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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?


Kat said…
Julie, I'm going to be honest and I hope it doesn't sound too brutal.

Does Judy have a voice? Why doesn't she use it? Why didn't she use it at her first job with Anne? Why did she just take the fall for this passive-aggressive micromanager?

Halfway through reading the post all I could think was, what kind of martyr is Judy? I don't see where she once articulated any of her legitimate feelings about how she was being held back by this person. Not to Anne, and not to her boss. If she's too timid to speak up for herself, she is going to find it hard to do well anywhere in my opinion.

I understand leaving a job because of a micromanager, I've done it. I even understand being apprehensive about confronting a tough situation like this one, but we are all responsible for allowing ourselves to be rolled over if we just allow it. Judy seems to think she has no power to address the she doesn't. She gives her power away to Anne without once saying a word in her own defense, or confronting Anne about her own behavior, about not meeting deadlines and making Judy look bad, etc. For all she knows, if she'd talked to Anne when the opportunity arose, Anne might have learned something and changed her behavior. OR she might have approached her own boss about the issue of deadlines not being met because of Anne's shortcomings, not her own.

Judy needs to learn to stand up for herself. She should have told Anne that she'd had nothing but praise from the other managers on the project, and was confused as to why Anne was unhappy with her performance. She should have told Anne that she felt stifled by having to clear every single decision with her, and that she felt that clearing every little thing was not conducive to her growth as an employee. She should have told Anne that she was concerned that she was handing in work timely and then being asked about it later because Anne hadn't held up her end, and that in the future she would be honest about why a report hadn't been submitted instead of allowing people to think SHE was the one who hadn't got the job done.

There are lots of Annes in the world. They can generally only treat us the way we allow them to. I know that in a work situation this can be more difficult to navigate, but just saying nothing and then "wondering" what went wrong is not going to work with difficult people. I hope that in the future Judy will look at herself and how her passivity is contributing to her career woes.

Great post, Julie!
Anonymous said…
Hmm Kat. I'm in a tough spot on the choices Judy made. I didn't ask what she said to Anne in the meeting and I wonder what difference that would have made here. I didn't get the sense she was soooo passive as I made it sound, apparently. My bad. I don't know if I can get her to reply though I have permission to report the story to ask what she should do. Also I can say this isn't par for the course with her. I think what I took away was her genuine dismay that it didn't seem to matter what she said or Anne did and that's ultimately why she left. I told her I wasn't so sure Anne was there seriously interviewing but then I'm not there so it's hard to say and I've been out of the office and that industry for a while so the politics, well I felt a little distanced. But you make a lot of good points. I'll try to get her to read and reply.


(excuse anonymous - have fired AT&T and haven't got my router set for my computer yet with new comcast)
Anonymous said…
I just re-read and I see I just kept asking her "and then what happened?" I feel so badly like I left who Judy is out of the story.
jeanie said…
I can understand it, as I lived it to a degree in 2 instances in a previous career.

One of them I felt I could speak out as he was so OTT about it - but the boss who was my "best mate" and so sweet but whiteanting - that is hard.

I have no advice - I left the industry - but best luck to your friend finding a way to use her voice. Perhaps she could request not to be in direct line of command with this woman - or if not possible, another manager be bcc'd on all information so the workflow could be monitored...?
Kat said…
Julie...I'm sure I would have a different opinion if it seemed as if Judy had confronted the situation in some way. I know it can be hard for a lot of people (me included!) to confront. It's just not comfortable. Don't feel badly, it's a really well-written post! Just the perspective I got of Judy is that everything was going on in her head, but she never said anything. If that were true, that kind of person can be as hard to work with as Anne is because you never know how they really feel about anything.
Anonymous said…
Judy should breath and just do her job instead of assuming that her new boss is too stupid to see through Anne as she has or to assume that no one at her former workplace saw through Anne.

Some people just skate through life without visible consequences for their actions despite the fact that they are fooling no one.

This is a new job and a new day and nothing "bad" has happened yet. Panicking in advance is probably not the best plan.

If one of my employees came to me with tales about a potential new hire (and if the industry is truly that small - I already know these stories) I would not be pleased. It's middle school behavior and has no place (though I know it happens) in the workplace.

Judy seems poised to try to micromanage in her own way when she should just let her work speak for her. If Anne is hired and starts up her old tricks, then it's time to confront, until then, she is making trouble where none currently exists. jmo
Anonymous said…
Kat, Judy is thinking of coming by lol. She said she did discuss her POV and expressed disagreement to Anne. She said her only regret was not stealing my line of, "Why do you want to do that?" and put Anne on the explanation hot seat. Lol. She admitted she did spend too much effort trying to smooth over and avoid confrontation. I said I thought she had a lot she wished she had done differently but hindsight is 20/20 and to focus more on now, by which I mean let that past go.

Which brings up Annies point. Yes my default advice was nose to grindstone and don't borrow trouble.

Julie Pippert said…
Here's the good thing about being slightly aged: you have this long perspective that what goes around comes around. For everyone, self included lol.

So in my experience, maybe you don't see the consequence but if you go along doing your best and maintaining a good rep on your own, that's the best thing (best revenge lol).

I guess a year isn't a long term view per se, but back when a sort of slightly similar thing happened to me (which is why I think this is such an interesting situation -- I figure we can universally relate) although it was a colleague not any kind of boss or leader...I did end up moving on (for many reasons) but without ever directly confronting the person and eventually, yes, people saw the situation for what it was.

It's funny -- for each situation I can think of that in any way relates to this general theme, it seems as if about a year elapses. Weird. Also OT but just this point that occurred to me.

So, Judy...keep your mind on your driving and your hands on the wheel (and I know you know what song I'm quoting there lol).
Ed T. said…
Ooh, this one doesn't look like a lot of fun. For years, I wondered how my mother could *ever* let herself be used as a doormat by a co-worker/boss. Later on (after her passing), I had the "pleasure" (or not) of experiencing what she went through first-hand. Needless to say, after doing so I have a far deeper appreciation of just why it is that some folks can "go postal" (though I don't condone such activities.) I survived that "era", but to be quite honest I came out more than a little damaged and gun-shy (metaphorically speaking), and have honed my sense of snark as a self-defense measure (some would say passive-aggressively so.)

I truly don't know what would happen if I were put in a position of having to work with/for the person involved again, nor what I would do if I ever met up with the person who my mother had to deal with (this is really difficult, as my mother worked for a church, and I can't help but run into some of those folks from time to time. As you said, it's a small world after all.) I do know that the possibility did raise its ugly head once (during a reorg, the possibility of returning to work with/for this person was mentioned), and I spent far too many $$$ on antacids to keep my stomach under control.

Ed T. said…
BTW, one thing I forgot mention had to do with the whole "it is hard to confront" thing. Yeah, it's hard. My current boss can't believe that people have problems going though our ombuds and conflict-resolution processes. I don't know about others - well, actually I do. When you have a lot of time invested in a job (I have 30+ years in mine), you tend to get more than a little gun-shy with open conflict, as it is often perceived as "playing office politics" and seen as a career-limiting move. Esp. as one gets older, one places a lot of value in the job one has, and the possibility of putting said job in jeopardy tends to make one very nervous indeed. Hence, the reference to antacids in my previous comment.

Julie Pippert said…
Ed, I've had limited success with confronting, even in a "productive" way. I've had far, far more success focusing on doing my own good job and waiting for what is probably usually a temporary kink to work out. When it's not, I have to find a workaround.

One time I did follow appropriate channels of dealing openly and correctly with a problem (sexual harassment) with the worst consequence. I am cautious now in my trust of HR, protocol or policy again.

It's probably why I never castigated Judy for what she did or didn't do.

I don't know what to attribute this to, honestly. I know some say it's taking away the wrong lesson, or not doing it right, or something along those lines.

Again, it usually works best IME to focus on doing your own good job and watch -- it usually smooths back out.

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