etc down to the nearest farthing; lots of arithmetic. As if the poor man didn’t have enough to do writing the Canterbury Tales.

      1. Morning reader*

        Chaucer was a government employee? The things I missed, not being an English major…

      2. KateM*

        When my country went over to euro, they translated all government supports more or less exactly. It’s easy to realize that the amount hasn’t been raised after that – it is something like €17.32 (random number). At least my GP has changed their visit fee (which they take only in cash) from €1.72 to €2.00 after several years – I don’t understand what took them so long!

  4. Observer*

    #2 – Unprofessional Community partner.

    The question here is not whether you should tell the supervisor, but why would you NOT tell them?

    Would you hesitate to tell them if you were paying for the service? Would you hesitate to tell your mechanic shop if the mechanic assigned to your car tried to convince you to install high power speakers in your car instead of changing the oil and checking the brakes?

    I think that you have MORE standing to mention the specific problems than just a service provider that totally fell down on the job. Because you and the community partner have a mission and this guys behavior goes against that mission. So you have standing both for yourself, but also to give the other organization the information it absolutely needs.

    1. Observer*

      By the way, this doesn’t have to be a deal and conflict. Just matter of factly telling them that one school has explicitly told you that they won’t have him back, and your staff’s description of what happened.

      You’re not telling them what to do or what to tell them. But now they have the information they need, and going forward if you continue to work with them, they know that you won’t be using this guy and they can react accordingly.

      1. Viette*

        So agree with this. OP’s anxiety may be suggesting that speaking up about this will cause conflict, but it’s very unlikely that the community partner will come into conflict with the OP about shared feedback from a work site.

        The community partner might come into conflict with John about it, but that’s different (and appropriate). Just because you tell someone information that may disappoint/upset them doesn’t mean they’ll be disappointed/upset with you.

        1. Lydia*

          Having invited people who do this kind of education into the classroom to work with students, my experience has been the organization apologizes profusely and wants to make sure the relationship is still good, then assures you they will schedule someone else for the next presentation.

      2. Eldritch Office Worker*

        Yes. Some people are really conflict adverse, to the point where they don’t want to say anything negative. But this is not conflict! It’s reporting the facts and letting them do with that information what they will.

        1. Margaret Cavendish*

          Maybe “conflict” is in the eye of the beholder? Either way, it sounds like OP is trying to avoid an uncomfortable conversation! The bad news is, it can’t be done.

          You could avoid/ ignore/ put off the conversation with the community partner, but that puts you in a position of conflict with the school who told you they don’t want John coming back. One way or another, you’re going to be having an uncomfortable conversation. And the longer you put it off, the worse it’s going to get.

    2. Tinkerbell*

      Adding to this: if you still feel you need to soften your language, come from an “I’m worried about him” standpoint. After all, if he’s their usual go-to guy but he’s doing his job so badly, maybe something is wrong? Not that you have to speculate specifically, just let them know that the school felt he was unprofessional in X, Y, and Z ways and you wanted them to have a heads-up in case something in his personal life is causing him to have issues with how he’s doing his job?

      1. WishIWasATimeTraveller*

        Unless LW has a specific reason to actually be concerned, this would run the risk of sounding a bit false. I think it best to just keep it factual, say that they don’t want John again and why. If their employer is concerned about John’s wellbeing they can take it from there.

        1. FashionablyEvil*

          I find taking a tone of, “I’m not sure if there’s something else going on with John/more context I’m not aware of, but…” covers it. Because those things are certainly true and it gives John the benefit of the doubt in case, I dunno, he’s in the midst of a family emergency, mental health crisis, etc.

        2. Totally Minnie*

          I totally agree with you. When I was working in libraries, we booked a series of presentation with a local radio personality who we’d used before and had never had issues. But this series was. Whew. He tried to make our staff run his PowerPoint for him, tried to sell things to attendees which was a violation of his contract with us, gave a two hour presentation in a rambling stream of consciousness, and at the end of the program started hugging staff against their will.

          We were taken aback because he’d never done that at any of the other presentations he’d done for us, but we didn’t lead with concern for him on a personal level in our feedback to the radio station. We just told them simply and clearly what his actions had been and that we could not invite him back.

    3. Artemesia*

      It isn’t a guy who is disorganized — you could roll with that. It is a guy whose approach undercuts the mission and is a menace to the students. You need to let them know, you do not want this guy back in the classroom with your students because of his inappropriate behavior and to tell them why.

      1. Bonnie*

        Exactly – “John told the students that high school isn’t important, so I’m sure you’ll understand that we won’t be asking him back.”

        1. Observer*

          Exactly what I was trying to say with my last paragraph. Thanks for putting it better than I did.

        2. Miss Muffet*

          Yes, that “I’m sure you can understand” — and I have to believe they will probably WILL be totally aghast when they hear this list of feedback that runs exactly contrary to the mission he’s meant to be supporting.

    4. El l*

      Yeah, agree, this isn’t just a minor slip-up, this is actively working against what they’re trying to achieve, and it fits with a wider pattern of (at the very least) unprofessionalism.

      I’d be put it this way:
      “__, I need to pass along the feedback I’ve heard about John – and what I plan to do about it. According to the teacher at his last session, he told students actively counterproductive things, like that high school wasn’t important [and other relevant quotes/behavior from that session.]

      “Missing a session is one thing, but I have to be candid with you, this sounds harmful. I encourage you to verify for yourself what happened, but we just can’t feel comfortable working with him again on our projects. Please let me know what you think, but for now I’d like to discuss what we can do for alternative arrangements.”

    5. Formerly Ella Vader*

      Yes, I agree.

      If I were in the OP’s place, and I didn’t hear the presentation but I heard these comments from credible staff and students, I would definitely be giving feedback as soon as possible to/through the partner organization, about ways in which his presentation tone/content didn’t fit with the mission or with the needs of our students. I have been the person in charge of a group of teenagers when visiting presenters misjudged what was appropriate for our group, and I always gave that feedback as soon as possible – directly and immediately when I was listening to the presentation, or within a day or two of collecting observations from the staff who were in the room and whichever kids brought it up to staff members at nightly check-in. Sometimes presenters who weren’t familiar with the needs of this group or of teenagers in general tried to act “hip” and “cool” by, e.g., making jokes about the kids sneaking out at night with the flashlights they were handing out, using casual slang which some people connected with racist assumptions, gamifying their presentation in infantilizing ways like giving out prizes for asking questions. In fact, young people in our program loved being treated as adults by professional presenters (they might need to provide a little more context and definitions, but in general we asked them to provide a tone of “very good undergraduate lecture” or “Ted Talk”, and most of them did).

      It’s also useful to give the organization a note about the issues with responsiveness and the no-show. You could offer to have someone from your group go to talk to the organization’s presenters about what is expected from a schools talk. If you don’t need to book again for a while, maybe don’t commit yourself one way or the other until it’s time to book again. Then you could say “who do you have doing these presentations now?” and if it’s just John, say “We identified some concerns with him last year – can you tell me how you followed up with John?”

    6. elle *sparkle emoji**

      OP should consider that the community partner should want to know this stuff. It sounds like they’re a charity advocating for a cause– if John isn’t asked to come back to these schools that means he is limiting their reach. He’s harming their ability to complete their mission.

      1. tangerineRose*

        “OP should consider that the community partner should want to know this stuff.” Exactly!

  5. Heidi*

    I suspect John’s employers do not know that he’s saying these things and would really want to know about it. Even without the career planning session that does not endorse graduating from high school, the failure to show up and poor responsiveness to scheduling inquiries are reasons enough to request a different speaker.

    1. nightingale*

      Oh sh*t I think I glossed over the part that said it’s a career planning session. That makes it feel even worse, like John has got some hang ups about his own life/ status and is like “it’s ok to not finish high school” to prove some kind of point.

      Honestly though, it’s so hard to do anything these days without highschool much less college that regardless of his reasoning (none of which reasons look great!), that’s just really irresponsible. I think OP is right to want to speak up, make sure it never happens again, and say they want a different presenter, etc

      1. For sure*

        Hail yes, as a parent, if my child came home from school and told me he was counseled by an “expert” (not a buddy) — and the students do view these guests as “experts” — that not finishing High School was fine, I would be at the school the next day, and at the next school board meeting as well, to make sure this was corrected for all the students AND the assurance this would not happen again. Serious serious problem.

        1. Margaret Cavendish*

          Same. And this goes back to what I was saying above – there’s no avoiding an uncomfortable conversation here. And it’s better to have the conversation with the community partner than with a bunch of angry parents!

      2. Heidi*

        I really wonder what the content of that career planning session was. On some level, it would be really interesting to learn about how people built careers without graduating high school because there are alternative paths out there. But there are ways to explore that without sending the message that graduating is unimportant.

        1. elle *sparkle emoji**

          I have a hard time believing John’s words were based on any sort of reality. It’s definitely possible to be successful without college and I think those career paths deserve some attention, but high school? I’m sure it’s technically possible to be successful without a diploma, but I certainly can’t imagine how not graduating would be beneficial.

    2. HonorBox*

      Totally agree with you. The “advice” about not graduating high school is bananas in that situation, which absolutely warrants a phone call. But the poor responsiveness and bailing on a session reflects poorly on John’s employer as a partner org to this school, and for that I’d want to know if I was his supervisor.

    3. madge*

      Agree. If it was just the bro dude personality, I could possibly chalk that up to a really clumsy attempt to connect with teens. He could be spoken to and given one more chance. But I’m pretty certain teachers, of all people, do not have the time or get paid enough to chase people down just so they can undo the teachers’ work (who needs a diploma???).

    4. Dust Bunny*

      This was my thought: Whatever organization employs him hired him but hasn’t checked in on what he’s actually saying and has no idea about his content. They need to know, and the LW/school board need to know what their reaction is when they’re told (that is, if they don’t act on it or make excuses, maybe it’s time to reevaluate this partnership).

      1. GreenDoor*

        Please report this guy! Especially if you work with a student population that is disproportionately affected by things like lack of access to mental health/social services, generational poverty, or students who may be the first generation in their line to graduate/go to college. I work for an urban district with a high poverty rate and we use a lot of outside providers like your org. There are plenty of ways to build trust and establish rapport with young people. Making light of their needs and blowing off their aspirations just so you can come off like a “bro” is not how you do it!

        1. Hydrangea McDuff*

          Yes for sure. And as a high school teacher who invited a lot of guest speakers to my CTE classes, I would have been semi livid to have a scheduled speaker not show up. Even if it was an understandable emergency (and you always have to have a plan B) I would likely not keep this org / this person on my list. You only get 180 hours a year with your students!

      2. elle *sparkle emoji**

        Yeah, John’s behavior has to be undermining their ability to succeed unless they are a GED prep company.

  6. Genny*

    LW 5, one of the reasons federal government salaries aren’t round numbers is because of the way cost of living adjustments are made (I assume the same is true for state governments, including public universities). Even if, say, a GS 13, step 1 position earned $100,000, that number would no longer be a nice round number once the next COLA goes into effect. At least federally, the COLAs (and federal pay rates more generally) are hotly debated within the legislative branch and between them and the executive branch. Consequently, if a COLA is authorized and appropriated, it’s typically been negotiated to the nth degree, leading to rather specific percentage adjustments like 8.7%, 5.9%, or 1.3%.

    1. RightSaidDread*

      Almost correct. Federal employees do not get COLAs (Cost of Living Adjustments), but some years federal employees get pay increases to the general schedule and/or locality adjustment. In my 20 years as a fed, I have never seen any increases nearing 5.9% much less 8.7%, so I have no idea where you are getting your numbers. Most years it is around a percent, but I remember multiple years with 0%!

  7. Malarkey01*

    LW3 The comment that this might be a red flag that the company doesn’t value work life balance may not be realistic when asking for 6 weeks vacation in a new job. (Assuming you’re in the US), it would be very difficult for most businesses to give a long term employee 4 weeks off, even those with generous leave allowances have trouble with a month long absence taken all at once, let alone a brand new hire that will be at the beginnings of transitioning and training into the new job.

    It’s absolutely fair to want a yes/no answer (although I suspect a fast answer would have just been no), but I don’t think this is even a yellow flag in regards to work/life balance.

    1. Decidedly Me*

      This is what stood out to me, as well. Not having an immediate answer to long amounts of time off (for a new employee no less) doesn’t indicate the company doesn’t care about work/life balance.

    2. Tinkerbell*

      Yeah, six weeks in the next few months (even if they’re pre-planned and negotiated) sounds like a lot. Presumably they’re hiring because they need someone doing the job NOW, and it’s kind of a tall order to ask them to put the work on hold for that long already! I guess it’s possible there are places this wouldn’t be an issue – if summer is their slow season anyway, or if training someone up usually takes years instead of weeks/months – but I wouldn’t be surprised if they’re stalling because they’re shocked he’s even asking.

    3. Captain dddd-cccc-ddWdd*

      Yes, if I was in the hiring manager’s position and the new person pushed and pushed for an answer before I really knew the answer, I’d have to say no. I would also be willing for them to change their mind about the offer based on that. (would I rescind the offer – no – but that is the first thought that went through my mind. It wouldn’t start us out on a very good footing.)

      1. Artemesia*

        they should have when they made the offer agreed to unpaid leaves for the 4 week vacation and committed one way or the other to the other one.

        1. Captain dddd-cccc-ddWdd*

          Sorry, I disagree that they ‘should’ have agreed unpaid leave for 4 weeks. The trips are in the ‘summer’ which I think the latest that can be is September. So potentially he would be away for a month, 3-4 months (or less) into his employment. I bet 4 weeks unpaid for a vacation wouldn’t be approved for an existing employee (it’s a massive ask) or only approved for a real one-off like a once in a lifetime trip.

          1. Colette*

            And often having the new person out for 4 weeks means the existing employees can’t take as much time off. But either way they owe her a clear yes or no.

      2. I have RBF*

        When they are trying to arrange international travel for a reasonable price? I would expect them to push for a timely answer, because every day they wait could be hundreds of dollars. Travel is best booked with long lead times.

        He may need to just tell them that he is taking that time, unpaid if necessary, and then just books his tickets. If they balk, it just shows that they aren’t good for their word.

        1. Dancing Otter*

          But they haven’t given their word in the first place. How can they go back on it?

        2. Captain dddd-cccc-ddWdd*

          > He may need to just tell them that he is taking that time, unpaid if necessary, and then just books his tickets.

          What a great way (not) to start the relationship with your new employer…

    4. GythaOgden*

      Yup. Also if they were booked already, that would be different, but if OP hasn’t bought the plane tickets yet, that’s not something the company should be expected to honour. Six weeks of vacation is stretching it even for our European public sector leave allotment; I get 29 days AL (exclusive of bank holidays; it makes up for the rubbish pay) so if I used it all on trips like that, I’d have nothing left for anything else. And it’s the privilege talking — a lot of people wouldn’t be able to afford that kind of vacation, and the jobs that pay the money to finance that kind of trip are the ones where the person takes on more responsibility in exchange for the pay that allows you to take off for six weeks of actual vacation.

      I’m looking for a new job and in addition to having to keep days in hand for interviews (even generous UK AL can get eaten up very quickly if you’re not careful) because I’m interviewing in the town where I live and it’s hard to do anything here when I have a two hour public transport commute. It’s one of those things that you have to postpone in order to be able to get the job that will pay for it.

      1. Caliente Papillon*

        These were my thought exactly- it’s one thing of you’ve already booked and paid for the trip but you haven’t so I wouldn’t even call it a landed vacation really, more like a thought.
        They should get a clear yes or no but their proposal actually seems slightly ludicrous to me. Maybe they should just not be officially hired until after the month and half in vacations? Imagine the employees already there- oh we hired someone! Guess what they’re going on vacation for 4 weeks next week!

      2. I Wrote This in the Bathroom*

        “Also if they were booked already, that would be different, but if OP hasn’t bought the plane tickets yet, that’s not something the company should be expected to honour.”

        That’s my thought too – I had a friend take a job offer at a place that offered 0 (ZERO) PTO days for the first six months, when his family already had a vacation fully booked for a 3-week trip to his wife’s home country; first they’d had in many years, if not ever. He told them during the interview process that he had a long trip already booked, and they were fine with him taking that time without pay. I understand how being told “we kinda sorta plan on those two trips, but nothing is final yet” can come across to the employer as, well, there not being anything final yet, so nothing they have to give a yes or no answer to.

      3. MCMonkeyBean*

        Yeah, I was surprised when I saw the comment about tickets getting more expensive. You’re asking for half the summer off! That’s a HUGE ask–one I would generally expect people are only making because the trips are already paid for and can’t be cancelled. IMO, unless the trip is for something significant and immovable like a wedding, if you haven’t bought the tickets yet then you should not be expecting to still take that trip.

    5. amoeba*

      Oh, not just in the US, even! In Europe, it would seem super out of touch, actually. (Might be even worse because additional unpaid leave is really not a thing that’s regularly done here – once you’re out of PTO, you’re out of PTO – not counting sick leave, but no more holiday, for sure.)
      You do get your PTO for the year up front, so if you start in May, you’d have 8/12 of the yearly days available. But that would be something like 15-20 days, not six weeks. And while it’s fine in most workplaces to negotiate pre-planned holidays within the first few weeks/months, it would not be the rule to take your entire allotment during the first summer (there’s also frequently a company closure at the end of the year that you need to save 3-5 days for).

    6. Allonge*

      Even if not in the US – I am in Europe and our basic rule is that you only get to take leave in exceptional situations in your first three months (illness or similar). So the answer absolutely would be ‘no’ and we have decent work-life balance otherwise.

      Still, this would be clarified at the interview at the latest, so I also agree that wanting an answer is fair, it’s just likely to be a no.

      1. Captain dddd-cccc-ddWdd*

        I think it’s more likely to be a ‘flag’ about how decisive (or not) the company is, more than about work life balance. They do seem to be waffling and putting off the decision. I wonder if that is how they operate in general.

        1. Pretty Generally Happy, Mostly*

          in my company, the waffling would mean, “technically the answer is no and there’s no precedent for something different, but we’re trying to figure out if we can do something different for you anyway.”

          ….. and yeah. that’s very on brand for how we operate in general.

        2. Sola Lingua Bona Lingua Mortua Est*

          I think it’s more likely to be a ‘flag’ about how decisive (or not) the company is,

          That’s how I read it. It sounds like indecision torture to me, too. LW3 should proceed with the de facto answer being no–the trips may well pass before any decision is made.

      2. amoeba*

        Hm, for us that used to be the rule (during the probationary period) but pre-planned holiday could certainly be negotiated at the offer stage. But only if you actually have the PTO for it, so certainly not six weeks. (And I’d probably still avoid asking for something like 3 weeks within the first two months, unless it’s my honeymoon or something!)

        And in general, at least in my field, it seems to be getting more relaxed in general – when I started my last jobs, it was never a problem to take PTO in the first months. Some employers seem to prefer it by now because otherwise new employees tend to end up with a ton of unused days at the end of the year…

        1. Allonge*

          Oh, I didn’t mean to give the impression this is a universal rule, sorry! Obviously within Europe there are still dozens of different laws and thousands of company practices on this.

          But yes, for us if you wanted to take six weeks off in the first two months, most likely you would be asked to start two months later. The only thing this would not apply to is, again, illness, medical procedures, pregnancy and such.

      3. Emmy Noether*

        Depends on the country within Europe, too. When I worked in France (a while ago, so may have changed), vacation accumulated May-April for some reason and could only be taken the next period, not the current. So if you started in May, you were SOL for 1 year (other types of leave did accumulate quicker, and my job let me take an advance, but still, it suuuuuucked as a system). In Germany I’ve always had no advance leave during the probationary period as a rule, accumulating monthwise. Employers/bosses have some flexibility, but no-one wants to have the employee owe nearly a year’s worth of leave if the probationary period doesn’t work out.

        1. Earlk*

          This seems really odd to me, in the UK you can use your leave during your probabtion, even if it’s technically over what’s “accumulated” (although it wouldn’t look great if you wanted to use all of it within the first 6 months) and I thought we had stricter leave rules than most of Europe.

        2. Allonge*

          no-one wants to have the employee owe nearly a year’s worth of leave if the probationary period doesn’t work out.

          That’s an interesting issue – everywhere I worked you got credited your entire yearly leave on your first day so you could use it, and most had some limits on how much you can take while in your first X months.

          But if someone does not make it through the probationary period, they are only owed compensation for the proportion of leave for the period actually worked – so your leave allotment is two days per month, you worked two months before concluding it did not work out, then you were compensated for four leave days if you did not take them, not for your whole year’s worth. That’s part of the point of not allowing people take a lot of leave in the first period.

        3. amoeba*

          Huh? That’s really interesting, I would have said the opposite for Germany – I’ve always had the full PTO for the year available from Jan 1st. (Although technically it “accumulated” – so, it was fine for you to take all 30 days in the first half of the year if you wanted, but if you left, say, in September, you’d be “over” the leave for that time and would need to “give back the days” – mostly by deducting from your final salary.)

          1. TechWorker*

            Right, they get around this because leave is almost always less than a month => less than a months salary so if you give notice then it’ll be taken out of your paycheck. I don’t know what they’d do if you took leave and then quit with no notice immediately after getting a paycheck but I would guess they would try to get the money back…

          2. Emmy Noether*

            Most companies make all of it available in their system from the start, yes, but the legal situation is different. I actually looked it up recently when I left a job and it’s quite complicated, so I’m not confident repeating all the details here – easily searchable if you want to know the full absurdity though. There’s a difference if you leave first half of the year or second half, and the probationary period is different still (don’t have a legal right to your full yearly vacation for the first 6 months). In no case can you be obligated to pay back anything, or even have it deducted from a paycheck, though – worst case it will be deducted from your vacation at your next employer (no, I don’t know how that’s supposed to work in practice, either).

            A lot of companies will do it simpler/more lenient than what the law says, because it looks like a headache to implement and control – which is not a problem of course as long as it’s in the employee’s favor.

            1. amoeba*

              Huh, interesting! Guess I confused it with Switzerland – here, unfortunately, it does appear to be possible to ask for the money back (no idea whether this is actually enforced as I haven’t run into the situation, luckily…)

            2. Myrin*

              Re: how the deduction at your next employer works in practice: when my sister last changed jobs, her former boss had to fill in a form where it states how much vacation she’d already taken and she got to take the rest at her new/current job.

              1. Emmy Noether*

                Ok, that’s the easy part, but do the companies transfer money between them? Because if the employee doesn’t take exactly the amount of leave corresponding to the time at each job, then the company where he took more than the prorated amount is effectively subsidizing the other company.

        4. rebelwithmouseyhair*

          That is more or less right, the first year you can only take unpaid leave or a few days here and there as they accrue. But the accrued days are supposed to be for next year, so if you take too many, you won’t have anything banked for the next year.
          And yes it’s really weird that it runs from 1 June to 31 May. Especially since other types of leave (especially compensation days for working more than 35hrs a week) starts on 1 January and accrues through to 31 December.
          If someone wanted to have six weeks off their first summer, it would have to be unpaid. There’s a good chance it would be granted if it was the condition for accepting the offer.

    7. Emmy Noether*

      6 weeks a few months into a new job would raise eyebrows even in countries that have that much legally required vacation. Most places one can’t take paid leave in advance during the probationary period, so it would probably have to be unpaid, and given grudgingly. I’ve seen people take up to 3 weeks for already booked long distance travel if negotiated before starting, but 6 is really pushing it, especially since it doesn’t seem to have been booked yet.

      1. Chocolate Teapot*

        My previous job recruited a young woman who I was supposed to train up. Due to timing I was on holiday for her first full week and when I returned, she had put in numerous holiday requests including a time I had planned to be away.

        It transpired she had informed HR before she started of pre-booked holidays which could not be cancelled/rescheduled. On top of when she was on holiday she was often not in the office due to sickness, so in fact she wasn’t much help at all!

      2. umami*

        Yes, I am surprised they haven’t already assumed the answer is no and moved on. It definitely sounds like they have intentions of traveling, not that actual plans have been booked and paid for, so I would be really surprised if the company felt any obligation to honor the request they way it’s been described. I’m puzzled by the work/life balance thing; do they really think it’s reasonable to ask for such a huge amount of time at once at the very start of employment? I wouldn’t think so if I were hiring someone, especially if there isn’t a compelling reason (like a special occasion) for needing to book both of these trips this particular summer.

        1. General von Klinkerhoffen*

          Yes, I think there’s a difference between LW’s situation which is effectively saying “hey at some point I’d like to take some vacation, how does that sound?” and their saying “yeah we’ll see what we can do”; and starting saying “I have travel already booked for the first two weeks in June, how should I put this into the system?”.

          I think the employer in this letter is hoping they’ll get the message, reschedule, and shut up.

          1. Lydia*

            I mean, the OP maybe should just move on, but the employer should not just waffle on the answer and hope the situation solves itself. That’s crappy. If the answer is no, just tell them that!

            1. umami*

              I think an extenuating factor is the person hasn’t even started working yet, so it might not actually be possible to give a response when they haven’t even onboarded yet. It would be necessary if they were still negotiating an offer, but that’s already passed. So now it’s a ‘we’ll see what we can do’ once you’re here kind of thing, I suspect. I can definitely see not prioritizing a decision on a soon-to-be employee’s potential vacation needs over other pressing work.

    8. Jackalope*

      To me the red/yellow flag is not that they aren’t excited about so much vacation early on in his employment. It’s that he asked for the time off specifically when he was negotiating his hiring, and they a) couldn’t give him a firm answer but said they’d try, and b) have waffled for a month since then. Are they going to do this every time he wants to take leave? (Or if not for all leave, any time he wants to take more than a day or two?) I think we can all understand that taking 6 weeks of leave so early in his time at the job might be a hardship for them, but they need to give him an actual answer. It’s not great to put him off for that long, and making the answer no just by holding out on a response until he can’t go anymore (or the time has passed) is a bad way to deal with this, whether they do that intentionally or just by dithering too long.

      1. Manic Pixie HR Girl*

        Yeah, they just need to give him an answer. And, if it was me (as the employer) I would be less concerned about the 2 weeks in June vs. the 4 weeks later in the summer, but that’s a separate issue.

        A job I worked a number of years ago did this – I was new-ish but not new, and I had plenty of accrued leave to cover the request, and they would. not. give. me a straight answer. I finally just rescinded the request on my own because it was getting too close and plane tickets were getting too expensive, and my direct supervisor said, “Oh that was very good EQ.” … or you could have just said no.

        1. umami*

          Sounds like they were giving you space to make the *right* decision yourself. What a strange way of doing it though! I’ve always assumed a non-answer is an answer, and always not the answer I am hoping for.

          1. Manic Pixie HR Girl*

            There were … a lot of things about this job that in hindsight should have kept me away from it before I took it, and that’s where I will leave that. :)

      2. Kevin Sours*

        If it’s important enough to affect accepting an offer you need to make it part of the offer. If it’s not then you need to let it go. Because even if the whoever they talked to was responding in good faith (and they probably were), there was no commitment. And it’s not clear to what extent whoever said they’d try to accommodate had a realistic view of what the company was willing accommodate.

        But yes the company should figure this out so that everybody can move on.

    9. CheeryO*

      Right, I was a little surprised by the framing of the trips as two “somewhat long” vacations. 2 weeks is very long; 4 weeks is almost unheard of even at my government job with ample PTO. I would be checking in one last time and ensuring the employer that I know that it’s a big ask and that I would not expect to be paid for most (or any) of that time.

      1. Cmdrshprd*

        Maybe this is just a different frame of reference/semantics, but idk that I would agree that 2 weeks is a “very long” vacation.

        Yes people take one or two days off here and there, that to me is very normal standard that hardly requires much discussion. Yes you let your boss know, but generally it is more of I checked schedule we do not have anything on those days.

        I would say one week (5 days) is a pretty standard vacation time to request off, and two weeks (10 days) “long” but not “very long.” If you are doing international travel where travel to/from your destination can take 1 to 2 days each way, two work weeks off (for 16 days off in a row total) is not that long.

        I would say 4 weeks in a row would be a “very long” vacation, and would require more coordination to shift duties around during the absence. But two weeks would take a bit of coordination but not a ton, unless the position is one that requires daily coverage/job duties. For example a receptionist, or reviewing/approving daily reports that can’t wait until the person gets back.

        1. Shan*

          Yes, people at my company (Canada) regularly take two week vacations, and honestly, it doesn’t require much coordination. Obviously that isn’t the case with every single position, but it’s definitely more common than not. I just interviewed someone this morning who mentioned they need three weeks to attend a wedding in their home country in September, and it was an absolute non-issue.

          Now, that being said, two pre-scheduled vacations that would potentially go beyond the vacation day allotment would probably give me pause – but still wouldn’t be a definite no.

    10. cncx*

      I’m in europe where 3 and 4 week vacations are not unheard of and 2 plus 4 weeks so early into employment would still Not Be Done here. I feel like asking for the start date to be pushed out would work better here.

    11. Merrie*

      Counterpoint, if the person’s still training, why would having them absent be that big of a deal? It would push back the time until they’re fully trained, true, but if the company really wants that person for the long term, they should be able to work around it.

  8. Brain the Brian*

    LW4: Check your company handbook if you haven’t already to make sure you haven’t missed something. My employer’s explicitly calls out that if the company pays for an employee’s PD or tuition reimbursement and the employee leaves within a certain amount of time, the employee has to pay back the company. Really great way to encourage employees to build their skills and stay with the company (eyeroll), but it’s very clear in our policies.

    1. Captain dddd-cccc-ddWdd*

      > Really great way to encourage employees to build their skills and stay with the company (eyeroll)

      Curious – do you think policies like that are ‘wrong’? Stipulations about clawback are really common. It makes sense because otherwise what’s to stop people getting the company to pay for training etc and then just leaving, so the company doesn’t get the benefit of it after paying out. I think it has to be like this otherwise there would be no incentive for companies to pay for tuition etc. I do think 2 years can be too long though (I know you didn’t say 2 years, it is just a time that’s often stated); 1 year would be more realistic, although what would be better is a time period that takes into account the cost and individual circumstances (e.g. “using Excel effectively” is cheaper and should have less of a clawback period than a year-long leadership program).

      1. Poly Anna*

        Ideally, you would make it so the training is not the only reason people would want to work for you :) Part of that is trusting your employees, it may not make sense to nickel and dime them on every small thing in that regard. (I’ve personally only seen payback clauses on things over 2000-3000 euro and the terms were reasonable)

        Alternatives are things like a yearly individual development budget for each employee, but companies would usually still end up paying for new employees and courses that are relevant but not something people would choose for themselves.

        1. I am Emily's failing memory*

          My employer has both. Each department’s budget includes a line item from for employee professional development, for things like conferences and short training courses where they’ll be gaining knowledge they can directly apply to their current job. Each department has their own internal policies governing any maximum amounts available (including any travel, lodging, and/or per diem costs), how many workdays you can spend at training instead of doing your normal work, and it’s common for there to be a requirement to share your notes or give a short presentation to the rest of your team afterwards, so the department is benefitting directly from allocating funds for PD. The department head and direct manager gave discretion to debt specific requests that would be a hardship for the team or department to grant, and the internal department policies are subject to change at any time and technically never guaranteed – although I’ve never heard of a department axing their entire PD budget, I’ve seen the amount of the allowances be adjusted year to year. If you quit at any point after any costs had been paid you would not owe the money back, but if the event hadn’t happened yet it’d be expected you would no longer go, and they’d likely try to send someone else in your place if possible.

          Separately, there’s also a tuition reimbursement program that’s part of our official compensation package, which is in the employee handbook and in the benefits sheet that’s enclosed with a job offer. The maximum amounts and other criteria are set at the organizational level, and unlike the departmental programs, the organizational one is only available for courses that count towards degree-granting programs, only reimburses fees and tuition (not travel costs), and would require you to use leave if any of the sessions overlapped with your normal workday, but there’s no requirement for it to relate to your current job, there’s no requirement to present what you’re learning to anyone internally, and there is a clawback clause if you leave within I think a year of reimbursement.

          So basically there’s a clawback policy on the one that’s structured as an employee benefit/part of their compensation package, but not the one structured to be mutually beneficial for an employee and their immediate team.

      2. Brain the Brian*

        My company simply does not promote or provide other growth opportunities to employees who participate in professional development and / or get degrees / certifications, and so people leave even though it means they have to pay back costs (or they simply don’t ask for reimbursement in the first place, because they know that they will probably wind up leaving). In but one example, we had an accountant get her CPA on the company’s dime at her second-line manager’s request, and the company refused to promote her when she finished, instead elevating her utterly incompetent coworker — who did not have a CPA anyway — to be her new boss. She gave her two weeks notice exactly one day after the clawback period had ended.

        In short, it’s wrapped up in a toxic, excellence-averse culture that actively discourages employees to learn and improve. An exec said to me once “We can’t improve too much, or someone will question why we weren’t doing better before.” Senior management here sees employees here as simply replaceable, incompetent cogs in a broken machine that I’m convinced will never be fixed.

        I’m ranting, and this thread risks running afoul of the commenting guidelines’ rules about off-topic discussions (and frankly, kindness), so I’m going to put a sock in it now. :)

      3. Twix*

        In an industry where 2+ year clawback clauses are very common, I actually love my company’s approach to tuition assistance. You pay out of pocket, and the company pays you back as a tuition reimbursement in your paychecks (which is tax-exempt up to $5250/yr) over 2 years. If you leave before 2 years have passed, you don’t get the full amount back. Absolutely no other strings attached.

        1. Well...*

          One possible downside to this is that you need to have the $ to pay upfront, so it privileges people that aren’t on super tight budgets. It’s nice that there’s not some all-or-nothing 2 year deadline.

          I don’t love the idea of these programs, though, they feel a little too close to indentured servitude, and it’s another case of companies leveraging their power to minimize their risk aversion. Considering that academia nowadays sometimes looks like it’s just helped shift employee training costs from companies to the individual, this “you must work for me for X years if I pay the training/career development costs that 50 years ago I would have been responsible for” feels grosser.

          Then again, we live in the real world, and this might be the best/only way for people to be able to cover this tuition in the current state of things, so I can’t hate on it too much. It’s just a worrying large-scale trend.

          1. Twix*

            That first part is definitely true of tuition reimbursement in general, but salaries are high enough in my industry that it’s generally not an issue. I’d be much less on board with it at, say, a place that primarily employed minimum wage workers. The rest of your comment I 100% agree with, which is why I’m a strong proponent of publicly funded higher education. But until then, this is the system we have to work in. I also didn’t mention it in my first comment, but my employer offers fairly generous extra PTO for attending classes/studying/exams, so they are directly absorbing some of the cost there.

            It is worth considering that this setup often allows a lot more freedom in professional development than employer-funded workplace training would. I’m looking right now at a graduate program for a very hot new subspecialty in my field that would, among other things, drastically increase my hireability and negotiating power. I could potentially make use of it in my current role (or a higher one within the company) at some point in the future, but it’s not something we’re using anywhere right now or have any current plans to adopt. Broadly speaking it would be good for my employer to have someone on staff with that skillset, but the program would be far more beneficial to me personally.

          2. cabbagepants*

            I disagree strongly that it’s anything like indentured servitude. They’re not making you take the course and they’re giving you extra money on top of your paycheck rather than withholding your pay.

            I agree that there is a privilege aspect but that’s generally true for higher education and everything that costs money, and such a hypothetical pay-back program at least lessens the burden.

            1. Well...*

              I mean… they’re only paying you back if you keep working for them. If you rely on that money because the degree program is outside your means (say you took out a loan, for example), then you’re effectively exchanging future work for $ you rely on now, not work you’ve already done.

              It’s a strong claim to say the arrangements have absolutely nothing in common.

      4. WishIWasATimeTraveller*

        I worked for a company that had generous tuition funding programs and no clawback clauses. That surprised many people, but it was very rare that people would leave soon after their training. I think it made them feel more committed to the company because they felt like the company had invested in them.

      5. Brain the Brian*

        I suppose they’re not inherently wrong, but in my employer’s case it’s wrapped up in a general unwillingness to promote or otherwise offer growth opportunities to employees. They simply don’t promote people who upgrade their skills — whether through participation in professional development or by getting a new degree or certification — and so the clawback policies feel inherently predatory.

        In perhaps the most egregious example, one of our accountants went and got a CPA on the company’s dime at her second-line manager’s request, and after she finished, the company refused to promote her into the vacancy above her, instead promoting her utterly clueless coworker (who didn’t have a CPA regardless) to be her new boss. That employee put in her two weeks’ notice *the day after* the clawback period for her tuition reimbursement ended. And then after she left, the company doubled the clawback window. (again, eyeroll)

        Basically, this is all wrapped up in a mindset that is deliberately anti-improvement. I quite literally had a C-level exec say to me once “Don’t improve too much, too quickly, or clients will notice and wonder why we weren’t doing better before.” Knowing that the company will refuse to recognize improved skills in any meaningful way and that you will have to leave to get the promotions you deserve, most low- to mid-level employees simply don’t bother asking for reimbursement for tuition and PD — or they don’t bother getting them at all. It hurts the company more than anything, frankly, since our employees are basically broken, replaceable cogs in a malfunctioning machine all the time.

        I digress. I am quite close to the line on the commenting rules about staying on-topic and remaining helpful to a LW’s circumstances now, and I will put a sock in it.

    2. bamcheeks*

      Tuition assistance is often subject to a clawback, but in the UK that would be specified at the time the agreement was made with the individual employee, not a general rule. The sliding scale from “conference/professional development opportunity/networking event/ongoing leadership programme/professional credential/qualification” would make it incredibly hard to have a blanket policy rather than one which looked at the specific timescales and type of programme on an individual basis, IME. But it is worth checking your handbook to see if there is anything. What they shouldn’t be able to do is make you retrospectively responsible for it: if they do want to make you pay for it if you leave within a specific time, that should either be made clear when you accept your place or should be written in your handbook (even if it’s super generic like “company ~~may~~” or “company reserves the right to…”

      That said, LW4, when I was having my postgraduate credential paid for and changed jobs, I asked my new employer whether they’d be happy to pick up the ongoing cost of the programme I was on and they were happy to. So you can definitely make it part of your salary negotiation if/when you’re offered another job. “I will be worse off if I move to you because I’ll owe my existing company X for my qualification [the benefit of which you’re going to get], do you have any flexibility to make that good” is a very straightforward thing to introduce when you’re discussing salary and benefits.

      1. LW4*

        That is an interesting suggestion I would not have thought of! It reminds me of when cell phone companies offer to pay any cancellation fees attached to your current cell phone plans.

        That said, the cost of the program is $500, which to me is in that range where I definitely don’t want to pay for it myself but also is not so big a cost that I would feel the need to ask for help getting out from under from a next job. If that makes sense.

    3. LW4*

      Thank you for your suggestion! I don’t think the handbook says anything about that, but I will double check.

  9. GythaOgden*

    Re: Jane. No, you’re not the asshole. Even amongst my friends, everyone expects to pay their own way and gets lucky if someone decides to cover it all. We’ve all taken turns at doing that as well as picking up the tab for someone falling on hard times to ensure people can join us even if they’re broke, but they are then expected to return the favour by other means. It’s not necessarily transactional — just one of those fluid ‘I’ll scratch your back…’ things that people do in friendship groups.

    Jane needs to be told to stop this right now. She’s a mooch and if you don’t speak up now, she’ll continue to mooch. Even if she’s not all together financially, that doesn’t mean she gets to put others in a difficult position themselves.

      1. elle *sparkle emoji**

        That doesn’t mean she gets to unilaterally decide on a new job perk without communicating that. If she has an issue with the pay she needs to ask for a raise or look for a higher-paying job.

  10. Akcipitrokulo*

    LW1 – no, I don’t think you handled it well.

    Not paying for tacos was fine – because she had suggested it – but embarrassing her at the restaurant instead of talking beforehand? Yeah, that was not a good move.

    You should have clarified beforehand.

    Setting someone up for a fall is not a good move.

    1. Thistle whistle*

      the only embarrassment should be felt by rhe employee who was trying to take her employer for a ride. she should have been called out when she dodged the ice cream bill and that would have stopped her cadging right at the start. at least she now knows that she can’t dump the bill on you any more. lesson learned.

      1. Allonge*

        Yes – of course with hindsight the conversation should have happened before, but that goes both ways!

    2. Kat*

      Agreed, after the ice cream thing, LW should have clarified that they would be each paying for themselves with Jane when she saw the Taco Tuesday invite. Jane obviously had the wrong impression re who would cover these outings – but the LW’s solution was to make things super awkward for their only employee, which is not going to improve their relationship. Not exactly a result LW should be patting themselves on the back for.

      1. Well...*

        I’m not sure what’s super awkward about this though? It is a little awkward, and it would be smoother to have addressed it up front. Still, asking someone directly to help pay for a bill isn’t a horrifying social nightmare that must be avoided at all costs.

        It seems like the employee overreacted a little with embarrassment, which is nice if it can be avoided, but sometimes these things happen.

      2. Ladida*

        The reason it was super awkward though is that Jane went to the bathroom right after the bill came. If she hadn’t, the OP would have said “it is 20 each” and Jane would have realised that she needs to pay for her share. This is probably what OP expected to happen.

      3. elle *sparkle emoji**

        Jane made it awkward by rushing to the bathroom to skip out on the bill. OP simply didn’t hold on to the awkwardness hot potato.

    3. Ladida*

      I agree that she could have warned her beforehand but it is possible she was not sure whether the employee was expecting them to pay. The ice cream incident was an indication of course, but an ice cream is a small expense and very different from lunch. It is very strange for someone to arrange a meal, suggest a restaurant and expect others to cover the bill, so it could be a bit presumptuous to accept the invitation and tell her “we are not paying for this”. A normal person would have replied, yes of course I would not expect you to pay for this and could also be offended that they thought this.

      1. Artemesia*

        handled badly and now the employee is embarrassed. It was obvious after the ice cream thng and the graceful way to handle it is before going for tacos to say as Alison suggested. This sounds like fun but we don’t have the budget to expense this to the business this often, so it will have to be dutch treat. This way the employee is not embarrassed and treated like a dead beat in the restaurant.

        1. Ladida*

          I don’t think it’s that obvious, an ice cream is like coffee, your boss or manager might treat you to it even if it is not expensed because of the difference in income. Yes, Jane not offering to pay for her ice cream was a bit of a red flag but, just from this, you can’t tell Jane is the sort of person to set up a lunch appointment at a place of her own choosing and expect her boss to pay for it.

        2. elle *sparkle emoji**

          Jane was presumptuous. She deliberately tried to skip the bill by running to the bathroom. Her choices made things awkward and it’s ok for OP to make her deal with the awkwardness she created.

        3. elle *sparkle emoji**

          Running to the bathroom when the bill comes is a pretty well know move for trying to avoid the bill. If she wants to behave like a deadbeat, then she can deal with the embarrassment.

      2. I am Emily's failing memory*

        I had the same thought – it had only happened once at that point and with a snack, so LW might not have been able to anticipate that she was going to pull the same thing for a full meal. In hindsight she sees the two incidents as part of a clear pattern, but it’s not crazy that she might not have seen it before it happened for only the second time.

    4. Aria*

      > embarrassing her at the restaurant instead of talking beforehand

      I think this goes both ways. Jane went to the bathroom when the bill came. That’s the most common trope for getting out of paying for your meal, right next to “oops I forgot my wallet, I’ll pay you back later”. There’s no way she didn’t know what she was doing.

      > Setting someone up for a fall is not a good move.

      There’s a difference between OP not thinking to clarify who’s paying for lunch and setting Jane up for a fall. I agree that after the ice cream incident OP should have specified, but it also seems like Jane was testing the waters with getting a smaller expense covered and then trying to go for a whole meal.

      1. Allonge*

        Exactly – this was a misunderstanding, and low-key embarrassing for everyone, and could have been prevented with clearer communication, yes.

        But there are no bad guys here and no need to paint anyone as one.

        1. Sasha*

          Was it a “misunderstanding”, or was Jane trying to manipulate LW1 into paying by legging it to the bathroom when the bill arrived?

          Seems like the second one to me.

          1. Allonge*

            Could be but this is one of the cases where – unless Jane brings this up again – there is no reason for to investigate the full intentions behind the actions as it will not lead to anything productive.

            Both sides hopefully learned something – it’s ok for everyone to be over this, and everyone should be over this.

            I know that we as commenters tend to litigate any and all small issues here but that is only ok as a commentariat, not when you are actually in the situation.

            1. anxiousGrad*

              “there is no reason for to investigate the full intentions behind the actions as it will not lead to anything productive.”

              This is such a good point for so many social interactions!

            2. bamcheeks*

              Yes! there are so many things where it’s just fine to chalk it up to a misunderstanding between two or more people, without assigning blame on either side. You don’t have to assign asshole-status to anyone!

          2. Well...*

            Eh, or Jane might have just felt awkward about the bill in general, but somehow had it in her head that the boss always pays, so went to the bathroom to avoid feeling weird about it.

            It’s more likely that it’s deliberate, but I wouldn’t say it’s totally implausible that the whole thing was caused by awkwardness/social anxiety/mistakes. I know that when my anxiety tells me to do stuff, it fires kind of randomly in my brain and sometimes suggests the worst, most embarrassing, weirdest thing to do in a situation. There’s so much panic going on in the background that I don’t have the capacity to think calmly through the options and choose a rational course of action, and sometimes I do misstep weirdly at the level of low-stakes social niceties stuff. Sometimes trying super hard not to do the Wrong Thing can be hella counterproductive.

            Anyways it doesn’t really matter. If Jane was being manipulative, it seems pretty low-level and easy to shut down, as was done passably by LW already.

      2. YetAnotherAnalyst*

        In fairness, I’ve also gone to the bathroom while my boss got the bill during team lunches. It’s the least disruptive time to excuse yourself, and you’re ready to work when you get back to the office.
        Which doesn’t mean Jane’s not out of line; just that I don’t think you can use her bathroom timing as proof of bad faith here.

        1. Gemstones*

          I think the difference, though, is this wasn’t a team lunch with a whole bunch of people…it was just three people, and Jane was the one who organized it. Inviting someone out and then dipping to the bathroom when it comes to pay…it’s just a little tacky…

          1. I am Emily's failing memory*

            It’s tacky during a social occasion where there’d normally be an expectation of paying your own way, but if Jane had genuinely gotten the impression that the company foots the bill for workday lunches, even though her impression was wrong, it could very easily just be the most convenient time to get up and use the restroom – the meal is done, it’s going to take a few minutes for the boss to request and take care of the check, and you don’t want to have to hold it till you get back to the office, so of course you’d go now.

            Maybe she was trying to avoid the check on purpose, or maybe she truly believed her presence during the check-paying wasn’t necessary and she had to pee.

      3. Random Bystander*

        I agree.

        By jumping up to head to the bathroom when the bill came, Jane appeared to be trying to force her share being covered/avoid the conversation at the table (there’s no way to miss that the LW expected to split the bill when there’s clear calculations “this is my/our share” going on).

        The LW1 knows now that it is necessary to clarify about who’s paying for lunch going forward, but it does seem odd for Jane to have suggested a very specific meal and then expect someone else to pay.

      4. HonorBox*


        While it would have been great to clarify after the ice cream, I’m not sure I’d have completely picked up on the move Jane was making right then. A few bucks for a cone… whatever. And then she made the invite for tacos. This is a Jane issue. She got up from the table before the bill was delivered, so there wasn’t even an opportunity to have a short conversation when the bill arrived. She put herself in that spot and I don’t think OP needs to feel bad if Jane was embarrassed.

    5. I should really pick a name*

      Because the ice cream incident had already happened, yes, I think the LW should have clarified beforehand with the tacos.

      But just because they didn’t doesn’t mean they’re obligated to pay for Jane. Jane initiated the event, so there really isn’t a reason for her to expect the company to pay for it.
      If Jane was embarrassed, she caused the situation that embarrassed her. She set herself up for a fall.

    6. CTT*

      I’m not sure if there’s any situation where it wouldn’t be embarrassing – taking her aside beforehand could feel like a reprimand, same with an email (at least it would feel like that to me). It’s an awkward situation, and it’s hard for a lot of people to tackle those perfectly.

      1. Blue*

        And also the conversation would have been weird if Jane *hadn’t* been expecting the boss to pay. It’s a situation where with hindsight, it would have been better to address it beforehand, but I don’t think OP was in the wrong for not divining the outcome.

        1. Ladida*

          Yes exactly, this conversation would have been pretty weird if Jane did not expect her bosses to pay for lunch.

      2. Essess*

        It could have been a non-awkward “Hey, tacos on Tuesday sound great. Just want to make sure you know it wouldn’t be covered by the business but I’d enjoy joining you for a shared lunch outside the office to destress.”

    7. Beth*

      The employee set up her bosses. She ducked out to the bathroom at the critical moment when the check came, hoping they’d Be Nice and feed her again, rather than calling her on her BS.

      I just hope she hasn’t tried to pull another one of these since then.

    8. HearTwoFour*

      Jane was trying to “train” her boss to pay for her meals, and it failed. I wonder if she also regularly comes in late…

        1. Thistle whistle*

          Thats only relevant IF the company had a track record of paying for food on long work days. They didn’t.

          Whilst it’s nice if companies can afford to do that, if its a tiny place, that would be anachronous and so wouldn’t be expected (unless you have a brass neck).

          1. DisgruntledPelican*

            It’s relevant as a response to HearTwoFour suggesting Jane probably comes into work late.

        2. Lydia*

          No, the OP clarified. Jane works 9-5; OP and her husband regularly work 12-14 hours days.

      1. bamcheeks*

        This is such a weird interpretation of the power dynamic between staff and manager. If your staff tries to “train” you to pay for their lunch, you can just … not do that.

    9. EPLawyer*

      OP wasn’t setting up Jane to fail. She was just following convention that everyone pays for their own food — unless explicitly stating who is paying. Jane knew what she was doing when she bailed for the restroom right when the check came.

      Should she have talked to Jane first? Yes. Should Jane not have scheduled lunches that she assumed her bosses would pay for? Oh yes.

    10. Betty*

      I don’t see how the OP “set her up for a fall”? To me that suggests that the OP was attempting to play gotcha, when all they did was say “we’ve paid for our lunches, here’s your part of the bill”– which would be a totally normal and non-embarrassing thing if everyone had the expectation of paying their own way. Just because Jane *felt* embarrassed doesn’t mean the OP *acted with the intent* to cause her embarrassment.

    11. I have RBF*

      No. Jane set up “Taco Tuesday”, so she was trying to set up her manager, the LW, for paying for lunch without even saying so. The person who was being railroaded into paying was the LW, and they were blindsided. I sure would have been embarrassed to find out that I was supposed to be paying for everyone (or expensing it) if I hadn’t announced that earlier. The LW just returned awkward to sender.

    12. EvilQueenRegina*

      While clarifying beforehand might well have been the better course of action, what would be best in a situation where the OP/equivalent had no idea at all that Jane/equivalent thought it was being paid for until it got to that stage? Say something in the moment as happened here, or just pay at the restaurant to avoid a scene and have a conversation back at work afterwards?

    13. Just why*

      How were they setting up Jane for a fall? She didn’t realise until Jane came back from the bathroom that Jane had no intention of paying and so LW1 had to step in and let her know it was unpaid.

  11. Storm in a teacup*

    In my old sector (healthcare) it was common for hospitals to fund relevant post-grad and leadership programs for staff. Short courses were never bound by this but for longer courses with significant outlay in cost and time out of the department we used to have to sign before starting the course that we understood we may have to pay back some or all of the cost of the course if we left within 12 /24 months.
    In reality a lot of people negotiated with their new workplace to cover costs and this is certainly what I did when I left.

    1. LW4*

      Thank you. I think what is confusing to me is that it feels in-between. It’s a yearlong program and it does involve taking days away from my desk and counting it as work (maybe like a half-day every month, a full day quarterly-ish?) but a lot of it is on my own time. Much of it is meeting with people in my sector that I often already meet with too. So, it’s not like a training that’s only a day or two, but it also does not feel like it gets to the ‘university course’ side of the spectrum.

      Another comment also mentioned the next job covering the ‘pay-out’ cost, which never occurred to me.

  12. ABat*

    LW 1 – because this started right after a big lunch, I wonder if you or your partner said something offhand like “we should do this more!” which she took at an instruction?

    1. YetAnotherAnalyst*

      Oh, that’s a great thought – that makes a lot of sense! I wonder if it’s worth OP clarifying that with her now? I’d be pretty miffed if I thought I’d been told to arrange weekly team lunches and I had to pay for my lunch.

    2. Sloanicota*

      Reading that one, I was thinking “Hmm, how often are you asking your employee to work 12 hour days? Is she salaried or hourly? How screwed would you be trying to replace her? 12 hours is a lot of hours! Lunch a little more often doesn’t seem like a crazy way to say thank you if you really need her to hang in for that long.

      1. Allonge*

        This may be true in general but it’s not the point here. Even if OP was willing to pay for lunches regularly, that has to be their decision and not something Jane tricks them into doing.

        1. EPLawyer*

          THIS. Jane doesn’t just get to decide her bosses are paying for lunch now. If Jane does not like working 12 hours days without lunch being bought, that is something for Jane to consider about whether to keep working there or not. She does not just to get decide that her employers are buying lunch.

          1. Lydia*

            Jane isn’t working 12 hour days. OP clarified that Jane works a regular 8hr/day schedule, but she and her husband often pull much longer days during the tax season.

      2. Random Bystander*

        Well, since it referenced tax season, the 12 hour day did seem to coincide with the crunch time of filing deadline, so it doesn’t seem like it’s all the time (but a predictable event for anyone working in tax prep, as it appears this company is).

      3. Yorick*

        Sure, OP could take the employee out to lunch a little more often. But the employee shouldn’t expect it and certainly shouldn’t try to trick her bosses into buying her lunch.

      4. Courageous cat*

        I don’t think we need to bend backwards to find justification for letting employees run roughshod over the owners on this matter. It’s totally ok to say that “deciding your employer is paying for lunch for you whenever you want them to without even saying so” is a pretty bad move as an employee, entirely regardless of your working conditions.

        Even if it *would* be the fair thing to do for Jane, there’s a thousand other ways to communicate that than what she’s doing.

  13. MK*

    Ok, but is it common in these companies for the subordinate to actually “ask” for these lunches? I wouldn’t think it odd if it was the OP suggesting it, or if it was a more spontaneous thing, but I don’t understand how she got from “my boss invited for lunch once” to “work lunches are a weekly thing! I can make suggestions about where to go!”.

    I do thing the OP should have had the “this isn’t a business lunch” conversation when Jane put the taco lunch in the calendar rather than wait for the check.

  14. Aria*

    I’m surprised Alison’s answer to #1 didn’t include more of a reference to the fact that Jane was scheduling these events of her own volition and then expecting them to be paid for by the business. There was absolutely no reason for her to be doing that, and while OP should have been clearer (especially the second time, after the ice cream experience), it’s pretty clear that the first offered lunch turned into Jane thinking she could somehow finagle more free meals out of her employer. When would it ever be an employee’s turn to just start scheduling team lunches for her boss apropos of nothing? I do think that Jane isn’t likely to do it again now that she’s been called out by OP, but honestly the whole thing would have me questioning her professional judgement. Engineering situations to take advantage of people is always a red flag in my book.

  15. Dog momma*

    I would never assume that the boss would be picking up the lunch tab eternally. and would be mortified if somebody had to point this out to me. Something like this usually happens as a one time treat , or around the holidays. at least when I was working.

    1. Ferret*

      At my current company there are regular team dinners which the business pays for, usually the manager will pay on their card and claim back. But this is clearly set out in advance and definitely isn’t a weekly event

    2. MK*

      Eh, I think this could be a natual mistake for someone whose previous boss always picked up the tab (or who has been tild by their parents that it’s normal). What I find odd is her making suggestions for outings, twice in a row, after only one invite from the boss. I could see an employee whose boss has been inviting them for months and paying doing that.

      1. elle *sparkle emoji**

        Agreed, there are times where this could be a natural mistake but suggesting these lunches when there is not an existing “we all go to lunch weekly and the manager pays” culture is bold.

      2. lucanus cervus*

        Yeah, I worked in one very small company where we often ordered lunch in on a Friday, and the company paid. But it wasn’t every Friday, and it certainly wasn’t us who got to decide when those Fridays would be! Our boss would suggest it once a month or so and pay over the phone, and the newest person would be in charge of walking around the corner to pick up the food.

        Anywhere I’ve worked, if it’s the employees who decide for themselves to go out/order in, then we pay for our own food. I could never inform my boss that they were taking me out to lunch. My toes are curling in horror at the thought.

    3. Ellis Bell*

      It’s a really standard etiquette across a lot of situations that the person coming up with the idea to go out and making the invitations at least pays for their own food. That doesn’t mean the invitee doesn’t pay anything, but you can’t ask someone to dinner just to cadge a free meal off them. While I definitely would expect a boss to pick up the tab if they invited me out – there’s an implied pressure for me to attend and they picked the price range of the restaurant – they get to set the parameters. If I decide that I want Tacos for no particular business reason on a Tuesday? Then, yeah I’m going to be paying for my own lunch because the boss didn’t invite me, or offer to treat me.

    4. Rachel*

      Did you ever work 12 hour days during tax season?

      Because in those jobs, employers have a tendency to pay for more meals and coffee breaks and things of that nature.

      1. HonorBox*

        But it sounds like the OP did that during a 12 hour day / busy week.

        And when the employer does pay for meals and coffee, etc. they’re doing the inviting. It doesn’t mean that when an employee is feeling like they’re working hard they can schedule a lunch just to get free lunch.

      2. Allonge*

        Sure, but even in those cases you cannot randomly order any food/coffee and expect that it will be reimbursed – you would talk to your boss first or do it based on a policy/custom in place.

        Boss invited me once for a coffee = I never pay for coffee again is NOT how things work in most places.

      3. Oh, please*

        Given that the employee *isn’t* working 12 hour days (per the OP in the comments) and is making more than the letter writer – maybe the employee should stop be the one paying for things? Honestly…

    5. I am Emily's failing memory*

      It sounds like she was mortified (“hid from me the rest of the workday”)!

      1. Thistle whistle*

        Sounds like she should be embarrassed. inviting people out for lunch then trying to stick them with the bill.

        1. Parakeet*

          This wasn’t a social lunch, or at least she apparently didn’t understand it to be such. The rules of social etiquette don’t apply. It’s not a peer relationship – managers and staff are not on equal footing in terms of power and resources.

          The staff member missed the boat here – and there could be plenty of reasons for that, including just misunderstanding how norms work, or assuming that these were paid for with a corporate card – but this isn’t “inviting people out for lunch” in the same way that one would do with actual friends.

    6. Eldritch Office Worker*

      My company covers lunch all the time – but I don’t schedule a lunch anytime I feel like it. You need to know the norms of your office (which are often set by the person who knows the budget) and not create your own, is the main thing.

  16. Chocolate Teapot*

    My previous job recruited a young woman who I was supposed to train up. Due to timing I was on holiday for her first full week and when I returned, she had put in numerous holiday requests including a time I had planned to be away.

    It transpired she had informed HR before she started of pre-booked holidays which could not be cancelled/rescheduled. On top of when she was on holiday she was often not in the office due to sickness, so in fact she wasn’t much help at all!

    1. For sure*

      HR should have informed you of that, they were the ones who dropped the ball.

  17. I should really pick a name*


    Has your partner mentioned the time pressure?
    Have they asked if the first trip could be confirmed one way or another independent of the second trip?

  18. Rachel*

    #1: I think Alison gave a really great script for setting expectations around bill payment.

    But I can’t help but notice the casual drop of 12 hour days. A lot of people work in industry that has really long days during tax time. It is certainly not unheard of that the employer pays for more meals during this time.

    Also, I noted that you see a delineation between your corporate card and your personal card. I wouldn’t expect an employee dining out with you to be able to distinguish between these cards as you are paying. It just looks like a credit card.

    I mean, I agree with Alison that it’s okay to set some boundaries on this. But I also think maybe the contributor and other posters here are going a bit too far in dragging the employee.

    1. Oh, please*

      Given the OP’s updates in the comments (that employee makes more money and does not, in fact, work 12 hour days) I’d say the amount of dragging is just right.

  19. Minerva*

    LW 1- Perhaps uncharitable, but based on how this was described (particularly the part about going to the bathroom when the bill arrived and then saying “thanks for lunch” when she returned) I think Jane knew exactly what she was doing in trying to establish that she gets lunches and treats paid for by the boss. She got embarrassed because she didn’t think the boss would call her out on not paying.

    1. Olivia*

      Yeah, that was my read too. It kinda seems like she engineered the situation so that someone else would pay.

    2. K8T*

      Agreed! I wonder if the people defending her missed that part of the letter – her intentions are very clear

  20. bear*

    LW1 – I agree it’s weird that your employee is just scheduling these lunches without any prior discussion beforehand. That seems a little off to me.

    But I do think you should consider that it might be nice for you to pay for lunch or at least coffee/treats/snacks more regularly during tax season. If your employee is working 12 hour days regularly, it’s probably hard to find time to eat in the first place and I’m sure providing food of some sort would be appreciated. I’m a CPA and maybe I’m biased because I’ve only ever worked at large firms where this was the norm during busy season, but I would honestly be upset if my employer wasn’t willing to pay for at least one meal during weeks where I’m working anywhere from 60-80 hours. Usually the norm was if you had at least 10 billable hours in a day, the company would let you expense a meal that day.

    1. Some Internet Rando*

      I agree with this. The way Jane handled it wasn’t great, but it sounds like she works very hard (12 hour days during tax season!) and is your only employee. A little moral booster would go a long way to keeping her.

      It might be a good idea to go back to her and diffuse the embarrassment by explaining that you were caught off guard at the restaurant since she initiated the lunch but you really value you her (assuming you do). And then maybe have a plan about occasionally treating to lunch/food if that is possible and clarify that you would let her know in advance if its going to be covered by the business. Could you afford something 1x per month or throughout tax season when you are asking a lot? If she is a valuable employee a taco or ice cream cone is a small price to keep someone happy in their job.

    2. theletter*

      I’m of this mind too – part of the reason Google offered three free meals a day was that it helped keep engineers focused for those long shifts. They didn’t have meal prep or leave the office for nourishment.

      It might be useful to stock a fridge with snacks, sandwiches and treats during tax season if people are expected to be there from 7 AM to 7 PM. Or set up a little schedule of lunch deliveries from reasonably priced restaurants.

  21. amoeba*

    I think the easiest would have been to reply to the suggestion with “oh, tacos sound lovely! Unfortunately we cannot do it as a business dinner this time, but very happy to join if we split the bill” (like Alison suggested). At least to me, that seems the least awkward choice.

    After the fact, yes, it would probably always be embarrassing, no matter how you handle it.

    I’d assume no more such situations will arise because Jane has gotten it now – but if not, that’s how I’d handle it in the future. (And if you do invite her for something, make it clear that it’s a special occasion – “to celebrate xyz, today’s on us!”, “from now on, we’ll do company lunches roughly once a month, we’ll put them on the calendar!” or whatever…)

  22. Hiring Mgr*

    I don’t think Jane did anything *that* out of bounds… It’s pretty common that employers will cover a lunch like this. Was she a little cheeky? Sure, but sounds like a minor issue overall. Nobody is the AH here in my view

    Plus, as the third person in a three person business where the other two are married owners… she probably has a free lunch or two coming her way :)

    1. Happy meal with extra happy*

      Where the employee schedules it without any prior discussion? I’ve never ever heard of that being pretty common.

      I feel like there are multiple comments here acting like that those who think Jane behaved wildly outside of the norm are actually taking a position that it’s super weird for bosses to pay for meals, flat out. We fully get that bosses should and do pay for work lunches, but an employee scheduling a free lunch on their own initiative without any go ahead is bizarre.

      1. Allonge*

        Also there is a difference between the company paying (especially in a large org) or boss paying out of their own money.

      2. K8T*


        If it ended after the ice cream ..sure I would assume no real ill intent and move on but taking the initiative to schedule the lunch and then just /happen/ to go to the restroom once the check is dropped? No chance she wasn’t being sneaky about it.

        1. Eldritch Office Worker*

          I don’t know that it was sneaky, I think there could have been a real misunderstanding. People make social faux pas all the time. But it’s definitely not normal and she overstepped.

          1. Yorick*

            She was at best unsure whether they were going to pay, so she left the table when the bill came to avoid the awkwardness and in the hope that they’d decide it’s just easier to pay the whole bill while she’s gone.

            1. Parakeet*

              If she thought the employer was going to pay, “when the bill came” would be prime time to use the restroom!

              1. lucanus cervus*

                Yeah, she could have genuinely thought that since she wasn’t needed for the bill, it was a good time to go. I know that hiding in the bathroom when the bill comes is a cliche, but that doesn’t mean doing it in good faith is impossible.

                She made a weird overstep and it’s easy to be suspicious of a mistake when it benefits the person who made it, but it’s not ridiculous to extend some benefit of the doubt. Maybe she learnt a weird norm from a previous office, or read way too much into a ‘We should do work lunches more often!’

      3. Hiring Mgr*

        Agree, that’s the cheeky part.. Just saying it feels more like a minor misstep than anything else

  23. Enginerd*

    LW3 – Would your husband be willing to take unpaid leave for the trips? If they are hung up on the amount of PTO for a new hire and not on the amount of time away from the office, offering to make some of the time unpaid may help them with their decision.

  24. Slowpoke*

    Oof, I really feel for the awkwardness in letter 1. My guess is not that Jane was trying to pull something, but that she assumed all lunches were expensed and doubly so after you pulled out the credit card for ice cream (seeing this as offering to pay). It’s a shame it wasn’t able to be resolved later (such as by eating the cost and then having a separate, seemingly unrelated conversation about the meal budget going forward), but I understand why. I think this is just one of those situations that feels painfully embarrassing for a few days and then everything is fine again.

    1. EPLawyer*

      She scheduled lunch. I can see it being akward for Jane if BOSS said let’s do Taco Tuesday and then expect Jane to pay. But Jane scheduled the ice cream AND Taco Tuesday expecting both times that boss would pay. Which is pretty audacious of Jane.

      1. Slowpoke*

        Sure, but like Allison says, different workplaces have different norms about the boss always paying or not, and if Jane was expecting that norm, she may have interpreted agreeing to lunch as agreeing to pay. Or maybe she was trying to manipulate the owners, as other commenters are suggesting, but money misunderstandings are pretty common and I think it’s more generous to assume that’s what it was.

      2. Eldritch Office Worker*

        Agreed. My job is pretty generous with the paid lunches but that would still feel like a huge overstep for me.

    2. umami*

      That’s my take, too. I don’t assume bad intent on Jane’s part; she seems to legitimately have thought that boss would cover when she took out a credit card at the drive thru, and then put money in the bill holder the next time. If Jane had assumed I was intending to pay by saying thank you, I would have gone ahead and paid, and next time would have clarified ahead if Jane suggests another outing (but really, any time I am out with staff, I am going to pay regardless of who initiated the outing unless it’s specifically for something like boss’ day where they want to treat me).

  25. madge*

    “Universities — like government employment — often list their salaries as very specific, non-round numbers because they are weird bureaucracies.”

    For anyone considering a role in higher ed/government, this sums up what you need to know about those cultures. Thank you for making us feel seen, Alison!

  26. Katie*

    NTA. Your employee was taking advantage and knew exactly what she was doing when she avoided the bill by taking off to the bathroom.

    1. umami*

      This makes me laugh because when I was a teenager, I would go to the bathroom after dinner, and my mom ALWAYS thought I was trying to get out of helping to clear the table or do the dishes. But I wasn’t! I really needed to go to the bathroom! I’m sure she still to this day believes that to be the case lol. I would hate to think that if I go to the bathroom after a meal in a restaurant it’s presumed that I am avoiding the bill.

      1. Minerva*

        I would assume the timing was innocent if it wasn’t followed by “thanks for lunch” the moment she came back. There was no offer to pay.

        Her scheduling the lunch + bathroom when the bill was presented + “thanks for lunch” instead “what do I owe” screams to me that this was intentional.

        1. Parakeet*

          But if she thought, for whatever reason, that the employer was paying, why would she say “What do I owe?” instead of “Thanks for lunch”?

          1. Minerva*

            Why did she assume the employer was paying?

            *She* scheduled the lunch then assumed her employer would pay. That is the crux of the issue.

            If I scheduled a lunch with my boss I would not in a million years *assume* my boss would pay. It would be very nice if they did, but the assumption is what gets me.

    2. Peanut Hamper*

      It’s not uncommon for people to use the restroom after they are done eating in a restaurant. Sometimes you just need to wash your hands.

      It’s pretty cruel to this employee to suggest that they had nefariously planned all of this to bilk their employer out of five dollars.

  27. LTR FTW*

    Re: letter 1 — brings me back to my first job after college. The first day, three of us were starting and our boss took us out to lunch. I was *pretty* sure the boss was supposed to pick up the tab for this, but just to be safe I only ordered something I could afford to pay for with the cash I had on hand. (This was the absolute cheapest appetizer on the menu and a glass of water, because I was flat broke!!!) Well, this was the first time my boss had reports and she didn’t know to pay for us, so I wound up paying for myself with my last few dollars and then walking home from work because I didn’t have bus fare. I’ve always looked back on this as my *boss’s* gaffe and not my greedy expectations!!!

    30 years later and I’m still pretty sure the boss is supposed to pay when we go to an official work lunch. I always pay for my team when I’m the most senior person.

    1. kiki*

      That was definitely your boss’s gaffe!! I think what makes it different in this LW’s situation, though, is that Jane is suggesting outings. If the suggestions were coming from LW, I would 100% believe LW should be paying since they’re the boss.

    2. Allonge*

      Yes, this is on your boss – either to pay or at least to clarify in advance that everyone will be paying for themselves.

      Nobody here is saying that expecting a manager to cover lunch is outrageous, it’s just that there are specific situations where that is a reasonable expectation (and as you have learnt, even then it can go wrong because sometimes bosses are clueless).

      For me the overall point is that if you are in doubt about the payment arrangements, it’s best to ask.

      1. Angstrom*

        Yeah, it shouldn’t be a big deal to ask “Is the company buying today?” or if you’re the manager, to say “The company’s buying today” or “I’d be happy to grab lunch together, but it’s not a work function.”

  28. your friendly airline hater*

    Quick tip for OP 3: if you know the plane prices are going up because you’re checking them regularly, check in incognito mode! There are rumors that some airlines work with Google to artificially inflate costs for people who look repeatedly because they want to scare you into making a quick purchase. I’ve seen it happen before where after my mom has Googled a flight about a dozen times it’s significantly cheaper in incognito mode. Of course that’s anecdotal evidence, the prices also might just be going up, but it’s worth a shot.

  29. HonorBox*

    LW4- We had someone who was signed up for a leadership program for which work paid the bill. They left the organization suddenly. The bill had already been paid and it was far enough in that we couldn’t just swap someone into that spot, so we told the departing employee that they were welcome to continue to participate, but they just needed to clarify that they were not representing our organization any longer.

    Like your situation, the cost for the program wasn’t THAT much, so our organization eating the cost was not a make or break situation. If it was a longer term situation where we were reimbursing tuition or a program was a multi-year deal, it might change the equation. I’d check your handbook, but wouldn’t worry too much about it if there’s nothing explicit in there.

    1. LW4*

      Thank you! Your situation is probably most like mine. The program costs $500. Which I certainly don’t want to pay out of pocket but could if I had to, but it also feels noticeable but not extravagant even for a smaller non-profit. Potatoes you can feel but small ones.

  30. Bunny Girl*

    #2 reminds me of the speaker who came to my high school health class to talk about drugs, and started his speech off with “I’m not going to lie, I had a lot of fun when I was on drugs.” The look on both of our extremely conservative teacher’s faces was just **chef’s kiss**

    1. Eldritch Office Worker*

      It reminds me of the DARE presentation where they explained how an orgasm was the peak natural pleasure a brain could experience and cocaine went like 3x over that threshold. Like…I never did cocaine but I thought about it really hard after that.

      1. Bunny Girl*

        Wow my teacher wouldn’t even say the word “orgasm.” Abstinence only and you weren’t supposed to enjoy it when it did happen.

    2. Generic Name*

      Hilarious. Was it DARE? I read somewhere that DARE was a giant failure. I remember a police officer coming to our classroom with a bunch of pills and baggies glued to a giant board, and he proceeded to identify each one and tell it what it was (and possible what it did?). I’ve were all like 10. I remember wondering why they were telling us all that.

      1. Bunny Girl*

        It wasn’t DARE it was just through our health class. We did have DARE in middle school but I immediately discounted everything she said when my friend and I passed the speakers vehicle in the parking lot and she was in there chain smoking.

      2. Eldritch Office Worker*

        I read somewhere about a DARE officer who passed around two joints for people to look at and was sternly like “I better get these both back” and when he got the tray or whatever back there were three joints.

      3. Silver Robin*

        DARE was a failure, but an interesting one! Learned about it in a project design course for grad school. Interesting because all the participants had positive experiences – the teachers, the police officers, the parents, and even the students generally quite enjoyed it and gave positive feedback. But, it did not actually reduce drug use (explaining what the drugs do and how to identify them does not actually scare kids straight, it helps them decide which ones they want because, impulse control etc.)

        The program has been adjusted and now focuses on peer pressure, sticking up to bullies, making your own choices, and navigating interpersonal dynamics. Turns out drug use is a social thing influenced by social dynamics, who would have thought? (sarcasm). The newer program focus does actually help reduce drug use.

    3. Hiring Mgr*

      I may be a bit older, when I was a kid we had David Toma (former undercover cop who the TV show Baretta was based on). come speak to us. It was pretty “real” in that same way – kind of a “scared straight” type presentation based on his experiences

      1. Francie Foxglove*

        Toma…We had him too, but he lost a lot of us when he started telling how Satan possessed people and made them sacrifice animals and cut their own faces off. The real problem at our school was gangs. He didn’t say a thing about that.

    4. Irish Teacher*

      We had a speaker at our 6th year (much the equivalent of 12th grade) retreat who a) started by saying he was sure we were all wondering why he’d move to Ireland from California (like yeah, just begin by implying an insult to our country), b) boasted about all the celebrities he knew in California and when asked “like who?” struggled to name any, c) said something along the lines of how we were probably thinking he had great fun drinking and doing drugs and was now telling us not to, d) claimed to have taken so many drugs that…it sounded extremely improbable and e) informed us he didn’t “believe in social drinking,” that that was just an excuse to get drunk (as if nobody could ever drink responsibly).

      The next day, our teacher asked our advice about the following year’s retreat and the general consensus was “do not ask that idiot back!”

      But yeah, among other things, he was telling us “don’t drink or do drugs. There is no such thing as a social drinker. Anybody who drinks at all is getting irresponsibly drunk” while boasting about how much drugs he’d taken.

    5. Lydia*

      I was a very young college student in the age of DARE, but never experienced it myself. My time in elementary school was pre-DARE and my time in high school was overseas. Anyway, I had my Psych 101 class where the professor stated to everyone, “If drugs were as bad as they say they are, nobody would ever do them again. That’s a lie. Drugs feel great. That’s why people do them.” He then went on to explain why those good feelings have a downside and how it affected the brain. I paid attention to that!

  31. Samwise*

    Universities, especially public universities, may list their salaries as “weird” exact numbers because that’s the mandated pay range for the position. (For instance, the monthly salary for a $50K/year is $4167)

    If you are offered the job, ask about what benefits are or can be offered as a pre-tax deduction, as that can make a difference for you. For instance, my retirement contributions are pre-tax, as are health insurance premiums and parking.

  32. Observer*

    #2 – Unprofessional partner

    An additional thought. Please start looking for a different organization to partner with. Unless their response to your information is perfect you absolutely do not want to depend on them to any extent. And even if they do respond perfectly, you should find backup.

    I’m a bit concerned with how his supervisor handled his failure to show up to a session. By itself that would not be the end of the world, but given the rest of what you say, I have to wonder if there is some level of mismanagement here.

  33. CPA Spouse*

    As a manager, I would never go out to a meal with my employee(s) and not expect to pay. If I wasn’t in a position to do so, and they were the ones who scheduled the outing, I would decline the invitation. Was Jane presumptuous? Yes. But the way LW1 reacted caused a really awkward situation.

    PS: As a spouse of someone who owns their own CPA firm – having the boss buy lunch / snacks / ice cream throughout tax season can go a long way for morale. Tax season is brutal. Lunch / snacks / ice cream for staff is a great budget line to have.

    1. umami*

      Same, I always pick up the tab for my staff, even if they make the suggestion (really, we are talking about ice cream and tacos). But I get that YMMV and not everyone (like LW) thinks that way. I would feel bad about making Jane feel bad, though; if she came back and saw money already in the bill holder, it’s not weird to presume the entire bill had been covered.

    2. Pink Candyfloss*

      I’ve never worked for a manager that didn’t pick up the tab whenever we all went out to eat together. It is the expectation in my industry.

      It was a bit weird in this case since the employee was the one who did the inviting – which I totally understand the manager’s confusion. Hopefully a lighthearted conversation will clear the air.

    3. Adele*

      I agree with you, although I get that this could vary by field. My boss (law firm partner, so also owner) told me plainly when I first started and tried to pay for myself at a casual lunch out that he would never let his employees pay when out with him. Clear communication is your friend here. I most definitely take advantage of this and invite him to lunch that he’s going to pay for–and he’s happy to accept the invitation, because I make him way more money than a lunch costs and keeping me happy with a little perk is worth it to him.

  34. Interview Coming Up*

    Regarding letter #1, maybe you’re not paying her enough if she’s that excited about a free meal.

    1. Eldritch Office Worker*

      There’s nothing in the letter to suggest that, and it’s unkind to the letter writer.

      Have you ever seen people around free food? They turn feral, even if they have no financial constraints. There are plenty of letters around that.

      I’m not calling this girl feral, but free meals warp the judgment of otherwise reasonable people.

      1. Interview Coming Up*

        I meant that to be a question instead of a statement (and an honest question!). So that was a typo to not have it be a question mark. I don’t know if it’s uncharitable… I think it’s good to be aware of power dynamics with restaurant bills as well as economic differences.

        I’m in an incredibly underpaid field and although I’m always excited about free food, I did read a bit of trickery/moxie into the employee’s actions and I could only see myself being that bold if pushed to. I realize that some people are just that bold in general.

      2. Interview Coming Up*

        Yeah I did not mean for that to come out sounding so accusatory and stark.

    2. Colette*

      I’ve spent years in high tech where everyone was very well paid, and there was still a rush for free food in the break room.

    3. Lydia*

      OP did follow up that Jane is paid pretty well, and more than the OP and her husband are right now since the business is new. That doesn’t mean it’s enough, but I think this is a case of Jane making some assumptions rather than not getting enough food because she can’t afford it.

    4. Courageous cat*

      This is a weird/unnecessary conclusion to jump to. There’s nothing suggesting that. Like Eldritch said, some people just go nuts over free meals.

  35. Sitcom Writer*

    I just finished up a year-long leadership program last year where a few people changed jobs partway through! It really depended on the company on how it was handled. A couple had to drop out because the original company paid for it and did not want them to continue on their dime, but they did not have to pay it back. I think one had to drop out and pay it back, and two paid for it themselves and stayed in the program. I changed jobs about three months after graduation, and I was not expected to pay it back (my bosses seemed to mostly forget I was in the program at all).

  36. Nonprofit4*

    I used to have a boss at a large and well-resourced nonprofit who would schedule mandatory team meetings during lunch hour at a restaurant, then make us pay for our own meals. One time she was running late and asked me to order (and pay at the counter) for her, then declined my reimbursement form later that week. It was a really crappy thing to do and has stuck with me for years.

    1. Cheesesteak in Paradise*

      That shouldn’t even need a reimbursement form! That should be, “Boss, your meal was $16.75” (with hand outstretched).

      1. riverofmolecules*

        Yeah, the reimbursement form is suspicious to me. If a reimbursement form is involved, that suggests to me that the lower-level staff were paying for their own lunches but the manager’s lunch was being paid for by the organization? Did the boss normally get their personal lunch reimbursed?

  37. Gemstones*

    LW #3 sounds like they haven’t even bought the plane tickets yet…is the vacation really planned/set in stone? Couldn’t they just postpone it? Like, it would be one thing if they already had the tickets, but if nothing is in stone yet, it seems weird to be so wedded to it.

  38. Pink Candyfloss*

    LW #5 you lost me at $900 for 60 hours (pre-tax, good lord). I hope that you just made up those numbers and that’s not a real expectation!

  39. Immortal for a limited time*

    I second the comments of others about non-round numbers being totally normal and not due to any weird bureaucracy. Pay adjustments are often percentage-based and the organization might express the pay range as a total annual amount or a monthly amount in the job posting, or even an hourly amount. For payroll purposes, the annual pay has to be divided by the number of pay periods in the year, which might be 12 or 24 or 26 or 52, or whatever your organization does. I am salaried, but my pay is also reflected in our payroll system as an hourly amount, which is also not a round number (sorry). It might have several decimal points (e.g., 38.33417 per hour, or something odd like that) simply due to dividing the annual amount by 2,080 hours, then multiplying it by the number of pay periods. It’s just math! It’s not a conspiracy to confuse applicants.

  40. Jennie*

    Okay, I’m not gonna lie, I’m perpetually scared of being Jane from L1. Obviously I do not invite my bosses out to lunch and then expect them to pay. But I have been in situations where someone in management way above me invites me to a coffee or a lunch, then they start putting their card down, and I’m never sure whether I should be offering to pay my share or whether it’s obvious that they will pay it because they’re management??

    1. CPA Spouse*

      If someone higher up than you invites you to coffee, lunch, etc. then I absolutely would assume they were paying. Let them pay and give a hearty “thank you!” The weirdness from LW1 came from Jane scheduling the outings and then expecting her bosses to pay.

    2. Minerva*

      If you’re unsure just offer to pay and let them say “oh no I’ve got it”

      When the situation is unclear offering to pay is never rude.

      1. Heidi*

        Yes to this. You could say, “Should we split the check?” or “How much do I owe?” or “Can I venmo you my share?” Then they get to say, “Oh no, I’ll take care of this.” Or they’ll let you look at the receipt and figure it out.

  41. Rebecca*

    The first letter is a cringe situation no matter how it’s handled, but I can tell you that if someone told me “We’ve covered some treats lately but we can’t do that as a regular thing” I would quite simply die of mortification, especially since “treats” implies that this grown adult is asking for a trip to the candy store. Yes, Jane should always assume she will be responsible for her own tab, but I think next time, just decline the Taco Tuesday invite.

    1. MicroManagered*

      This is a situation where some cringe/embarrassment is completely appropriate and warranted. Jane SHOULD feel weird about needing to be told she can’t schedule lunches and ice cream runs herself and expect her employer to pay for it (especially as the only employee? wth). Sometimes a little embarrassment is an important social tool.

    2. I should really pick a name*

      A bit of mortification isn’t the worst thing in the world. I don’t think you can get through life without it happening occasionally. No reason never to have taco tuesday again now that the situation has been clarified.

  42. Sad CPA*

    OP1 – Companies expensing meals is industry standard during tax busy seasons – since individuals are working 12 hour days for 2-3 months it’s seen as a way to keep them in the office, healthy, and (reasonably) happy. Given the industry, I think you are off base here.

    Even in my tax role before COVID I would expect daily meals from my firm during busy season. Post COVID this expectation has increased significantly – I now would be surprised if I didn’t get a meal everytime I go to the office. 17% of CPAs quit during COVID and retaining them is even more difficult now. I chatted with my peers about this letter and those who switched firms a few months ago noted they have always had coffee and lunch for them when they work in office.

    I think is becoming an industry norm in tax that you may need to begin budgeting for. if you have enough work to ask your employee for 60+ hour weeks, you have enough money to feed them as well.

    1. Sad CPA*

      they have always had coffee and lunch *bought for them when they work in office.

    2. Lydia*

      Jane is not working that many hours. OP clarified that Jane works a normal 8 hr day while she and her husband work 12 to 14 hours during tax season.

      1. Sad CPA*

        It is still standard in the industry – admins who work 40 hour weeks get taken care of as well (regardless of role or seniority, tax season is stressful). I can’t speak to other work environments, but in tax it is not appropriate to not pay for your employees lunches during busy season.

  43. Tech writer*

    In regards to question 5: That’s fascinating. I didn’t know that about university salary numbers being weirdly specific. But I would also assume that it would be hard to predict a salary post-tax in the United States because don’t health insurance premiums and 401ks get taken out pre-taxed? So you wouldn’t know which of the 3 health insurance plans the employee would pick and you wouldn’t know what percent they want taken out of their 401k, if any?

  44. Nancy Drew*

    LW3: Why not book refundable fares? I know sometimes that can add to the cost a bit, but it’s possible to book refundable fares while they’re low and get the money back if you need to cancel the flights.

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