my friend is a bad employee — how can I help?

A reader writes:

I’m looking for some advice to pass along to a friend. I’m a huge fan of your blog (it has helped me in two job application process, and I recommend it to everyone I know). My friends and I can’t seem to figure out what the best way to handle this situation.

I’ve to come to realize that my friend is a bad employee. I think we’ve all worked with bad employees, and I always wondered what is going through their heads. Now that I’m friends with one, it’s offering me great insight. But I’m trying to figure out what I should tell him.

Some back story: Last year, out of law school, he got a job with a small firm. He would constantly complain about the partner he worked under complaining about his work. He would get upset when he was told to write papers in a different format, and I often urged him to understand that as his boss, it was his prerogative how things were formatted and he should learn to adapt. He also grumbled about the occasional long hours or having to work weekends to get projects on deadline wrapped up. I also suspected there was a personality clash going on. After a few months, he was fired with almost no notice. I can’t say I was shocked.

Fast forward a year and he is at a new job. After a few months, the grumbling about work has started again. What leads me to believe this isn’t just a series of bad bosses is the attitude I’m seeing from him outside the office. There seems to be zero initiative or drive. Most importantly, he often complains about being criticized for making mistakes. I’ve always worked with the approach that if I make a mistake, I need to work doubly hard to fix it and not make the mistake again. Instead, he seems more upset that someone called out the mistake and less interested in fixing them.

Recently, he complained about having to stay late to fix a problem with seemingly no remorse for creating the problem himself. We also work in a city (Washington, D.C.) that is famous for expecting people to work long hours and give more than the standard 40-hour week. He almost flatly refused to work late or go in early. (He’s salaried.) I understand that he might just want to be gainfully employed with a 9-5 job and is unconcerned with advancement. But I worry, based on the complaints I hear (and the frequency that he’s mentioning mistakes), that he might find himself out of a job again before too long.

He’s also a total introvert and really doesn’t enjoy people. He avoids his office at all costs. He is a horrible networker. Plus, he’s one of those people who thinks he’s the smartest person in the room. I’m not sure humility is one of his strengths, and I’m sure that shows in his office.

I work in a different field and I have tried to offer some of my own personal experience that has led to professional success. It doesn’t seem to be sticking with him, plus he thinks the two worlds are too different for it to matter. Do you have some advice on what you can tell someone who seems to an awful employee with a bad attitude?

Well, I’m not sure this is your problem to fix.

I understand the impulse to want to help, and I can imagine how frustrating it is to be on the receiving end of all of this complaining when you can see that he’s the problem, but ultimately, you’re his friend, not his career adviser, and you’re limited in what you can (or should) do.

That said, there are a few things you could try … but you should do them with the understanding that it’s very possible that nothing you say will make a difference, or you might find yourself more frustrated than he is.

The biggest thing I’d try is nudging him away from complaining and more toward doing/thinking/changing. For instance, when he’s complaining, say something like, “It seems like your office really values X, Y, and Z. If those things are annoying you, is it the right fit for you?” Or, “Law firms in D.C. are pretty well-known for operating like that. Will you be able to be happy there, knowing that?”

Part of this is about taking the value judgment out of it (i.e., that he’s lazy/obstinate/etc., even if he is) and really zeroing in on the part of the problem that you as a friend have standing to care about: He’s unhappy with the situation he’s in.

But you also have standing to function as a reality-check, as long as you do it with a fairly mild and non-judgmental tone. For instance: “Hmmm, what you’re describing seems pretty normal to me. Most managers want A, B, and C.” Or, “Mistakes at work can be a really big deal, especially if your manager doesn’t get the sense that you’re taking it really seriously. What’s worked for me in the past when I’ve made mistakes is….”

But you’re going to have to be careful not to make his problems your own. Be a sounding board and point out where what he seems to want is at odds with where he is, but don’t get drawn into feeling responsible for changing him beyond that.

(The one exception to this: If you have an extremely close friendship and think that he would value a kick in the ass from you, then you can have one serious heart-to-heart with him — as in, “I want to talk to you about something that’s really worrying me. What I’ve seen from you is XYZ, and I’m worried that it is impacting your career and ultimately will make you far less happy than you could be.” But that’s for extremely close relationships only, and you pretty much have to drop it after that.)

Read an update to this letter here.

{ 90 comments… read them below }

  1. Kelly L.*

    I also think it’s important to realize that he may not exhibit that attitude in the office. I don’t think someone’s steam-blowing-off to his friends necessarily correlates to his work or attitude while actually at work.

    1. Anonymous*

      Considering the friend was fired from his last job, I’d say it’s a safe bet that this is more than just blowing off steam to his friends.

      1. Kelly L.*

        Could be. Or it could be something else, but the OP doesn’t necessarily know; she’s only speculating.

  2. Anonymous*

    Before you follow Alisons advice Id ask your friend if he even wants your advice or not.

  3. Portia de Belmont*

    I’m sorry your friend is in such a bad place; these days law offices can be brutal environments. I’ve seen way too many first year associates go from bright, capable, and energetic to burned out husks getting through the day on rage and caffeine. From what you describe, he might be better suited to a different type of law practice, like a corporate legal department, or even as a sole practitioner. I’d encourage him to think about what he likes to do professionally, and try to find a place that’s a better fit.

  4. College Career Counselor*

    If he’s a BrandNewLawyer(tm), he may not have the experience or skills to do a transfer to a new type of practice yet. He may also have a boatload of debt (average indebtedness for law school grads was $98,000 in 2012) that is keeping him yoked to a salary in a job/environment that’s not a good fit.

    All that said, speaking as a career counselor, he does sound like he needs a kick in the ass because he will get himself bounced out of another job right quick and there are a ton of lawyers stacked and waiting to apply for said job.

    The unwritten rules of the workplace (how late you stay, how you approach people, how team-focused you appear, the format of your reports/research, etc.) are all critical to success and frankly, continued employment. He sounds like he’s in the process of sabotaging himself by coming off as an entitled recent grad with a lackluster work ethic. As others have noted, perhaps he doesn’t present that way at work, but if he’s been fired once after just a few months, I’d say it’s likely that his attitude is leaking through.

    Bottom line: Alison is correct about this not being your problem to fix, because you can’t. Your friend won’t change unless he actively wants to.

    1. Vicki*

      What in the world was he THinking by going to law school?
      And how dod he get through law school without having to reformat things according to standard, work late, etc?

      1. Ruffingit*

        Having survived law school myself, I can say that it’s a very different experience of stress than working in a firm. There is a lot of formatting according to a standard (The Bluebook is the citation formatting bane of every law school student in America) and there are a lot of late nights.

        But, there is no one really watching over your shoulder and if you don’t produce your work product daily (that is, keep up with your outlines so you can pass the one exam at the end of the semester that determines your grade), that’s on you. No one else cares if you do that or not.

        So while there is a great deal of stress in many ways, it’s much, much different from the stress you handle in the working world of law firms.

    2. FYI*

      This. Lots of us lawyers are stuck in jobs we hate. I do a good job at work most of the time, but I’m not super-employee and refuse to spend time networking or at nonbillable events. And I complain to my friends.

      (Also, while I haven’t been fired, getting fired in the legal field can have a lot more to do with your firm’s financial state than your skills/attitude.)

  5. Tiff*

    If this is a friend and not a co-worker….I’d give it to him. Straight, no chaser, may have to yell it out and have a drink later.

    That’s what friends are foooor…….

  6. AnotherAlison*

    “Plus, he’s one of those people who thinks he’s the smartest person in the room.”

    So, yeah, he’s probably not going to listen to much of what you have to say.

    I would only be concerned if you actually worked WITH him, because the perception by mgmt can sometimes be “birds of a feather” and it would reflect on you. But you don’t work with him. It’s kind of like with my teenager. I can keep reminding him forever to set his alarm, get to school on time, do homework, etc. OR I can let him experience ramifications of being a bad student and make his own decisions to change his ways. People generally have to make mistakes to grow.

  7. TRB*

    I’m pretty much with Alison on this one. Just a few comments and first and then if you’re really close, a serious talk.

    I have a few friends that are similar and sometimes the issue is that they just don’t work well under authority (or want to work well under it). These people usually do better when freelancing/consulting/starting their own businesses. The problem is, if you don’t get any experience you can’t work for yourself because who is going to hire you/use your services?

    Hopefully your friend sees reality (through either your advice or getting fired from basically every job) and can use these jobs to gain experience so eventually he doesn’t have to work for anyone or realize that this how the world works and he’ll have to deal with it.

    1. Katie in Ed*

      +1. I’m one of those workers who tends to bristle under authority. That, coupled with a general lack of patience, particularly when I get the idea into my head that things are being done the “wrong” way, can make for a frustrating work life. I’m lucky though – I’ve been able to successfully work in consulting for a year now, and having a sense of power and choice over my work for the most part dissolves the attitude. If I don’t want to work with a client, I don’t have to. If I need a day off, I can take it. And I am eternally grateful and feel privileged that I’ve found a way to live my life that way. I don’t have to submit to my negative qualities – just work around them.

      It sounds like your friend doesn’t feel like he has a lot of control over his life/career, thus all the grumbling. Maybe there’s a way you can help him delineate between the aspects of his career he can control and the aspects he can’t. This might be a bit too much if he feels like he’s completely lost his grip on it, but it might be worth a shot.

      I definitely agree with Alison as well – take away the value judgement. There’s no utility in labeling someone as “bad.” It won’t help either of you.

  8. AnonForThis*

    Ugh, this makes me wonder if I’m a bad employee. I’ve always had lots of praise and stellar references, so I’m hoping that means that I at least hide this kind of thing well at work.

    I’ve struggled to find work that feels like a good fit. This means that I complain or worry out loud to my husband, and to a good friend at work that struggles with some of the same concerns I have.

    I think that I really do want a 9-5, individual contributor, do-it-excellently-then-go-home-and-forget-it kind of job. I don’t have this kind of job; never have. I’m saddened by how the (nonprofit – I have no idea what the rest of the working world is like) world seems to be moving toward longer, crazier, more demanding hours – it just doesn’t seem like a healthy way to live.

    Anyway, just mourning that I might be a crappy worker. Sigh!

    1. Not so NewReader*

      Anon, I don’t think OP’s friend EVER wonders if he is a crappy worker.

      By the simple fact that you wonder about this, makes me think you are probably not a bad worker at all.

      1. LisaLyn*

        Ha, I agree! Plus, I don’t think wanting a 9 -5, work hard while you’re there and then LEAVE it there, means you are a bad employee. Even in the example in the OP, the friend didn’t want to stay late to fix a problem he created. Now, that I would see as an issue. But just in general? Naw.

        1. Jamie*

          No – not a bad worker in many positions at all, but it is something people choosing professions should think about.

          The work a solid 40 and leave it at the door is great – but it’s not realistic in a lot of professions. This attitude will be the death of your career in most IT jobs and for most lawyers I know. In some industries I’d throw Project Managers in there. Most upper management (until the very end when you are just waiting to retire – those people tend to scale back to a solid 40 while others are being groomed as their successors.)

          If the normal schedule is important to someone they need to take that into account when choosing a path.

          (none of this is directed at Anon for this – just typing out loud)

          1. AP*

            I think that’s one of the big takeaways for the interns at my company. Office experience, firsthand knowledge of the documentary filmmaking process, and an up close and personal look at the work/life balance (or lack thereof) that pretty much the entire industry abides by. Better to make those decisions early…

    2. Ash*

      What in the world? If you aren’t getting fired from your job and get good reviews, why would you ever think you’re a bad worker?

      1. Not so NewReader*

        Really. There are different types of people with different goals. Just because someone wants to work 75 hours per week and someone else wants to work 40- does not make one person “better” than the other.

        It is just different that is all.

        Some people see a job as part of life and some people see a job as ALL of life. We need both types of people to make our society function.

    3. Joey*

      Here’s what I do: no matter how bad things get on the job you can’t let it show at work. Nothing, nothing, nothing good will come of it. It might feel good initially to release your frustration, but by doing that with co-workers you are creating a perception that you’re unhappy at work. That’s going to seriously limit your career at that employer and the potential highlights you may be able to add to your résumé.

      Go home and tell your SO about all of your work problems if you need to talk about them. You may not even be looking for solutions. You might feel better just getting it out. Whatever you do tell your SO exactly your intentions. Too often spouses (or friends)unnecessarily assume you need a real solution when the solution is simply talking about your work issues.

      And don’t feel bad about complaining about aspects of your job. There’s no perfect job- there will always be parts of it that are frustrating.

    4. Sarah*

      I sympathize with you, and much of your experience is my experience too. I think some of it is fit. I have had nonprofit/public organizations that strive to achieve work/life balance, but my current job has none of that (and it’s driven by the director). I do good work, and I meet deadlines, but I have no interest in staying here long-term because of the lack of work/life balance (among other dysfunction).

    5. Katie in Ed*

      I think a lot of folks in idealistic fields struggle with this. You can love the mission, but it can ask things from you that you aren’t prepared to give. Coming to terms with that can be very painful and not an easy choice. Try your best not to sweat it, and make a choice that’s good for you.

  9. Anonymous*

    To be honest, if I were a mediocre employee and one of my successful friends who is not even in my field tried to step in and “help”, I’d be annoyed. But that is just me and I tend to be overly independent, and only you know how your friend may react to unsolicited advice. Your friend may also need an outlet for blowing off office steam, which we all need to do.

    1. Jessa*

      I think the issue here is why the friend is venting. Sometimes people vent because they want to vent, not because they want a solution. The OP can try Alison’s advice, but the best advice for the OP may be “Hey I get you wanna vent about this but I’m not up for it right now. I always want to try and help you fix it and I don’t think you want that. So, how’bout them “fill in team?”” And stepping back and NOT engaging when the venting happens.

  10. S3*

    Reading your question, I was reminded of 2 situations I’ve been in.

    First, I had a friend who became a coworker. She was a great friend, but a terrible employee. For the sake of my job & my professional standing at the office, I had to distance myself from her significantly at work. It was a shocking lesson for me on how different the same person can be in a professional vs. non-professional setting.

    Next, I managed a recent college grad who suffered from similar delusions of grandeur while being a real menace to the workplace. I couldn’t seem to say or do anything that could convince him that he needed to work much, much harder if he wanted to advance his career.

    I went to my supervisor for coaching on how to help the employee. My boss said, “It sounds like he may need a life lesson.” Your friend might find himself in a similar boat.

    I like the Kris Carr quote, “The only time you can change someone is when they’re in diapers.”

    Perhaps your role in your friend’s life is to pick up the pieces when he finally has the maturity to recognize the life lessons the universe has been sending his way.

    1. Jberry*

      I’m going to second this advice. I’ve had a similar experience with a co-worker who I really liked, and often went to bat for with senior-level staff; however, that co-worker is transactional, doesn’t push herself, and finds so many opportunities to blame her failings on others. She just does not see that she doesn’t produce quality work, but in her mind it is always the other person’s fault. I avoid her now, and explicitly ask to not work with her since it only adds to my own workload. I think time and more experience are the only things that will ultimately allow her to understand why her work style is not sufficient. Maybe your friend is the same way.

  11. Mike C.*

    Like Joey said, make sure that your advice is welcome.

    Remember to separate the actions from the person – rather than saying, “I think you’re a bad employee”, say, “I think these behaviors are holding you back”. Not only is it easier to swallow the medicine, but it goes from being a discussion about “what you are” to a discussion about “ways to improve yourself”.

    I can’t help but think that the extreme shyness is acting as a multiplier, but I don’t really know how to address that issue.

    Best of luck!

    1. Katie in Ed*

      Exactly. You can’t change “what you are,” and it’s painful to be told you should. You can change “what you do,” and it doesn’t have to be personal.

  12. Elizabeth West*

    You know what I was thinking as I read the OP’s question? That the friend HATES his new field. Plenty of people go to law school (or teacher school, or med school, or [insert specialized training here] school) with a skewed vision of what the job is really like. I did–and ended up quitting teacher school because I realized it was not for me. If I had seen it through, I might have ended up in the same position.

    The OP might make a suggestion, worded kindly as in Alison’s answer and Portia de Belmont’s comment, that the friend explore options where his training would be relevant but without the cons of working in his current environment. OP might also offer to help research these (but don’t do it for him; just help him if he asks). Plenty of these skills are transferable. And like Portia says, he might even be able to find something in the field with less pressure.

    1. fposte*

      Elizabeth, I was thinking the same thing. This all sounds like somebody who desperately doesn’t want to be a lawyer, or at least the kind of lawyer he’s stuck being right now. Unfortunately, screwing up badly enough to get fired doesn’t enhance your options, it diminishes them.

      But I’m inclined to think this is something the OP can’t do anything about. And if “friend” is code for “boyfriend,” I’d certainly be careful about financial entanglements with anybody with this approach.

  13. JMegan*

    My ex husband is an alcoholic, and I spent a lot of time trying to “manage” our marriage. In addition to which, some of the things he told me about the way he works were absolutely horrifying to me – he’s rude to customers (and proud of it), calls in sick as often as he can get away with it, and so on. If he were my employee, I’d have fired him years ago.

    But the thing is, he really genuinely didn’t want my advice, or suggestions on how to change his behaviour either in our relationship or at work. No matter what tactics I tried – friendly advice, pointing out consequences, swift kicks in the ass, etc – he just wasn’t going to change. Not for me, or his boss, or his colleagues or his friends. (Hence, why he is now my ex instead of my husband!)

    Now, this is not to suggest that your friend has a substance abuse problem, and of course the dynamics of a friendship are quite different than those of a marriage. But the TL;DR here is what Alison and many others have been saying – this is not your problem to solve. All of your good advice and best intentions won’t do a single thing to change his behaviour, until he himself is ready to change.

    1. Apostrophina*

      You don’t need a substance-abuse problem to have that personality, either. One of my relatives was always one of those “smartest guy in the room” people and has pretty much left a trail of irate clients and irritated coworkers everywhere he went. You can’t tell him anything; it will always be the problem of Those Other Jerks, and a world of 7 billion provides an inexhaustible supply of Other Jerks.

      (On the other hand, when I had to have a sensitive conversation with my boss once, Mom’s advice was “Just don’t call her a @^&!! the way Relative did HIS boss [when he quit his last job], and I’m sure you’ll be fine.” I didn’t, and I was. :) )

  14. Amy B.*

    I used to think when people complained or told me their problems, they wanted my advice. Otherwise, why would they be wasting my ear-time (I can only handle hearing a certain amount of whining a day). Then I realized they just wanted someone to side with them and console them regarding the meanies in the world.

    Now my auto-response is, “You have two choices: Change it or Accept it. And I can’t make the decision for you.”

    1. Elizabeth West*

      I like to say “Do you want me to give you advice, or do you just want to vent?” I wish people would ask me that. Sometimes I just want a sympathetic ear, and they leap in with both feet telling me what to do.

      1. Lynne in AB*

        I usually want advice, and so I default to problem-solving, but my friends usually want a sympathetic ear – so I am mindful about this and try to strangle my automatic problem-solving urge, but sometimes it’s hard to remember to do. :/ It didn’t even dawn on me until my mid-twenties that often people DIDN’T want to go into problem-solving mode, and wanted sympathy instead. (That still doesn’t feel natural, but I’ve mostly learned to compensate for the way my instincts lead me astray in this. Mostly. I can definitely understand why some people leap in…)

  15. anon lwyr*

    “He’s also a total introvert and really doesn’t enjoy people. He avoids his office at all costs. He is a horrible networker. Plus, he’s one of those people who thinks he’s the smartest person in the room. I’m not sure humility is one of his strengths, and I’m sure that shows in his office.”

    Hmmm. Sounds like most lawyers I know. I wouldn’t worry too much about him, if he’s any good, his work will speak for itself, if he’s a terrible lawyer, he’ll eventually find a place where he can succeed at doing mediocre work. (I am a lawyer, by the way).

  16. Anon*

    I guess this falls under Alison’s “if you are really close” comment. If you are this worried, I would guess that you were really close and I would say that you should give it to your friend straight. Then next time he complains, use it as an opportunity. And to be honest, I’d probably harp on it if I saw the behavior continue.

    But maybe this is me and how I do relationships. My husband and his best friend are very, very close. It’s a bromance in every sense of the word. But he watches his friend make some serious life mistakes and downright refuses to make any more than an oblique comment. And nothing changes. I don’t get that. But that might be a guy thing.

    1. Ash*



      Anyway, don’t mark something down due to sex/gender when it’s most likely to do with people. Maybe years ago your partner and his friend got into a fight due to unwelcome advice and he doesn’t give any now? Maybe he doesn’t care because his friend is an adult? Or maybe because he realizes it’s not his place to change other people?

      1. Joey*

        Nope. Guys do this a lot. I don’t know if women do to, but guys definitely do.

        I think its this: guys assume one or more of the following:

        1. Someone else (like his wife or gf) already told him he screwed up.
        2. The screw up was so bad he already knows.
        3. You’re not going to change him so why bother.
        4. Discussing it is going to kill the good time we’re having.
        5. Guys have fun by showing off or making fun of each other. Having a serious talk about problems isn’t fun.

      2. Elizabeth West*

        Joey’s right; guys generally (not always) don’t act the same way about this stuff with each other that women do (and vice versa).

        That’s why I hit up my guy friends when I need to know what my male characters might do or not do in my fiction. Like, would a guy who likes this do this, or talk about it this way, or at all? I know what I would do, but it’s typically different than what they would.

        1. HR Abnormal*

          I’m a guy, work in the commercial seafood industry which is full of guys. I’m confident I speak with authority.

          Joey hit it square.

  17. VictoriaHR*

    Everything I know about the law or being a lawyer, is from reading John Grisham novels. That said, even I know that first-year (or second-year or third-year) lawyers get the scut work, the long hours, and the rush to bill clients as much as possible for the benefit of the firm. How did he not know this?

    I find it hard to believe anyone is friends with this person.

    1. Amy B.*

      “Everything I know about the law or being a lawyer, is from reading John Grisham novels.”

      Me, too!

    2. Cat*

      Oh, come on, I think most of us have friends who have gone through rough times that made them less-than-always-pleasant to be around; it doesn’t mean they’re not worthy of having friends or that we don’t stick with them out of a reasonable and deserved loyalty they’ve earned.

      1. iseeshiny*


        It’s really easy to judge on the internet, where all we see is the aspect that has people writing in to an advice column – I am sure this person has some qualities that make him the kind of friend that OP is willing to help.

    3. Liz T*

      Some people head to law school because they think it guarantees them a 6-figure income for life, and because they can’t think of anything else to do. Both my parents are lawyers, and loved law school, and still think that very few people who become lawyers actually should.

      Plenty of people think they know what they’re getting into, but really really don’t.

    4. Pussyfooter, aka. OneoftheMichelles*

      Many people have never read a John Grisham novel…I’m 40, read other things, and I never heard of any of that until I “heard” your post.

      *I did make a mental note, higher up the thread, to ask the normal work hours/expectations of any future career possibilities. But I have the life experience of a 40-yr-old, not some young person just out of college and new to the work world.

  18. Not so NewReader*

    Wow. Can’t fix people who don’t want to be fixed.

    OP, try not to get too bogged down in your friend’s trials and tribulations. I think general questions like Alison suggested are best.

    “Gee, Friend, you seem so unhappy. I would love to see something better happen for you. What do you think you would like to do to help your happiness level?” Repeat as needed.

    From the sounds of it you have put everything you have into helping your friend already to no avail. Sometimes friendships like this just wane and vanish. The reason is eventually the difference in life style/attitude/quality become too great to bridge anymore.
    You can’t stay on his path and he can’t stay on yours.

    I hope for his sake he turns himself around, not everyone gets a caring friend like you.

  19. JR*

    It sounds like he chose the wrong field to get into… Lawyers work notoriously long hours, especially as a new graduate trying to break into the field. I worked at a downtown firm for a few years as a librarian, and the partners/juniors both worked 60+ hours a week.

  20. FD*

    I feel you, OP. I have a few friends who keep shooting themselves in the professional foot, and it’s very frustrating.

    In my experience, some people are ready to be helped, and some people aren’t. Don’t forget that in general, people don’t change until they’re ready to change; you can help them figure out *how* to change, but change always starts from within. Just as a person who’s depressed can’t be ‘fixed’ from the outside until they’re ready to seek help (even though you can provide support and encouragement), a person making professional mistakes isn’t going to change until they’ve decided they *want* to change.

    It’s frustrating, especially when it’s someone you care about, but conversely, learning to tell the difference between people who are ready to be helped and people who aren’t will save you a lot of frustration.

    In general, there’s a fairly simple litmus test I’ve found useful to assess whether people are ready to be helped or not. Usually a few simple leading questions will help clarify the situation.

    OP: “Wow, that sounds frustrating. I wonder though, is it possible the expectations of your office are that everyone works late? I know some law offices are like that.”

    You’re likely to get one of two categories of answer.

    “No, they’re just being unreasonable. I hate the politics there.”

    “Maybe, I don’t know. I just don’t feel like I fit in there, and I don’t want a job that requires me to stay late all the time.”

    Both answers express negative feeling towards the situation, but the second answer *acknowledges the possibility of partial responsibility for that feeling*. This is really, really important! Change is only possible when a person first realizes there is something THEY can change, whether that thing is ‘find a new job’ or ‘change my attitude towards work’. If a person expresses the first idea, they probably aren’t ready to change yet.

    It helps sometimes to me to remember that change is always uncomfortable. And people usually don’t change until they’ve come to the conclusion FOR THEMSELVES that the discomfort of changing is less than the discomfort of the status quo. And no one in the world can make that call but them.

  21. LisaD*

    I lived for a year with the woman who, incredibly, had a horrible boss, mean coworkers, and terrible work at EVERY job she took. Magically no matter where she was employed, everyone else had serious problems and she was doing a great job but nobody recognized it, and she was then fired unfairly! It never occurred to her that the problem might be her…

    Bite your tongue would be my suggestion, this issue is bigger than your friendship and probably goes deeper than you know.

    1. periwinkle*

      Been there, done that, bought the t-shirt. In my friend’s case, though, the same thing also occurred with evil family members, neighbors, landlords, random fellow store patrons (backed up by the evil salespeople and store manager), and so on. I suspect she was a perfectly competent (possibly even excellent) employee at each job until the craving for drama kicked in.

      You can’t fix your friends. Goodness knows my friends can’t fix me.

      1. LisaD*

        Haha. Oh boy does that sound familiar.

        Parents and siblings didn’t appreciate her, boyfriends weren’t trying hard enough to keep her, friends were stabbing her in the back left and right… honestly felt really badly for her, something must have happened in childhood to make her feel so persecuted at all times.

        1. CathVWXYNot?*

          Ha! I used to have a colleague like that. One day she was commenting to a friend and me that she seemed to have major problems with a lot of people that everyone else liked just fine. After a loooooong pause, she tipped her head quizzically to one side and said “maybe it’s” – but before she could get the word “me?” out, we were interrupted and she went off to deal with an emergency of some kind. My friend turned to me and said “ohhhhh, she was so close!

          The moment was not repeated. She continued to have major problems with people that everyone else liked just fine.

  22. Michelle*

    First, I empathize with you. It came as a great shock to me when I realized a family member was a bad employee. I completely understand that you would want to help your friend, to shake them and say “just be a better employee!” But you can’t or more accurately, shouldn’t. The truth is, you cannot make them a good employee. What you can do, is just be a friend. This means focusing on your friend’s happiness, not their performance. What do they want out of work? What types of things do they enjoy doing? These are normal “friend” conversations that focus self-discovery, not performance management. You are not their boss and you don’t really know how they behave at work. But you do know that you care about them and want them to be happy and successful. And you can also tell when they are not happy and successful.

    Good luck. I know this is difficult.

    1. MadtownTanya*

      If you’re close friends, I would also consider whether this person has Asperger’s Syndrome. Lots of Aspies are socially unaware and/or inept. If they haven’t had training in HOW to behave in different situations (work, romantic opportunities, groups of friends), they may not be very good at performing according to expectations. Social or environmental cues don’t always register; it can make the person seem self-centered when they’re really just plain oblivious . . .

      1. Elizabeth West*

        Could be, but it really sounds to me more like he didn’t realize what he was getting into, and now hates it.

  23. Garrett*

    One of my best friends is not a great worker. She has had several jobs in Accounting (her background), but she would often call me to help her with basic math issues. I was glad to help, but also not surprised when she was let go from those jobs, mostly for being too slow on completing tasks.

    She knows she isn’t a great accountant, but it’s hard for her to find other jobs, since all her experience is in that area. So, I just help her as best I can, be a good sounding board, and encourage her when she’s feeling down.

    This is a bit different from the OP, but the similarity is that there isn’t much you can (or should) do. It’s out of your control.

  24. nyxalinth*

    He’s also a total introvert and really doesn’t enjoy people.

    This, especially the first part, don’t make someone a bad person nor a bad employee. I’m very introverted. There’s only so much yik-yak and interaction with others I can handle in a day. I can still do my job quite well, though.

    If there’s any aspect to law that would work better with his introversion, it would likely be a better fit for him.

  25. Grace*

    I would say that if you do talk about it with him, bring it up once and then leave it. You can even ask him to stop venting to you about his work – nothing frustrates me more than listening to someone complain about things that are not issues to begin with, heap abuse on people who are probably only trying to help/follow policy, and then refuse to improve their own situation.

  26. Interviewer*

    Full disclosure: I work for a law firm, managing a branch office.

    I don’t think there’s anything you can do here, except be a sympathetic ear, and possibly prod him (gently) into considering whether this career is something he actually wants to do. What makes him happy? Is it dealing with the clients? Is it working on a document? What work at the firm does he enjoy doing? What does he think lawyers need to do to succeed at their jobs? Are there any fellow associates he admires? Just ask questions, let him talk. I think his answers will point the way on whether this has been a total career misstep (i.e., going to law school, becoming a lawyer) or if he just hates the long hours (i.e., shouldn’t have joined a DC firm).

    From there, do you want to help him? Realize it is not the job of friends to make better employees – that’s the boss’s role. It’s admirable to want to help him, but I can guarantee by your description that he’s not going to be open to your advice on the workplace. Having said that – if he asks your advice, you should be honest. His bosses are giving him reasonable instruction and constructive criticism. So starting there for his fixes would help him.

    I feel for you. I absolutely HATE when my husband brings home his workplace complaints, because he’s an amazing employee who gets kudos and bonuses from his boss, but he’s got co-workers who can’t get it right. I see the most obvious fixes, and at first I tried so hard to help him “fix” it but then it became a 2-hour conversation (and sometimes a fight, if he didn’t agree with my “fix”). I have learned that if I nod and say “mm-hmm” and “oh wow” in the right places, we’re down to about 20 minutes, tops. Lesson learned.

    PS – We have a nickname for your friend’s personality in a law firm: Sharp Elbows. Pokes everyone out of their way on their climb to the top. Hoards work. Routinely disregards instructions from partners and others on the team. Doesn’t have the client’s best interests in mind at all times. We actively avoid hiring those lawyers.

    1. Elizabeth West*

      I think his answers will point the way on whether this has been a total career misstep (i.e., going to law school, becoming a lawyer) or if he just hates the long hours (i.e., shouldn’t have joined a DC firm).

      Like Marshall on HIMYM–he wanted to be an environmental lawyer (even though it didn’t pay much), but hated being a corporate one. At one point, I think I remember him wanting to bail on the whole thing.

  27. Vicki*

    FYI: Tip to the OP

    “He’s also a total introvert and really doesn’t enjoy people.”

    These do not equate. There are many introverts who enjoy people. There are also introvert lawyers.

    The I/E difference is about how you get/expend energy. An I lawyer has to do things differently from an E lawyer, but please don’t assume that I means “doesn’t enjoy people”.

    1. Victoria Nonprofit*

      Yeah, but it’s perfectly reasonable to say “He’s an introvert” and “He doesn’t enjoy people.” They can stand alone and both be true.

      Anyway, I recognize myself in that part of what the OP is saying. My introversion absolutely gets in the way of my work sometimes; I avoid the phone more than I should, overuse email, struggle to maintain the energy required to be “on” by the end of the week, and hate the hell out of small talk and other social lubrication.

      (And yet nobody – NOBODY – ever guesses that I’m an introvert. I’m super outgoing, too often the first person to jump into a conversation in a group meeting, etc.)

      1. Not so NewReader*

        Ditto for me. I find I grow extroverted if my role is defined, such as “meeting attendee.” Put me in a roomful of people just chatting with coffee and donuts and I just want to run away.

        I think that more people than we realize feel this way.

        Even in situations where my role is defined there comes a point where I must call it a day and go home for quiet time.

        I do admit though the problems have shifted with age and with practice. I sincerely believe I will always be one who recharges by being quiet, though.

        1. FD*

          Ugh yes. My manager’s helping me work towards manager skills, and one of the things he’s got me working on is getting more comfortable in social settings (my line of work, being able to network with vendors or go to social events is important). I feel like walking over hot coals would be easier.

        2. Catherine*

          Oh this is me to a tee. If I have a role to fill then I can excellence. But if the role is please make small talk with people who have never met, I just want to run away. In fact, I have run away. Now every time, I don’t, I count it as a win.

  28. CAndy*

    The comment about “total introvert” is unnecessarily disparaging.

    In my experience, intelligent introverts understand the bits they need to work on to fit in and be successful, in certain situations.

    I have seen far far fewer extroverts with the ability to understand when to tone themselves down.

  29. Anonymous*

    I didn’t see any evidence that the friend sees himself as having a problem that needs fixing.

    If he surfaces and says, “WHY IS THIS STUFF HAPPENING TO ME?” well, then you have a reason to say something. Without that, if he’s not worried, then there’s nothing to worry about.

  30. Sophie*

    If this was’t an American writing in, I would swear it was a recent lawyer in our office!!! (I’m in Australia).

    He was on a fixed-term 6 week contract, with the possibility of full time work after that. His contract wasn’t extended. He was lazy, he made so many mistakes, I had to explain tasks to him multiple times and he still didn’t do it, when I asked him to double-check something before I wrote to the opposing side about it, he had a hissy fit and yelled at me for being irrational! But once he had checked, it turns out he was wrong. But he walked around like he was the smartest person there and that I was below him.

    I think those kind of people definitely need a kick up the bum, otherwise they will never ever get proper jobs or careers. If you’re close enough that you can, definitely give it to him.

  31. Crisp*

    Speaking as someone who went for decades without knowing I has aspergers syndrome, this letter could have been written about me. Tread carefully, but know that aspergers people don’t know what we don’t know. We need people to tell us what may seem common sense (things like we don’t get to define our jobs – the first time I read that comment from Alison it knocked me over. I had never considered that concept before).

    That isn’t easy by any means because it can come across as condescending. I probably wouldn’t have accepted advice like that a few years ago – but I get it now. Good luck to you both.

  32. Miss Displaced*

    Oy! It sounds like he is very unhappy with his chosen career/profession (Law) and it not being what he thought it would be.

    If this is the case, it will not get any better for him.

    Hopefully you can help steer him to some real soul searching about his expectations and what he wants to do in life as a true friend.

  33. JuliB*

    This Christmas, give him ‘What Color is Your Parachute’ as a gift. That book really helped me, but I’m not sure how it will come across if given out of the blue.

  34. Dulcinea*

    OK, so I am a lawyer who has worked (albeit briefly) in a few other fields before settling into law and I *will* say that the most micromanaging, egotistical, anal, irrational, and insanely ridiculous bosses I have ever had have been in law, specifically litigation ( I count 3 and one is a family member). I truly believe that law (ESP litigation) attracts those particular personalities. So it’s totally conceivable to me that the friend in this case had bad luck 2x in a row and in fact ended up with crazy bosses.

    But, in my experience, law is a field that requires certain social skills to be successful in, and all the subcultures of law require their own social skills…so maybe the friend just hasn’t found his people yet? I am a legal aid lawyer and I truly feel that (example) the corporate attorneys I know have their own language/culture that I just don’t know.

  35. Dan*

    This situation makes me particularly sad. My son, although he’s only 8 yrs old has all of these personality traits – he’s got ADHD and Oppositional Defiance Disorder and this is exactly what I’m picturing his future to be like. Although he’s on medication, he doesn’t like to listen to authority, loses interest in things very quickly (ie. Quits!), doesn’t like when you give him constructive criticism – can’t even tolerate it if you tell him he did something wrong when he thinks it’s perfectly fine … I could go on and on. I wonder if this guy maybe has some psychological stuff going on that effects his personality – a chemical imbalance of sorts. If so, lightly suggesting anything to him will fall on deaf ears and may even annoy him. Best of luck to both of you.

  36. Elizabeth West*

    We need an internet rule, like Rule 34 and Godwin’s Law, regarding Asperger’s syndrome. Inevitably, on these types of posts, someone will always pipe up “Maybe he has Asperger’s.” We could call it Rule ASP or something. :P

    I don’t think Asperger’s syndrome is that common!

  37. Decimus*

    The current practice of law is simply a nightmare if you don’t have the right type-A personality or aren’t in the right area of the law. I say this as someone who got a law degree but quickly realized I hated law school, liked the research, but couldn’t stand the necessary 11+ hour 7-days-a week working days. I changed fields. It’s less remunerative but I’m not going insane either.

    I think the best thing to do is perhaps gently prompt the friend to think about what he really wants to do.

    1. Ruffingit*

      Same here. Law grad, practiced awhile, changed fields ASAP. Just wasn’t my cup of tea.

  38. Helen Cowles*

    You are describing the way I was in my last job. The only thing that made me change was a talk from a co-worker/manager when this person almost fired me for my bad attitude. I promised that I wasn’t going to lose my job and I would do whatever it took to keep my job. Your friend needs to learn how to change his perspective. When your friend complains, ask your friend what is the exact opposite, ask your friend to see the good in the situation. Read the book Peaks and Valleys. It changed how I view the world of work. Your friend has to want to change. Your friend has to get fired from a job he wants and loves, or almost get fired. He needs a wake up call and no one knows what that wake up call will be except your friend. Otherwise, tell your friend you can’t and don’t want to listen to him complain, or it will bring you down as well. Take it from someone who has experienced being clinically depressed most of my entire life.

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