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I read and agree with Karla also. I personally don’t want to be in a car for two hours with my boss, whether I like them or not, unless they frame it as being for a specific purpose such as discussing a review, preparing for a meeting/proposal, etc. which would remove the pressure of having to decide what to talk about for two hours.

I vote for her suggestion below and going a bit further to offer the ride only if there are at least 2 other people who would go (if this is about cost savings for the company). Topics could be focused on upward feedback or ways to make the department better.

“Instead of putting the onus on them to opt out of traveling with you, flip the default to make it an opt-in: “I plan on driving in tomorrow; if you want a ride, we can meet up at the office [or other public meeting point] at 8. Otherwise, I’ll see you at the client’s at 9.”

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I read the article and Karla's response. I think Karla is right. Although the boss was trying to be considerate, his statement does raise a lot of questions. He needs to make the same offer to everyone and take out the word "uncomfortable." Say something like "There is a mtg, and you can ride with me or order a cab and expense it.", enough said. He may need some training in order to lead across genders in this modern era.

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