ask the readers: do I tell my oblivious colleague why he’s not working as much as he’d like?

It’s Book Week for me, so I’m throwing this one out to readers to weigh in on. A reader writes:

I’m in a freelance profession that’s very close-knit. One of my colleagues moved to my area almost 2 years ago. He tried to break into the scene right away, and because of his attitude and some issues with his work, he had trouble. He came across as pompous and like he knew it all, tried to immediately get work that was already being done by others, and he pissed off some really important people. I was not a fan of his at first myself!

Over the past several years, he’s toned things down a LOT. I’ve grown to like him very much, and I think he is very talented and I now enjoy working with him personally. He just fell pray to a couple of freelance faux pas that unfortunately, as these things tend to do, still make things hard for him. I feel bad for him because my other colleagues are notorious for holding grudges. I’ve tried to speak more highly of him to them, but they are still leery. This also makes it difficult for me personally, because they don’t want me to hire him for things, especially when it involves collaboration.

Yesterday he expressed frustration to me that he wasn’t getting hired for things. He seemed to have no idea why, and it made me wonder if he actually wasn’t aware to the extent that he blundered when he arrived here. I responded sort of lamely that the scene is really hard to break into and I had trouble myself at first, which is true. But that’s not the whole story, obviously.

The question: do I tell him what my colleagues have said about him, and how he was perceived? I feel on the one hand it’d be a kindness for him to be aware and then try more actively to repair the mistakes, some of which actually involve the work itself. On the other hand, it seems mean to tell someone, “hey, you behaved badly two years ago, your work had [these problems], and people sometimes still avoid you because of it.” I feel there is literally no way to say this without being extremely hurtful and upsetting — especially since it is things people have been saying about him when he isn’t there.

This affects me personally, too — my colleagues get annoyed with me when I want to hire him for things. I enjoy working with him and want to do so without people getting pissed off. But he’s upset some people so much that I don’t think they’ll forgive him without a flat out apology.

What do I do?

{ 169 comments… read them below }

  1. Emi.*

    If it’s just “you don’t get work because no one likes you,” with no path forward for him, I might hold off. But it sounds like if he *did* offer a flat-out apology, it would help him a lot. So I would.

    1. Seriously?*

      I agree. If it is something that he can address if he knows about it, then telling him would be the best thing to do. If he can’t do anything about it, then there is no point.

      1. DJ Roomba*

        But even if he can’t do anything to rectify this situation (so it’s not “actionable”) it may actually be something he can use for the future (ex/if he ever moves again, in social circles, etc). I think sharing this with him is a greater kindness than leaving him in the dark wondering why everything is so hard. And even if YOU can’t find a path through this situation, maybe he can (so not actionable become actionable). And as his friend, you should give him that opportunity.

        I think it’s actually great that you were put off by him but then he won you over. Rather than piling on with what others have told you, it would be best to speak from your initial experiences with the implication that others may have felt the same. And as a way to figure out a solution, maybe you can share what he did since that bad first impression to change your mind.

        So again – tell him! It may not feel like it but it is actually the kind thing to do.

        1. Roscoe*

          Agreed. Even if the situation isn’t salvageable now, at least he knows.

          I think for him, its better he know that its because of his personality and not his skill. Because if he thinks he isn’t getting hired because he sucks at his job, that can be a whole other mess for him mentally and emotionally

          1. Jesca*

            +1. But in the script replace the word “personality” with “behavior”. I think it softens the tone a bit when someone says “people in the industry like a certain type of behavior” as opposed to “people around here don’t like your personality”. The second phrase sounds a lot more personal than I think is warranted here. He just sounds like he came off too strong in the beginning, and the kindness would be to point THAT out.

            1. JM60*

              I think the phrasing of behavior instead of personality is a lot better in part because people can change their behavior, but ‘personality’ can be a bit more enduring.

            2. Steve*

              Yes. I would also use “behavior” instead of “personality.” I think it is more precise. “Personality” is vague and can be confusing; “behavior” is more clear and actionable.

            3. Susana*

              Spot on, Jesca. Reminds me when my sister (8th grade teacher) had a student who said to her, I know you think I’m a bad kid. She said no – I think you’re a great kid. It’s your behavior I’m having a problem with…

              1. Analyze All The Things*

                This is the exact reason we tell our kids that they’re “making naughty choices” rather than just being bad.

          1. DD*

            That’s a really great point! It softens the blow, it’s truthful and it shows him what he could do more of.

        2. Seriously?*

          I think it depends on whether the OP thinks he is likely to repeat his mistakes. It sounds like he has gotten better. I think in that case I wouldn’t bring it up unless he does. Lying to him about why no one will hire him is not being kind.

    2. JerryLarryTerryGarry*

      Even if there isn’t a clear path forward, it’s a kindness to let him know. This is his profession, not a friend group. Even just replying, “yeah, I get resistance to bringing you onto my projects- you didn’t make the greatest impression when you first arrived.”
      If he wants specifics, supply a few, and any actionable ways to remedy. But if he knows, he can actively work towards repairing the damage instead of blaming the economy or whatever.

      1. Indie*

        This is brief and impersonal. I like it because it’s just factually non patronising and gives the friend an opportunity to ask for more detail if he wants.

    3. stk*

      Yeah, this. He actually could probably do himself some good by being nice and dropping the right comment of apology at the right time.

      That said, not everyone appreciates this stuff so I’d maybe ask him whether he DOES want to know. “Hey, so you were talking last week about finding it hard breaking in to the field and getting work. I actually ended up having some thoughts on that, if you’d like my thoughts on what might be going on?” is how I’d put it, I think.

    4. JSPA*

      This goes beyond a first impression. He didn’t over-imbibe at one party and knock over the hot dogs. He blundered, like a clueless mooing calf, into and through a lot of people’s back yards, for a matter of weeks or months, while in full possession of his faculties. That’s a much harder memory to supplant.

      Being a boundary-crossing, loud blow-hard is clearly not all that he is. It’s not how he’s learned to behave. But if he fully established that it’s a facet of his personality, people may never actually get around to seeing him as anything other than a pest-in-waiting–whether or not he apologizes.

      Tipping him off that he started off on the wrong foot with a lot of people–and kept wrong-footing for a considerable while–may help him put the current situation into context. That being, some people may never want to deal with him. Some may begrudgingly come around, but it’ll be a slow process (and one that he can derail by defaulting to “calf mode,” even briefly, no matter how irked he is at how hard he has to work to even reach neutral status). He might want to do extra, “good guy bonus points” stuff (whether that’s volunteering at the food bank or joining the OddFellows or being the dunk tank target for some industry-tangential Good Cause).

      Repeatedly mentioning how green he was when he started, or apologizing, will likely just remind people of things better forgotten.

      Alternatively, he might do better starting fresh elsewhere–but only if he’s the sort of person who will have learned the process of how to suss out a new area’s culture. Some people don’t learn process, they just slowly learn (often through hard knocks) the rules of the one place they are now.

  2. JokeyJules*

    if you consider him a friend of sorts, tell him.

    I’d phrase it something like “dude, at first, I think you made some really bad first impressions. I think a lot of people were really put off when you did X, Y, and Z. You know that can stay with people, and i think that’s why they’re hesitant to give you work. I know you’ve changed a lot and aren’t that same person, but they don’t know yet. I think you should apologize to help make up for some of it, and then the way you are now will help with the rest.”

    I’ve had similar conversations, and if the friend is secure and mature, it should be a very constructive conversation

    1. Irene Adler*

      I like this.
      One thing: might preface this with asking him if he is open to hearing the observations the OP has made regarding the reasons for not getting hired. Or is he just venting his frustrations to a friend?

      1. JokeyJules*

        “I don’t know why i’m not getting jobs!” is a VERY different statement than “why do you think this is happening?”

      2. k.k*

        Another vote for this approach. No use trying to give him advice if he’s not open to it.

    2. SierraSkiing*

      That’s a good approach! And I like how you don’t try to exactly quote the coworkers; OP should give him the information he needs (“people remember him for X, Y, and Z and he might have better luck if he explicitly apologizes for them”) without adding in whatever painful details of what people have said about him. He doesn’t need to know that Thor called him a know-it-all jerk or that Quill was laughing about him with Gamora.

      1. TootsNYC*

        or maybe not apologize, but try to find a way to clearly demonstrate that he doesn’t do that stuff anymore

        I don’t want apologies; they’re awkward, etc. And I don’t want an apology if someone just had an unpleasant style; I only want an apology if they’ve specifically wronged me. And even then, I’d rather just be proved wrong.

        I think apologies can sometimes focus the attention on the wrong thing, and they can mess up the power balance.

        But knowing that he interrupted too often to impart his wisdom to people who were already experts can help him remember to ask more, listen more, express admiration for other people’s expertise.
        I’ve done that very sort of thing w/ someone, and essentially wooed them around to be more welcoming of me.

  3. Murphy*

    As much as it’s going to suck to hear it (and there’s no avoiding that!) I would lean towards telling him. I think you can soften it by telling him how much you enjoy working with him, and that some of the things he did are common among freelancers, but it seems like things will never improve for him if he doesn’t know what he did!

    1. Spooky*

      I agree. FWIW, I’m also a big fan of delivering hard-to-swallow news digitally, rather than in person. It’s always difficult to have to hear that kind of thing, and to hear it in person and then continue your meeting/dinner/whatever you were doing when you told him is even worse. Give him the time to read it, digest it, and compose himself on his own timeline.

      1. TheCupcakeCounter*

        I probably wouldn’t send it out of the blue though…maybe have something pre-written and next time he says something send it with line about him mentioning it several times you you’ve really given it a lot of thought and then list the things you know. I agree that this is one of the few times that softening the language and delivery is warranted.

      2. Thursday Next*

        Although then you lose the benefit of a friendly, light tone, which can really soften difficult news. Also, an email can seem like the product of premeditation in a way that a conversation isn’t, and that could make things awkward in a different way, because now the friend/colleague might think, “Wow, I’m such a disaster that someone took the time to really think about this and write this down.”

        I definitely see Spooky’s point about email giving the recipient privacy and time to digest info, but in this case I’d recommend a face to face. It gives the person a chance to ask follow up questions (“I had no idea peopl thought this. What do you think I can do?”) and gain reassurance from the tone of the response. LW can emphasize that they were won over after a negative initial impression, so all I see not lost.

      3. Yorick*

        I wouldn’t send this digitally. It’s likely to hurt his feelings and not hearing the friendly tone would make it worse. Also, he won’t be able to ask questions.

      4. nr*

        I’d do this in person, but if possible (and that’s a big if possible – unless OP is going to bring it up, she can’t control when he asks), do it while, like, walking around the block or something. (I guess you could respond to the question with “let’s go walk around the block,” but that might make it sound Big And Heavy.) Gives the person a few more potential ways to process, there isn’t someone staring at him, and it doesn’t take very long, so he can escape pretty quickly if he wants to – but they can also continue the conversation.

        I’m a big fan of walking conversations, though, for these reasons, and that’s obviously dependent on people and circumstances.

        1. Laura*

          Driving conversations also work well in this context, for the same ‘don’t have to look at the person’ reasons. Some of my most open and honest conversations with people (although mostly family rather than co-workers) have been whilst I was a passenger in a car and talking to the driver.

      5. Sunshine on a Cloudy Day*

        Le sigh… it seems like whenever anyone recommends giving tough or uncomfortable news in a written form (rather than verbally) a bunch of people jump in to say “NO DON’T DO THAT”…

        I’m someone who would strongly prefer to receive this sort of information in a written format. For me – I’d much prefer to process privately and then followup in person if I have any additional questions (or have concerns about tone/intent/etc.).

        Of course I understand that some (maybe even the majority) of people don’t feel the same way that I do. And that’s totally fine and I completely respect that. But – it’s really frustrating to hear constantly “no! no! never ever deliver difficult news in a written format” whenever the suggestion comes up.

        What I’d recommend is – delivering the uncomfortable news in whatever manner you believe the recipient would appreciate most (and also within what is doable for you, yourself – ie: if you are a terrible writer, or if writing would cause you extreme anxiety, then weigh that against what you know of the other person). Sure, it might not be something that is easy to tell about another person (and in that case, just do the best you can), but I also suspect that if more verbal people (who seem to be in the majority) were a bit more open to the idea that some people, do in fact, prefer this method, then maybe they’d also be more aware if someone they know would prefer this.

        1. Gen*

          I recently found out that I’d been ostracised from part of a semi-professional group without me ever really noticing- those people were chilly but I had assumed that they were just like that. I didn’t get any work from them but my style isn’t necessarily theirs. So getting a Twitter private message that it was deliberate was a shock (in my case it was because someone who stole money from me had started a smear campaign rather than because of anything I’d actually done so it is different in that respect). On the one hand I appreciated getting this information digitally because it gave me a chance to reread the information a few times and really digest it before getting into the ‘wtf?!?’ response. It also gave me some time to make that response more gracious because honestly my initial reaction would probably have lost me even more work. Also not everyone is going get upset over information like this but not having to worry about other people seeing me cry was definitely a benefit

          1. So and Sew*

            Being able to reread it is actually exactly why I’d prefer to deliver difficult news verbally. My spouse, for example, can get really thrown by bad news. But if it’s in writing, he’ll keep going back to it and finding new sources of panic/frustration in the message — anxiously overthinking the exact phrasing.

            Doing it verbally let’s you get the tone of voice right, and means it’ll fade into memory more easily (in a good way).

            1. jo*

              This is so true for me, too. When something difficult to hear arrives in writing, it’s so much harder to leave behind when you need to move on to constructive next steps. Hearing it in person can feel harder in the moment, but at least my brain can protect me later by blurring the memory. And the heart of the message still gets through–that part is generally impossible to forget. It’s the painful exact wording that fades.

        2. Lissa*

          I agree to an extent but there’s a big social change that would need to happen before I’d feel comfortable delivering news textually unless I KNEW the person would prefer it, because of the difference in perception. If I deliver the news verbally when they’d rather have it digitally the person is likely to be frustrated with the situation, and perhaps take it less well than if I’d said it digitally. But if I deliver news digitally when they prefer verbal, both these things will be true plus they are likely to think I am a super inconsiderate/terrible person. There is just such a widespread “thing” (that I don’t personally agree with but it’s there) that it’s really callous to give bad news non-verbally. I would love to see this changed though. But you just hear it so often I wouldn’t want to take the risk.

          1. Sunshine on a Cloudy Day*

            This is totally fair/true! You’re right that the consequences of guessing “wrong” are worse (currently) if the person prefers verbal news vs if they’d prefer digital.

            Not to open a whole can of worms (and this isn’t directed at anyone specifically) – but it just sort of seems like *for the most part* those in the minority (who prefer news digitally) are more likely to acknowledge/respect those who prefer news to be delivered differently (ie: verbally) than those in the majority (who prefer news verbally). Mostly because, as you said, this is a just a “thing”.

      6. YB*

        Just a different perspective: I’m sure you’re right that it’s less awkward for the deliverer to just send an e-mail, but as someone who’s had to *receive* news very similar to this (I sometimes don’t come across the way I’d like to), I find this sort of news much easier to receive in person. E-mail is so cold and impersonal and it’s harder to read tone, whereas in person, you can pick up on the person’s kind and empathetic intentions more easily. Also, there’s a certain permanence to e-mail that makes it less ideal. If someone tells me in person that others think poorly of me, it hurts, but the memory fades. If someone e-mails me the same thing, I’ll read the e-mail ten times a day every day for the rest of my life. It’s something to think about.

        1. So and Sew*

          My goodness, I should have read your comment before I replied. This is exactly the same thing I meant.

          1. jo*

            I think it bears repeating! That’s three of us so far who feel the memory/self-flagellation aspect is important.

  4. That Cat Lady*

    Since you have a personal relationship with him now (from the sounds of it) and since he’s asked you for advice I think it could be OK to gently tell him that he didn’t make the best first impression when you met him and you wonder if that might be the reason he’s struggling today. I think he deserves to know otherwise he could continue to put people off, even though you know that once you get past that first impression he is a nice person to work with.

  5. Observer*

    The key question is whether this sis actionable information. Can he make changes or do anything that would change things?

    If nothing he does is going to change matters, then you need to keep this to yourself. But, if you think that he can change things, you would be doing him a kindness by telling him. Not “You were a jerk and incompetent”, because that’s just mean. But “People see you as X. If you do Y, you may be able to change that perception.”

    1. Snark*

      It’s a good question. If there’s no meaningful action he can take other than to feel bad about stepping on toes years ago, I’d hesitate.

      1. animaniactoo*

        Eh, I think there’s value in hearing that it’s going to take longer than he might expect to overcome people’s first bad impression of him.

        He might still be frustrated, but his frustration might have more patience and understanding mixed in with it.

      2. Yorick*

        I had an extremely long job search, and it was demoralizing. You start to attribute it to any possible flaw, especially those that you’re more sensitive about. I think knowing an actual reason why people didn’t hire me would have made me feel better, even if that reason sucked.

        1. Me*

          I also recently had an extremely long job search. Part of it was being in a competitive and declining profession. Part of it was being older. As poor Yorik said, it was demoralizing. I longed for someone to tell me what was wrong with ME and how I could change to get a job. I’ve done a lot of temp and contract work these last five years. It doesn’t help my confidence when assignments end far sooner than I expected or I don’t get offered a permanent job.

    2. Totally Minnie*

      I do think it’s actionable information, whether it changes the current situation or not. Even if his industry relationships in this area are irreparable (which I hope they’re not), knowing that he came on too strong in the beginning can help him in his next career steps. If he were to move to a different area or change to a different segment of the industry, knowing that he got off to a rocky start here could help him prevent that from happening again.

  6. Turquoisecow*

    I think it might be helpful to offer some specifics, rather than a generic “you rubbed them the wrong way” or “people don’t like you,” since those aren’t really actionable criticisms.

    For example, if you can point to a specific incident in which he tried to steal a person’s work, you can say something like, “Wakeen doesn’t appreciate that you tried to steal the Llamas Inc. project from him. I know you were just starting out and you’ve learned better, but he’s not as sure, so maybe if you apologize, he’d be more amenable to collaboration.”

    You can also mention that other people who saw these actions might have been put off, if he doesn’t come to that conclusion on his own. If he disregards or dismisses your advice, there’s nothing more you can do for him.

  7. Technical_Kitty*

    If you think he’s worth the trouble and does good work, say something to him. Point out the things people have issues with, and offer a way forward if you want to. He’s an adult, apparently knowledgeable in your industry, so he should be able to address the issue himself.

  8. Clorinda*

    Can he take some action now that would improve his status moving forward? That is, would the apology really help? If so, you should tell him directly, even if it’s awkward. Otherwise, answer specific questions only, and only with specific examples, and only if you know for sure.
    “Why can’t I ever get a gig at Puppy Cuddlers?”
    “Well, last time you were there, you stepped on a chihuahua, and everyone knows it was an accident, but you didn’t apologize, so you might be off their list for a while.”

  9. LSP*

    First, I’d make sure he actually wants feedback from you, because he may be interested in simply moaning about his lack of jobs, but may not be interested in taking steps needed to improve that.

    If you feel it out, and he seems like he might be open to hearing some constructive criticism, just speak about it kindly and let him know that some of what he did were some really common freelance pitfalls. As for the other, more offensive pieces, just try to be gentle and direct and let him know you’d be happy to help him figure out how to mend any broken fences, etc.

    You are right that it would be a kindness to tell him what others think of him, but it is not your responsibility and if you don’t feel comfortable approaching this at all, you are under no obligation to do so.

    1. Turquoisecow*

      Oh, that’s a good point. Some people just like to complain, and don’t actually want advice.

    2. Emmie*

      Excellent point. Do you want advice, or do you want me to listen? It’s a pretty powerful question.

  10. Snark*

    I don’t know. If you have the kind of relationship with him where you can bring it up as a friend, it might be a kindness. “Hey, I was thinking about our conversation about your difficulty getting your business started here a few years ago. Would you be open to hearing some of my recollections from that time that might clarify why you got wrong-footed with folks here, even if they might be difficult to hear?”

    What I wonder, honestly, is whether there’s anything actionable for him to do here. Emi’s suggestion of an apology might be well-received, but if it’s been a couple years it might strike people as weird that he’s apologizing for being a butthead way back when.

    On the flipside, if this guy is more of a professional acquaintance with whom you are friendly when you work together but otherwise aren’t friends per se….this might be overstepping. This is more of a friend conversation than a colleague conversation, and unless you have the standing to drop some hard truths on him, it could come off as weird that you’re doing it at all. It’d also be worth considering whether a dude you describe as being “pompous” and a “know it all” a few years ago will be receptive to hearing it.

    1. WolfPack Inspirer*

      This is where I’m at too –
      IF you are more friends than colleagues
      IF you ask him directly if he wants clear feedback or just wants to b&m (b!tch and moan)
      IF you feel like he has grown as a person or is mature enough to actually hear and accept some unflattering info
      IF there is something specific that knowing this info will allow him to do that might mend fences

      Then yeah, it would be a kindness to him and a benefit to the overall profession to try and get things rolling along more genially. But that’s a lot of ifs.

    2. Penny Lane*

      We’ve discussed the “apologies for past behavior” thing several times here – such as in the person who had bullied someone else in high school and thus was unable to get a job with her company, that type of thing. I think the consensus has been – can the person apologize because they are truly apologizing and looking to make amends for past behavior, versus is the person only apologizing because they are hoping to get something out of it (=a job, referral, reference, etc.).

      Depending on the personality of the person – some people can get away with a self-deprecating “Hey, you know, a few years ago I really came on strong with XYZ but since that time I’ve reflected …. blah blah blah.” Of course, I have no idea if the OP’s acquaintance falls in that category or not.

      1. Snark*

        I don’t know. In this kind of case, I think the two motives can coexist. Obviously, he’d personally benefit from making meaningful amends, because it would improve his professional reputation and he’d get more business. I think if he can make genuine and honest apologies, the fact that it will improve his business is not a reason not to do it, and won’t necessarily be held against him. If he’s just obviously going “ok, apologize to Fergusina so she’ll throw me some work” then it’s going to be rather obvious, and it will backfire.

        I’m thinking of a particular colleague from some time back who got a bad review due to….less than impressive soft skills, let’s say. And he came to me and personally apologized for some things he’d done that made him less than easy to work with, and backed it up with an apparent and genuine good-faith effort to work on those things. Did I perfectly understand that he was doing it to save his job? Sure. But I also did appreciate the apology, and it did smooth things over between us.

        1. Emi.*

          I think it works better with professional offenses (including soft skills) than personal ones like childhood bullying.

        2. AMPG*

          I think the difference has to do with whether you’re apologizing for behavior in a work context that hurt you professionally, or personal behavior that’s now having unexpected professional consequences. It seems that people would be less willing to believe an apology in the second category, and I think that’s understandable. In the OP’s case, the friend/colleague would be apologizing for work-related behavior, so I think it would be more well-received.

      2. serenity*

        Those behaviors in past letters are *much* different than what we’re talking about here (someone who at one time came across as pompous and has now softened, according to the OP) so I’m not sure it’s a helpful comparison.
        I think your example of a self-deprecating prelude in this guy’s next conversation with potential employers wouldn’t be a bad idea.

      3. Moonbeam Malone*

        Based on the info in the letter and assuming the friend isn’t just reaching out to apologize to people when/if he’s looking for work from them (which, yeah, he should definitely steer clear of,) it sounds like he probably has room to say something to people he’s offended, so long as he’s genuine. “Hey, I was talking with OP about some of my missteps when I was starting out in this area and she let me know that when I tried to take on that teapot assignment from Mad Hatter Inc. that I was trying to snipe a job you were already working on and my behavior there didn’t speak well of me at all. I think I’ve grown more aware of the culture and norms since then, but I’m really glad I know about it now when I can reflect and learn from it and I’m sorry I did that to you!” That script could probably use some work but you get the idea? It could be tricky for him because it’s something he has to do for himself and OP would probably have limited/no ability to coach him there, but I think it might still be worth it for him, if that’s the direction he wants to go.

  11. Temperance*

    Honestly, he sounds like a blowhard, even if he has toned things down a bit. I think you’re putting your own reputation on the line by advocating for this guy and pushing others to accept him.

    If you do tell him that he came off badly, there are two things that will happen, depending on his personality: 1.) he’ll start harassing your colleagues about forgiving him, and let them know that you told him what they think of him, or 2.) he’ll make amends.

    From your description, he sounds more like #1 than #2, and I think you should just let him flounder or get a regular 9-5.

    1. And So it Goes*

      I concur. I think there is too big a risk that #1 will occur and hurt your bottom line. If this was a close personal friend it may be different for all the obvious reasons. However….do you really want to stick your neck out for this person?? Spot on, Temperance.

      1. Ali G*

        Something else that worries me for the OP is, even if he is sincere, gets it, and wants to make amends – is he going to expect the OP to be his “champion?” What happens when he apologizes or whatever and still can’t get work? Is it the OP’s fault? Or is he going to harass her all the time to get him on her projects?
        There are a lot of possibilities for the OP in trying to do something kind, having her life messed up in the end.

    2. TootsNYC*

      well, our OP can deliver the news with info about what he observed Boorish Friend to have done (“you tended to interrupt people and lecture them, when really they were already experts; that kind of thing can contribute to people being pretty hesitant to hire you”).

  12. MuseumChick*

    I’m going throw up a caution flag because I witnessed a similar situation that ended badly. Basically Person A asked Person B “Why does no one in this field seem to like me?” Person B said “I’m telling you this as your friend. *Insert reasons person A wasn’t making it in the field*. Person A stormed off and has remained resentful ever since.

    I don’t know if your colleague will react the same way but it is a possibility. If you still want to go forward with talking to him I would word it something like. “Ok, I’m going to tell you something that might be hard to hear. When you first got to this city you made some mistakes that people are still holding grudges over.”

    1. Snark*

      Yeah, the hazard with “honestly, tell me why people don’t like me” is that, well, occasionally people will do just that.

    2. Temperance*

      It could go worse, like if LW decides to confront the people who dislike him and mention that LW told him so.

    3. Kate 2*

      That actually sounds like a good ending to me. Anyone who constantly complains and then throws a tantrum when someone honestly tries to help them is not a person worth calling friend.

    4. Penny Lane*

      Right, but then Person B is clearly in the right, because Person A isn’t a likable / reasonable person if he storms off and is resentful. And then Person B shouldn’t really feel bad that Person A isn’t getting jobs. I don’t feel bad when unlikeable / unreasonable people don’t get what they want; do you all?

      1. MuseumChick*

        Well, the OP here seems to want to maintain a good relationship with this colleague. What I’m saying is that if she goes ahead and tells me why he isn’t succeeding it could end with this colleague resenting her not matter how kind/thought/accurate her insights are.

  13. fposte*

    I think you can ask him if he’d like your insights, rather than just either volunteering them or keeping schtum. Next time he complains, you can say something like, “Would you find it helpful to get an external perspective on this, or do you want to just work this through?”

    1. Phoenix Programmer*

      Man I wish there was a vote or bump system this should be near the top!

  14. Shadowette*

    “hey, you behaved badly two years ago, your work had [these problems], and people sometimes still avoid you because of it.”

    It will be an awkward, difficult conversation but it would ultimately be a kindness. Deliver it with compassion and sensitivity with lots of comments on how you have seen the good work that he does and that you enjoy working with him.

    Ultimately, it will take time and patience to fix his reputation. The responsibility is his, not yours. It sounds like you are already trying to help but you can only do so much. However, he will never be able to fix his image if he doesn’t realize that it is an issue. My advice is to have the awkward conversation with him so he has an opportunity to fix the issue.

    1. grace*

      This is where I fall, too. I can’t imagine learning after the fact that my friend/someone I respected knew why I was having trouble finding a job, listened to me talk about how I was having trouble finding a job, and chose not to tell me.

    2. Temperance*

      I can see this blowing up in LW’s face, though, if his colleague decides to confront people who he sees as the gatekeepers to his industry.

          1. animaniactoo*

            Probably not much. LW has a solid reputation already, and can probably easily smooth over any “WTH did you tell Jerk that I said?” “I’m sorry – he’s been really great lately and frustrated and I was trying to make him aware how badly he came off at the beginning. Clearly that was a mistake and I’m sorry you had to deal with it.”

          2. bb-great*

            Eh, I don’t know. Maybe if LW gives names and direct quotes, those people wouldn’t appreciate knowing that LW was parroting them to the person they’re criticizing. But if LW keeps it to a general, “The way you acted rubbed some people the wrong way,” and this guy uses that as a reason to harass other people? I think that’s pretty clearly on him, not LW, and people will see that.

      1. TootsNYC*

        Our OP doesn’t need to name names! She can focus on what she observed about his behavior, and frame any “people tend to hold on to that” as her own observations as well, and leave out what anybody else said.

  15. SophieK*

    Can I ask you why you are more invested in protecting the feelings of a jerk than honoring the feelings of his victims?

    I’ve never understood this mindset.


    1. Andy*

      I think I understand where you’re coming from, but sometimes good people act jerky out of inexperience or ignorance and sometimes it’s incumbent on us people who want to consider ourselves good to accept this and, if not actively help people move on from jerkiness, understand that it genuinely does happen that people improve.

    2. Murphy*

      Because it sounds like he’s good at what he does and, more importantly, has made great strides in improving his behavior.

    3. Turquoisecow*

      I think calling them victims is a little harsh.

      Ordinarily, I’d agree with you, but this guy doesn’t seem to be a deliberate jerk, just a guy who made a few mistakes. He’s already seemed to be improving, so punish him for some mild rudeness in the past? Also, his “victims” seem to be handling themselves just fine.

    4. Snark*

      I think this is amped up a little high. People offended by a jerk may be, but are not necessarily, victims. And seeing as everybody is a jerk at some time or another, I don’t think being a jerk a few years ago really merits being ostracized or not given helpful and actionable feedback on how to not be a jerk. It sounds like the guy reined it in, and I still think it’d be a kindness to both him and the folks he pissed off to give him the information he needs to make meaningful amends.

    5. Roscoe*

      It sounds like he wasn’t trying to be a jerk, just unfamiliar with the norms of the industry in that area.

      And it sounds like their feelings are more like holding a grudge needlessly, based on this sentence “my other colleagues are notorious for holding grudges”. Just because someone pissed you off once, doesn’t mean you have the right to be a jerk toward them forever.

      And do you think people don’t deserve a 2nd chance ever?

      1. Snark*

        Or maybe he overcooked it trying to project confidence and capability, and did in face end up in pompous jerk land! NOT THAT I CAN EMPATHIZE WITH THAT OR ANYTHING.

        Either way, I don’t think he deserves to have the letter J branded on his forehead so all the Nice People can shun him forevermore.

    6. bunniferous*

      Jerks do not have to stay jerks, and people can change. If we do not allow for that then what incentive does anyone have to stop being a jerk?

      1. bunniferous*

        Also, I have been a victim of jerks more times than I care to remember. I find it healthier to acknowledge change when I see it. And in my case it was way more than violation of work norms. Not everyone has to handle things the way I do but I do get to choose how I handle things, and if I were one of the people in this work group I would want to know that change happened.

      2. Countess Boochie Flagrante*

        Jerks don’t have to stay jerks, but I would say the onus is on them to demonstrate that they are no longer jerks, rather than on anyone else to open up and give them more space to inflict their unknown quantity of current jerkitude on others.

        1. Snark*

          And I think, in this case, that the colleague has demonstrated that he can display better behavior and work nicely with others – which is at least a reason in the “pro” column for letting them know.

        2. Aurion*

          But he already has. He won LW over when LW was, at best, lukewarm towards him in the beginning. That is a solid point in the “demonstrate he is no longer a jerk” column. Maybe the chicken has come home to roost either way, the question is whether to tell him that because he hasn’t made the connection for himself.

        3. TootsNYC*

          to demonstrate that they are no longer jerks,

          I agree!

          And that’s why the OP does have an opportunity here to help him by helping HIM see the problems with his behavior, so that he can then demonstrate that he’s no longer a jerk.

    7. Overeducated*

      The world isn’t necessarily divided into “jerks” and “nice people/victims.” For instance, I used to be VERY shy, and realized over time that it could come off as standoffish; now I make more of an effort to be friendly but it is honestly sometimes awkward, I’d hate to be put on the “jerk” side forever because I got it wrong while trying to learn. It sounds like the colleague is trying here, I wouldn’t assume he’s irredeemable.

      1. serenity*

        The world isn’t necessarily divided into “jerks” and “nice people/victims.”

        Bingo. Anyone who says differently is naive, stupid, or a combination of both.

      2. Colette*

        And people who pride themselves on being nice often are selective about who they are nice to because they don’t consider the whole picture. For example, they let someone ahead of them in line, which is nice to that person but not to the 10 people waiting behind them or they let a poor employee avoid consequences because they need the job and inadvertently make everyone else’s job harder.

      3. MamaGanoush*

        Yes, exactly. People I’ve worked with for over 10 years still say to me, Oh when I first started working with you, I thought you were a stuck-up smarty pants, but now I know you’re reliable and helpful and “just being MamaG”. I will always have to work hard at not being shy, awkward, and smarty-pantsy. And I didn’t know I needed to do it until a colleague sat down and told me. I am still grateful for their willingness to do something hard, awkward, and risky. OP, let your colleague know.

    8. Jaguar*

      Someone being obnoxious is not the same as someone being an abuser and it’s kind of ridiculous that you frame it that way. If there is any victimizing at all going on here (and I would say there isn’t), it would be the “nice people” holding a grudge against someone for years and those grudges affecting the person’s career. Nice people and unforgiving don’t sit easily together. “Why are you trying to hire Ted? I hate that guy,” is not the sort of thing nice people say.

      1. Working Hypothesis*

        I don’t think I’d hold a similar grudge, unless the guy were *presently* still behaving like a jerk (which I can’t tell from the letter — it’s clear the LW thinks he has gotten somewhat better, but less clear whether that means he’s left jerkdom behind or simply gone from 90% jerk to 75% jerk). But I don’t think anybody has the obligation to hire a freelancer if they don’t personally think he’s going to be comfortable for them to interact with. If that impacts his career, it’s not their “grudge” which is affecting it, but his own past actions; and it is on him to change them in ways which give enough people reason to WANT to hire him that he can get past it, professionally.

        I agree that the whole ‘victim’ thing was a bit much, and I’m skeptical about any approach which divides the world into Jerks and Nice People. Everyone behaves badly sometimes, and nearly everyone also behaves well sometimes. But I do think it is entirely up to individuals how much and what types of jerky behavior they are comfortable with in the freelancers they choose to hire. If someone’s career is affected because they’ve offended enough people that they can’t get enough work, that’s on them, not on the people who don’t choose to hire them.

        1. Jaguar*

          I agree with your broader point. Nobody has an obligation to interact with anyone they don’t want to. My point was that holding grudges and trying to block someone from getting hired because you don’t like them is not commensurate with being a “nice person.”

          I don’t agree with your strict “that’s on them” idea of responsibility. The people blocking the guy from employment are taking a specific action (they aren’t just not hiring him – they’re telling OP not to hire him). When you take action, you have a responsibility to act ethically, and I wouldn’t call this action particularly ethical. I can see acting the same way myself, so I wouldn’t condemn them, but acting ethically would be interviewing the guy and raising your concerns directly with him.

          1. Colette*

            I assumed they are telling the OP not to hire him on projects she is doing for them – i.e. he’d be a subcontractor on their job. That’s the kind of thing they get to decide, particularly since it sounds like some of his blunders where in work quality.

      1. Snark*

        Cruella was really abrasive when she was getting her fur business going, but I hear she’s really toned it down.

        1. Sci Fi IT Girl*

          I heard Scar gives great motivational speeches and works well with freelance teams. Don’t think he’s up for any feedback though. (You guys – I just snort-laughed so loud my coworker heard – thanks for making my Thursday funny Snark and Indie!).

          1. Snark*

            His last freelance team wasn’t that happy working with him, as I recall. He’s best in an individual contributor role.

            1. Indie*

              Whereas Jafar really is a jerk. He gives his genies the tiniest offices and tried to steal credit for Aladdin’s cave project. Don’t get me started on Evil Queen. She runs her business ‘like a family’, which is just code for being poisonous.

              1. Cat owner*

                Gaston is an amazing guy to work with. Ask Tom, Dick or Stanley – they’ll tell you whose team they’d prefer to be on.

    9. bonkerballs*

      People who hold grudges for years and refuse work to someone who made professional mistakes that he has rectified are not nice people.

      1. Colette*

        I mean, if I hire you to dog-sit for me and you forget to feed my dog for 2 days, you may get much better at the job but 10 years later I’m still not going to hire you to dog-sit. Refusing to work with someone who will cost you more time/effort to work with than someone else, or who messed up the last time they worked with you, is a perfectly reasonable decision to make. It’s not about holding a grudge, it’s about doing what is best for yourself and your business.

        1. bonkerballs*

          It is holding a grudge when they’re telling OP not to hire him or work with him. And I think there’s a big difference between someone who acted pompous and someone who didn’t feed your dog for several days.

          1. Colette*

            It sounds like there were actual work implications, but even if all that happened is that he came across as arrogant or selfish, why do you think the OP’s contacts are obligated to hire him instead of someone they like better? It’s OK to not hire, or date, or befriend someone because they were rude or obnoxious to you.

    10. Yorick*

      I don’t think it’s really reasonable to call someone who found a colleague annoying or whatever “his victim.”

    11. Yorick*

      Some people are actually perfectly nice but don’t know how to navigate the workplace, and so they come across a different way. Once they realize this or become more mature, they can become great coworkers.

    12. LilySparrow*

      I got the impression this was about professional courtesies and work habits, not predatory behavior.

      A victim is someone with less power in a situation, who is harmed. Being a pompous know-it-all or delivering poor work doesn’t create “victims.”

      These are senior colleagues in positions of influence who are rightfully pissed off. They don’t need their feelings taken care of. But if the friend can improve his relationship with them, they could all benefit, since apparently he’s good at his job.

    13. Bea*

      She’s not protecting anyone here, she’s not making excuses for an abusive person from the information given.

      He’s an arrogant obnoxious guy who toned it down is how I’m reading. So he’s now suffering consequences from past behavior and OP has information he could use to smooth the feathers of those he’s ruffled two years ago.

      So it sounds like everyone here is nice and one of them had a conflicting personality at the beginning.

      I’m a nice person and think it’s crass to define these other freelancers as victims when he’s not even being outlined as a bully or predator, just an awkward jackass.

  16. Andy*

    ok, so I see a lot of good in talking to him, but with a few solid conditions in place: you know he’s mature enough to take it in the spirit with which it’s given, the info will be put to use to advance his career (and not even by accident torpedo yours because you went out of your way to coach him and people are weird and WANT to hold grudges), and regardless of an accidental sabotage (so (THIS PERSON) told me you hate me because (reason)) the disclosure will benefit you in some way. Then tell him how it benefits you, explain that you wouldn’t be going out of your way except you think (insert reason here), so you ensure he knows that you’ve got skin in his game and you assume a level of investment on his part toward your good or benefit.

  17. SJPxo*

    I’d maybe say to him either if he brings it up again or wait a couple of weeks and say “I’ve been thinking about what you were talking to me the other day about the problem about getting work, and I wanted to ask if you’d potentially like to hear some honest feedback from what I am hearing from others? It might be hard to hear but it is what is being said within our professional circle and I think maybe their is value in hearing that so you had some context as to why you hadn’t been being booked and it may help you grow and improve to help get booked in the future. If you feel like you’d rather not know I do respect that but I feel honesty here will help you” and see what he says. Do try and be gentle, as hearing not so flattering stuff about you can be hard, but personally I prefer to hear and so I can grow and be more conscious..

    1. TootsNYC*

      or maybe “from what I’ve observed”–no need to start a convo about “which others?”

  18. CTT*

    You mentioned that your colleagues are bothered when you work with him as well – what do you say when they bring this up? Are you acknowledging that he was hard to deal with it first but you’ve since had good experiences? Indicating to people that you know he was a handful would help your colleagues understand that you’re not just working with him because he’s never been a jerk to you; you know the negative aspects to his personality and they’re outweighed by how good he is to work with.

  19. Roscoe*

    Yes, you should definitely tell him. I think its fine to say, “When you first came, you did X, Y, and Z, and people, including myself, didn’t really like working with you. I’ve seen you improve, and you may just need to make an effort to help others see how you’ve changed”. I’d want to know. I’ve also told friends of mine that I didn’t like them when we first met because of certain behaviors.

    As far as you are, if you are hiring people, you can hire who you want. If people have a problem with it, thats on them. You don’t owe them an explanation. They still need to be professional. And maybe once they see how he has matured over time, they will come to respect him as well.

  20. J.B.*

    I like what everyone has to say above. I’m on team talk to him – IF you think he will apologize sincerely and let it go/not feel wounded himself. Sometimes with grudges everyone is just stomping around. A simple direct apology can help, maybe a “here’s what I’m doing differently now”, but then stop. The word “but” would undo any good from apologizing.

  21. Leave it to Beaver*

    Assuming that you have a good relationship and the feedback would be beneficial (meaning he would consider it beneficial and isn’t the type to shoot the messenger) – I would tell him, should he ask you again directly. But, would avoid discussing things that you heard from others. Rather, since you had an experience with him that was less than ideal, you can speak to that. Something along the lines of — Friend, I’ve come to know you and enjoy working with you, but I must admit when I first met you, I was put off by X and Y… others may have had a similar experience and that could be impacting your ability to get work.

    1. Kiwi*

      That’s a good idea, because then there’d be no risk of him going to other people in the industry and saying “OP says you said X about me. Well, here’s why you’re wrong.”

  22. Aphrodite*

    I think I’d take a two-pronged approach. First, ask him if he is open to hearing suggestions. If he (truly) is, explain exactly what he did two years ago that put people, including yourself, off. Focus on your reactions, explaining how in those two years you came about, what he did right, what you learned, and how you feel now. Then mention that others are still in the initial phase and haven’t gotten to know him and what ideas you have for how he can begin to change that. Walk him through a process of repairing the damage but don’t suggest everything. Lead him but let him come up with ideas for this phase.

    The other part of my suggested approach would be to those who still dislike him. Explain your experience to them with details so they understand you once felt as they did, why you feel differently now, and how the journey went, what you saw and felt, and why you think they may want to reconsider their feelings as well.

    Don’t do either with the intent of solving his problems. I think if you see yourself as a kind of mentor to both sides, bringing a larger perspective, that you might be able to help both sides find a great solution. (Or maybe not; it really depends on your staying neutral and on their being open.) Good luck!

  23. Umiel*

    I think you should tell him. I was in a similar situation in which I had made an enemy at work who was in a position prevent me from moving up. No one wanted to talk about it, but finally someone clued me in. I had suspected this was the case, but it still hurt to have it confirmed. Even though it hurt, I was grateful for the information, and I wish someone had told me earlier. If I had known for sure what was happening, I could have worked earlier to repair the damage. I might also have realized that nothing I could do would help, and I would have worked harder to leave the organization I was in. Even if you don’t think there is action he could take to remedy this, it may be the trigger for him to realize that he should try something else or go somewhere else. I would have been so grateful to have gotten that feedback sooner so I wouldn’t have wasted so much time.

  24. Sci fi chicka*

    I am a big fan of feedback and if I were him I would be sad that I had such a negative impact and was not given feedback. Now, I realize my view at work is different than most – I believe in trying to help others grow (if they are interested in feedback) and let’s them make the choice of what do with that perspective. They can get mad, ignore it, take some aspects, address the mistakes and move on ,etc. I feel not giving the opportunity of feedback (I.e simply going away) in these situations is actually not desirable (again I realize I am the odd one, I come from a music performance past where every performance you sought feedback, even the final one, and even though it can be difficult in the job I have now I feel an obligation to give folks a chance). I am surprised at how often in the workplace it is “don’t give feedback” “not your place” etc. if we don’t how can we expect folks to maybe change? Even jerks.

    Now, if he is resistant, you are done. The main thing is he made that choice.

    If anyone is interested, there is a great book called “Thanks for the Feedback. The art of receiving feedback well* even when it is off-base, unfair, poorly delivered, and, frankly, you’re not in the mood. “ yep, that really is the title.

  25. Indie*

    “Are you just venting or would you actually like me to get you some feedback from people?” would sort out whether he genuinely wants to know. When that’s established though, I’d present the observations as my own.

  26. Alice*

    Maybe poaching is not how things are done in this industry… but being notorious for holding grudges isn’t a great advertisement of professionalism either. No one in this story comes off well except for OP! Good for you for attempting to handle things with sensitivity and professionalism.

  27. DeeShyOne*

    There’s a lot of good advice here, and the general consensus is: tell him.

    It’s going to be an awkward conversation, no matter what, so prepare for that at the very least. You’ll find out very quickly based on his reaction to the conversation if he’s venting or actively looking for assistance on how to move forward.

    What he does with the information after you share it is entirely up to him.

    My own personal discovery in “planning” conversations like this, is they NEVER go the way they happen in my head. Go into the conversation open and listening with the intent of just getting a message across that is helpful to him.
    Continue working with him if you wish as you see value in his work and eventually, that will get around as well.

    Good luck.

  28. animaniactoo*

    OP, I absolutely think you should mention the basis of it to him, along with the idea that it takes people awhile to rebuild a reputation when they’re overcoming a bad one.

    However, I think that you should be really careful about your own perspective here because you’ve either got a giant typo or you’re minimizing a lot. You state that he moved to the area almost 2 years ago, but then note that he’s toned down a lot over the last several years. These statements are logistically incompatible. Possibly you meant last several months?

    Whichever it is, I think the key to this is going to be making him aware that he is going to have more of an uphill battle; along with encouragement for his current path. “I see the difference, but many don’t yet – when I try to suggest you for a project, I get *REALLY* strong pushback about using you. I think you need to be aware that’s how bad an impression you made. But I don’t think you should be discouraged by that. You’re good now to the point that I DO want to work with you and DO keep trying to suggest you whenever possible. I think it’s just going to take some more time and exposure on the chances you do get, and you’ll make it through this period.”

    If there are specific apologies or actions he could take in your opinion, ask if he wants those suggestion. Otherwise, it really hasn’t been long enough for the bad impression from *last year* to be worn away and both of you should be more realistic about that.

    1. Oxford Coma*

      Good catch on the timeline! Perhaps LW knew him before his move, but forgot to mention it? It might affect my decision to tell/not tell him about this, if they had a prior relationship.

    2. Star Nursery*

      I took it to mean two years ago he pissed people off initially when he arrived and since then has toned things down.

      I read it thinking when the letter writer described the timeframe of “several” (which sounds like it could be two or more in a broad non specific description) they just meant in the two years since arriving.

  29. AVP*

    I’m in a hiring position in a very similar industry and I also want to point out that while two years probably seems like forever ago to your friend, it’s still pretty recent history to people with a longer work track record. There’s a TON of inertia when it comes to hiring freelancers – you don’t always have time to go through a formal process so you’re really relying on “who was good last time” and “who’s been recommended by someone I trust” and once the ball gets rolling, it’s rolled already.

    All that is to say – I think it really takes 5 years to correct a reputation like this, and a lot of people don’t outlast that period and end up finding different work or a different city. If you think his work is good and that he could make it, I would explain all this to him and see if there’s something he wants to change on his end to get through this, and I think it’s a conversation with happening.

    by the by – this works the other way, too. I have acquaintances who used to do great work who no longer do – and the people around them know it – and they still get hired all the time from people who remember them doing fine a few years ago, and they’re still coasting on that. I would estimate that this can’t last more than the same 5-year stretch.

    1. Argh!*

      “who was good the last time” and sometimes also “who I’ve relied on for ten years!”

  30. Boredatwork*

    I agree with the other posters who suggest making sure he wants some constructive feedback. To pretend to be Alison – who always encourages direct communication – next time he laments, ask him “would you like some constructive feedback based on my observations”.

    If he says YES, Please! Say something along the lines of “you ruffled some feather when you first broke into the industry, you did X and Y and those things are frowned upon. I enjoy working with you but your initial impression has left others wary. Have you considered reaching out to colleague A and apologizing for doing Z?” (You don’t have to be specific about the person, maybe a generic, those projects you tried to steal by low balling the quote even though they has already been assigned.)

    The risk to you is if “Unpopular guy” goes and whines to your colleagues that everyone is mean to him, and it’s so unfair. But this will basically reinforce their previous opinion and I doubt your industry will fault you for telling someone who has been a jerk to apologize for being a jerk.

  31. saffytaffy*

    My feeling is that it’s not going to be useful to tell him this unless you can also give him feedback on how to remedy the problem.
    I managed to do this successfully with a friend who loves community theater and didn’t understand why she never gets cast (in anything except her husband’s shows, after decades of auditions). I gently explained the issue and then said, “if you did X, Y, and Z it might change things.” She did, and it did. So make sure to offer him some kind of advice with which to move forward.

  32. Argh!*

    Yep, you should say something!

    It doesn’t need to be harsh. You can tell him he rubbed a few people the wrong way when he first got there and a few people are holding it against him. I don’t know if there’s a fix for that problem, though. In a crowded field, almost any misstep can be damaging to a career. Branching out to nearby cities might be the best bet, especially with a good track record with the work that he has been doing.

  33. Former Computer Professional*

    “You started out roughly here and even with your best intentions, many people found you could be a bit abrasive. I think they may still remember this and that’s why they’re hesitant to work for you. Please consider reaching out to these folks and saying something. People respect those who can own up to their past. Saying that you apologize for your previous behavior, that you’ve learned from your experiences, and that you hope you can work with them in the future, might go a long way to smoothing over the rough edges.”

  34. Llama Grooming Coordinator*

    I think there are three steps – and that’s if he’s open to it (though sometimes you might have to force the door open, so to speak):

    1) Tell him. Be nice about it, but say that when he first came in he made poor impressions. Acknowledge that even you had a poor impression of him at first.
    2) Acknowledge that you think he’s gotten better. Because you do.
    3) Provide a suggested solution. Like apologizing to people he’d directly wronged (and to be sincere about it).

    It also sounds like in your industry, first impressions matter quite a bit. And unfortunately, people have kind of decided that Fergus is…well, a Fergus. So he might not be able to repair his reputation entirely in your area, which quite frankly sucks for him. But it’s also his own doing, so he may just have to live with it. But also – is there someone who isn’t quite as adamant about holding a grudge? Because that might be an inroad to repairing his reputation with others.

  35. Bea*

    If he is told he’s built a bad reputation, there’s a lot more he can do. Including apologizing and going out of his way to show he’s no longer an arrogant turd that makes others bristle.

    Sure he won’t fix everyone’s thoughts on him but he can approach things differently and at least try. Right now he’s kind of just lost and confused why he’s getting so much static in his endeavors.

    Hell if he’s just like “oh. Well ef them then!” at least he’s aware and not left questioning his skills and has confirmation others just think he’s a dick. As much as that can hurt, plenty of people don’t seem to care either. You never know but being honest with someone you appreciate and truly want to help is the best choice since in the end, you’re all professionals. We had a broker years ago that is a diiiiick, people started cutting him out and he was shocked. He only responded when my boss told him “dude. You’re an unlikable dick. Stop yelling at me. Never speak to my employees again if you can’t be nice.” It’s incredible how people do not change until they feel the pain of their actions.

  36. katherine*

    By any chance are you and/or your colleagues female? Because if your close-knit field is anything like my close-knit field, there is often a gendered and/or Shitty Media Men aspect to such pompousness, which could play into why people don’t want you to hire him.

  37. Rectilinear Propagation*

    I feel there is literally no way to say this without being extremely hurtful and upsetting…

    But it’s hurtful and upsetting to him now. Being unable to get work is hurting his ego and his finances. Not knowing why has to be frustrating at best.

    If this is the only reason you have not to tell him then I say tell him because you aren’t actually sparing his feelings by not saying anything. If anything he’s going to be hurting a lot longer if he has to figure this out on his own (or worse, he never figures it out at all).

    Caveats: Don’t use specific peoples’ names and don’t do this if you can’t absolutely trust him not to do anything foolish in response. If there is a chance he’s going to run out and start confronting people over whether or not they like him then don’t do it.

  38. CALISO*

    I’m curious – what type of field is both freelance and collaborative? I’m not trying to out the LW or ID their particular profession, but as a corporate drone living in cubicle land, my experience is limited. When I hear freelance, I think writing, web design, consulting…none of which bring to mind a reason to hire a fellow freelancer.

    As to the question – I’m with everyone else. Tell him, kindly, in person, but tell him.

    1. AVP*

      I work in film production and it struck me that they could be talking about my work! No idea if that’s what it is though. My fiance edits a website and I think he might describe his work as both collaborative and freelance-based as well. Event planning also comes to mind.

      1. Moonbeam Malone*

        Yeah, a lot of video/media work can be collaborative (but is not always.) I do some animation freelance and it can go either way depending on the nature of the project.

    2. Anna*

      It sounds a lot like the comics community in Portland, honestly, but it could be one of any creative industries.

    3. LilySparrow*

      My first thought was theater, film, music, or some other kind of performing arts.

  39. Michaela Westen*

    I used to have problems like this from being raised in a toxic family. I honestly didn’t know how to behave or why I was having problems.
    I’m grateful to the people who said something, even if they weren’t very nice, because it helped make me aware and get me started working on it.
    Of course you want to be as nice and gentle as possible. Maybe start by saying what you like about him and why, and then mention why he’s having problems, and then say again why you like him. :)

  40. Gypsy, Acid Queen*

    Would it soften the blow to say, “Would you like for me to find out?” He says yes, then you take a few beats (days, or whatever) and then tell him the truth?

  41. NicoleK*

    Sometimes, there is no nice way to give someone negative feedback. My coworker complained about not being promoted. I kindly informed her that she needed to work on self confidence and her improve her computer skills. Our boss didn’t provide any feedback on areas for improvement. While those are correct, in reality, she’s super needy as an employee (she’s been in her role for 5 years, but needs the level of support of a new hire 7-9 months on the job). There is no “nice” way to give her that feedback especially since she’s unlikely to ever make significant improvement.

  42. Old Admin*

    I remember trying to help a colleague who’d had a similar bad start by advising about previous slipups / stepping on toes.
    His reaction was pretty bad – he flew into a rage and immediately demanded names and details. When I refused to give them, the fallout was on me. Oh well.

  43. Auntie Social*

    I’m a little late to this, but I think it’s a great thread. Having lived in various cities myself, I think it is really important that the freelancer is gently clued in on his surroundings; what might be completely acceptable and common on the west coast might be considered intolerable in the midwest. As we don’t know the any real specifics about the situation, I think it’s easy to assume the worst.

    I once worked on a mixed team of freelancers and FTE, all in a small room. The FTE staff talked and joked around while they worked, but the freelancers worked quietly during while the FTE staff had a good time — it was implicitly assumed that as freelancers, we weren’t welcome to join in the conversation.

    One of my fellow freelancers was determined to break in (regardless of warnings of other freelancers) and started chatting during the day and joining in the conversations that the FTE staff were having, and they resented her for it and would make comments about her being pushy and bossy and too talkative. After a few weeks, they fired her for not being a “good fit”. She never understood that she violated the unspoken social rule in that work environment and in doing so — despite the quality of work she did — the pissed off the FTEs.

    It seems so playground schoolyard to me, but back to the OP — it would be doing such a kindness to this person to tell him why he is not getting work, and why he has the impression he has built.

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