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Advice / Succeeding at Work / Work Relationships

Help! My Boss Won't Leave Me Alone

Welcome to our first advice column Q&A! Have a question for Fran? Email

Dear Fran,

I was recently on an international trip with my boss, and, quite frankly, traveling with him makes me uncomfortable. After we finish up our client meetings each day, he wants to spend the evening together—eating dinner together and then working together in the hotel lobby. This isn't really that uncommon at my company (though usually there's a bigger team traveling together), but I just want to go back to my room and be alone.

Then, the other night, the hotel's Internet was slow and I couldn't attach any large files to the emails I was sending him. He insisted on coming by my hotel room to pick up my files on a flash drive—and then sat down on my bed and wanted to chat and hang out. I was furious and told him to leave—which he eventually did—but I couldn't help but feel uncomfortable. I don't want to travel with him anymore, but the project we're working on lasts another six weeks. What should I do?


Dear Uncomfortable,

There’s an old Chinese proverb: The beginning of wisdom is to call things by their right name.

Your first task is to name the situation. Is this “sexual harassment,” defined by law as “unwelcome and severe or pervasive conduct of a sexual nature that affects working conditions or creates a hostile work environment?” If so, start keeping a paper trail.

My guess is we should call this ambiguous, like most things in life. Which is not to say that your boss isn’t a big fat jerk! Unfortunately, some situations are simply not in our control, and some people are jerks. And some of them get to adulthood, even into positions of power, without learning to recognize social cues. The psychotherapist in me could diagnose this, but I’ll refrain.

There could be reasons for your guy's boorish behavior, such as he’s having a hard time in his life (not your problem, of course). On the other hand, he may just feel entitled to nightly (non-sexual) companionship as part of the organizational culture, and also be a jerk. Can you discreetly find out whether you are alone in disliking him?

In any case, you need to set boundaries about what you will and won’t put up with, but you also need to be smart in dealing with people, men and women.

Don’t, for example, do what I did. My first job was at a two-person start-up in the entertainment field. The only other person in the office was my manic, married boss. I really liked the work, and the guy was brilliant, but he was constantly inviting me to dinner, looking at me longingly, telling me how beautiful I was. I told him I had a boyfriend (now my husband of 35 years), but nothing dissuaded him. After about six months I felt so uncomfortable I just quit.

But acting impulsively is almost never the right choice.

So I would ask you to determine whether you can tolerate six uncomfortable weeks in service of fulfilling your larger goals. In the grand scheme, six weeks is a short time, especially if you generally like the job, your other co-workers, and the advancement possibilities. Especially if you don’t have another job option.

You say you he “insisted,” and you were “furious.” Ask yourself honestly if you’ve actually set and expressed your boundaries clearly and firmly. One of the reasons you may feel uncomfortable is because on some level you recognize that allowing him into your room was a kind of triple foul: you permitted him to violate reasonable boundaries, sent him a mixed message, and needlessly lost control. Next time, you “insist”—on delivering your flash drive to the lobby.

On the plane next time, politely but firmly tell your boss you’re happy to review the day’s work for, say, two hours, in the lobby, but you need time to decompress alone after that. Perhaps even say you need to call your boyfriend, even if he’s mythical. And don’t go down the path of telling him about your feelings of discomfort, which could set the stage (in his mind) for more sharing of feelings—his!

You need to set your boundaries and be firm. But after that, your only real option here may be to learn to deal with your discomfort. Try meditation or progressive muscle relaxation. Exercise. Distract yourself. Keep a journal. Writing can help you integrate the emotionally reactive, impulsive part of your brain with the logical, narrative part. Try writing down negative feelings toward this guy and the situation, and be sure to focus on some positive things (and people) in your life too.

Way back when, maybe I should have stuck out my discomfort with my own boss; it’s not as if he threatened or insisted. But I was too naïve to understand sacrifice for a larger goal, too timid and confused to set boundaries clearly and firmly, and too mired in the socio-cultural idea that women should make as few waves as possible. And the fact is, that guy eventually turned that two-person start-up into one of the most innovative, successful entertainment marketing companies in the world.

Focus now on getting through the next six weeks and getting assigned next time to someone in the organization whose work (and personality) you do admire, but not by saying bad things about this guy.

Good luck!


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Photo courtesy of Ambro.