One of the hardest decisions you’ll ever make as a leader is letting go of someone you like. Someone who’s been loyal. Someone who means well. Someone who’s trying. But here’s the truth most leaders avoid: you can care about someone and still need to let them go.
Keeping someone who’s not aligned with the business—out of fear, guilt, or comfort—isn’t kindness. It’s dysfunction. And over time, it rots your culture, slows your growth, and drains your energy. Leadership requires courage. Especially when it’s personal.
Why This Is So Difficult
Let’s be honest: firing someone you care about sucks.
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You’ve built a relationship
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You remember their early wins
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You want to avoid hurting them
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You think more time or coaching might fix it
But leadership isn’t about keeping everyone happy. It’s about protecting the mission and doing what’s right—even when it’s hard.
The Cost of Keeping the Wrong Fit
When you delay a necessary firing:
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Your A-players carry dead weight
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Standards start to slide
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You build resentment
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You create a gap between what you say and what you allow
Everyone feels it. Even if you never say it out loud, your silence is a message.
Culture doesn’t break from one bad hire.
It breaks when leaders protect the wrong ones.**
Red Flags It’s Time to Let Go
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Repeated underperformance despite clear expectations and coaching
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Attitude problems that impact team morale
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Inconsistency that creates delivery risk
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Resistance to growth or feedback
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Lack of alignment with your company’s mission or values
You don’t fire for one mistake. You fire when patterns don’t change—and start costing your company time, trust, and traction.
How to Fire Well (Even When It’s Emotional)
1. Be Clear—Not Cruel
You can be direct and still be kind. Say what isn’t working. Say what you’ve already tried. And say why this decision is final.
Bad: “This just isn’t working.”
Better: “We’ve talked about the missed deadlines and how it’s impacting client delivery. We’ve tried coaching and adjusting your role, but the pattern hasn’t changed. It’s time to go in a different direction.”
2. Keep It Short and Clean
This isn’t a debate or therapy session. Stay focused. Don’t get pulled into emotional loops. You can be compassionate without apologizing for the decision.
3. Protect the Rest of the Team
After the conversation, communicate clearly with your team. Don’t throw anyone under the bus. Just reaffirm your commitment to the mission and the standard.
4. Learn From It
Ask yourself:
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Did I set clear expectations early?
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Did I avoid this too long?
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Was I honest with them—or just hopeful?
Leadership means learning. Every decision—especially the hard ones—shapes you.
Personal Story: When I Had to Fire a Friend
Years ago, I hired someone I cared about deeply. We’d been through a lot together. I wanted to give him a shot. At first, things went well. But over time, deadlines slipped. Communication got weird. Clients started noticing.
I made excuses. I gave too many second chances. I avoided the conversation until the damage was done. When I finally let him go, it was painful—but necessary. I realized that protecting him was hurting everyone else—including me.
It taught me that loyalty is important—but alignment is non-negotiable.
Final Thoughts: Lead With Heart, Decide With Clarity
Letting go of someone you care about doesn’t make you a bad leader. It makes you a real one. Because you’re willing to do the hard thing to protect what you’re building.
👉 Book a leadership clarity call if you’re stuck holding onto the wrong person—and need to move forward with strength and integrity.
You can care about them.
And still let them go.
That’s not betrayal. That’s leadership.
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