how do I get my rich boss to pay me back for lunch?

A reader writes:

I work in a small office (about five people) and probably once or twice a week, we will do a group order of delivery/take-out for lunch. I’m the most junior at the company, and often I end up asked to place the lunch order, so I put it on my personal card and have everyone pay me back. All of my other colleagues are quick to ask how much they owe and reimburse me, but on the occasions where my CEO joins the lunch order, he has never paid for his food or even offered to do so. I honestly don’t think it crosses his mind to wonder who paid for the meal, and I have a sneaking suspicion it’s often because my other colleagues simply pay for him. (I have another sneaking suspicion it’s because he’s a white man who has had a great deal of wealth his entire life.)

After the meal there’s always a conversation, initiated by my colleagues, in which everyone ask me how much they owe. We are in an open office space with our CEO, but he seems to be entirely oblivious to these conversations. I would love to be able to simply Venmo charge him, but alas he has made it clear that he is “anti-Venmo” (what?).

I’m feeling very bitter that he is in a position where he doesn’t have to think about the cost of a $14 salad, and frustrated that my other (wealthier) colleagues are all willing to eat the cost to avoid asking him to pay. He knows how much I make, but how do I gracefully make it clear that he should be expected to reimburse me like everyone else (and ideally, should do so without being prompted)?

You can read my answer to this letter at New York Magazine today. Head over there to read it.

{ 266 comments… read them below }

  1. HugsAreNotTolerated*

    Honestly the CEO probably thinks you’ve been putting the lunches on a company card, or expensing them. I’ve found that once someone reaches a certain level within an organization they kinda just.. forget about stuff like that. If he’s been C-suite for a while, he’s probably used to an assistant who has his card information ordering his lunch and assumes you’re doing something similar. If you’re not comfortable approaching him, maybe go to his Administrative Assistant. They’ve usually got a good rapport with the executive and can help guide you how to best handle this type of thing.

    1. That would be a good band name*

      I was going to suggest going to his admin as well. Or just double checking with another coworker that has handled the ordering and find out what they’ve done. I wouldn’t assume that your coworkers are buying the CEO’s lunch. It’s much more likely that they already know that you should be getting the boss’s corporate card or getting reimbursed from petty cash or something else but forgot to pass that info along. I’ve found that once “everyone knows that’s how that works” they forget that it isn’t knowledge that magically appears in the new person’s brain.

      1. designbot*

        Agreed. Also if he had an admin assistant, why wouldn’t they be the ones ordering lunch in the first place?

        1. SS Express*

          If the CEO has his own assistant, who works specifically for him and not as a general admin support person for the entire team, that person wouldn’t necessarily coordinate lunch orders for everyone.

      2. Derjungerludendorff*

        But if the company is that small, it can also be easier to raise the issue. Since presumably they know the CEO personally.

    2. Veronica Mars*

      Yes, this. I recently started working with execs more and am learning that 90% of what I attributed to assholiness is actually just them being completely out of touch. Not that that’s an excuse, but generally when people are brave enough to point it out to them, they’re surprised/shocked/mortified and take immediate steps to fix it.
      I’ve actually started to view it as part of my job to be the person who is brave enough to just be candid with them.

      P.S. I’m a millennial and I can’t handle Venmo. I dunno, I’m fine with most social media and I’m good at PayPal but Venmo is too cool for me.

      1. TiffIf*

        I’m a millennial and I never used Venmo until my new landlord (who is 60+) let me know I could pay rent via Venmo instead of mailing a check.

        1. Diahann Carroll*

          Ha! My 60+ year old therapist hipped me to Venmo since I usually get my EOBs from my insurance company after our sessions long after said session took place – I was walking my payments over to her office during lunch breaks or mailing it, but she was like, “No, just Venmo me – it’s easier” and she was right.

          1. Quill*

            I try to avoid using it because I’m not that convinced that any app is secure in using my banking information, especially if people are using it on their phones!

            (That and it’s yet another piece of financial paperwork to keep track of, I have enough of those.)

            1. Lauren*

              Also, don’t ever say ‘cuba’ or ‘syria’ as a message for payment. They lock it and takes 1-2 weeks to get it unlocked. $100 took $200 to send money to my hiker bf while he was on the CDT in Cuba, NEW MEXICO.

      2. These Old Wings*

        I’m also a millennial who doesn’t use Venmo. I actually tried to set up an account recently, but apparently if you have a joint checking account, only one person can have a Venmo account and since my husband already had one, he just sends money.

        1. AGirlHasNoScreenName*

          Yup, same issue for me. I just feel weird having to ask my husband to send money on my behalf to people he’s not likely to meet. So I always hope for another e-payment option since I don’t carry cash, either.

            1. Barefoot Librarian*

              I second Square Cash. I’ve been using it for years and haven’t had any issues.

      3. I Wrote This in the Bathroom*

        I’m on the older end of Gen X and I love Venmo. But I admit that I first learned about it from my younger-millennial younger son. Most people in my age group have no idea what it is. Whenever I want to settle up with someone my age and tell them I have Venmo, I get this look like “that’s too much information, I don’t care what weird thing you have”. Paypal is very popular though. I have also heard of security concerns with Venmo (which I have not yet researched and haven’t had issues with it myself).

      4. GothicBee*

        Also a millennial, and I refuse to use Venmo purely because one time when my credit card info was stolen, Venmo was one of the charges. Which is probably a dumb reason and has nothing to do with Venmo directly, but I still won’t bother using it.

        1. Diahann Carroll*

          No, that’s a pretty valid reason IMO. I wouldn’t use it again after something like that if it happened to me either.

          1. AnonEmu*

            Yeah fair, that’s the same reason I don’t use Lyft anymore (they were the source of said leak, but customer service were utter jerks about it and I wound up having to cancel said card and it took ages to fix)

    3. kittymommy*

      Same. I had a boss like this and he was very wealthy and it really didn’t occur to repay because in his personal life most of his bills got sent to his personal banker/accountant and was paid that way (still his money though) so for business he just thought their was an expense account. He was mortified when told otherwise.

    4. putt putt*

      There are only five people in the office and OP is the most junior. It sounds like OP is the admin (or at least takes on the admin responsibilities).

    5. Enginear*

      This. I would bring it up to the boss that “hey, I’ve been putting all these lunch expenses on my personal credit card and been asking everyone to send me their portion. Whenever you get a chance, you can send me your portion via paypal/venmo/zelle. Maybe I could get a company credit card to eliminate this hassle?”

      1. Diahann Carroll*

        Yes – the company CC is a good request, and really, they should have one since there are only five people in the office they’d have to worry about. It’s just much easier than having to worry about reimbursing people directly.

        1. TechWorker*

          The company isn’t currently paying for the lunches though, so putting it on a company credit card doesn’t solve the problem of getting people to pay up. It just makes it the companies debt (which is likely better than the current situation but CEO may not see it that way).

      2. Lauren*

        You prob won’t get a CC, but this script should work and it eliminates CEO from having to pay anyone back and forces everyone to pay him.

        – I can’t afford to keep using my debit card (i’m paycheck to paycheck), and that I just can’t keep giving Vemno a 1% fee for immediate access to that money. Can i grab a card putting lunch orders on your card moving forward?

        1. Lauren*

          OOOOOO – Send an email with the break down.

          Lunch is here! I fronted the money today, here is the breakdown of what everyone owes.

          Sansa – $11
          Arya – $14
          CEO – $728 (you owe for the last 5 months)
          Rob – $17
          Theon – $13
          Bran – $32 (you still owe me from last week)

      3. T2*

        I had this come up when I was younger. The solution was to say “ ok. What card do you want me to put this on since I don’t have a company card.”

        And if they say my personal card, Well. I forgot my wallet that day.

    6. Just Another Manic Millie*

      “Honestly the CEO probably thinks you’ve been putting the lunches on a company card, or expensing them.” Not necessarily. I’m reminded of one of my previous companies, when it was Wakeen’s responsibility to run errands, including picking up breakfast for Fergus, the company’s owner. Quite often, Fergus would say, “Wakeen, I know I told you to get me a roll, but I changed my mind. Take this back and tell them to give me a muffin instead.” And he wouldn’t give Wakeen the money for a muffin. He acted as if the deli would be glad to take the partially-eaten roll back and hand over a muffin without asking for extra money. So Wakeen had to pay for Fergus’ muffin out of his own pocket. Don’t tell me that Fergus thought that Wakeen was using a company card. There was no company card!

      In case you’re wondering why Wakeen put up with this, it was because he was afraid of getting fired if he refused. And he was afraid that if a future company should call Fergus, Fergus would say, “Wakeen knew that it was his job to run errands. But when I asked him to get me a muffin, he refused.” (This was back in the day when bosses weren’t afraid to tell companies that they fired people, and they weren’t afraid to include the reasons, and if they didn’t give the whole story, well, the potential hirers didn’t care.

      Alison said, “It’s incredibly unlikely that your boss will flagrantly refuse to pay once it registers for him that you’ve been buying his lunch with your own personal money.” I disagree with her as to how unlikely such behavior is.

    7. AnonOffice*

      You say “I can’t afford to pay for lunches” and ask everyone to prepay. Just say it casually. Or stop going out altogether. This is insane.

  2. Annie Porter*

    I couldn’t agree more with Alison’s advice, although I do think there are people who try to get away with not paying for food by banking on it being uncomfortable to ask for reimbursement. It’s insanely obvious that when food is ordered, a cost is involved. Anyone who doesn’t ask what’s owed or pay up knows darn well that they are eating food they didn’t pay for.

    The only acceptable explanation here, IMO, is if the CEO assumes stuff is being ordered on a company card (and since it’s a small org, this even sounds unlikely. Doesn’t he review the credit card statements and notice that there’s no Jim’s Steakout charge, ever?)

    1. CmdrShepard4ever*

      Darn you Annie Porter, I have not had Jim’s since I moved out of the area 5 years ago and had forgotten about. Now you reminded me and I miss it!!!!

        1. ThatMarketingChick*

          Now that I’m thinking about it, I don’t think I’ve ever had a CFS when I’ve been sober. It was always a 4:30 AM post-bar stop.

    2. sunny-dee*

      Why would the CEO review the credit card statements? That would normally be the bookkeepers job (and they probably have a bookkeeper, even if it’s outsourced). I would assume that it was going through some kind of company payment (credit card, account, petty cash) or that the employee was asking for reimbursement.

      1. Diahann Carroll*

        Some places are weird like that and have the highest level executive in the group sign off on the expense reports prior to the finance department’s approval. I worked at an insurance company that had our division SVPs and sometimes division president(s) reviewing and approving expense reports before they went to accounting/finance for final approval and reimbursement.

        1. TechWorker*

          In a company of 5 I wouldn’t find it at all weird if the CEO approved expenses, here it’s the managers job no matter how senior. (Eg senior directors approve directors expenses, etc).

      2. cacwgrl*

        I managed HR for a decently sized company doing business in 10+ states with 300 people on the books. CEO allowed 6 company cards and monitored the statements every. single. month. He saw them after accounting first looked at them, assigned cost codes and reconciled most receipts. He would not sign the check (lord I hope they’ve finally gone paperless!) until he had everything reconciled to his satisfaction. Every Single Month.

  3. Kristine*

    CEOs are crazy busy and probably not grasping all the details since they don’t manage the day-to-day minutiae. Explain you’ve been putting lunches on your card but cannot do it anymore. Probably, being a CEO, he will appreciate your initiative if you approach the conversation respectfully and frame it in terms of your problem-solving abilities.

    1. valentine*

      He said he’s anti-Venmo and it would be extremely odd if he’s able to completely tune out every single repayment discussion.

      I hope OP will stop paying for everyone.

  4. Cookie Captain*

    I don’t think there are many situations where sending someone a Venmo charge instead of talking to them at least once is a good idea. I could be a 20-something Venmo enthusiast (I’m not) and I would still find that incredibly rude.

      1. HugsAreNotTolerated*

        Frequent vemno user in 30s here; it’s totally fine to send a pay request to a friend if you’re splitting bills or had a shared dinner and they said “oh I’ll venmo you my part” and forgot to send within a day or two. But sending a request out of the blue weeks or months after the fact? Nope, not okay!

        1. Mary Richards*

          Agreed, as a 20-something Venmo lover, but I’d always say something first! I think we’re saying the same thing in different ways. :)

    1. Washi*

      I could see announcing to the group when you place the order “ok order is placed, I just venmo charged each of you for your stuff, thanks!” which might be what the OP meant. I would actually appreciate a Venmo charge, since it would mean I didn’t even have to remember about paying what I owed.

    2. 1234*

      If my roommate forgets to pay me for the internet bill (in my name), I will send a Venmo charge without saying “you haven’t paid me yet” but that’s because we’ve established that we will Venmo the other person what’s owed.

    3. Tzeitel*

      Agree. I once got a venmo request for a charge and the comment was that it was for a drink an aquaintance bought me at a party. I thought that they were offering to buy me the drink, not giving me a loan! There was no discussion about it at all. I thought that was bizarre behavior. If there was a text like “hey, I spotted you for that drink, do you mind Venmoing me?” I probably would have complied (even though it’s strange to charge someone after offering to buy them a drink…).

  5. Mary Richards*

    Have you considered asking one or more of your colleagues what they do? I get that you suspect that they’re paying for him, but is it possible that they aren’t and they know something you don’t about how to get the money? Just a thought!

    1. Duvie*

      Good advice! They may have a process you haven’t heard about. Even if they laugh and tell you “Good Luck”, you’ll still have more information than you do now.

      1. Jen S. 2.0*

        And if they do laugh and say good luck, then you know to start getting the money upfront instead of expecting reimbursement.

  6. Trek*

    I would pop into his office and say you are collecting on outstanding lunch tabs, have a list like you are collecting from a few people. Then provide him his total. Hopefully he will pay out or will state I will pay you on x date and then you just need to follow up on that date and ask for your money. Of course the obvious question is what’s next if he won’t pay or acts like he will be never does which makes it even more difficult.
    In our office people sign up for group lunch and pay when they order so no one has to be out the money. You may want to consider doing that as well. Of course you could ‘forget’ to include CEO with the lunch order a few times but that depends on your office and how he will react.

    1. Jdc*

      Ya I’m wondering why you don’t just ask. I can almost guarantee he’d pay you right then. Or what my old boss did, just hand me $100 for the week and he was kind enough to have that include my lunch too since i was doing the work.

      1. JimmyJab*

        Because LW is the most junior person there and its stressful and scary to ask someone that senior for money, even if its owed to you?

          1. Derjungerludendorff*

            How people feel isn’t up for debate, and acting dismissive about it isn’t helping anyone.
            There is a real power difference in this situation, and most people rightfully take that into account. Emotionally or otherwise.

            1. Play A Doctor On TV*

              I mean, it basically up to the person whether they feel so uncomfortable that they would rather take the financial hardship than speak up. But it’s not like there’s some magical third option out there…either OP takes the tiny risk that the request will anger the CEO or they don’t.

        1. fhqwhgads*

          I surmise the part that gives them pause is the open office and the conspicuous discussions with everyone else repaying what they owe for lunch, unprompted, plus the power differential. To the OP, it seems like it should be obvious to the CEO what is going on because it’s going on outloud with everyone else every time. That doesn’t mean OP shouldn’t be direct and just ask as Alison indicated – but I can see how given the way it’s gone, OP has concerns that the boss might not be reasonable, because from their perspective it seems like there must be some reason why among all this obvious repayment, CEO did not participate. I do think obliviousness is a probable reason, but it makes sense to me OP had the concerns in the first place that it might go sideways.

    2. putt putt*

      The tricky part is that this has been going on for a while without OP asking for money. If OP suddenly starts asking for money when it hasn’t been done before, it could come off as a bit awkward. I think OP has to directly acknowledge the fact that the boss hasn’t been paying. It doesn’t need to be a big deal, just something like, “I won’t be able to pay for lunch on my personal card anymore. How do you want to handle this?”

  7. Rainbow Roses*

    This is the reason I refuse to be the “lunch lady” at work unless it’s part of my job description. Too complicated. I don’t order other people’s lunches and I don’t ask other people to order for me.

    As for your situation, I agree you should speak up. The boss is probably just clueless. If he refuse to pay up after being clued in (and I also mean paying back what he owes you so far), then stop including him for lunch or ask him to pony up before placing the order.

    1. Annie Porter*

      Amen to this. I went vegan, and any and all office food issues were immediately sorted, if anyone wants an “easy out” :)

    2. Kristine*

      Probably best to avoid the “lunch lady” role altogether, yes. Or, at least collaborate with one other employee. These things dovetail into drama pretty quickly, even with the best of intentions.

    3. WellRed*

      Yes, it’s one thing to occasionally decide to all call out for lunch, but don’t make it part of your regular duties just b/c you are the most junior. It won’t help your career.

      1. Kat in VA*

        Depends on her career. I’m an EA and catering/lunches are absolutely part of my regular duties.

    4. JayNay*

      this is great advice. Be busy next time people are collecting lunch orders, or say “ah, can’t today, can somebody else take care of it?”
      This whole situation reminds me of other questions we’ve discussed here on AAM about the power dynamics of who gets asked to do coffee runs and lunch orders for the whole office.
      I find it offputting to unload this on a junior team member.
      If being “too busy” for lunch duty doesn’t solve the issue, i would bring it up with your team lead. It could be along the lines of “I like our lunches together, it’s just that I noticed I get asked to handle the organizing of orders a lot of the time. It’s more frequently than others, for example three times just last week. Can we spread this out more evenly? I want to contribute to the team in other ways and not become the designated lunch person.”

      1. CmdrShepard4ever*

        But often times certain people’s time is more valuable than the time of a junior team member. It does not make sense for the CEO at a pay rate of $400 an hr or a Senior teapot maker at $200 an hour to spend an 30-60 mins ordering lunch when it could be done by an entry teapot analyst at $50 an hr. If there are 5 entry teapot analysts and 1 of them specifically is asked to order lunch more often than the other 4 entry teapot analyst then yes they should speak up. But it might not make sense to say every single person should take a turn ordering lunch.

        1. Massmatt*

          I agree with this overall, junior employees should naturally do more junior tasks, but these should not fall on someone by gender, which is often the case.

          And in this case we have the person making the least buying the lunch of the person making the most, which is terrible.

        2. Burned Out Supervisor*

          Meh, unless lunch is required for a work meeting, I still think it’s crappy to make the junior staff order it all the time. If eating out for lunch isn’t mandatory, then ordering it should rotate.

          1. Diahann Carroll*

            This. My last job was very big on group lunch orders for no particular reason other than x amount of people wanted the really good Mexican food that day, so our CRM manager would send out an email to everyone asking if they wanted to join in on the order and, if so, send her an email with your food choice and she’d collect payment before going to pick up the food. If she didn’t have time to do it, or if other coworkers decided they wanted to eat something else and wanted to know if anyone else was interested, they would send it out – it wasn’t done by seniority or who’s title/job grade was higher. That made it fairer.

        3. TechWorker*

          Does a lunch order for 5 people really take 30-60minutes..? (Not that it makes much difference, but like that’s more ‘family takeaway’ sized than ‘massive event’)

          1. CmdrShepard4ever*

            I think it can depend on what kind of ordering it is. If it involves walking around getting everyone’s order calling it in, walking to pick it up and coming back it could take that long. But even 15 mins of the CEO’s time is still more valuable than a junior teapot analysts time.

        4. Derjungerludendorff*

          They should probably do it every now and then, even if it’s just for team morale. And especially if they’re not actually busier than the junior employees at that moment.

          Always pushing the fussy menial work off on people below you just isn’t a good look, especially if they have to take on a financial burden.

        5. Seeking Second Childhood*

          Sounds to me like the junior person was doing this on their LUNCH BREAK so pay scale wasn’t relevant.
          Yet another re-run letter where I wish there were an update.

        6. GothicBee*

          I don’t have a problem with the junior person doing the ordering, but I don’t see why they can’t say, “I’m not able to put the entire order on my personal card, what should I do?” and leave it at that. It’s really not reasonable to expect the person making the least amount of money to front the expense for everyone’s meals, even if it’s a fairly immediate reimbursement. That’s what I’d do in that scenario.

          1. Diahann Carroll*

            It’s really not reasonable to expect the person making the least amount of money to front the expense for everyone’s meals

            This is the crux of the issue for me.

    5. Washi*

      Agree. I hate it so much that at my last job, I kept snacks in my desk so even if I forgot my packed lunch, I didn’t need to order out. (For me it was less the money and more keeping track of “I want tuna salad but with peppers instead of tuna and if they’re out of peppers then I want avocado and greens, but only if there’s arugula, not spinach, and if they’re out of that, my second choice is…”) Some offices have a super ingrained culture of ordering for everyone if you order out, and in those cases, I choose to save my political capital and just bring my own lunch.

      1. AndersonDarling*

        I HATED doing the lunch ordering. “Make sure they don’t add mayo!” or the “Tell them they cut my sandwich diagonally last time and I want it cut straight!” not to mention if an order isn’t correct and it’s my fault because didn’t check all 10 sandwiches.
        And then they all want fountain sodas! How am I supposed to carry all those sodas! UGH! So very, truly, happy that I don’t have to do that anymore. And when someone does a lunch run for me, I make sure to place a simple, easy to bag and carry order.

    6. CmdrShepard4ever*

      For OP and anyone else located in a major metro area there is a great app called “ritual” that allows everyone to pay for and place their individual order from their account and then have just one or two people go pick it up. We have used it and it is great. Everyone places their own individual order (can’t blame anyone for messing it up) under their name, and pays from their account with their individual card no need to hound people for payment afterwards. It also allows for “online ordering” for smaller local restaurants that might not have their own website. You also earn reward points for ordering and for picking things up for people that you can use as discounts towards future purchases.

      P.S. I am not a paid spokesperson just a fan.

      1. Caramel & Cheddar*

        Seconding Ritual. I use it so frequently that one of their people once took me for coffee to bounce ideas off me as a frequent user; the “let one person pick up everyone’s order” thing was one of the ideas!

      2. CB*

        Seconding some type of group ordering! Many popular chain restaurants (like Chipotle) are also starting to roll out similar features where each person picks their meal and pays for it, and then it’s all packaged together for one person to pickup.

        Alternatively, I have a close friend who is a junior assistant to the CEO of a large arts organization. They don’t have corporate cards, so she has the details of one of his personal credit cards saved on her computer. She gets his lunch every day and found it was easier to just save the card number, order online, then go and pickup the lunch. Depending on OP’s relationship to the CEO, this could be an option, especially if lunches are a regular thing.

      3. zora*

        Caviar has this option, also, if you are in a place that they operate. You can create a “Shared Cart” and there’s a setting that can require each person to pay for their portion by credit/debit card.

    7. Burned Out Supervisor*

      I quit going to big get-together dinners with an online group I’m a part of because people would leave the amount of money for what they ate, but wouldn’t consider tax and tip on a gigantic tab. Twice I ended up being part of the last three that had to deal with the bill and had to throw in quite a bit of money to settle up. Separate checks for life.

    1. Respectfully, Pumat Sol*

      That’s really not going to go over well with this person’s BOSS. I am an easygoing person, but if someone did this to me without bringing it up politely a few times I would be livid. This is the nuclear option you use as you’re walking out the door to a new job. Not the option you use as the most junior person in the office to the CEO.

    2. zora*

      Yeah, this is terrible and so passive aggressive.
      This could be a good opportunity to show the CEO that the OP can handle an awkward situation professionally and directly, like a grown up.

  8. Don't blame Millennials*

    Funny… Dumping on the old rich white guy. Seriously, just talk to him. Or is that too much for Gen Z? Bet $100 that he assumes it’s going on a company card or submitted for reimbursement, etc.

    1. Mary Richards*

      While I also think mentioning the fact that he’s always had money is a little…gratuitous, I just can’t believe that you don’t see the power imbalance and awkwardness here.

    2. Sick of Workplace Bullshit*

      I’m Gen X, for what it’s woth, and I think this rich, entitled white dude is doing this completely deliberately. Especially when he can hear discussions about payment. He’s getting a thrill out of it.

      This is an asshole-taking-advantage-of-power-dynamics and preying-on-women-not-wanting-to-rock-the-boat problem. It has nothing to do with age. I’m sure he’s well aware the OP doesn’t have a company card.

      1. WellRed*

        This seems a little over the top. I also must have missed the part where the letter writer says they are female? Or is that an assumption on your part?

        1. Sick of Workplace Bullshit*

          You’re right, that was an assumption on my part, given the dynamics. I should not have made it. I stand by the rest, though. Sadly, through more experience than I’d like.

      2. Herding Butterflies*

        As a woman in a male dominated field who combats this BS, and has often and successfully rocked the boat (and still do at 25+ years in), I am still going to play devil’s advocate.

        The OP’s letter did not identify gender and Alison admits that she usually defaults to female in her replies. Why did you default to the OP being a woman? Would your response be different if the OP were a guy?

        1. Sick of Workplace Bullshit*

          Because I made a mistake based on experience. My apologies. I still think the boss knows what he’s doing.

          1. Herding Butterflies*

            We’ve all had a**hole bosses. I’m sorry to hear that you have had them too. That’s why learning how to stand up for oneself – whether it rocks the boat or not, or whether OP is man or woman – is an important skill set to learn.

      3. Socrates Johnson*

        WHAT?! What a crazy jump. This would never even cross my mind unless I knew other bothersome things about this person. What in the letter makes you think he is entitled?

        I would feel embarrassed and bad if this happened to me (I’m a boss) or even if this happened with friends when I didn’t know I owed.

        1. Sick of Workplace Bullshit*

          I don’t think it’s crazier than any other opinion given here. I’m commenting based on my experience. I hope for the OP’s sake I’m wrong.

      4. Dust Bunny*

        I’m Gen X and my first thought was that he’s just used to stuff being expensed, and doesn’t remember that the LW doesn’t have the ability to do that on his behalf. Clueless? Sure, but we all get used to stuff happening “automatically” in our lives–I have to remind my parents to feed the cats breakfast when I’m away from home because they’re used to me doing it before they get up and occasionally forget that I’m out of town and not just at work.

      5. Pollyanna*

        Obliviousness is far likelier than some hypothetical thrill. I generally try to look for the charitable interpretation first, rather than automatically think the worst. If he proves to be a cheap SOB who won’t pay for his own food, that’s unfortunate — but there’s no reason to assume that’s the case.

    3. Lu*

      This feels like an incredibly mean spirited comment. If you’ve never felt uncomfortable speaking up when there’s a clear power difference, good for you, but I’m having a hard time squaring your display name with the weird Gen Z attack here. Pointing out that someone coming from a place of privilege (ie being an old rich white guy) might make him blind to the burden he’s putting on his employees is a valid point to make and isn’t “dumping on the old rich white guy.”

      1. Odie*

        If barbs informed by identify politics and directly targeted at an individual are “mean spirited,” then that cuts both ways: the LW has done exactly that in crafting a narrative about what’s happening (a narrative that traffics in fundamental attribution error and that most of the commenters here have implicitly disagreed with).

    4. Another Millenial*

      I find it hard to believe that he assumes it’s going on a corporate card when they are discussing payment RIGHT IN FRONT OF HIM.

    5. Massmatt*

      Waaah, poor rich guy, getting his lunches paid for by his junior employees! Yes, let’s all feel sorry for him! Not!

      You seem to have missed the part that this is a small office of 5 people, talk of “company credit cards” and “submitting for reimbursement “ are nonsense.

      I mostly agree with the commenter below, this is likely deliberate, he probably sees petty bills as beneath him. I’ve encountered rich people like this, instead of being generous (or even decent) they excuse themselves when the restaurant bill arrives or bluster “do you know who I AM!?” when asked to pay their bills.

      This guy is acting like a jerk and should be DEEPLY embarrassed by his behavior. Why isn’t he just picking up the check or using his credit card for lunches for his employees? If he can’t bother to pay for his lunch I guess he can’t afford to eat out. Stop paying for his lunches.

  9. Heidi*

    This is going to probably be less convenient, but is there any way you could collect all the money up front? Once you’ve paid for it and and the food is eaten, there’s basically no incentive for people to remember to pay you other than moral compunction. You should still tell your boss that you’ve gone XX dollars in the hole paying for his lunches and not getting reimbursed and it’s no longer within your budget to do so, but this prevents the deficit from happening in the first place.

  10. Chili*

    Since the office is so small, payment conversations have gone on in CEO’s presence, and he owes you quite of money by this point, I would talk to him before you order lunch again and directly ask if there’s a way he thinks payment should be handled. Mention that you’ve been paying for everything on your own credit card and that you know he doesn’t have Venmo, so you need to figure out a convenient way for him to pay you back or set up a company card for these expenses. I like to give people the benefit of the doubt, but because the office is so small and it seems like there are enough conversations going on that would lead most people to realize they need to pay, I think I would approach this more directly than I would otherwise.

  11. Hope*

    I was in this exact situation at work. Stewed for months. Till I finally just did exactly what Alison suggests – right after the last time I paid, I sent him an email saying “Hi boss, total for today plus the last few months is x (chicken wraps x6). Here is are my bank details [a very typical way to do it in the country where we live].” And bingo, done!
    He was not trying to scam me… he’s just a thoughtless and busy guy and doesn’t think about these sorts of things. And was probably expecting me to follow up.

    1. Herding Butterflies*

      My last boss was this way too. Always assumed that group lunch orders were being handled by the office manager who had the corporate card. He was always embarrassed – and quick to pay up – when he found out he was in error.

    2. Lily Rowan*

      Yeah, that’s a good point to keep in mind — the bigger the boss, the more likely they are to rely on other people to follow up with them. Especially when it’s something the other person cares more about, even when it’s something as obvious as who is paying for my lunch (answer = me).

    3. The New Wanderer*

      I like this framing, I think it might be something the OP can adopt even as a junior person without feeling overwhelmed by the situation. Assume as the junior person you are responsible for following up with the CEO on CEO’s obligations, and provide a clear reminder:

      Hi boss!
      Your lunch bill is $xx for the Oct-Dec lunches, payable to OP’s name. If you would like me to send a bill more often (monthly or per lunch), please let me know.
      Thanks!
      – OP

  12. Buttons*

    If you ever feel guilty about quitting a job ask yourself this “Would they hesitate to lay me off ?” The answer is no. if they have a business case to lay you off they will, and they will not think about it if it is a convenient time for you or not.

    1. sunny-dee*

      That’s not universally true. I can think of three occasions (two where I work, one where one of my best friends works) where they delayed firing someone for an extended period because of extenuating circumstances. But those were firings for cause, not layoffs — I guess a layoff could be different, if they were (for example) getting rid of an entire department or closing a branch office.

      1. Tongue Cluckin' Grammarian*

        My workplace let a toxic employee hang on far too long before firing for cause (multiple) because that employee had experienced some personal life hardships right when they planned to do it.
        They were trying to do right, but in this specific instance, they really really really shouldn’t have.

  13. WellRed*

    OP, stop taking lunch orders. It doesn’t sound like it’s in your job description. Bring your own lunch until you break them of the habit of seeing you as the lunch getter.

    1. Skitch*

      If you’re junior in an office or on a team, getting lunch is just something you might have to do, job description or not. It wasn’t in my job description when I started in Big 4 public accounting, but I did it, as did all junior staff.

    2. MissDisplaced*

      I hate being the lunch getter! But when I do, I collect the money beforehand. Makes It easier

  14. TootsNYC*

    This sort of stuff does happen.
    And it’s part of why people chicken out–they leap to that possibility as a probability, and then they won’t say anything because they fear it’ll sound like they’re accusing people of being thieves and con artists (which is what that behavior is).

    HOWEVER: If you just blithely assume that everyone is a well-meaning person who just happened to not realize, then there’s your script. And your tone.

    And the shysters can’t really defend themselves.

    1. Veronica Mars*

      Yeah, definitely. It’s a complete falsehood that we can guess what’s going on in people’s minds, and trying to do so often leads to us treating other people poorly.

      A few months back my mom said “you spend an awful lot of time making up in your mind what people think about you, and it’s always negative. What if you starting thinking in best case scenarios instead?”

      That advice has been serving me pretty well.

      1. sunny-dee*

        My manager is HUGE on saying to assume good intent. I think in general, it does lead to a happier approach to life and people.

        1. TootsNYC*

          the thing is, even if there IS ill intent–your actions would be exactly the same.

          And assuming (and assertively moving toward) good intent allows the crummy people to save face, which means they’ll pay you back (or whatever) with much less drama.

          1. hbc*

            Totally agree. And in my experience, when crummy people turn down such a face-saving offer, they’ve got no more room for plausible deniability on the non-crumminess.

            OP: “Hey, boss, lunch was $17, is this cash or reimbursement or what?”
            Crummy face saving boss: “Er, um, cash, I guess.”
            Crummier boss: “No, I’m not paying for my lunch.”

      2. TootsNYC*

        smart mom!

        (also, most people aren’t really thinking about you at all–how often do YOU spend time judging other people? and if a person does, maybe they should stop?)

        1. Veronica Mars*

          I think your second point is very relevant to this situation… The LW assumes that the boss has spent time thinking about lunch money and decided not to pay it. But chances are, he isn’t thinking about it at all. Even if he’s in the area while y’all are talking about it, chances are it’s not big on his mind.

    2. hbc*

      I totally agree. And not only can you approach someone better if you haven’t pre-judged them to be scammers or jerks, you can avoid major embarrassment. I’ve had the people come in with “It’s so unfair that X has been done to me for Y reason for months!!,” and had to go, “Whoa, no, Y is not at all what is happening, and I would have fixed X in a second if I had known about it.” Of course I still fix X (if in fact X was actually an issue and not part of the misperception about Y), but I don’t forget that the person jumped to the worst possible conclusion about me and the company, ignoring a whole alphabet of possibilities.

  15. Close Bracket*

    Re: Lunch OP

    If there is someone in the office who OP trusts to give good advice, I recommended going to that person to ask how people typically approach the CEO for reimbursement. If the boss even has an assistant, that would be a good person to ask, but in an office of 5 people, maybe he doesn’t have one. OP says they are the most junior but doesn’t say how new they are. If they are fairly new and the most junior and it’s an established custom that everyone covers the CEO, they might get a lot of side eye and silent judgement if they just up and ask. Taking the temperature and maybe even getting an ally to back them up is a better approach.

    1. Daisy-dog*

      My thought as well. I doubt there’s an admin in that small of an office (because otherwise why isn’t that person ordering lunch??). With a seemingly hands-off, fairly oblivious CEO – there may be someone who is his right-hand employee that can give advice.

  16. HugsAreNotTolerated*

    Another way to handle this when you’re asked to do the lunch run, just reply with “Sure, I’m ordering from XYZ today. I’ve just placed my order online for for 12pm pick up. Let me know how many orders I need to grab.” That way you’re 1) determining where YOU want to eat your lunch from. 2) Not making multiple stops. 3) Forcing everyone to place their own orders and pay the restaurant directly online.
    If someone asks to you pick up their order from ABC, you respond with “Sorry, I’m heading to XYZ and need to run an errand on the way.”
    But overall?? Yeah push back on this lunch stuff, you definitely do NOT want this to become what you’re known for around the office. Wash your hands of it as soon as you can.

  17. coffee cup*

    Not ‘a boomer’ (presumably anyone over 45 these days) but I had no idea what Venmo is until I just looked it up there! It does look really useful but yeah I agree not ideal for this situation. I think Alison’s advice is good. And even if he wasn’t rich you’d still be entitled to ask for the money back!

    1. bassclefchick*

      I am over 45 and I am Gen X. I have also never heard of Venmo. Nor would I use it. I refuse to use my phone for banking.

    2. Alienor*

      I don’t think there’s widespread understanding of how old boomers are–my mom is one and she turns 70 this year! I doubt many people who complain about “boomers” are really working in offices full of 70-year-olds; they’re just annoyed by anyone more than a few years older than they are. That said, the boss is absolutely in the wrong here, even if he doesn’t realize it, and the OP deserves to get repaid, as well as paid for every lunch going forward.

      1. pentamom*

        That’s the oldest Boomers. The youngest are 55, so there are still plenty in offices.

        But I agree the term is used loosely, and I (an Xer) don’t get why it has become widely acceptable to use an age-related term derogatorily.

        1. Alienor*

          True, but since the peak of the boom was in the late 1950s, I think most of them are in at least in their 60s by this point. I’m also a Gen Xer, and after a youth of being called the invisible/forgotten generation in thinkpieces, it guess it just really chaps my hide to be lumped in with boomers in middle age. :)

          1. Old Biddy*

            same here. I’m an early Gen Xer (1968) and get annoyed when people assume Gen X is clueless about tech when we were at the forefront of much of the 1990’s tech boom.

      2. The Man, Becky Lynch*

        Boomers are 1946 – 1964

        So the youngest is 55.

        Generations span about 20 years on average ;)

    3. Seeking Second Childhood*

      BabyBoom “officially” ended in 1964 so no, you’ve just hidden ten years’ worth of people. Call us Baby Bust, call us Gen X — but do not lump us in as boomers.
      As I’ve said here before, many of us who are Baby Bust are touchy on this because we’ve spent our lives being invisible. Schools closed around us for lack of attendance. Our generation’s tastes were labelled “alternative” because it wasn’t popular with the generation ahead of us. We knew that we would have to fight extra hard for jobs because of a traffic jam in the generation ahead of us. And many of us figured out in middle school Social Studies class that there would be a funding-vs-population problem with Social Security just when we started thinking about retirement.

      1. Bleh*

        Yes, to this. Gen X is invisible because we are not big enough to be marketed to. So leave us out of the whole Boomer, Millenial conflict, whatever it is.

  18. Black Hole Sun*

    To be honest, the “boomer” comment got my back up, because quite frankly despite his age or wealth, as the CEO he should be responsible about this kind of stuff and it’s unnecessary to demean the man for being from a different generation or not using Venmo. The CEO is already being a (lots of bad words), using derogatory terms or mocking his inadequacies just diminishes the LW’s argument, which was stronger without noting his generational deficiencies.

        1. Jungkook*

          That’s shocking to me too. Can I assume someone won’t pay up because they’re a stingy Chinese woman, for example? Why is it okay to make a negative assumption about anyone based on race and gender, instead of giving them the benefit of the doubt?

          1. Fikly*

            It’s more relevant in terms of priviledge and life experience. What a white man experiences is tremendously different than your example of a Chinese woman.

            1. Quill*

              Being an asshole knows no race, gender, or age, but boy do those three things matter when it comes to getting away with being an asshole.

          2. none*

            It’s shocking to me also when neither race nor sex have anything to do with this. Wealth and power, maybe. Or maybe just obliviousness. But really, to call out that he’s a white guy makes no sense. The important context is that this is the CEO and letter writer is the most junior employee.

            1. Derjungerludendorff*

              Privilige definitely has something to do with this though. Whether the CEO is just oblivious or actively malicious, it’s much easier to ignore or perpetuate a problem if you never have to deal with it yourself.

              1. none*

                sure, privilige related to not having to worry about money. Privilige of the well to do. Surely you are not equating that with whiteness?

                1. Ask a Manager* Post author

                  We aren’t going to pretend here that being an older white man running a company isn’t in many ways a huge amount of privilege.

                  Per the above request, move on.

  19. SongbirdT*

    Side note re: Venmo — am not a Boomer, solidly Gen-X, but I too am anti-Venmo as they have / had major security holes you could drive a truck through. That’s not to say I can’t send you digital funds – my bank can do it. But there are good reasons to not Venmo that doesn’t make one a Luddite.

    1. Quill*

      Yes. Also, overall: I’m not going to use a finance transfer system that’s based on an app, because I know that the internet security on your phone can easily be much less rigorous than that on your average computer with an average household antivirus.

    2. Rexasaurus Tea*

      THIS. I’m extremely hesitant to trust a phone app that wants direct access to my bank account.

      I have the app because some of my family members prefer it, but it’s not connected to any account. It’s like a little side pocket of available funds in case I need to pay someone else and they only want Venmo.

    3. Booklover13*

      Millennial who is also on the anti-Venmo train. Venmo is basically just PayPal in App form, which is to say, they want to hold my hold my money without any of the protections of actually being a bank.

  20. blink14*

    This is pretty presumptuous statement about why he hasn’t paid you back. I’m thinking that this has been going on long before you were hired, and your other colleagues for whatever reason had a hand in starting the trend of not asking the CEO for his share, but covering it on their own. You need to speak to one of them or all of them, and say you simply aren’t going to order lunch anymore until this has been cleared up. Open the door for someone who knows your boss better to approach him about the subject.

    The CEO may think this is coming out of petty cash, on a company card (in an office this small, that’s questionable), or something other arrangement that may have been how the lunch orders were when they first began, but now it’s not that way. It’s entirely possible that he knows its coming out of your pocket, but the chances of that are lower than the other options.

    And for what it’s worth – I’m in the older end of the millennial generation, and I’m still not that comfortable with Venmo. Don’t judge someone by the fact that they don’t want to use an electronic payment app, it’s pretty common.

    1. annakarina1*

      I’m also of the older millennial generation, and it took me a while before I got comfortable with Venmo, it felt weird to attach my bank info to it. I use it so my roommate can pay his rent half because he prefers sending it as opposed to handing in a check or cash, but I don’t use it for anything else.

      1. blink14*

        Same here – I use it so my roommates can transfer utility money to me and for the occasional splitting a check with someone. Otherwise, not really into it!

    2. The Man, Becky Lynch*

      I just don’t see the point in the even changing options for money transfering. I have had PayPal for years, just use that. It frigging owns Venmo, y’all. It’s just another “fancy” gadget that isn’t necessary.

      I’m not old. I just don’t buy into each latest technology craze. I capped out at an Original Nintendo and had cassette tapes in my car until I wrecked it and only then did I get a car without a tape deck, lol. It’s not about age ever.

      1. Black Hole Sun*

        I’m a young Gen Xer, but I had to reply to your car with a tape deck because it reminded me… I was so sad when my old 1988 car crapped out and I realized that my new car didn’t have a tape deck (roughly the year 2000). I hadn’t even considered that not having a tape deck was a possibility and didn’t notice until I drove the damn thing home. All those mixed-tapes made as a teenager became obsolete… So sad.

        1. The Man, Becky Lynch*

          WTF, a 2000 car didn’t have one? What kinda bootleg…I’m sorry that happened to you!

          My 2017 doesn’t even have a CD player though *blinks* It’s all bluetooth, be still my heart. Thankfully my partner “shamed” me into getting a smartphone 5 years ago [it’s in quotes because he only said it in passing and I was like…oh shoot…well if you’re gonna point it out, lol]. so I can use that option. Otherwise I’m stuck with the radio.

          1. Rexasaurus Tea*

            Same here – my 2017 doesn’t have a CD player and I am sad. (also fully aware that this First World Problems and I don’t really have anything to complain about.) My kids’ music is all on CDs and I haven’t yet gotten around to putting it on a USB stick.

          2. Black Hole Sun*

            To be fair, I think you could get a CD/tape deck, but you had to ask for it and it was more $$$. I had just assumed that getting the basic (i.e. cheapest) version would get you a tape deck, but alas, no. But, I still have my one-disk, dual cassette (for making mixed tapes!!) stereo I bought for my 16th birthday. So, I do occasionally bust out an old mixed-tape.

    3. Fikly*

      Why, if they are present when multiple frequent conversations are going on about repayment, would you think the CEO doesn’t know exactly what is going on?

      Yes, without any additional context, your assumptions might be right, but we have additional context.

      1. blink14*

        Maybe he thinks owing the OP means owing the corporate card, maybe he’s totally oblivious, and maybe he knows exactly what’s happening and doesn’t care. However, without straight out asking to be reimbursed for personal funds laid out, nobody knows what his response will be.

        1. Fikly*

          If you have to bend over backwards to come up with a reasonable explanation, it’s unlikely the explanation is reasonable.

          Yes, he should be asked. However the odds that this guy is oblivious are low.

  21. No Coffee No Workee*

    I’ve been in this exact situation. I started working for this one company when I was 20. As the most junior person, I often placed lunch orders. A few times, my rich boss wouldnt give me money.

    I started sending emails to everyone on the lunch order, saying “here’s what you ordered – please confirm its correct. And this is how much you owe.” Didnt help my boss pay up,

    After a couple of times doing this, my boss (who generally was NOT an A-hole) said to me that it was tacky I’d ask him to pay, because I’m fortunate to be employed at a great company and he often treats us for lunches, happy hours, and other fancy dinners.

    Being so young, and not having anyone else around me that was in a white collar profession, I kind of let it go. But then i started to push back on people, saying that I couldnt afford to put the whole amount on my card, so can someone else offer up their card, etc.

    I had kept track of how many lunches I covered for my boss. I ended up creating an invoice for like $300 (or whatever the amount was) and submitted it to the accountant. I then sent an email to my boss and other co-workers, saying that I appreciated all of the freebies he gives us, but that I alone couldnt afford to pay for all his lunches. I offered other employees to start taking turns to “show their appreciation”.

    I think he got embarrassed. He promptly paid my invoice and started having someone else with a corporate card place lunch orders. This way, people technically would pay him for lunch.

    I ended up working for him for another 15 years (it really was a great company and a generally good boss!) But I always remained conscious of the younger people in the company and what we ask them to put up financially.

    1. Is it Friday yet?*

      I’ve found that this is the unfortunate reality of a lot of Fortune 500 companies or “dream job” offices where there’s a large candidate pool of people who would love to work there. More often than not, the compensation and benefits are garbage, and the attitude from leadership is that you should just be thankful to be working for Really Awesome Company Doing Really Cool Things.

      1. Amethystmoon*

        Yep, and also we’re supposed to be grateful for getting a paycheck above minimum wage. Just because it’s above minimum wage doesn’t mean that all of life’s expenses are covered with a lot of wiggle room to spare for everyone.

    2. The Man, Becky Lynch*

      And this mindset is why it’s important that Alison keeps drilling the “Gifting flows down not up” into everyone. I’m glad you eventually got paid and that he’s generally just a weirdo when it comes to thinking he’s super special for “treating” his employees. Gurl, that’s just normal retention behavior, it doesn’t mean that your staff ever owe you a free lunch.

      Wait. Wait. He had it set up so someone used a corporate card…but then still collected everyone’s cash? LOL okay. At least y’all liked him enough to put up with that kind of weird petty cheapskate ways.

        1. The Man, Becky Lynch*

          Well, he’s so KIND and AWESOME for giving all of them jobs…it’s the least they can do *rage face*

    3. Coco*

      Omg. You are so awesome for this!!!

      I offered other employees to start taking turns to “show their appreciation”

    4. Diahann Carroll*

      After a couple of times doing this, my boss (who generally was NOT an A-hole) said to me that it was tacky I’d ask him to pay, because I’m fortunate to be employed at a great company and he often treats us for lunches, happy hours, and other fancy dinners.

      LOL! The audacity.

    5. Gazebo Slayer*

      Sometimes it takes public embarrassment to make people behave decently, unfortunately.

  22. Dumpster Fire*

    I feel for you, OP1, but please remove the “alas, he’s a boomer and so therefore….” from your repertoire. As a boomer who’s FAR more tech-savvy than any of my millenial/GenX/whatever colleagues, that’s a really good way to lose all credibility with the people who are, in fact, likely to be your supervisors/bosses/C-level execs for the foreseeable future.

    1. The Man, Becky Lynch*

      My older millennial ass just learned recently that this “boomer” nonsense isn’t actually targeting the generation itself but the stereotype of the generation that’s held across many age groups….

      I originally jumped at the #NotAllBoomers but then found this information along the way.

      It’s up there with the “Thanks Obama” nonsense when everyone was blaming him for random AF things. Sigh. I’m getting too old for this sh*t!

      1. Tongue Cluckin' Grammarian*

        It seems to be a reaction to all young people being called “Millenials” more than to the actual specific age group, yeah.

        All people older than me = Boomer
        All people younger than me = Millenial

        Regardless of what generation category would actually fit.

    2. Blackbelt Jones*

      Amen.

      I’m a boomer also, and have been using computers since the mid-80s, with a STEM degree and 20+ years in tech fields, including programming. (*And* female.).

      Those little “boomer slights” are tiring.

    3. Boomer*

      I completely agree – I’m a young Boomer (age 55) and I have Venmo, Insta, Snapchat, etc. Making ageist assumptions about your boss or anyone else is going to backfire on you big time.

    4. Triplestep*

      Totally agree in the credibility point. I am 56. I don’t know what that makes me in terms of generation labels, but my kids both come to me for tech support. One is 24, and the other is 30. If I thought for minute that one of my employees was making assumptions about my technical acumen based on my age, that would be very career-limiting for her indeed. It would also color my opinion about her general critical thinking abilities.

  23. Coco*

    Is there a reason you’re using your personal credit card? When the boss gives his order can you ask for the corporate card? Or his own? Def let people know what amount they owe so you can recoup your costs but please stop using your own card.

    1. anon4this*

      She can get points/reward points/coupon codes/etc by placing large orders on her personal credit card. It’s probably why she hasn’t asked for a company card.

      1. Coco*

        These are lunch orders for a small group so assuming they aren’t $$$? I can’t imagine the points or perks of the card are in way close to the hassle of chasing people to pay her back?

        1. anon4this*

          Well, if everyone gets a $10 meal, that’s around $50 a week or $100 if twice a week (for 5 people). Times that by 4 weeks (for 1 month) and you’re looking at $200-$400 monthly. With places like Panera, McDonalds, Wawa, etc. you can certainly accumulate tons of reward points (same goes for booking plane tickets = free miles, etc.).
          Also, it seems like every co-worker is trying to pay her back ASAP, except the CEO, so I’m not sure there is a hassle of chasing “people”; it seems like the OP wants to keep using her card and is just looking for advice on getting the CEO to reimburse her in a more timely fashion.

      2. 1234*

        Not everyone gets a company card. Old Job had a rule where only Senior People got company cards when they started. The rest of us either had to be personally reimbursed by the company or use a Senior Person’s company card.

        1. NotAnotherManager!*

          And sometimes having a company card is more of a hassle than it’s worth. I would still have to do expense reports and reimbursement, so I just use mine (fortunate to have an accounting team that reimburses expenses within one week) for the points/rewards.

    2. The Man, Becky Lynch*

      Lots of companies that are that small don’t have corporate credit cards available or are very weird about how they’re used.

      Hell. I have a customer who is not a micro sized company and they swear they don’t have credit cards available either. Sucks for them, since their accounting stinks and therefore they have to pre-pay everything. So I was like “We accept credit cards, no additional charge…….” “Yeah we don’t have those.” Okie-doakie.

      But I agree that it’s one of those things that you have to be vocal about if you’re going to play the “we’ll put it on my card” game.

      1. hbc*

        My company couldn’t get unsecured credit, so we had a secured credit card, which was a pain. We had to have a separate bank account with our limit ($5K) for them to hold against it, and even if we paid off the balance early during the month or sent them a check for $10K, we couldn’t spend a penny over 5K during any month. Giant pain in the rear.

        1. The Man, Becky Lynch*

          Yeah it took years to get cards for our company too, I’m told! Thank God it’s not secured though, holy moly my head exploded.

  24. frida*

    ha! I was in a similar situation recently, except my boss took our team out to lunch, told us to get whatever we wanted, and then DINED AND DASHED. Like he left just as the waitress approached with the bill. Well over £100. We split it amongst the rest of the group. No one has mentioned it since.

    1. DANGER: Gumption Ahead*

      I could see this happening on the Office and that is the only place it should happen. What a tool

        1. Quill*

          I think I’ll save it for Friday open, because it’s wildly off topic, secondhand, and a doozy. (Happened to my mother’s ex-colleague who I’m friends with.)

  25. I'm Not Phyllis*

    I know for sure that my boss (who is the CEO as well) would never expect me to pay for his lunch and would be mortified if he found out that I had been doing so while also resenting him for not paying his share. I’m sure that, like Alison says, he is assuming it is being taken care of some other way. Please ask him about it (or his assistant if he has one) and/or just stop paying for his lunch, even if it involves not ordering anymore (if that’s an option). It is not worth the resentment or financial issues involved!

  26. Miss Fisher*

    Why not just send out an email to everyone ordering when their totals after. This is what we do. And then you can track who has paid or not and resend the email if not by end of day.

    1. Seeking Second Childhood*

      Ooo… and set it up with your best buddy as the fall guy.
      1pm email :”Lunch is ready for pickup; here’s what you all owe me: Dopey $11.75, Doc $12.15, Grumpy $13.00, Snow White $13.00, and Prince Charming $15.50 Signed, Bashful”
      5pm email: “Hi Bashful — I picked up my lunch when you weren’t there and have been tied up ever since. Can I bring $13 to you now? Signed, Snow White. PS PrinceC, Want me to swing past your office and bring your $$ to him too? I can hear you’re still on that conference call.”

      1. Carlie*

        I’m on team collect the cash before the pickup. Tell everyone including the boss that you can’t use your card any more, give them a week’s notice, have a pile of $50 or so in singles to give people change, and they’re out of excuses. If someone does forget cash, they get to go pick up the food so they can pay with their card there.

        As for the boss’ back bill, if it feels awkward you can say you were doing a semi-annual personal budget analysis and “happened to notice” that you had never collected from him. That way the timing isn’t so weird, you’re giving him a polite out, and it’s a good example of why doing it via cash only is a better plan. (so debts don’t accumulate to such a big amount)

  27. Amethystmoon*

    Yeah, this is why I generally don’t go out to eat unless it’s with family. It’s expensive for the average person. Groceries already cost quite a bit if you’re trying to eat healthy. Our cafeteria is not too bad, but the food tends to be contain the cheaper carbs such as white rice, white pasta, or potatoes that if you’re dieting, you’re constantly told not to eat, so I only get stuff from there a couple of times a month.

  28. The Man, Becky Lynch*

    I understand that you think that it should be enough to nudge him into throwing in his share because you’ve spoken in front of him with the others about how much they owe, etc. But in reality, many people are simply aloof and don’t take hints. So I would go the direct route. “Hey Dale, I put this lunch on my personal card, your share was $15.”

    I doubt that he thinks that it’s on a company card, he’s the CEO of a micro sized company, he knows that these aren’t hitting the books and you don’t regularly fill out an expense report the same way you’d do in a large company. He probably just thinks someone is treating when he’s invited to join. The others may have waved him off previously as well, so he’s not aware that when you order, you do expect to be paid. I’m extra guilty of doing the “Don’t bother, it’s on me.” when in a group setting like this, so some people would need to be nudged and told that this is actually a pay for yourself arrangement.

  29. Imaginary Number*

    Has anyone actually asked him to pay directly? You said he’s been within earshot of conversations about paying for lunch but that’s not the same as telling him he owes a certain amount. He really may just be completely oblivious and doesn’t think about these things. It might just take a, “Hey, do you happen to have X-amount for lunch from this week and two weeks ago?”

  30. Kevin Sours*

    OP#2. It’s not your responsibility to stay on. It’s their responsibility to make you want to.

  31. I don’t post often*

    I agree with the many commentators here- if he has a good assistant he isn’t used to thinking about the details because he doesn’t have too. Sounds odd unless you have had an assistant or have been an assistant.

    I worked as a catch-all project manager but also assistant to the executive of my department for a few years. After the first three months I scheduled his flights automatically with dates, times, seating arrangements etc he liked. He literally never knew why he was always assigned the first row seat until six months later he commented on it while we were traveling together. He assumed some sort of automation based on preferences and valued customer status. Nope- I knew he wanted front of plane aisle seat, and felt it was my job to make sure that happened.

    Just a quick conversation about the lunch issue likely clears up the problem. Either with his assistant or with him directly.

  32. RUKiddingMe*

    “ After the meal there’s always a conversation, initiated by my colleagues, in which everyone ask me how much they owe. We are in an open office space with our CEO, but he seems to be entirely oblivious to these conversations.“

    Do he sits *right there* hearing them arrange pay back and doesn’t offer his share…ever?!

    Sorry but this sounds less like oblivious and more like deliberate.

    OP in the future get a way to pay that isn’t your card before placing the order. If he says he will pay you back ask him if he will also be paying for all past purchases.

    1. Gazebo Slayer*

      Also, the “but I’m anti-Venmo” excuse without offering an explanation of why, a check, or cash makes me awfully suspicious. I’d act as though I were giving him the benefit of the doubt, for the sake of getting along with him at work, but I wouldn’t expect the best.

      1. Jennifer Juniper*

        Maybe he’s suspicious of new technology. I’m aware Venmo is something used to pay for stuff, but not quite sure what it is.

      2. NotAnotherManager!*

        Lots of people don’t use Venmo and don’t feel comfortable hooking their bank account to an app. However, if one feels that way, one needs to pony up the cash for their meal or otherwise reimburse the person doing the heavy-lift on your lucnh order.

        1. RUKiddingMe*

          And that’s perfectly reasonable.

          In my family a lot of money goes back-and-forth between family members for…reasons.

          One brother in law resisted anything other than sending a check through the mail (snail mail) for the longest time because he got screwed over in a financial thing.

          I finally told him “dude It wasn’t the tech it was trusting the wrong person.”

          We finally got him to open a bank account just for sending/receiving.

          He keeps only enough in it to keep it open. Now he doesn’t worry about being “hacked.“ Even though he was never hacked first place.

          I mean if they’re gonna do this money back and forth thing they need to make it easy-ish on everyone else.

          But if OP’s boss doesn’t want to do Venmo, he could….I don’t know…give her cash, each time.

  33. Fikly*

    #2

    Whenever you feel bad about the timing, think about all the reasons your company is giving you to want to leave, and think about what they could have done to make those reasons go away. Then hand in your resignation.

  34. cosmicgorilla*

    You…use your words. Like a grown up. And stop making up stories about how the issue is because he’s wealthy and privileged.

    1. ThisColumnMakesMeGratefulForMyBoss*

      This. Mistake #1 is putting everyone’s lunch order on your own card. Mistake #2 is not popping into CEO’s office and saying “you owe me $15, thanks!”

    2. Amy Sly*

      It’s amazing how many problems can be solved by cutting out the hints. Whether a problem employee, an annoying coworker, a spouse who doesn’t read your mind … try using your damn words.

      And if getting the same advice that toddlers get is embarrassing, well, it ought to be.

      1. NotAnotherManager!*

        It will sound weird, but having a child on the autism spectrum has done wonders for me on this front. Kid does not get hints at all but is great with explicit directions and stated expectations. Because we’ve changed our communication style at home to accommodate, it’s spilled over into other areas of life as well. I didn’t realize how much I was expecting people to “know” things or get hints until we had to change our communication strategy at home.

    3. Fikly*

      When the only person doing this is wealthy and priviledged, how is it making up a story to think this is a factor?

      1. cosmicgorilla*

        It’s a story because the person doesn’t know that’s the reason why. Tons of other factors have been discussed already in the comments, such as the exec thinking the meal is being expensed. Unless the exec specifically says, “I don’t have to pay for things because I’m so rich!”, it’s not a fact, and the letter writer is making massive assumptions.

        1. Fikly*

          Except that the LW has stated that the exec has been nearby in hearing during multiple conversations about repayment, thus you are going through strange contortions to find an explanation that doesn’t involve the exec doing this deliberately.

          It’s not a story, it’s a likely explanation. There is a bit of an assumption, but not a massive one by any means. On AAM, we take the LW at their word.

    4. CM*

      All the “use your words” answers are not taking into account the power imbalance here. This is not two peers dealing with an issue. It’s the most junior employee in the office asking the CEO for cash. The OP is not being less of a grownup by having difficulty handling this.

      I am in a senior position and I would think twice, or three or four times, before saying, “Hey CEO, can you give me that $15 that you know you owe me but have never bothered to pay before, even when you see other people paying me right in front of you on a daily basis? Or better yet, make it $300 to cover all your past lunches too, thanks.”

      You can see from all the stories here that the CEO could have a wide variety of motivations and reactions. There are stories of CEOs being horrified that they didn’t realize the person was paying out of pocket, and stories of CEOs saying that they deserve a free lunch because they are doing their employees the favor of employing them. We really can’t assume either good or bad intentions on the part of the CEO.

      1. cosmicgorilla*

        I don’t know that I would ask for reimbursement for past meals, but I don’t see that it’s that hard to say hey CEO, your part of the meal was x. If someone can talk to the CEO to get their lunch order, then they can talk to the CEO to say hey, your salad came to 16.75 with tax and tip. Since this is an on-going issue, the letter writer can say hey, I’m collecting cash up front since I put these meals on my personal card. If they’re really feeling froggy, they can say, I’m collecting cash up front, or would you like to put this on your card?

        I don’t assume any good or bad intentions on the part of the CEO, but the letter writer seems to be.

        The letter writer asked how do they let the CEO know he’s expected to pay. The answer remains – with words. You ask. You open your mouth and you say words. There is no way around that.

  35. Nephron*

    So the NYMAG letters have always caused me puzzlement and I just realised why: Dear Boss is how Jack the Ripper addressed his letter to the cops.

  36. mf*

    I would tell your coworkers or boss, if you don’t report to the CEO, that you can no longer put group meals on your personal card. Not everyone has been paying you back for their lunches and it’s becoming a financial burden. You’ll be happy to keep placing the orders but from now on, you need to use someone else’s card or a company card.

    Another alternative: start bringing your lunch to work. If you’re still asked to do the group order, do it but insist on using someone else’s card since you are not buying any food for yourself.

  37. Old Cynic*

    re: Venmo. I’m in a group of 15-20 guys who dine out every couple of weeks. When we tried Venmo, the person who paid was always short changed at the end of the process. We went back to pitching in cash the night of the event.

    1. The Man, Becky Lynch*

      OMG how’d that happen, who was shorting?! I’d be hunting down names but I’m a savage like that.

      Is it because of the tip? Did they short the tip…THAT is a nightmare I’ve heard about. And reason 13423 why I don’t split checks but I also don’t go out with someone that I’m not willing to buy a meal for either.

  38. Jennifer Juniper*

    If the CEO simply refuses to pay his share, or you get in trouble for speaking up, another option would be to simply bring your own lunch and not join in with the others when they order lunch.

    This would be a last resort if your office is extremely dysfunctional.

  39. Black Hole Sun*

    White men have fundamentally have more privilege and wealth than others. That’s not an assumption, that’s fact. That also means, they may not be aware that the privilege and wealth afforded to them is not afforded to others. That’s not prejudice or bias, that’s ignorance. That doesn’t mean all rich, white men or white men in general are ignorant. But, it does mean that there is a possibility that rich, white, men may not be aware of the disparity between them and others. In the context of this particular situation, where a rich, white man is not paying for his lunch — it very well may be caused by the fact that he is unaware of the disaparity or that he assumes someone else will handle it. Either way, the LW is under the impression that it may be caused by privilege. Our role as human beings is to seek out the truth and not wallow in clickbait (which gets harder and harder these days) The LW is just as responsible for finding out the truth about her boss and whether he is being a **** or whether he’s just obtuse, as you are for determining whether privilege comes with bias or not. In the end, it’s your call, not mine or Allison’s or anyone else’s here.

      1. Les*

        “White men have fundamentally more privilege and wealth than others…they may not be aware that the privilege and wealth afforded to them is not afforded to others.”

        Fascinating. To which stereotypes should this behavior be attributed if the CEO were African American, Japanese, or Latinx?

        Obliviousness, indifference, or selfishness are aren’t the sole domain of any one race or gender.

        1. Black Hole Sun*

          This was in response to a comment further up and not a sole reaction to the letter. Since you chose to distill my argument to the first couple of sentences, I’m not quite sure what you want my response to be. But, I don’t ascribe character traits to a specific race or gender. I also don’t ignore the reality of white privilege. Both those sentiments can exist together.

    1. What the What*

      “White men have fundamentally have more privilege and wealth than others.”

      Not in the US state I live in. Very high poverty rate, one of nation’s highest suicide rates, early mortality rates, low access to physical and mental health care, low wages, higher taxes, big meth and opioid problem, etc. Not much privilege for ANYONE of any race here.

      1. Ask a Manager* Post author

        White privilege doesn’t mean that you’re lucky in all areas of life. Please do some reading on it, but this isn’t the place to debate it so let’s leave it here.

  40. Heat's Kitchen*

    THIS: “You shouldn’t put your career on hold until your boss is back. And no manager worth doing that for would ever want you to.”

    I put in my resignation yesterday. My boss is sad and surprised I’m leaving and would “do whatever necessary” to keep me, but he also said multiple time, “I get it. You need to do what is right for you, your career, and your family” and he has been nothing but supportive. I’m lucky and I know that, and hope to be this person going forward.

  41. Kaaaaaren*

    I think the OP should stop putting these lunches on her credit card and just pay with cash when the order arrives. She can say “I’ve recently paid off my card and I’m trying not to use it except for emergencies, s, from now on, when I order the weekly lunches, please have the cash ready so we can pay the delivery guy when he arrives with the food.”

    This will also make getting money from the boss a bit easier, since it’ll be made clear that the lunch is being paid for in cash right now vs. by some mysterious lunch fund he presumes exists.

    1. Jess*

      That seems a bit contrived, I don’t think you need a fake excuse about paying off a credit card that makes it sound like you’re in more dire circumstances than you really are, and that would require you to keep up the ruse by not using your credit card in front of your co-workers in the future.
      I think it makes sense to just ask clearly for reimbursement, to make it clear that you paid with your personal credit card and everyone else owes $x.

    2. CM*

      I agree, except I don’t think the OP should make an excuse. She should just say, “Sorry, I’m no longer able to put these lunches on my personal card.” There are plenty of other solutions — company card, someone else’s personal card, CEO’s personal card, gather cash from everyone, petty cash from the office.

    3. The Man, Becky Lynch*

      Depends on how they’re ordering but many places won’t take cash upon delivery! Only places with traditional delivery that they’re offering tend to do that, most delivery is done through 3rd parties now.

    4. Kaaaaaren*

      I guess my larger point is that even if reimbursed, it’s still on the OP to manage these charges on her personal card, to do the legwork of chasing people down to get paid back, having to worry about how to approach the boss about his share in an office where many coworkers have felt more comfortable simply paying for him in the past, making change for people, etc. And while not the HUGEST deal, it is an added burden that shouldn’t be placed on an employee, especially the lowest ranking and presumably worst paid member of the team and I don’t think it’s “contrived” to say she can’t do it anymore. Nor do I think people will hyper-focus on her personal card use and call her out if she uses it for non-emergencies in the future.

  42. Blue Eagle*

    This won’t help you get paid for the balance owed, but in the future you may want to collect the money BEFORE you place the order and put it on your card. If you don’t have the cash in hand before the order, then don’t order it. Ask me how I know that this will work.

  43. What the What*

    The OP is in an unfortunate position and I totally get that. I hate when people are careless about other people’s money or squirm out of paying (one of my parents is like this). It’s one of my Top 10 Pet Peeves. The CEO might well and truly be a jackass but there could be other factors as discussed by other commenters.

    I really don’t like how the OP said the CEO’s poor behavior was possibly due in part ”because he’s a white man….” That’s a really broad and presumptuous generalization. Of like an entire race. And of an entire gender. If we substitute the race and gender, it sounds like a pretty harsh and jarring assessment of someone, doesn’t it?

  44. June First*

    Alison: “It’s incredibly unlikely that your boss will flagrantly refuse to pay once it registers for him that you’ve been buying his lunch with your own personal money. There are people who would try that, but they’re relatively rare…”

    But if he IS one if those people we absolutely want to hear about it in the updates!

  45. Llellayena*

    I’m borderline millennial/genX and if you said “Venmo me the money” I’d have to say “huh?” Getting outraged that someone doesn’t use Venmo so you can’t send them a request is ridiculous. Just ask! There’s nothing wrong with directly reminding him!

  46. Wait,what?*

    ” (I have another sneaking suspicion it’s because he’s a white man who has had a great deal of wealth his entire life.)”

    I read this blog almost daily and it is interesting and useful. I realize that most of the folks here tend to be left of center, but I’m a little disappointed that Alison didn’t call this out. There are people of all colors, shapes and sizes that are a$zh0Le$ and conversely that are amazing and wonderful people. That statement was just racist and does not belong here. What skin pigmentation a person has is irrelevant. Please just stop with this sort of nonsense.

    1. What the What*

      I agree with you, Wait, What. I hate the way people—who are perceived to be a certain way (ie, rich, poor, skin color, background, ethnicity, region)—are publicly crammed into little pigeonholes. It’s a slippery slope when society begins to believe in absolutes like white-males-are-inherently-privileged-and-therefore……..enter bad adjective here.

    2. Ask a Manager* Post author

      Racism isn’t just about bias, but also power — an institutional power imbalance and systematic oppression, not simply bias alone. (Same thing goes for sexism.) Pointing out that someone is in a demographic group that has more power and privilege isn’t racism, just as it isn’t racism to be thoughtful about when someone’s membership in a marginalized group might be relevant as well.

      Race does matter, because we live in a society where it impacts all kinds of things. Pretending to be colorblind makes it impossible to do the work necessary to work to combat racism.

      1. What the What*

        I appreciate Alison’s well laid out response. My comments weren’t focused on racism, sexism, privilege, colorblindness, etc., but rather the danger of buying into absolutes. Absolute thinking drives me up a wall because I’m learning as I get older (wiser?) that life’s kind of like an iceberg: a lot going on under the surface that we aren’t privy to.

        I’m not sure who the comment was directed at, but I think it’s somewhat presumptive to say someone is “pretending” to be colorblind or that it’s somehow NQR to be colorblind. It’s okay to see others as unique individuals first. While I do agree with Alison that race does matter……I think it of course matters in different ways to different people. (For me, it makes me curious about others, their history, stories, experiences, etc. People fascinate me.)

  47. Amethystmoon*

    So, this is probably just a dumb question, but is there some reason boss can’t pay you back in cash? If he doesn’t want to trust an app, I would think at least cash should still be a legal option. Yeah, not everyone carries around cash, but if he knows he’s going out to eat, he should be able to withdraw some in advance. Or check? I know they’re old-fashioned, but they’re still legal tender.

  48. Prof. Space Cadet*

    I’m not saying the CEO has bad motives, but I’ve noticed that some people don’t think about the power dynamics involved in these situations until they get pointed out.

    Several years ago, I attended a business dinner about 9 or 10 people at a conference. There were about 3 different organizations present between the 10 of us. We paid on one check with separate cards. “Herman” the dinner organizer) said “Clara will be responsible for figuring out the tab, because she’s the youngest person at the table.” Clara (a 22-year old intern) looked like a deer in the headlights, so I jumped in an said I’d do it. Herman replied, “but it’s tradition that the youngest person do it.” I shot back, “tradition according to whom? That’s just weird.” Herman immediately backed off and hasn’t said anything like that since then.

  49. Scarlet*

    OP I have a couple of questions –

    1. Why do you “have another sneaking suspicion it’s because he’s a white man who has had a great deal of wealth his entire life”? Those sorts of assumptions about people are unhealthy and breed discontent. Also I’m reminded of Hanlon’s Razor – “Never attribute to malice that which can be adequately explained by stupidity”. Many CEOs (not all of course!) started at ground and worked their way up. Why don’t we try to assume the best in people?

    2. Has anyone ever asked you or told you to put the lunches on your personal credit card? A simple conversation like “I am unable to put these expenses on my debit card today – can you give me the business credit card for the order?” would be an easy solution, if applicable.

    3. Have you asked the CEO directly, or perhaps his admin about repayment? CEOs operate at a really high level and often avoid the day to day minutiae. In fact, it’s their job to act that way after a certain level. That’s step #1.

    You seem really young in your career, but I can pretty much guarantee a little pro-activeness/assertiveness will resolve this issue. However what I would do right now is STOP putting the expenses on your credit/debit card ASAP until you have a resolution for this.

    Also, any CEO/human being worth their weight would be REALLY embarrassed the junior employee has been footing the bill for their lunches. I mean hell, I’m only mid-level and I would be horrified and go to the ATM ASAP to pay it back. One thing I’ve always found helpful in approaching business conversations – they’re not personal, you’re not taking a swipe at them. This is business, these are professional relationships, it’s 100% OK to be upfront, straight-to-the-point, even curt as long as you remain respectful. Good luck!

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