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I have a direct report that overall does good work. They are responsive, document things well, follows through, is willing to work after hours as necessary for the role, and in general gets things done for the role as it stands today.

The employee has been with the company for 8+ years and 5 years ago switched into their current role. At the time there wasn't much demanded of them and they had a senior coworker they could rely on for help if they needed it. They chose the opportunity because they thought they wanted it at the time.

Fast forward to the last year or so, and the employee is stating they don't like the role anymore and has mentioned multiple times they are considering going elsewhere. They often complain that the company isn't what it used to be, and that they aren't happy. In addition, their skills are more suited for what the role was 5 years ago, not for today or the future. They have stated they don't want to grow in the role either.

I'm torn because I like the person, they have been somewhat of a friend and the team is pretty close knit, and their work in general is good and fills the gaps in some areas of the team. I don't necessarily want to lose them, but I also know the role really requires newer skillsets and a better overall attitude about the workplace going forward. I've asked them about finding a new role within the company but they don't think that's for them either. Do I placate them somehow or just nod my head and leave things as is hoping the situation will work itself out with them? Force things like training or required new skills on them to force them to make a career decision? Something else?

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    What outcome do you want? It's not clear from your question Sep 24 at 14:37
  • Your question could be condensed easily to, ‚how should i make them happy, or do i just let them leave‘ …to be honest i expect almost all answers will say something alone the lines of ‚this person has already checked out, expect them to resign soon, no matter what you do they will leave‘
    – morbo
    Sep 24 at 14:42
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    Help them find their next gig, in exchange for them helping you find and transition in their replacement. Think of it as a win-win.
    – Pete W
    Sep 24 at 14:57
  • give them a new role or let them go
    – Tiger Guy
    Sep 24 at 16:41
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It sounds very much like the person and the role/the company aren't a good fit any more. Probably the best thing you can do is for everyone to be grown-ups about this and work out a way of ending the relationship amicably:

Thanks for your time here. You've said you're looking to move on, and I'd agree that's probably the best thing for all sides. Let us know when you're interviewing and we'll give you a good reference.

and at the same time, start hiring their replacement.

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  • "I'd like you to stay, and we can work together to find a role you'll enjoy. But if you decide at some point you'd rather leave, let me know, and I'll reach out to my network..." Sep 24 at 16:41
  • @MichaelMcFarlane This situation seems past that: "I've asked them about finding a new role within the company but they don't think that's for them either." Just time to move on. Sep 24 at 16:49
  • Precisely what I said. Sep 24 at 16:53
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It sounds like they're telling you that they want and intend to leave. It's not about them telling you they want a different role, it's about them telling you they don't want the current role and aren't interested in any other role. Let them go. This is a natural thing. Don't attempt to circumvent it. Employees come and go every day. This is not a big deal.

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  • "Let them go" as in "Let them resign on their own accord" is easy enough. The difficulty is making a decision that either forces them out now or firing them when the team is already short staffed and they are still in good standing from a performance perspective at the moment.
    – TheCleaner
    Sep 24 at 18:18
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Sometimes, the fit between a good worker and the role isn't what it needs to be. The best thing you can do for a good person, a good worker, is to be honest.

If you need something different from the role, explain what you need and indicate how you will help this good worker get there.

If this individual isn't interested, then try to find or create a new role that they can do well and in which they would be happy. In some teams, that wouldn't be possible.

If all else fails, you need to decide if you can live with a role that isn't providing everything you need, or not. If the latter, this individual will have to find a job elsewhere. Offer to give them a great reference.

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