Bearer of Bad Tidings: When should you take the risk and tell a boss about a difficult coworker?

"I knew my boss was interviewing someone for a new position," my friend told me, "But you could have knocked me over with a feather when she walked in!"

My friend Judy and I were talking about her experience with a difficult coworker. Judy lives in another town and works in a small-world-after-all industry -- one I used to work in, and truthfully, the one I'm in now is very much the same: you tend to cross paths over and over with the same people.

Judy actually had worked with this difficult coworker at a previous job. When Judy joined that company, this woman, Anne, was already well-established. She was cheerful, friendly, outgoing, and one of those people who loved to accentuate the positive. She took Judy under her wing on Judy's first day.

"I went home that night and told my husband that if she was a reflection of how this company was going to be, it was going to be my best job ever," Judy recalled.

For the first few months, Judy felt like she'd never had a better colleague or had ever performed with such enthusiasm at a job. Anne was not her direct supervisor, but she was Judy's team lead, and so, in a sense, Judy looked to her for leadership.

Slowly but surely, Judy found herself deferring more and more to Anne, even though Judy considered herself a very independent and opinionated person, "For some reason, I just kept turning my head to seek Anne's reaction in meetings, and things like that. At first I thought it was a sign of my respect, but later I realized Anne was very passive aggressive and would, under the aegis of being helpful, express her disapproval of me being too self-starting."

Judy found herself feeling stunted and frustrated in her job, and worst of all, really frustrated with Anne. Then she'd chastise herself about that, rationalizing that everyone loved Anne and Anne had always been so good to her. Judy felt angry most of all at herself for feeling this annoyance about Anne. Anne was successful, looked up to, and well-respected in the company. She was included in high-level meetings, constantly referred to as someone to ask, and plugged in to many projects that were considered "career makers."

"One time, while Anne was on a two week vacation, this opportunity came up to do a project. It would be a sort of cross-team deal and I was really excited about it. I told my boss it sounded great, and as soon as Anne returned, I talked to her about it and she was enthusiastic. The project was a go.

"Anne was plugged in nearly full-time to another project, so I got a lot of latitude and lead on this new cross-team deal. I thought, here we go, this is great, just the opportunity I need, and Anne seemed so great again after her vacation. She seemed really supportive of me doing all of this. I liked the other team lead a lot, and was flying with the project."

Judy was happy and confident, back to loving her job. Until the meeting.

"Anne called me in for a chat. She said she wanted to touch base about the project I was on. As my team lead, I'd kept her in the loop, sent progress reports, etc, but the other team lead was really empowering, trusted me to handle things on my own. With Anne, I'd gotten in to the habit of reporting every single little thing, but on this other project, I'd let that go. Initially I'd been in constant contact with Anne, but she seemed so busy with her other project, and sometimes days would pass without her even talking to me, which was fine, unless I was asking for an okay. Sometimes she wouldn't even acknowledge or reply to some of my emails, other times she'd reply when none was needed. Overall, though, I figured she was letting me run with this, which made sense."

In the meeting, however, Judy found out that wasn't the case. Anne had been keeping an eye on her, and was displeased with the cut back in reports.

"Most of all," Judy said, "She was angry that I hadn't sought her approval before each decision."

Judy was stunned. Her boss and the other team lead were completely satisfied with her work. She'd received nothing but praise and positive response.

"Actually, I was relieved, a bit, to have a break, because Anne had gotten to where she was really micromanaging. I'd put together a project report, which really I should have been able to send straight to my boss, but I had to pass it by Anne first, and sometimes it felt like she'd change things just to change them, you know what I mean? What bothered me the most, though, would be times I'd sent in a report or whatever to Anne, and she'd be so behind, probably due to micromanaging more than just me, that she'd miss the deadline. So I'd be walking down the hall and my boss would stop me to say, 'Hey Judy, do you have a projection of when you're gong to be able to get me that summary?' and I'd feel awful because if I said Anne had it, somehow I felt culpable and nasty. But if I didn't, then how was I supposed to respond."

Judy alternated her answers to her boss, but all the time, she felt as if she were covering for Anne, which she began to resent.

"My boss would pop by my office and say a client was wondering when we'd have the quality results, and I would have completed it but I was waiting on Anne. I was so frustrated. The worst was, no client ever got mad, my boss was always such a nice guy about it, and there was never any crisis or explosion."

Until that day in Anne's office, Judy had no idea that she'd built up such anger or that things were as bad as they were.

"Once Anne began talking, it was clear to me that she had acted out this entire scene and drama in her head and worse, I suspected with my boss. I felt like a cornered animal. What had she said? And to whom? What was going on? What would be the ramifications? I nearly quit on the spot. In the space of one workday I went from the heights of feeling so confident about my work and my reputation to the depths of despair."

Judy didn't quit, but she did go home and start job hunting and sending out resumes.

"I didn't really want to leave my job; I wanted it all to work out. The thing with Anne was like a bad dream. She wasn't mean, not at all. She just flayed me with kind rebukes and allegedly helpful support that largely entailed cutting me down to nothing more than a computer mouse she moved and executed tasks through. I felt like a total tool."

Judy found that Anne was good to her word. She did expect that once again Judy would pass every thing by her before making any move decision, or completing any task. But Anne didn't make it easy by being readily available or by giving Judy a timely answer so that Judy could stay on task and on her timeline.

"After our talk, she jumped in to the other project practically full-time. I didn't get cut out, but I felt as if all my authority had been stripped.

"The thing is, nobody seemed upset. I felt like the only person who wanted to scream about the craziness of this, the only person who was furious and upset. Every now again someone would wonder when they'd get some answer or information, but that's it. No crisis. I felt like a chicken running with my head cut off, constantly frustrated, stressed, ripping my hair out. But everyone else seemed fine, and I thought you know, that's probably because I'm just keeping on and trying to smooth things out as best as I could. But I was losing my mind and had no idea what to do.

"Did I confront her? Did I talk to the other team lead about how the project changed? Did I go to my boss? It seemed as if every angle presented a lose scenario for me. Anne continued to be well-respected and important, but I felt as if I had lost all credibility.

"After that project was finished, I was practically cut out. I started getting more menial things to do, wasn't included in meetings, and communication deteriorated. The other team lead would drop by my office, but to ask if I knew where Anne was. I'd see projects and opportunities come in, but they'd all go straight to Anne. I started basically showing up for work and surfing the Internet and Anne didn't even seem to notice or care. She went from micromanaging me to never even noticing me."

Judy felt confused about what her job was, where expectations of her lay, what she was supposed to do, and how she was supposed to act. The hardest part for Judy was not knowing how it all went so wrong, and why things went so badly.

"I thought I did a great job. I never heard a complaint or a negative word, until that day with Anne. Even so, her complaint wasn't so much that I was doing a bad job or that there was a problem, but it was more that I wasn't doing it exactly as she would do it."

The next hardest part for Judy was why people respected Anne so much when she frequently missed deadlines, kept people waiting for answers or information, and dropped balls.

"I don't know if she did it to everyone across the board, but things that I was involved in, yeah, it happened. I guess she got away with it because in those cases, it felt like I was the one who ended up with egg on my face. I just don't know how or why I ended up in the patsy seat."

When Judy found an opportunity to leave, she grabbed it, but she had to leave diplomatically. It's a small-world-after-all industry, and she knew she'd take her reputation with her, and knew that it was possible someday she'd have to interact with former coworkers again.

She'd barely been at her new job a couple of months when she saw Anne walk in to meet with her boss. Anne saw Judy, and waved, but didn't greet her or act friendly.

Judy felt a rush of anxiety. She doubted Anne would say anything negative -- that wasn't her style -- but somehow, she'd make her opinion known. Judy feared another deep freeze, but most of all, she feared that she'd have to work with Anne again.

I didn't have any insight for Judy into the why of Anne, much less the how, or the what. I also had no clue how Anne managed to skate so easily over what would be majorly dangerously thin ice for most other people.

What Judy really wanted to know, though, is whether she should tell her boss anything about Anne, and her work history with Anne.

"If I'm proactive and approach my boss, say 'hey I noticed Anne was here meeting with you the other day,' I can hope that maybe she'll tell me what's going on, but maybe she won't and she'll be curious what I'm driving at. I could be direct and say I'd like to talk about my experience working with Anne and focus on the performance facts of micromanaging and missed deadlines. or I could wait and see what happens, Anne might not take a job with us, or she might not be offered one. I like Anne, she's a person who wants to be a good person, honestly, but I just prefer to never work with her again. What should I do?"

What would you advise Judy to do? And why?