Do you ever struggle with how much to lean into office politics? I’m wondering if I should get my boss a holiday gift this year. Nothing huge, maybe just a nice box of chocolates or coffee sampler. But I can't tell if that’s normal or if I’m overthinking it. What do you all do?

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I’ve never considered getting my boss a gift.

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Yeah, I’ve actually never considered getting my boss a gift before, which is probably why I’m second guessing it now.

Do it if you want to (are you a natural gift giver?) and don't do it if you feel too weird about it. Gifts have always been one of my love languages so I often give gifts to my managers, but if I expected a big return from it or if I was doing it to suck up, I feel like it'd be a lot more stress than it's worth.

That’s a really good way to look at it. I guess it does come down to whether it feels natural or forced. I’m not usually a big gift-giver, which is probably why I’m overthinking this. I definitely don’t want it to come across as trying too hard, just something small and genuine if I do it at all. Appreciate the perspective!

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