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)?

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    I myself would avoid bringing up the past lunch payments and just assume that money is lost now

    I'm also not sure if you can ask your boss to pay stuff without prompting... In my experience a lot of bosses tend to be a bit distracted and air headed. So there would be no point getting worked up over that.

    however it's obviously not right for you to pay for his lunches... So what I'd probably do is actually try prompting yourself the next time you pay for the food.

    If you have a slack with a public channel, you can just make a post that you bought the lunch and what the price was for everyone.

    or if you can bring the courage (you should) just text or tell him face to face casually and friendly what the cost of the lunch was and ask if you should drop him your account number in a text or something so he doesn't forget...

    you might need to remind him everytime though. He probably doesn't mean to wrong you. Don't be afraid to talk openly with your boss
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    He might just be used to everything getting billed to the company when he eats somewhere and simply forgot all this time that you obviously can't do that.

    Ask your colleagues about it. They know better than you what this is all about.

    Maybe it is something he expects from his employees. Then try to get everyone to pitch in or leave the company

    If they just don't want to bother him or if they are too afraid to ask. Then just do it yourself and ask when he's not busy.

    If you have a significant amount owed to you by him, I would just send him an invoice via e-mail. Don't know about you, but that seems like the most professional way in my opinion.
    Nice list of items and prices, maybe even a vat section above the total.
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    14$ for a salad?! Sounds absurdly overpriced to me...
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    You should really take charge over your own finances. I would just be as bold to ask "how do you want to pay for this" and not drop the subject until the money is back in your hands.

    And if that turns out impossible, refuse to use your own money to pay for other peoples lunch from that point onward. I would even be as bold as to point out the guy ruining it for everybody.

    And use my pause time, to which I am legally entitled, to organize myself a meal without the company's involvement.
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