How to Tell Someone They're Underperforming Without Losing Them

There's a conversation most managers will do almost anything to avoid. The one where you sit down with a talented person and tell them their work isn't landing.

So they wait. They hope it corrects itself, or they drop hints in team meetings that the wrong people pick up. Months pass, the results don't move, and the story hardens: this person can't do it.

Usually that's not true. What's true is that nobody has told them the truth in a way they could actually use.

I've watched a lot of these conversations go badly. The manager either softens it into vapor, "just keep doing your best," or unloads three months of frustration in one sitting. Both leave the person confused, and neither changes anything.

Start with what's real

The version that works starts with genuine appreciation. Not a compliment sandwich. Name the things this person actually does well, and mean it. You're not managing them out. You're raising it because you want their effort to have the right impact, and you want them to move forward in their career. Say that part out loud.

Then describe the gap plainly. What you see from them, and what the results have actually been. Be specific about who it affects and how. "This is a problem for your coworkers because," and then say the real because. "Be more strategic" is a personality verdict, not a request. It gives someone nothing to do on Monday.

Leave room for their side. Things aren't perfect where you work, and pretending otherwise costs you credibility. "I'm sure you have your reasons" isn't a throwaway line. It's you staying open long enough to learn something you didn't know was going on.

Then hand them the problem

This is the move most managers skip. Don't walk out of that room with your fix. Ask them to take three days and come back with two things: what they see as the problems, and how they'd solve them. Set the next meeting before you leave. Ask what they need from you to make it happen.

That last part matters more than it looks. When you hand someone your solution, you own their improvement. When you ask them to bring you theirs, they own it. People protect what they built. A plan they wrote beats a plan you assigned, every time.

This is the same principle behind everything else about leading well. The goal was never to be the person with all the answers. It's to build people who can find the answer themselves. Done right, an underperformance conversation is mentorship with a deadline.

Most of the people I've seen written off didn't need to be replaced. They needed one honest conversation, held with enough respect that they could hear it, and enough structure that they knew what to do next.

The kindest thing you can do for someone who's falling short is tell them clearly, while there's still time to turn it around. Avoiding it isn't kind. It's just easier for you.

If the same problems keep routing back to you because no one else has been shown how to handle them, you might be the bottleneck in your own business. Find out with the free Founder Bottleneck Checklist at jamiemasoncohen.com.