When Your Best Friend Becomes Your Employee (And It Starts to Hurt)
1. Brutal Reality Check (Opening):
You used to drink together on Fridays. Now he waits for your feedback in silent Slack threads.
He used to call you “bro.” Now he calls you “boss.”
He was your ride-or-die.
Now he’s the one slowing the team down. And you know it.
2. Execution Brief:
What hurts:
You’re torn. Loyalty says “protect him.” Leadership says “hold him accountable”.
You hate feeling like the bad guy. But the team is watching.
Where leaders screw up:
→ Avoiding the tough convo because of history
→ Overcompensating with favoritism or silence
→ Letting emotions stall decisions
What to do / say / avoid:
✔️ Address it head-on, privately
✔️ Separate personal history from professional impact
✔️ Be clear about expectations, not feelings
❌ Don’t vent to other team members
❌ Don’t hope it “fixes itself”
Real-life micro-story:
One founder kept covering for his old roommate-turned-CTO. Six months later, the dev team walked.
They weren’t mad at the CTO.
They were mad at him, for not stepping up.
If you only remember one thing:
You’re not leading just him. You’re leading the room watching how you handle him.
3. Action Protocol: “The FRIEND Cut Framework”
How to handle it without destroying the bond, or the business.
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Face It: Set a meeting. Name the tension. Don’t script it. Say what’s real.
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Reframe It: “We have history, but right now, I need to wear the founder hat”
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Inspect It: Outline the impact, I mean, facts, not feelings. “Here’s what’s slipping…”
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Expect It: Define what needs to change. Short timeline. Crystal-clear standards.
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Decide It: If nothing shifts, you choose: friend or leader. No in-between.
4. One Line That Hurts (Reflective Punch):
If you’re scared to lose the friendship, ask yourself: was it really friendship, or just comfort with no accountability?
5. 1-Minute Field Test:
Today, write down ONE team member you're protecting more than you should.
Ask yourself: Would I tolerate this if they weren’t my friend?
Then ask them for a 15-minute call. Don’t prep slides. Just say the hard thing first.
6. Real Question from the Field:
"One of my co-founders became my direct report after the re-org. Now he's passive-aggressive in every meeting. What do I do?"
→ Acknowledge the shift head-on. Don’t dance around it.
→ Give him clarity or an exit, not another vague chat.
→ You’re not equals anymore. Own it or step down.
7. No-BS Sign-Off:
This leadership thing?
It doesn’t come with instructions for when your friends become your reports.
But it does come with consequences if you pretend nothing changed.
Keep leading anyway. Even when it sucks. Especially then.
Pawel Pawlak
https://www.linkedin.com/in/dr-pawel-pawlak/
Zero Bull$hit Leadership: the shit no one teaches in business school, but every real leader faces by Thursday.
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