'What's the Best Way to Handle Lunch With My Boss?'

I am in the second real job of my career. It’s a great job with coworkers who respect each other, unlike my previous job, which was a place where everyone screamed all the time and the staff was underpaid and monitored by camera by the owner.

Several times a month, I am out of the office for meetings in the same neighborhood where my manager is having (separate) meetings. Maybe three out of four times, we'll finish around the same time and travel together to the office. Most of the time this happens, my manager will ask if I want to get lunch first. I don't feel any pressure either way, she lets me pick the place, and we enjoy each other's company. She even picks up the tab about half of the time. It's a good situation!

I have not been able to figure out the right amount of gratitude to show for the meals that she treats me to. I feel like working at my previous toxic job set a low bar for interactions with the boss, so my initial impulse is basically to grovel. Just a quick "thanks for lunch!" a couple times a month seems like not enough, but anything more effusive feels off. What to do?

As long as you’re making a point of saying thank you each time your boss picks up the check, that’s all you need to do!

In general, when a meal is eaten in a business setting, the convention is that the person with the most power will pay. If your manager takes you to lunch, she (or the company) will usually pick up the check. If you’re invited to lunch as part of a job interview, assume the company you’re interviewing with will pay. It is worth noting that the more social the occasion, the murkier this gets: At a team happy hour, for example, everyone might be expected to get their own drinks. But when it’s a one-on-one with your boss, she’s likely paying.

I suspect you’re right that your previous job warped your norms about what to expect from your manager—which is so common and one of the many ways toxic jobs mess with people—and as a result you’re feeling disproportionate amounts of gratitude for what’s actually a pretty normal thing for managers to do.

That’s not to say you shouldn’t be appreciative. You should! But “thank you for lunch—I enjoyed it” is an appropriate amount of acknowledgement. If she took you to a restaurant you especially enjoyed or hadn’t been to before, you could also comment on that, but much more than that is likely to come across as excessively effusive. It might help to imagine what you would like to hear if you were in your boss’s shoes—most likely you’d like a sincere, appreciative acknowledgement but wouldn’t expect anything beyond that (and might be weirded out by something more over-the-top).

But let’s talk about the broader question that I think is lurking in your letter: How grateful should you be—and how must gratitude are you expected to show—for fairly small acts of kindness at work? It could be a manager buying you lunch, or a coworker who grabs coffee for you when she’s getting her own, or a boss who goes out of her way to reassure you when you’re nervous about a client presentation. Those are fairly small in the scheme of things—they’re not really handwritten thank-you note level—but they’re kind gestures that make your work life more pleasant.

The best way to respond to small, kind gestures is twofold. First, give a sincere thanks in the moment. It doesn’t need to be flowery—just something like, “Thank you, this was so kind of you” or “Thank you, I really appreciate this.”

Second, let the gesture warm the whole relationship you have with that person. These actions are about connecting with you as a fellow human and expressing goodwill. Welcome that, and make a point of returning it with your own warmth and good will, whether it’s taking an extra minute to check in with someone when they’ve been out, or giving them the benefit of the doubt when you have the opportunity.

Of course, ideally you’d approach all your work relationships with warmth and good will, not just people who do you small kindnesses! But be particularly thoughtful about it when someone has gone out of their way to invest in their relationship with you. (There are exceptions to this, of course! If someone is mistreating you, you don’t owe them the benefit of the doubt because they once bought you coffee.)

Get more good advice from Alison Green at Ask a Manager or in her book. Do you have a pressing work-related question of your own? Submit it using this form.