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‘My Rich Boss Won’t Pay Me Back for Lunch’

Photo: The Cut

Dear Boss,

I work in a small office (about five people), 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. 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 asks me how much they owe. We share 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.”

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. 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)?

Oh my goodness, you need to speak up.

Yes, it’s crappy that he hasn’t realized he owes you money — especially when everyone else is discussing repayment all around him. And you’re right to be frustrated by having to constantly foot his bill. But if you haven’t specifically told him what he owes you, it’s premature to assume he expects you to pay for him. Does your company have an expense policy or corporate cards? He may figure that you’re expensing the meals or that his assistant is taking care of it or who knows what! So you’ve got to be direct.

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 (both because that’s probably the case and because taking that tone makes things less awkward for everyone).

In fact, if there’s any way to add up what he owes from past lunches too, you’re on perfectly solid ground asking for all of it. You could say, “Joe, I’ve been spotting you for lunch, and it’s been $X for the last three months. Can we settle up this week?”

I suspect you haven’t taken that obvious step here because the power dynamic is making you feel awkward and you feel like he should have realized it on his own. But if he’s even a halfway decent person — if he’s even a 30 percent decent person — he’d be mortified to know that you think he’s been trying to rip you off this whole time.

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.

He does sound a bit oblivious and self-absorbed, or maybe just absentminded, but he can be those things without being a horrible person too. Let him know he owes you money, and assume that if he’s not a monster, that will take care of it.

And if for some reason it doesn’t fix things — if it turns out that he is a horrible person — then stop ordering lunch for everyone, or insist on getting everyone’s money up front before you do.

‘Is It Okay to Quit My Job During My Boss’s Maternity Leave?’

Dear Boss,

I have been working at my company for a couple of years and started job searching a few months ago. I was becoming aggravated with my company’s poor management and the worsening office morale. Around the same time, my manager announced that she was pregnant and would be taking three months of maternity leave. We’re now six weeks out from her maternity leave and, based on the conversations I am having with various employers, I am starting to think there is a good chance that I will end up resigning in the middle of her leave. While this is never ideal, this is especially not ideal because our department is just two people, myself and her.

How terrible would it be to quit my job, given the poor timing? I would only be leaving for something that was a real progression in my career and/or an excellent organizational fit. I also believe I could train one or a couple of colleagues in a lot of my day-to-day work relatively quickly. 

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. It’s not ideal, but it’s just how things often go, since people generally can’t control the timing of a new job offer.

Most people aren’t able to ask a new employer to wait months before they start, and you can’t be expected to turn down a job that’s right for your career because it would inconvenience your current employer.

So no, it wouldn’t be terrible to resign in the middle of your manager’s maternity leave. It might be inconvenient, and it might be bad timing, but neither of those are reasons not to do it. Your employer will figure out a way to make do. They’ll pull in help from another team, or hire temp workers, or scale back on workload until you’re replaced. They’ll figure it out.

Of course, when you resign, you should acknowledge that the timing isn’t what you would have chosen and offer to do what you can to help make the transition go more smoothly. To be clear, that doesn’t mean things like offering to stay on longer than you want or to take time off from your new job to train your replacement. It does mean things like documenting your work processes, organizing your files, and leaving behind a write-up of where key projects stand. If you really want to generate good will, you could offer to be available for a phone call or two with your replacement after you leave, but even that is optional.

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.

Order Alison Green’s book Ask a Manager: How to Navigate Clueless Colleagues, Lunch-Stealing Bosses, and the Rest of Your Life at Work here. Got a question for her? Email Her advice column appears here every Tuesday.

‘My Rich Boss Won’t Pay Me Back for Lunch’