"You're fired."
Two of the hardest words any CEO will have to say.
I've fired dozens of people running AppSumo from $3M to $80M.
I've never regretted a single one.
What I regretted? How I handled my first.
After coaching hundreds of CEOs through this, here's the full playbook I wish someone had given me on day one.
The framework is simple:
GATED TRIALS FIRST
SAVE SECOND
FIRE ONLY AS A LAST RESORT
1 Have a CLEAR trial period with an OBJECTIVE pass/fail
Make it short. Make it measurable.
2 Sales In 10 Days
100 CS Tickets in 2 Weeks
5 Bugs Squashed in 5 Days
You don't have to fire poor performers if they never make it into your company to begin with.
2 Save
If they're a former A Player or someone that can be saved, try and save them.
Hard pill for CEOs to swallow: your star players WILL start slacking.
I once had a star player whose performance plummeted. Most CEOs go straight to "I need these KPIs to improve. Step up or ship out."
But if someone used to be an A-player and is no longer an A-player, this is not a skill issue. Something happened to reduce their will or their motivation. So bringing up KPIs? All that does is rip the relationship even more.
Instead, I pulled them aside and asked: "Is everything okay?"
Turns out someone in their family was going through major health issues. They were struggling to balance personal life and work.
Gave them time off to go handle it. Their family member recovered. They came back a high performer again.
Had I just demanded they step up, they would've walked away thinking "this company doesn't care about me."
Sometimes people don't need a lecture. They need you to give a damn.
That story taught me something most CEOs skip over entirely.
Most performance issues are fixable. Firing feels decisive. It feels like leadership. But most of the time, the person sitting across from you just needs clarity, not an exit.
And that brings you to the real question before you fire anyone: diagnosis.
Is this a performance issue or a personality issue? "Can't do" vs "Won't do." That distinction changes everything.
Performance issues mean they don't have the skills, the training, or the clarity on what good looks like. That's on you as the CEO. You owe it to them to try fixing it before you pull the trigger.
Personality issues are different. Toxic behavior, value misalignment, dragging the culture down. These don't get better with coaching. Move fast.
Here's the mistake most CEOs make:
They delay and ignore
OR
They jump straight to the firing conversation. They walk in with the decision already made and drop it on someone who never saw it coming.
The employee feels blindsided
The rest of the team wonders if they're next
You feel like an asshole
Don't start with "we need to let you go."
Flag it early
Start with "Hey, how do you think things are going?"
If they say "not great" you say "Yeah, I agree. Let's figure out how to solve it together."
If they say "great" you say "Here's where there's a disconnect."
That's the CEO's job.
A CEO is allowed to be unsure. They're not allowed to be unclear.
You should have clear KPIs that let you know things aren't heading in the right direction long before this conversation. The employee should never be surprised.
Once you've had the diagnostic conversation, you present Two Options.
Option 1: This is exactly what needs to change, the timeline, and what success looks like. We're going to work on this together. I'm in your corner. Whatever you need to succeed, let me know.
Option 2: If this isn't the right fit anymore, we'll help you land somewhere great with a good reference, severance if appropriate, and a real transition plan.
Let them choose. That's the most dignified thing you can do.
Most people pick Option 1. And then you watch.
If they go bitter, start complaining, and poison the team, that tells you everything you need to know. Fire them immediately. You gave them a fair shot.
If they try hard, show progress, take the feedback seriously? You might have just saved your best hire.
I've had B- players become future leaders with just this approach alone.
3 Fire
If it still doesn't work after the timeline, here's how to handle the exit.
Fire on Friday, not Monday. Give them the weekend to process instead of ruining their whole week.
Communicate to the team the same day. Don't let rumors fill the vacuum. Be respectful but clear: "This person is no longer with us. Here's how we're covering their responsibilities."
And then there's the part nobody talks about.
Saying goodbye to someone you've worked with, someone you've built with, is one of the hardest things you'll do as a leader.
If you do it with honesty and dignity, they'll remember that. Some of my best professional relationships today are with people I had to let go.
That's the part that can actually be beautiful. Not the firing. The way you handle it.
See you at $100M 🤝