I hired a friend and it’s not going well

A reader writes:

Late last year, when my company had some turnover and we needed a high performer in stat, I weighed the pros and cons and hired a friend, “Mike,” who I had previously managed.

He and I had brunch and discussed the friendship and work aspect, but ultimately the benefits to the business (at the time) outweighed the negatives I could see jeopardizing our friendship.

My issue now is that he seems to have incredibly low confidence when he isn’t in a familiar environment and has become self-deprecating and in need of constant reassurance, so not the high performer I thought I was getting.

That’s fine, and learning new skills can be tough, but at some point I need him to just perform. I also worry I’m approaching this more as a friend (“don’t worry, you’ll get there and I’m here to support you”) rather than a boss (“I understand you’re struggling and I’m here to support you to a certain point, but it’s also on you to make some changes”). What IS the right way to help an employee who has the skills but struggles with self esteem?

I also can’t be his sounding board for his feelings anymore and I don’t know how to discuss that. For example, yesterday he made a pretty brutal error and a client could have seen something they shouldn’t have on a live screen share. Now, they didn’t, as far as I know, so it’s a lot easier to mitigate, but obviously this is an issue.

It’s the first time it happened and I handled it the way I would with any other employee — “that shouldn’t have happened, we are lucky the client didn’t see it, and I want to know what steps you’re taking to ensure its never happening again, and if it does become a repeat issue we will have to have a more serious discussion.”

But then this morning he is texting me all woe-is-me and “I don’t want to come to work, I’m dreading it.” So far I’ve ignored the texts, but I want to say “what do you want me to do about it?” It doesn’t feel like a fair place to put me, as his friend and the person who delivered the much deserved criticism, but also I will own the fact that I have put myself here, by hiring him and failing at this boundary.

I’ve let it go but he will mope about it for days — and I don’t know how to handle his emotional self-deprecation (I think because we are friends, I hear more of his internal monologue than I would otherwise).

This is on me for hiring a friend, I know, but how do I set firm boundaries/help him with his struggling self esteem without crossing into friend territory? And how do I let him know that texting me that he is “dreading work” the morning after I have a disciplinary conversation with him is inappropriate/puts me in a weird position? Or do I say anything at all?

Are you prepared to lose the friendship?

I ask because there’s a pretty good chance that’s going to be the outcome here, and you can’t move forward the way you need to as a manager if you’re not okay with that possibility.

It’s hard enough to manage a friend under the best of circumstances, but it’s incredibly hard when that person isn’t performing in the way you need — and even harder when they are treating you like a friend rather than a boss.

It sounds like you’ve got to have a pretty serious boundary-setting conversation with him. It’s going to feel awkward and not terribly pleasant, and it’s possible he won’t handle it well — but it’s ultimately the least painful way forward here.

That means sitting down with him and saying something like, “While you’re working here, I’ve got to be your manager first and foremost, and that means you can’t send me messages about dreading coming to work. That puts me in a really awkward position, and it won’t work for the professional relationship we need to have. It also means you can’t look to me to be your sounding board for your feelings about work. I know you’re having a tough time and I sympathize, but because of our roles at work, I can’t be the person you talk that through with.”

I’d go on to say, “I know this is a weird spot for both of us, and if you decide it’s not for you, I’ll understand that. But while you’re here, I really need you to perform … and so I need you to figure out if it’s work you want to do and feel you can do, and if so, to focus on doing it without so much involvement from me.”

Because the thing is — it’s not your job to spend significant amounts of time shoring up his self esteem. It’s okay for a manager to do a little of that (“from what I’ve seen you do with X, I think you have everything it takes to excel at Y” … your presentation on Z in the meeting blew me away — you have a great command of the topic and a talent for making it interesting to others” … etc.) but you’re describing Mike as “in need of constant reassurance,” that’s not a reasonable way for you to spend your time.

You could also say, “Going forward, as long as we’re working together, I think we’ll each need to manage our relationship the way we would if we hadn’t know each other previously. That means I’m going to be less available for talking through your feelings about work, and I wanted to explain why so you understand the context.”

And then … start managing him the way you would anyone else. Don’t spend huge amounts of time on his insecurities; if the conversation goes in that direction, say something like, “Let me know if you have specific questions or areas you need help with, but otherwise I’m going to assume you’ll move forward with this” and then move to a new topic or end the conversation. That’s going to feel weird to you, and maybe rude, but you’re not doing him any favors at this point by letting him stay mired in these ongoing discussions of his insecurities.

If he texts you more complaints about work or comments about dreading coming in, first try ignoring them. If it keeps happening, then you need another “let’s clarify our work relationship” conversation.

But if things keep going in that direction despite this, it’s reasonable to call the question pretty quickly: Does he want to stay in the job or does he feel like it’s the wrong match? It’s okay to ask him point-blank: “Knowing that these are the expectations of the role, do you think you can meet them? Or realistically, is this not the right role for you long-term?” It’s not okay for him to stay in the role and keep signaling to you that he doesn’t think he can do the work — and if that’s what he’s conveying, you’ve got to bring that to the surface and ask him to decide either to commit and do the work or to move on.

And of course, even if he does commit, it may be that you end up deciding you need someone better suited to the work, and it’s wise to acknowledge to yourself now that it could go in that direction, so that you’re not operating through a lens of “must make this work.”

There’s a pretty good chance that this isn’t going to end with him having the warmest feelings about you. That sucks, I know — but it’s an outcome you’ve got to make peace with if you hire a friend.

{ 81 comments… read them below }

  1. Four lights*

    Even from a friendship angle, it sounds like he’s expecting to much from you. Friends vent and reassure each other, but it sounds like this is more than that and he’s expecting you to manage his emotions. That’s just not something you can do.

    1. OP*

      Thank you for this. I did end up telling him that, but I do have to check myself and try not to manage them.

      1. RUKiddingMe*

        This is so important. I commented further down (before reading any other comments) saying basically this same thing. It is not your job even as a friend to do his emotional labor.

      2. Artemesia*

        Best case scenario here is that he somehow got stuck in this whine and leaning on you and that he can in fact pull up his socks. I know that I can manage my anxiety if I focus on doing that and I can imagine oversharing with a friend and getting caught in a spiral of whine and neediness. Hope it works out that way — sometimes when people are told they need to get a grip — they do get a grip. And he might be able to perform if you have the conversation Alison prescribed. Hope so.

        1. selena81*

          The other day i read a piece from a recruiter ‘why a good recruiter is not a nice person’ and it kinda touched on this kind of thing: you need to be honest when something is wrong (when a match is wrong, when an employee underperforms), when we’ve all been conditioned to think that ‘a good person’ will downplay and excuse other people’s problems.

          Some people are pretty much lost cases (only redeemable with loooong therapy), but others are stuck in a selfdestructive loop that they can reasonably easy snap out of once someone plants that seed of ‘what the h*ll do you think you are doing??’

    2. pcake*

      Exactly this! Being a friend doesn’t mean being a therapist; you can be supportive, but if all the weight is falling on you for more than a brief period, it’s no longer what I’d consider friendship.

    3. AMT*

      I have a friend like that. I recently had to step back and realize how much conversation time he took up venting about the thousand things going wrong in his life, asking for reassurance, requesting advice he wasn’t going to take, or ruminating endlessly about how mean everyone was to him. I’ve started to realize that I’m happier when I don’t hear from him for a while, which doesn’t exactly bode well for our relationship…

      1. Princess Consuela Banana Hammock*

        Unfortunately, I had a friend like this, too. I realized that for my happiness, I had to pull back. She was being incredibly draining and relying on me instead of following up meaningfully with her therapist. We can’t do others’ emotional labor for them, and redrawing the boundaries can be really hard.. and may result in a loss of the friendship. But is it a functional friendship if only one person carries the weight?

  2. animaniactoo*

    Huh, I think my first instinct would have been to reply to that “Dreading coming to work” text with “Understandable, but you still need to do it.”

    At this point, I would be most prone to giving him the out: “This is not working as well as we hoped it would. I understand if you want to move on to something that is more in your wheelhouse, but if you stay here I need X, Y, and Z to be in place.” Where at least one of those points is “I can’t be your go-to for reassurance about your ability to do the job. It’s creating a work issue for me, and you need to find someone else that you can talk to about that aspect of what’s going on for you.”

    1. OP*

      My first instinct was to roll my eyes and respond with “are you d***king kidding me!?”. But I didn’t, I took deep breaths and later did say to him that it wasn’t fair.

      I really appreciate your comment and the wording around this!

    2. Batgirl*

      Really? Mine would have been “I don’t think this is appropriate . ” but Alison is probably right that it’s a face to face conversation.

    3. M&Ms fix lots of Problems*

      My thoughts went straight to: are you sure you’re texting the right number?
      I mean we’ve all thought it one time or another, but unless you have sick time to use you have to grab the bootstraps and get yourself to your job. It’s just never something you willingly admit to the boss!

  3. Suzy Q*

    This guy sounds exhausting. I think I would try to get rid of him since he doesn’t seem to be cut out for the job.

    1. OP*

      Exhausting, yes. Not cut out, no. I know his skill set and he is capable of doing the job – he’s just getting caught up in his own head. The problem is that when he is caught up in his head he becomes incapable of doing the job, which is something I need to address (and everyone has given me lots of great tips on how to address it)

  4. The Man, Becky Lynch*

    I don’t see this as a huge mistake on your part, you’re friends, true, however you mentioned you’ve managed him before. So you thought you were getting one thing but he is apparently a bumbling mess when he’s new to a job, which is a huge sideswipe you didn’t see coming at all. How could you see it coming?

    So now you have to see this other side of him and take action. Which may very well mean you lose a friendship but honestly, he sounds like a friend to lose.

    1. OP*

      Thank you for saying you don’t see this as a huge mistake. I appreciate that. I did manage him before, and it was totally fine.

      I’m ok with losing the friendship and being good at my job. It sounds bad, but he needs to step up or leave, and that’s what I would say to anybody.

      1. Snark*

        I almost wonder if he’s not stepping up because he, on some level at least, kind of thinks it’s okay not to because you’re friends.

        1. RUKiddingMe*

          Right? Maybe figuring OP will cover his mistakes, give him more leeway, etc. Since she managed him in the past he should know her management style, but who can say how he’s thinking…?

          1. Princess Consuela Banana Hammock*

            This is my suspicion. Even if it’s not a conscious decision, I think the friend is kind of wallowing because somewhere deep down he thinks OP will let him get away with it. Putting OP in that position is a not-great thing to do to anyone, but especially to a friend.

            1. RUKiddingMe*

              Yeah I don’t think it has to be an intentional decision on his part. Maybe just a subconscious assumption. It’s untenable though.

              1. OP*

                I really think Princess Consuela is on to something here -> and I do believe its unconscious but its a great point. Strong boundaries will only help me in this situation.

      2. The Man, Becky Lynch*

        I’m glad to remove that rock from your back, I truly believe it. It’s also something that you can see happen even if you just hire someone with a strong resume and references. If you hadn’t known him and he had the experience and some references, you’d find yourself in this same situation [only without the texting aspect perhaps but who knows, I’ve seen people complain to bosses without actually being friends before, it’s bizarre.]

        It doesn’t sound bad to want him to do-better or leave. I’m of the same thought process. Which is why I think that you have a few more steps but if he doesn’t leave on his own,you have to terminate him. This isn’t worth what you’re paying him both in actual wages and your time/effort/patience.

      3. RUKiddingMe*

        Agreed that you didn’t make a huge mistake with this decision. Sure it may have ended up not working out, but since you did have experience managing him previously you thought you were dealing with a known quantity. Don’t beat yourself up over this.

        1. OP*

          Thank you! I have been beating myself up a bit, I believe, over it. It’s a relief to have everyone say it isn’t that big of a mistake. I know the whole ‘don’t work with friends’ rule and try to abide by it, but because we had worked well before I assumed it would be the same.

      4. Sadie*

        My friend hiredme last year on a high stakes project after I’d been out of the workplace for 15 years due to physical and mental health issues.

        She’s given me a wonderful
        opportunity and I love working with her and her mix of faith, kindness and professionalism makes me push myself harder to be my best.

        I have struggled at moments and had to set some boundaries with myself and her about when my issues were applicable to mention as a potential problem versus making her feel responsible for me.

        It took a bit of wiggle room until we found a good fit for both of us. For example she’d arrange meetings at short notice and I’d panic it meant being fired so I asked if I could have an agenda to reassure myself it wasn’t a big deal. I also use therapy and work on not taking any criticism as personal but a chance to learn.

        And we have a strict rule of email for work, Whatsapp for personal that helps set a boundary. We both check in and ask if it’s a good time to chat about work stuff on the phone and we book in totally work free time too like we spent Christmas together and didn’t mention it once.

        But it takes both people to be balancing it and treating it like a partnership to work. One person cannot tip all the emotional labour into the other’s lap and play dumb. They cannot break confidentiality or create conflicting scenarios. My friend cannot tell me some stuff in her role and I respect that. I don’t disclose aspects of my disability that compromise her at work. We talk differently in the office.

        I love my job. I love working with her and my ideal scenario is to keep her as my business associate and my friend but jobs are easier to find that truly supportive friends so I will respect her at all times.

        This has the effect of balancing work and friendship because if I don’t respect her in both spheres why do I have her in both spheres of my life?

        Long story short: Mike needs to up his game on multiple fronts.

    2. President of the Lutheran Sisterhood Gun Club*

      Yeah, I agree that hiring him wasn’t a huge mistake. You’ve managed him before and had every reason to think he would be a reasonable employee. I feel like this is a case where you need to remind yourself that he is the one causing the drama, you didn’t cause the problem. You still have to deal with the problem obviously, but you definitely didn’t cause it. I had a slightly similar situation (except I wasn’t the one making any hiring decisions, and the person in question thought we were good buddies when actually we had only been minor acquaintances in school years ago) and assumed because of that that they could get away with all kinds of ridiculousness – didn’t end well for them, and I had to constantly remind myself that I didn’t cause this person to make bad work decision.

  5. Wing Leader*

    In my opinion–not as someone who is trying to diagnose anything but just as someone who has also struggled with insecurity and self-esteem issues–Mike needs a therapist. And that, OP, is just so far out of the scope of what you can offer him.

    I think the best thing you can do now is take Alison’s advice, stop being his friend, and start being his kind but firm and effective manager.

    1. OP*

      Totally, and I agree. But while I did think he needs a therapist I didn’t say it in our last conversation. Its not something I would say to any other employee and I’m getting pretty good about drawing that line now.

      1. The Man, Becky Lynch*

        Does your health insurance [assuming those exist] include any EAP?

        You can professionally refer him that that service without saying “You know what, you’re too much, go see a shrink.”

        Instead you say it like “we have this program [give him a flyer with the info], you may find it helpful in navigating the stress you’re feeling with your new position.”

        Or if you have HR, I would think of asking them about doing that, so that you can wash your hands of it and see if it’s something they could bring up. It’s a start to managing his issues.

        1. Anita Brayke*

          Yes! I love this idea, The Man, Becky Lynch! Refer him to EAP! Struggling with stress at work is a real thing and this could help both him and you. Plus, it sounds nicer to the employee than “shape up or ship out.”

            1. MtnLaurel*

              And also a great way for you to point it out as a benefit that he may not be aware of. Keeping it in the boss conversation. :-)

        2. Princess Consuela Banana Hammock*

          This is spot on. OP is right that it would be inappropriate–in the context of the workplace and from a manager to a report—to suggest he see a therapist. But a referral to EAP is a safe way to convey the same message in a more workplace-appropriate way.

      2. nonymous*

        I disagree about not telling him that he needs a therapist. Rather, I would approach it just like any other boss/coworker and point him to EAP resources. Your employee seems to need professional coaching and that type of consulting is part of the spectrum of EAP services.

  6. CoolInTheShade*

    My best friend (practically sister) was made my manager against her wishes a few years ago. The moment each of us found out, we were both devastated and knew there would be major impacts to the relationship. Our friendship definitely changed during that time as work was a major source of stress for each of us, and we didn’t have each other to lean on as friends.

    Fortunately she quit within months of that awful “promotion” and we’re super tight again. I would never manage or report to a friend ever again if I had a choice.

    1. CoolInTheShade*

      To add on to make sure this is relevant: during that period, we completely avoided all work-related texts to each other. It was definitely not okay for him to text you what he did.

      1. OP*

        No it wasn’t, and I did have that conversation. I don’t really want to text at all, actually and I think for the foreseeable future will be avoiding out of work conversation entirely.

        I do manage another person I’m friends with (it happens like you mentioned when someone gets promoted from within) and we are completely fine. Its the emotional aspect that really causes the struggle right now.

  7. CaliCali*

    I actually think this is a situation where “tough love” has the most potential to solve the problems involved, and I’d even approach it from the friend angle rather than the professional angle. I’ve sometimes been in the “woe is me, I’m feeling bad” pity party trap and it sometimes took a friend or family member to be like, well, this is your situation, you gotta either suck it up or change something (because often, that’s what it comes down to). You’d be doing everyone involved a favor to tell him “Mike, we’ve worked together before, and we talked about this. And right now, you’re putting me in a spot where you’re not performing, and it’s falling on me to make you either shape up or ship out. Which sucks, but that’s where we’re at.” He likely won’t react well, but it’s better for him to know the stakes.

    1. OP*

      That’s actually a really good line and if the conversation we have had doesn’t solve it I’ll be back here looking this up. Thank you.

  8. I was that friend*

    I was asked by a friend and former colleague a year ago to help her out by writing llama herding and herding tracking software how-to content for her employees in the field. This is a no-brainer for me, but I was never able to get it. The reason was that I never had consistent access to their development site- which I needed to be able to write the content, I had 4 laptops in 3 months- they kept breaking down, no one could teach ME how to use the software, so I was just in there bumbling around trying to figure it out. This was supposed to be only about 20 hours a week for me- remote. However, I had to go in (4 hour round trip) multiple times for them to fix the laptops, to meet with various people to show me how to even access the development site- because every person accessed it differently I had no idea how to get in- and where to go once I was in. As I said, this should be a no brainer for me- if I am given access and a basic overview of how something needs to be used, I can figure it out and write great online how-to documents. But I couldn’t even get access, it was so inconsistent, test data was missing… uggg
    I was honest with my friend and told her I didn’t want this to ruin our friendship. She told me that she had to figure it out on her own, and when I asked her how long that took, she said she didn’t really understand it all for a good 18 months. I said I wasn’t willing to have this level of frustration for 18 more months (for a part-time job I didn’t really need), and I was tired of her being upset that I wasn’t getting things done fast enough. So it was best if I quit.
    Manager please, make sure you have given him the tools and training he needs to be successful.

    1. OP*

      This is a great point. I think I did early on assume he would know some things he didn’t and through conversation have discovered those. I have offered more training and am filling the gaps – when he mentioned those things to me I took them seriously and claimed ownership over them, so I really appreciate your perspective here and will continue to do my best to support him.

  9. GreenDoor*

    In your conversations, if it’s seeming like he has serious reserveations/worries about his performance, maybe work it in there that you won’t think less of him if he decides the job isn’t for him and wants to move on. Perhaps, because of the friendship, he knows the job isn’t right but he doesn’t want to let you down, or he feels bad at the idea of making you have to hire someone new all over again. Maybe some reassurance that your opinion of him as a person won’t change if he moves on? (If it comes up organically in your conversations, of course).

    1. OP*

      I actually had to address the issue in this letter before Alison got to replying and I did bring this up, that if it was too much it’s fine to make that decision. So I’m glad that was a good instinct.

  10. Anon just in case*

    My current manager was my friend first and he can’t turn loose of that dynamic (with me or with most of the people he’s managing). Unfortunately, this makes him a pretty awful manager, he cares more about being liked than running his division. Awful problems are festering, he needs to fire a couple of people and won’t do it.

    1. OP*

      I’m determined to not be the friend manager with everyone and thankfully only this actual friend is someone I’ve run into the issue with. I really do appreciate the difficulty of friend managers. In my first management role I erred on that side accidentally and it did cause problems. I like to think I’ve learned from it.

  11. Celia*

    Hi OP. Sorry that you’re going through this with a friend. It’s possible that he really wants to quit, but is afraid that doing so will hurt your feelings or create more work for you. I mean, if one of my friends told me that they were dreading going to work, I’d tell them to find another job – any other job – because no job is worth your sanity. It might be the best thing for everyone involved.

    1. Okay, great!*

      I had that thought too. It ended up being not quite what he thought, and he’s hoping that she’ll be the one to suggest it’s not the right fit.

      1. OP*

        Totally, and I did actually suggest that in our next conversation. I think part of it is that but part of it is him not wanting to start again somewhere new but, direct quote “with a less supportive manager”.

        It’s that supportive line I’m trying to draw in the same way I would with anybody else that’s the trouble but I’m doing my best to think everything through and actually be a supportive manager, not a supportive friend.

        1. animaniactoo*

          Hmmm. It sounds like maybe the distinction you need to draw is that moving forward, as a manager, you’re going to need to be less supportive than you have been so he needs to understand that as a “new employee” he’s had a certain amount of leeway, and as a friend he got a bit more. But the level it’s been at is not sustainable on both sides in order for this to work.

          And then be clear about what you consider support to be that will be available to him as an ongoing employee. Access to stuff he needs to be able to learn the job? Honest review of performance? Performance issues addressed respectfully? Requests for help considered (but not necessarily fulfilled, and not necessarily the way he’d want them to be)?

          1. OP*

            This is really great feedback and provides me a good conversation starter and framework if the issue continues or arises again. Thank you

          2. BethDH*

            I like this a lot! It also helps you explain that things will be changing in a way that won’t automatically make him defensive. Especially if you mention what you WILL do (that you would do for all employees at this point) like clear feedback and fair goals, access to resources, and so on. I’m hopeful that a conversation that lays out what a good employee-manager relationship looks like can be more helpful than only telling him what doesn’t work.

        2. misspiggy*

          That’s interesting. Is he assuming that the starting troubles are his fault and therefore he needs an extra supportive manager because he finds it difficult to get to grips with a new environment?

          If that were the case, EAP could really help him identify how to assertively ask for help before a gap becomes a problem.

  12. JSPA*

    “As a manager, i need to be able to tell instantly if a situation is so serious that my reports are complaining officially. your recent text showed me that I can’t reliably do that, if you also (ever) complain to me, friend – to – friend, about work issues and work anxiety. I’m still here for you, when we’re both outside the workplace, for non – work – adjacent issues. But at work, we have to be in work mode. That means a correction from me should not weigh any more or less than one from some other boss. And vice versa. I know we all sometimes have to complain about work, or process work stress. You need to find someone else for that, though. I hope and i think we can both get there. I need both of us to follow those guidelines strictly for the next 30 days, focus on results, and then meet to confirm that this new normal is working for both of us. Can you commit to that? To be clear, if a personal crisis reaches the point where you’d be informing any manager, that official process is always on the table. But anything short of that needs to be directed elsewhere.”

  13. OP*

    OP here,

    Thanks so much Alison and to all the commenters so far. I really appreciate the perspective and the words of advice!

    1. SebbyGrrl*

      Your participation and willingness to come to this forum ready to WORK is awesome, GO You!

  14. JessaB*

    Yes but other employees wouldn’t expect you to be their emotional management go to person and if they did you’d have shut it down as weird. So I think you would have said it to another employee, maybe.

  15. AKchic*

    I’m going to come right out and say it – a lot of this sounds very much emotional labor. OP – do you think you are getting this much emotional baggage dumped on you because you’re his friend in general, or because you’re his friend-boss that he can dump on and garner sympathy from in hopes that it will lessen the impact of his potential mistakes?

    I bring this up because I see this sometimes when managing groups of volunteers. We’re all, to one extent or another, friends. But, with 400+ of us all working towards the same goal, we’re also coworkers. If something isn’t getting done, we do have to come down on someone at one time or another, and occasionally reassign work, or take a plum role/assignment away from a person. I occasionally see the “sob story excuse” come into play, and it tends to be directed towards female leadership more often than the male leadership. When the leadership roles come together to discuss it, it’s noted, especially if more than one sob story has been given within the same time frame. It’s always a woe is me, self-deprecating, low self-esteem issue combined with an actual concern (and a home-life issue). The “Perfect Storm” of drama that makes you want to feel sorry for the person and go easy on them so you don’t add to their mental/emotional burden so they can succeed and then feel better about themselves, thus getting that boost of confidence and doing better!

    The problem is – they aren’t going to. They’ve set you up to feel sorry for them and they are settling in to a pattern.

    The best way to get ahead of this sort of thing is to set the higher expectations and stop being the emotional outlet. Sorry not sorry, but you’re the boss and not his friend. You need to focus on the work aspect, so he needs to find someone else to be his emotional outlet. Refer him to the EAP if he continues. Treat him as you would any other employee.

    1. OP*

      I think because I am his friend in general, but I appreciate the emotional labor point here and bringing up if maybe it is a sob story. Your comment is appreciated greatly, and has given me food for thought!

    2. Alana*

      I manage a friend right now in a project manager role (so we have the same ultimate boss, and I don’t evaluate her or make hiring/firing decisions, but I do check in with her on deadlines, make sure tasks are getting done, etc) and the “sob story” thing cuts right to the core of it. There’s always a reason, and I’m sure it’s a true reason, and it’s fine to give your friends that context when you’re venting about work, but if you wouldn’t say it to our (mutual) boss, don’t say it to me.

      1. OP*

        I like this – I can use it too. “If this isn’t a conversation you would have with “Doug” (ultimate boss), then it isn’t one that you should have with me”

  16. Jennifer*

    No sense in piling on and reminding you of what you already know. I hope that he finds another role soon. It sounds like your friendship will be able to rebound if this ends soon.

  17. hotdirt*

    I wanted to comment, as I have been the managed friend who did not perform. In my case I wasn’t hired by my manager (she was promoted to manage our group), but I don’t think that matters much to the dynamics. We were friends, pretty close in fact, for several years before she became my manager. In my case, my performance was not terrible, or fireable, but we had some fundamental disagreements on how I should perform my duties (basically work style conflicts), coupled with a failure on my part on a task I was given. So: she was not happy with me, but I wasn’t in OMG fire this person already territory.

    I urge you to have this painful conversation now, because my manager (and now ex-friend) did not, and instead summarily fired me from my task for her, and tried (half-heartedly, but still) to get me fired all together from our workplace. That failed because there was nothing actionable in my record – the thing I had done poorly at certainly wasn’t great, but no other management personal thought it remotely rose to firing level. As it turned out, she was just fed up with me, and just could not deal anymore with her fed-uppedness. Had she had a painful conversation with me, say, a year earlier, perhaps things could have been salvaged, or even if not (I think our work styles would always have been incompatible), I could have moved on to other tasks amicably, and without what ended up being a fair bit of drama involving higher level managers that frankly damaged both of our reputations.

    TL;DR: suck it up now, because either way it’s going to hurt or end your friendship, and you may as well have that in the way that is least disruptful to both of your careers.

    1. OP*

      Thank you for this context and your own story – it makes me genuinely feel that addressing this now is the right instinct to have.

  18. Rookie Biz Chick*

    Hey, OP, I hired a prior colleague/friend in my small business a couple of years ago and let the drama around her low and eventual non-performance go way too far before I finally knew she had to go. It wasn’t fair to either of us. She invoked her anxiety when we had candid talks and I tiptoed around thinking I was giving her space to manage it. That wasn’t the right answer. My frustration with her – and ultimately with myself – spilled out in some really unhealthy and unprofessional ways.

    Sounds like you’re addressing some issues and have awesome scripts and guidance for the rest of it. I just write in solidarity of knowing how it feels to believe wholeheartedly that a person is the rockstar you worked with previously, then realizing they have a crippling lack of confidence and/or motivation that makes work life so difficult getting back on track.

    Definitely don’t let it go as far as I did without being clear and decisive – and then realizing once they’ve moved on how much freaking work actually never got done.

    1. OP*

      I really appreciate this – and I get what you mean about the “invoking anxiety” piece. Tiptoeing is definitely not what I want to do and I SO appreciate the solidarity. Clear, decisive, compassionate and boundaried is how I aim to be with all my reports, and there are a lot of great pieces of feedback here.

  19. RUKiddingMe*

    “…it’s not your job to spend significant amounts of time shoring up his self esteem.”

    i.e. Emotional labor.

    Even just in the realm of friends, without a work/boss/employee component it’s not your job to do his emotional labor *for* him.

    Some sure…friends and all that, but even as a friend you are not obligated to be his constant emotional dumping ground…on any topic.

    Alison, as an aside do you know if OP is a woman or male?

    1. Batgirl*

      I was debating whether or not to ask this question! I mean…it was entirely possible that Mike was trying to put his head on the shoulder of his close male friend; but I thought it more likely that OP was female and it was “yay lady bosses are nice, understanding and do free emotional labour!”

      1. OP*

        It’s a totally valid question in the context – and you’re not wrong. Although, I did check myself and ask if I rely on him in any way inappropriately to do emotional labour for me – when I’m having out of work issues, and the honest answer to that is I probably do. So I’m going to add an amount of personal ownership into the conversation – where I’ve relied on him and need to stop so we can focus on our work relationship. I’m not entirely innocent in this.

  20. Cat owner*

    Ug this one hits me cos I was a total Mike at my last job that I left about six months ago. Boss and I really should have had a lot more boundaries in place. I’m glad I left but I’m so embarrassed to look back now that I have an arms length relationship with my managers!

  21. Glengarry*

    I hired a friend once who I had worked with previously, and that also turned out to be a huge mistake. It actually really blindsided me, because at our previous employer she was fantastic and brilliant and amazing and respected by everyone. Luckily it was only a contract position for six months, and happily my managers were completely understanding and didn’t hold me responsible at all for her poor performance, but it was a really huge lesson for me. So no, I don’t agree that this is on you at all! You made a sound decision based on previous evidence, and it was just not possible for you to tell that it would turn out this way.

    1. OP*

      Thank you! This reassurance has made things easier for me to look at the situation objectively and really take a step back.

  22. Rez123*

    There is a lot more happening than just “not a good idea to hire a friend”. I think when you are good friends with the manager the boundaries do get muddled up, but I also think that most poeple know not to send texts about dreading to come to work for the friend/manager. Yeah, it’s time for a good talk about work relationship/personal relationship, It will propably have an effect on your personal relationship, but I think when Mike is an a better state of mind he will appreciate it.

    1. OP*

      I think you’re right too. It’s up to me to ensure that the boundaries are solid and address the relationship the way I would with any other employee. Thank you for commenting!

  23. A.*

    I know we’re focusing a lot on #5 so far, but I just want to say that #2 (heehee) is astonishingly out of line to me. It’s not okay to gossip about private client information in a relatively public area. And it’s not okay to call someone out for “eavesdropping” when I assume that OP was in the bathroom stall first!

    Also…who wants to hang out in a bathroom? Is this kind of gossip-y weirdness not what we invented the term “water cooler conversation” for?

  24. Shay*

    ” … hired a friend … I used to manage.” As a manager, you can be friendly but you cannot be friends. Sadly, this was doomed from the beginning. Are you prepared to lose the friendship or lose your job? One of these will go …

  25. Candace*

    I’m totally not piling on about hiring a friend because I agree you had every reason to think Mike would perform, but maybe for the future, if you do consider hiring someone you know otherwise, it might be helpful to have a very blunt conversation in advance. I’ve been hiring for 22 years, and only twice hired someone who was also a friend, because I was really, really confident that they were good for the role and that they wouldn’t be weird. But even so, before the hire was done, I said “In this arena, if it comes to a choice between boss and friend, I have to be boss, and if that means losing friend, it’ll have to be that way. If I ever have to fire you, I will. I cannot be your friend here. I realize you won’t be that way, but I have to be clear on that.” They were totally fine with it and did great jobs. If someone reacts badly to that, it might be a red flag.

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