They’re great.
They’re impossible.
And you can’t afford to lose them.
At least that’s what you keep telling yourself.
You have lots of evidence for the “great” part: They’re reliable. Everyone likes them. They know where everything is and they’ve been with you for years.
Then there’s the other part. The part about how their actual job isn’t getting done.
Or maybe it’s the other kind of employee. The rockstar who’s wicked smart, hits every number, and is faster than everyone else.
But no one wants to work with them. They act like they’re above the rules and talk down to people.
How You Say It
You’ve had the conversation four or five times. How things need to improve. They agree, but nothing changes.So the next time you talk, you try again. Like always, you lead with what’s working. Then you casually mention what’s not working near the end.
You finish by reminding them how much you appreciate them.
You don’t see this as confusing. You’re just being polite.
Besides, you don’t want them to get offended and quit.
You go around and around in your head:
They’re great. They’re impossible. They have to change. I can’t afford to lose them. They can’t keep treating people this way. No one else can do what they do.
You’ve been having this argument with yourself for a year. It never resolves. It just starts over.
Then the Email
And then they ask for a promotion. Or for three weeks of PTO during your busiest month, when the entire company knows it’s a blackout period.You read the email twice. You get angry, then you get anxious. You feel sick because now you know you have to say it out loud.
It’s time to look them in the eye and say what you’ve been avoiding:
“This isn’t working.”
It’s better for you. It’s fairer to them.
Maybe in the past they heard what they wanted to hear.
But maybe you spent five minutes on what they’re great at and thirty seconds on what’s not working. They can’t tell how much it matters.
Some version of this happens to almost every founder I know.
Why We Do It
The problem doesn’t go away. You just reassign pieces the of their job that they’re not doing, or continue running interference for the difficult player.And every conversation gets harder. You feel inauthentic because what you say doesn’t match what you think.
Meanwhile they’re making decisions about their career, expecting things will go on as they are. They may even be making big purchases thinking their job is secure.
When someone wasn’t working out, I almost always kept them too long. Usually because I believed someone was better than no one, and I didn’t think I had time to hire and train a replacement.
Sometimes the person was so well liked I was afraid other people would quit if I let them go.
That never happened. I just thought it would.
More than once, I kept someone because they were the only one who knew how to do that part of our process.
Every one of those reasons was about me. My time, my risk, my fear of what would happen next.
Maybe you have a reason that sounds better: You don’t want them to think badly of you for letting them go.
That one is about you too.
But none of those reasons has to do with whether the person is doing their job and working well with the team.
Two Questions
1. What does this person reliably contribute?2. What does this role actually require?
The answers don’t always line up.
You’re looking at whether this person, in this role, in your company, right now, is a fit.
If they’re not a fit, it doesn’t mean you’re calling into question their worth as a human.
But the job has to get done, and they need to know when they’re not meeting the standard.
Hearing you finally spell out what isn’t working and what happens if it doesn’t change may come as a surprise to them.
That doesn’t mean you should keep avoiding it.
As the owner, part of your responsibility to them is to be clear.
They need to understand the stakes so they can either step up or find a place where they can thrive.
Then the debate about what to do stops taking up so much space in your head.
And you get to stop second-guessing yourself.
