How to Know When a Team Member Is No Longer a Fit (Without Letting Guilt Lead You)

I used to have leaders come to me constantly about the same underperformers. Month after month, same names, same problems. But when I'd ask what they were doing about it? Crickets. Just more creative ways to avoid the elephant in the room.

Look, I get it. Nobody becomes a manager because they love having uncomfortable conversations about performance. But here's the thing: you're not actually being kind by avoiding these decisions. You're just spreading the misery around.

When Good Intentions Go Bad

Here's what happens when you let performance issues drag on like a bad Netflix series that should have been canceled three seasons ago:

The underperformer gets comfortable in mediocrity. They think everything's fine because nobody's told them otherwise. Meanwhile, they're missing out on finding a role where they could actually thrive.

Your high performers start wondering if you notice. Nothing kills team morale faster than watching someone phone it in while everyone else carries the load. It's like being the only one who shows up to help your friend move.

You lose sleep. And probably develop a slight eye twitch every time you see their name on your calendar.

The "Is This Person Still Right for Us?" Framework

Stop overthinking it. Here are four questions that cut through the noise:

1. Energy Giver or Energy Taker?

When they walk into a room, does the team perk up or do people suddenly remember they have urgent emails to check? Energy is contagious, and so is the lack of it.

2. Making You Money or Saving You Money?

This isn't just about direct revenue. Are they solving problems, improving processes, or helping the team hit goals? Or are you constantly playing cleanup behind them?

3. Are They Coachable?

This is huge. Someone who's struggling but actively working to improve is very different from someone who gets defensive every time you offer feedback. Coachable people ask questions. Uncoachable people have excuses ready before you finish talking.

4. Is the Team Picking Up Their Slack?

If other people are consistently doing their work or covering for their mistakes, you've got your answer. Your high performers didn't sign up to be understudies in someone else's struggle.

The 1:1 Dread Test

Here's a dead giveaway: Do you find yourself rescheduling their one-on-ones? Making excuses to keep them short? Mentally preparing like you're about to diffuse a bomb?

If you dread talking to someone who reports to you, that's not a personality clash. That's a data point.

Performance Improvement Plans: The Last Dance

PIPs get a bad rap as "firing someone slowly," but when used right, they're actually pretty fair. Think of them as the relationship equivalent of couples therapy—sometimes it works, sometimes it confirms what you already knew.

A good PIP should be:

• Specific: "Improve communication" isn't a goal, it's a wish. "Respond to client emails within 24 hours" is a goal.

• Time-bound: Usually 30-90 days. Long enough to see real change, short enough that you're not dragging it out forever.

• Measurable: You should both know exactly when they've hit the mark.

But here's the thing about PIPs: if you're surprised by needing one, you've waited too long. They should be a last resort after months of coaching, not a first attempt at feedback.

The Leadership Shift That Changes Everything

Ready for some tough love? You're not helping someone by keeping them in the wrong role.

I've seen managers hold onto underperformers out of guilt, thinking they're being compassionate. But there's nothing compassionate about letting someone fail slowly and publicly.

That person you're "protecting"? They might be amazing somewhere else. That designer who can't handle your fast-paced startup environment might thrive at a more structured company. That salesperson who struggles with your complex B2B process might kill it in retail.

By holding on, you're not just hurting your team—you're robbing that person of the chance to find where they belong.

How to Hold the Standard (Without Being a Monster)

When it's time to have the conversation, remember: clear is kind, cruel is not.

Be direct: "This isn't working out" is better than twenty minutes of corporate speak that leaves everyone confused.

Focus on fit, not failure: "This role requires X, and your strength is Y" sounds very different from "You're bad at your job."

Give them dignity: Have the conversation privately, help them transition gracefully, and resist the urge to bad-mouth them after they're gone.

The Bottom Line

Great leaders aren't the ones who never make hard decisions—they're the ones who make them with integrity.

Your team is watching. Your high performers want to know their effort matters. Your struggling team member deserves honesty about their situation. And you deserve to sleep without that nagging voice asking why you haven't dealt with this yet.

Stop letting guilt make your management decisions. Your future self (and your team) will thank you.

P.S. If you're reading this and thinking "But what if I'm wrong?" Here's a reality check: you probably already know. Trust your gut, document your reasoning, and act with grace. That's all anyone can ask of a leader.