Issue: Boss Troubles: A Gray-Area Behavior Problem

How should an employee contend with a well-intentioned but buffoonish supervisor who over-compliments and makes her uncomfortable?

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Tara Conroy* winced when her new boss would tell her, "You look especially lovely today" or "You have beautiful flawless skin" even though she knew he meant well.

"Pete was always looking for reasons to compliment people," says Tara, a sales promotion supervisor at a software company. "He was 20 years older than I was and 30 years older than most of the people on my team, so maybe it was his way of trying to be popular and fit in."

Instead of endearing himself to Tara and her team, however, Pete was losing their respect. "He'd thank people profusely for doing routine things, and it was just too much," Tara recalls. "People were thinking, 'Look, all I did was hand you the mail—I didn't climb Mount Olympus.'"

None of the women who worked for Pete thought he was hitting on them, but the compliments caused awkwardness just the same. "A couple of times, he came into my cube when I was putting on lipstick, and he said, 'Don't tamper with perfection,'" recalls Tara. "It made me feel self-conscious. And it was even more awkward when he complimented me on my appearance in front of other people."

Worse, members of Tara's team began making fun of Pete behind his back and teasing Tara about how "especially lovely" she looked.

"A Bad Example"

"It didn't seem really fair for me to let him keep up this behavior that led others to make sport of him," Tara says. "Plus, I was a supervisor, so maybe the underlings were thinking, 'Tara puts up with that kind of talk from her boss, so we all have to put up with this stuff.' I was setting a bad example. Plus, what if someone from another department heard the way Pete talked to me, and it got all twisted? It could start rumors."

Loath though she was to hurt anyone's feelings—especially the feelings of someone who clearly was trying so hard to be nice—Tara took a deep breath, walked in to Pete's office, and asked if they could talk.

"Almost on cue, he said, 'You look especially lovely today.' I said, 'Pete, that's what I want to talk to you about. I understand you don't mean anything inappropriate, but you frequently make comments about my appearance that make me feel embarrassed and awkward. A lot of times you say these things when others are present—it's something other people have said something to me about. So I need to let you know it's a problem.'"

Pete still managed to take it the wrong way. "He said, 'Tara, I'm madly in love with my wife' and started to continue. And I put up my hands and said, 'Pete, stop. This has nothing to do with my thinking you're hitting on me. Not for a minute. I know you're trying to be nice, but it's not appropriate in the office, especially in front of other people, but even when no one else is around, it's inappropriate.' I reiterated that others had commented on it and told him the last thing he or I needed was to have to go down to human resources and explain this."

"The Truth Hurts"

Pete looked embarrassed and a little annoyed, but he seemed to understand. "He said, 'Enough said, Tara. It won't happen anymore.' I felt sorry for him. It's hard to tell someone he's got spinach on his tooth, but it has to be done."

And Tara's approach did work. Pete stopped with the compliments on people's appearances and cut back on the effusive praise about their work.

Apparently, those higher up than Pete had some qualms about him as well, although for different reasons. "He was never really a big-picture, strategy guy, and he didn't understand a lot of the lingo you use at a software company," she recalls. "For a lot of things in life, he just didn't seem to 'get the memo.' If I had gone to HR with complaints about the inappropriate comments, that might have been the last nail in his coffin."

As it was, Pete hung on for a year more after Tara's talk with him—although things were always a little awkward between them—until Pete's supervisor told him he should start looking for another job. Soon after, he found a position at a medical publishing firm and left the software company.

Tara still wonders if she did the right thing by Pete, especially since his compliments didn't add up to sexual harassment. Rather, they fell into a gray area of behavior. Was it really her prerogative to tell another adult how he should behave in an office environment?

*This case study scenario is true. Names and identifying details have been changed.

Rebecca Reisner is an editor at BusinessWeek.com .