AskABoss: 'How do I gracefully make it clear that he should be expected to reimburse me like everyone else?'
I work in a small office , and probably once or twice a week, we will do a group order of delivery/takeout for lunch. I’m the most junior at the company, and often I end up being 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 reimburse me, but on the occasions where my CEO joins the lunch order, he has never paid for his food nor offered to do so.
The next time he places a lunch order, tell him on the spot how much he’ll owe. As in, “Okay, with your share of the tip, your lunch will be $17.” Or immediately afterward, say to him, “Joe, yours is $17. Can I get that from you before the end of the day?” And if he doesn’t pay you that day, remind him again the next day, just like you probably would with any other colleague. The tone you want here is utterly matter-of-fact, as if of course he’ll settle up once he knows what he owes .
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, particularly with this kind of power dynamic in play — so until and unless he flatly refuses to pay, there’s no reason to assume that will happen.
It’s really, really common to end up resigning at a time that’s inconvenient for your employer. That’s just part of doing business. People end up resigning in the middle of major projects, or right before big events, or while a key person is on leave, or right after another key employee just left, or when they’re supposed to be training someone new, or at the busiest time of the year.
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