I manage a friend and it’s not going well

A reader asks:

Late last year, when my company had some turnover and we needed a high performer in right away, I weighed the pros and cons and hired a friend, “Mike,” who I had previously managed. The benefits to the business (at the time) outweighed the risk of 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, and he is 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. They didn’t, as far as I know, so it’s a lot easier to mitigate, but obviously this is an issue.

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 it’s never happening again.” But this morning he has been texting me things like, “I don’t want to come to work, I’m dreading it.” It doesn’t feel like a fair place to put me, as 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).

How do I set firm boundaries? 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? Or do I say anything at all?

I answer this question over at Inc. today, where I’m revisiting letters that have been buried in the archives here from years ago (and sometimes updating/expanding my answers to them). You can read it here.

{ 34 comments… read them below }

      1. Too Many Tabs Open*

        I love the Andrew Rule; that’s a great way to maintain boundaries.

        (Summary: Andrew was another coworker who LW had a great professional relationship with; when deciding whether to tell Mike about some personal thing, LW asked “would I tell Andrew about this?” If the answer was “no”, then it wasn’t appropriate to tell Mike either.)

      2. Vio*

        Thanks. It’s great that things improved. A little sad about having to suspend the friendship but completely understandable.

  1. Telephone Sanitizer, Third Class*

    I feel really bad for the guy but I also hate the idea of having to manage a situation like this. Alison’s answer on the article was very sensible and I hope it worked out in some form.

  2. Mmm.*

    One thing I’m not seeing in this: What training has been done?

    I was a high-performer brought into a new job by a former manager/friend. In fact, I thought this was about me until the inappropriate texts about work! I would never.

    They relied on my history of high performance, not considering that I had been brought in for a different role, which also kept changing every couple of weeks. I received zero training at any point. When I asked for support, I was given the same response as here (albeit in different words): I just need you to perform.

    I ultimately got fired over all of this. The view from under the bus sucked.

    Was this previous high performer given the job-specific training they need to succeed? Sit down with them to figure out where they’re struggling in general, not on a case-by-casr basis before you decide what to do.

    1. OMG It's 2024*

      I feel you! I was hired away from the company I’d been with almost 10 years and had built a 22 person team and a large chunk of business for. The offer from other *big gov contractor* was too good to pass up, for a variety of reasons. BUT, then I got ZERO support. “We don’t have a Llama grooming capability so we can’t sell it for you.” “We have no contract vehicles in place for clients to get to your services through” etc… First year, I got “exceeds” because I was able to work around a lot of corporate deficiencies, but second year, our division was sold off and we lost “BIG C” support/access to resources and I had nothing to offer and my leadership just did a lot of shrugging. I wasn’t let go, but I let myself go….and am so much happier now 6 years on, with all of that nonsense in my rearview mirror!

    2. goddessoftransitory*

      Ugh, that is all too familiar to me from school days: when you’re a high performing student, an amazing amount of teachers will openly resent you if you don’t get something or are struggling with a subject. They saw you as the “easy” kid they didn’t have to worry about and suddenly you aren’t.

    3. Filosofickle*

      Yes, to most of this (just not hired by a friend). I’ve always been a high performer but right now i’m flailing — no training, no structure, bad fit, and constant changes. Was moved into a role that isn’t what I was hired for and doesn’t match my skills set at all. I’m just supposed to figure everything out! So, yeah, my confidence is in the tank and need more help than I have ever needed before. Who they see and who I usually am are not the same person.

      1. ferrina*

        Ugh, that sucks! I had that happen as well. Absolutely no training, what little training they did give was designed for other roles (maybe 10% applied to me), and the person who was supposed to be managing me went MIA for months, so I had no one I could ask questions of. It was so bad that I was told I was supposed to be managing a team, but never actually told who was on my team that I was supposed to be managing (I asked HR, managers, even the people themselves….no one knew if I was their manager). The Boss was so in their own head that they didn’t even realize that they did anything wrong in their (lack of) training. They just expected me to intuit the role.

        It didn’t get better until I left the team. Luckily I was able to find another internal role, but I recommend beefing up the resume. And it definitely did a number on my confidence and drive.

        1. Filosofickle*

          Yeah, I didn’t even mention that my boss went on a 6 month leave right as I was moved into the new role. I’m sorry there are so many of us!

    4. Elle*

      I’m experiencing this in a new position I was promoted to. My boss keeps telling me to figure things out independently but doesn’t give me the tools or background. Everything takes forever as I try to complete vague tasks (and not doing them well) and I’m falling behind. If my boss would just give me clear instructions things would move faster, be done correctly and I’d feel better about myself.

  3. Menace to Sobriety*

    Oh yeah. I’ve been there. I hired a former friend that I had worked with tangentially on a program (different companies, similar roles, no management responsibilities for either of us). We worked together GREAT. We used to joke we “shared a brain” because we were so in sync about how to get things done. Then I got hired by another company to build a team and he was my first hire. Started off okay, but it quickly devolved when we didn’t have the same “we’re equals with equal input into this decision/process/whatever” and I had to say, “I’m making an executive decision here and I need you to be on board with it,” etc… He basically wanted us to be “co-managers” of the growing team, but that just wasn’t sustainable because I needed him to focus on client delivery while I was focused on management, spend plans, hiring, etc… He stayed on for several years, once he was deployed to a client site and we weren’t in the same office all day, but our friendship suffered greatly and by the end of my time there when I chose to leave, he was cordial, civil, but didn’t even attend my going away party. Go into hiring friends with eyes WIDE OPEN and the fortitude to accept a relationship shift.

  4. Jiminy Cricket*

    What’s the advice when you’re not willing to lose the friendship? Is the only option then to leave?I’ve reached a point in my life where my close friendships are more important than my career. I need my people, and I’m not going to put a company ahead of them. (Maybe Mike wasn’t this lw’s “people,” just a friend.)

    And this is exactly why I have always refused to hire or manage friends, even in a couple of instances when their skills would have been a real boon to the company.

    1. Polly Hedron*

      Yes, I don’t think “Are you prepared to lose the friendship?” is a reasonable question, because if OP’s answer were “no”, it appears that the OP would have had to quit her job (which would have been even worse for Mike because a new manager would be unlikely to allow Mike’s dependency). Better wording would have been “Now that you are in this situation, to do your job, you must risk losing the friendship.”
      Fortunately, OP’s update said that it all worked out OK.

      1. Cyborg Llama Horde*

        A bit late now, but if you aren’t prepared to lose the friendship, I don’t think you should get into this situation. Or quit the job, but depending on how badly things go, even that might not save the friendship.

        1. tamarack and fireweed*

          Friendships get lost over just about any substantial change. Getting a romantic partner, getting married, having kids, professional changes, relocations … all and any of these, done by either partner, can end up costing us a friendship.

          Usually if this happens to us we end up thinking that the friendship was more conditional than we had previously thought, or that we were wrong about the friend’s values after all. Nonetheless, if you really aren’t prepared to do anything that could cost you a friendship then you wouldn’t be able to do anything at all.

          1. tamarack and fireweed*

            (I should say that if you already feel that *working* with your friend, or under your friend, or managing your friend, would be iffy, it’s completely reasonable to turn down a job where you’d have to do that. Below I described how I successfully managed a friend, but we were work peers first before we became friends, and then I was promoted.)

    2. Rebecca*

      I think the advice is to do exactly what is in yourlast line. If you know that your friendships are important and you’re not willing to lose them, don’t hire your friends in the first place.

    3. Your Mate in Oz*

      In the past I’ve turned down offers to work for friends because I don’t want to risk the friendship. It can go south a whole lot of was, even more so because I’m neurodivergent and what people see whan I’m feeling sociable is the 10% side of me. At work I’m the person who WFH when I can and tries to avoid people when I have to go into the office. I’m always balancing “being part of the team” against just how unsocial I can be. Working for someone who previously only saw me when I feel like being social seems like a recipe for disaster.

      I’ve had a couple of good experiences with close friends where I’ve said: this is what I’m willing and able to do, and what I expect out of it both financially and in terms of friendship. And they’ve been fine with what I’m willing to offer. But those have been “one of my hobby-ish skills is X, I’ll do X for you because it’s fun if cover my costs” type things where the wage side is more “you owe me a favour” than actual money. Importantly those have been week-ish side jobs rather than career ones.

  5. Jezebella*

    I wouldn’t be surprised if there was a gendered aspect to this – is LW a woman, and therefore more likely to be perceived as someone he can dump his emotions on? I’d bet dollars to donut LW is NOT a dude. I’m glad for the update, though, seems like they’re working it out.

      1. amoeba*

        True. She also does say that she realised she was also “dumping her emotions” on Mike though… so maybe not a huge imbalance, just not working well with the management situation!

  6. BellyButton*

    There have been a few times over the years that I have been tempted to hire someone I previously worked for. I always remember the AAM stories and reconsider. I haven’t ever been close friends with any former colleagues but close enough to get together every now and then for dinners, drinks, or the occasional house party- but I still think close enough it could be an issue.

  7. BellyButton*

    The update, linked above, is a good example a manger setting boundaries AND figuring out how to help a person gain confidence and utilize their strengths.

  8. tamarack and fireweed*

    I once managed a friend, for about 3 years as a team lead and then for another year as a manager (with a team lead between us). He was already there when I was hired, and we realized quickly that we had a home town and school in common and became friends instantly. Then, about 6 months later I was promoted to the lead position. After nearly 5 years in the job I was laid off, and he was laid off about a year later (they got rid of our entire function in our location). This was the European headquarter of a US company, with a lot more employees in the US and Canada, where I traveled regularly.

    Our Managing Director at the time, and American, was one of the best managers I’ve ever worked with – actually the first time I worked under *good* senior leadership, and it was an eye-opening experience. I still have very warm feelings for him. After he promoted me, he called me to a meeting at his office. He opened the meeting saying, and I remember this word-for-word, “[my name], you’re going to manage a friend. This is possible.” Then he proceeded to tell me that there would be times where I’d call him (most of my team was distributed over several European countries) and say “[friend’s name], I’m calling as your boss right now”. He advised me to make a clear distinction between talking with him as a friend or as their lead. He told some anecdotes, and took time to address some possible scenarios (eg. potential future performance / improvement points for him and my other team members, who all used to be my peers). He also talked about how it was valuable for me to have someone in the team who would feel comfortable to speak frankly with me, especially about problems, as long as there was no favoritism (real or perceived). (Until my second promotion, I wasn’t the ultimate sign-off on performance, hiring, firing, and also didn’t have insight into people’s salaries.)

    And overall it worked out great. Did we have to be careful to think about boundaries? Sure! Would it have worked if he, or I, had had a problem with compartmentalizing? No! Was there a limit to the depth of our friendship at the time and were certain topics too touchy to have boundary-free conversations about? Yes! But for two grownups who have good professional manners and care about preserving both our friendship and our professionalism it was totally doable. And work-wise I’m particularly grateful for the time he told me that the team really hated that I started meetings a few minutes late (on the old-style IP conferencing equipment, gah, in the bad, pre-Zoom times). And we were able to occasionally (like, once a year) hang out or go to a music festival together. We’re still friends.

  9. Going Against The Flow*

    Got to say I’m feeling for Mike. Gets recruited by a friend who is desperate to build the team and assumes he’ll be stellar right off the bat which doesn’t happen. Is it fit, lack of training, confidence issues who knows.

    Now it’s the classic advice to for the boss (seems all the writers are higher ranking) to decide is the friendship or career is more important and then unilaterally act on that decision. Now the person with less power gets no input and possibly has to move teams, maybe lose a job and/or friendship but we can all be happy the boss learned her lesson and created boundaries at the expense of someone else who didn’t get an equal say even despite being more affected by the outcome.

Comments are closed.