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.

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