Ask Amy: Boundaries in the Workplace

By Amy Dickinson | March 26th, 2021

What was once a normal tradition now seems questionable...


A hotel room or workplace

Dear Amy: I am about to take a job at a prestigious professional services firm.

My boss makes everyone stay at his house in a city out of state for regional group meetings a few times a year.

We have to stay in his house, in his daughter’s room, in the spare rooms, etc.

I think this is wrong, and it is not something I want to do. However, now I feel like I have to do this, because everyone else has been doing it for years.

I could get a hotel, but it will make me seem like I am not part of the team.

I worry about privacy, about feeling awkward, and about my tendency not to be myself when I stay at other people’s houses. What should I do?

– Home Alone


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Dear Alone: I could imagine a circumstance in which this might possibly be a fairly benign situation (very large house, very small workforce), but not in the context of “regional group meetings” with a larger professional services firm.

I shared your letter with John Challenger, CEO of Challenger, Gray and Christmas, a human resources consulting firm, whose reaction was unequivocal: “This might have been thought appropriate in another era, but it is not appropriate now. The boundaries are not right.”

The tougher call is how you should react to this. He and I agree that you should approach the person who organized this junket and say: “I’m so excited about coming to work here. I know I can make great contributions to the team, but I would prefer for an out-of-town event at night to have my own hotel room. Is this possible?”

Challenger adds, “There is some risk to this that things might not work out at this company, but if this is so embedded in their culture, you might not want to work there anyway.”


In the tradition of the great personal advice columnists, Chicago Tribune’s Amy Dickinson is a plainspoken straight shooter who relates to readers of all ages. She answers personal questions by addressing issues from both her head and her heart. A solid reporter, Dickinson researches her topics to provide readers with informed opinions and answers. Ask Amy, P.O. Box 194, Freeville, NY 13068

© 2021 by Amy Dickinson

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