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  • Writer's picturePeter Yawitz

Do I have to go to lunch with my boss?

Dear Someone Else’s Dad,

My boss invited me to lunch the other day. Although I know it’s important to have face time with him, I really dislike having lunch out with him because our conversations are superficial (“Oh, didn’t know you liked kale.” “Never tried mayonnaise on fries.”), and I never know what he wants from me. Still, I always accept so I don’t seem rude and unappreciative. At the end of this week’s lunch out (where we typically talked about nothing), he looked at the check, reached his hand to me and said, “Twelve dollars.”

I was shocked that he asked me for my share of the lunch, which of course I gave him. So two questions:

1. How can I make my lunches more interesting without resorting to boring food chat?

2. Should I say something to him or someone else about his asking me to pay for my share?


Likes Kale and Mayo

Dear Likes K & M,

Your instinct is right to find face time with your manager even though lunch has been painful chat-wise. You could, however, drive the conversation rather than just default to respond about your preferred sandwich cheese. So here’s a plan:

1. Think of three topics to talk about over lunch. Maybe two could be about work and one about a hobby of yours that you’d like him to know about.

2. Remind him of specific projects or tasks you’re working on and emphasize how you are solving problems. Bosses like to hear about your thought process.

3. Ask him about other initiatives going on in the firm. Try to avoid closed-ended questions like, “Are there any interesting things happening?” Instead, use conversation starters like, “I’d love to hear your thoughts about our pipeline.”

Now about the surprise “going Dutch.” Honestly, I think managers should always pay for lunch for subordinates in a restaurant, especially when they’ve invited someone. If money is an issue for you, you could say beforehand that you’re trying to be frugal with lunch these days, and would love to take a rain check. In that case he could be gallant and offer to treat you or ask when you’d like to reschedule. In any case you should look at the $12 as the cost of getting private time with your manager. Is that cost worth it to you?


Someone Else’s Dad

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