Sometimes the Kindest Thing You Can Do Is Cut Someone Loose

Sometimes the Kindest Thing You Can Do Is Cut Someone Loose

When good people become wrong people

May 24, 2025
3 min read
View On:Medium

The most brutal leadership lesson I've ever learned? Every day you keep someone in the wrong role, you're betraying everyone else on your team.

This is a story I've seen play out in different forms across multiple teams I've worked with. And it always ends the same way: with the best people walking out the door.

There's always a Marcus, the loyal tech lead who helped build the early architecture but drowns as the team scales. The founding product manager who thrives in startup chaos but crumbles under enterprise complexity. The engineering director promoted for tenure, not capability, who becomes everyone else's ceiling.

Look, I get it. These are good people. They've been with you through the hard times.

The Rope That Binds

Your team is like climbers roped together on a mountain, everyone moves at the pace of whoever is struggling most. When a leader hits their ceiling, they become a ceiling for everyone tethered to them.

In every version I've witnessed, the best people start leaving with some variation of: "I need to work for someone who can teach me something I don't already know."

Meanwhile, the organization clings to the struggling leader because they're "loyal" and "trying."

But here's the truth: that's not loyalty. That's comfort.

And every day you choose that comfort, you're betraying everyone else on your team.

The Warning Signs

Watch for these patterns:

Your best engineers are "exploring opportunities." (Translation: they're interviewing.) Ambitious proposals die in endless "let me think about this" cycles. Work flows around certain leaders instead of through them.

Innovation happens despite leadership, not because of it.

The math is brutal but simple: Team growth potential = Leader growth capability.

The Hardest Cut

In the most powerful version of this story I've witnessed, the conversation nobody wanted to have became the relief everyone needed.

When the struggling leader was finally approached about the role mismatch, the defensive reaction never came. Instead: "I've been drowning for months. I knew I was failing everyone, but I didn't know how to say it without destroying my career."

The transition wasn't punishment, it was liberation. Moving to a role that matched their actual strengths meant they could finally excel instead of merely survive. Platform engineering instead of team leadership. Strategy instead of execution. Individual contribution instead of people management.

The transformation was immediate. The team's energy exploded. Shelved projects suddenly became possible. People started proposing solutions they'd written off as "too advanced for current leadership."

And the struggling leader? They thrived. Finally free from drowning in responsibilities that had been slowly crushing them.

Holding onto someone in the wrong role isn't kindness. It's torture for everyone involved.

The Test

The moment of truth usually comes when you realize you've become the bottleneck you'd never admit to being.

Do you find yourself saying 'this isn't how I would do it' more than 'this works'? When someone proposes an ambitious solution, does your first instinct lean toward curiosity or caution about complexity?

If everything escalates to your desk, if bold ideas have stopped flowing upward, if your best people seem restless, you're no longer leading the climb.

You've become the weight dragging everyone else down.

The Uncomfortable Truth

Your growth as a leader isn't optional, it's everyone else's ceiling. You cannot guide someone beyond your own understanding. You cannot teach what you refuse to learn. And you certainly cannot accelerate a team when you're struggling to keep pace.

The mountain doesn't care about your relationships, your history, or your comfort. It only cares about capability.

Sometimes the most caring thing you can do for everyone on the rope - including the person who's struggling, is to make the cut that lets everyone reach their potential.

The Real Question

So here's the question that should haunt every leader: When your loyalty starts costing other people their potential, are you brave enough to cut the rope?


The hardest leadership decisions aren't about firing bad people. They're about moving good people who've become wrong people.