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[quote=Anonymous][quote=Anonymous][quote=Anonymous][quote=Anonymous]If it's not a cost issue, can you book them a nice hotel suite with living room + 2 separate rooms?  That way everyone has privacy AND you get quiet meeting space.[/quote]

I can, but that's not what he has requested--he sent me the link to the house he wants to book so he's done his research.  My question is, keeping in mind that I have a great relationship with my boss and he's a cool guy, is it worth me bringing this up to him, even though the woman hasn't expressed any ill feelings towards the arrangement?  Or, just keep my mouth shut and let her fend for herself if she's uncomfortable?  I don't want to overstep my bounds but I want to look out for my fellow female in the event she feels uncomfortable with it but doesn't want to rock the boat as the new girl.  My boss is a great guy but he's so laid-back (think tech start-up attitude) and I don't think he is looking at this from her view as a woman at all.  I'm also not sure how her husband feels about this but I'm not going there with my boss--that's her business.[/quote]

I don't think you can go to the woman behind your boss' back... he wouldn't like that + she is unlikely to have an honest reaction.

Best possible solution - you say to your very cool boss, "Hey Frank, I am about to book the accommodations for your travel to Texas with Alex and Jill.  I know the reasons you want to stay in a house versus hotel, but I wanted to flag something for you before I book.  This is a bit awkward for me to say and I apologize if I am overstepping my bounds, but I think it's important:  if I was new to the company and did not know you - like Jill - I would be uncomfortable staying in this type of causal setting with two men on a work trip.  Before I book, would you like to check in with her on the arrangement?"[/quote]

This is perfect. [/quote]

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