If you ever think “Should I fire this person?” even once—fire them kindly, but … well … now.
This is going to be controversial. But hear me out.
I used to think you should give people the benefit of the doubt. Coach them. Give them another quarter. Maybe they just need more time to ramp. Maybe the market is tough. Maybe they’re dealing with personal stuff.
Here’s what I’ve learned after 15+ years and watching hundreds of B2B companies: The moment you start questioning whether someone should stay, they should go. Kindly. With compassion. After all — it’s your fault for hiring them. But now.
Not in 30 days. Not after their next review. Not after you “give them one more shot.”
Why Your Gut Is Always Right (And Why You Ignore It)
Your subconscious processes way more data than your rational brain. When you think “Should I fire Jason?” your brain has already calculated:
- Their declining performance metrics
- The team dynamics when she’s in the room
- How customers react to them
- The excuses that keep coming
- The energy drain she creates
But then your rational brain kicks in with all the reasons to wait:
- “He’s nice and we like him”
- “Hiring is so hard right now”
- “What if we can’t find someone better?”
- “He’s still got potential”
That rational brain is protecting you from a difficult conversation. It’s not protecting your business.
The Hidden Cost of “Pretty Good” People
Here’s what happens when you keep someone you’re questioning:
They burn cash. That “okay” VP of Sales hires 2x more mediocre reps to hit their number. None of them make quota. Your CAC:LTV ratio goes to hell. What should be an 18-month runway becomes 9 months because you’re paying a team that can’t sell.
They lower the bar. Every A-player on your team sees you tolerating mediocrity. They start to wonder if they’re in the wrong place. The best people only work with other best people. Keep the B-player, lose your A-players.
They multiply the problem. B-players hire C-players. That one questionable hire becomes 5 questionable hires under them. Now you don’t have one problem—you have six.
They slow decisions. That VP who “needs more data” before every decision isn’t being thoughtful. They’re paralyzed. While they’re analyzing, your competitors are shipping.
“But What If I’m Wrong?”
You’re not. In 15 years, I’ve never seen someone regret firing the person they were questioning. Not once.
I have seen countless founders regret waiting. They always say the same thing: “I should have done this six months ago.”
What About if They’re “Good” But Not “Great”?
Here’s the thing: if someone is actually good, you won’t be thinking about firing them.
Let me be clear about the difference:
Good performers make you think: “How can I help them get to the next level?” or “Maybe I should bring in a CRO above them” or “What if we got them a coach?”
Questionable performers make you think: “Should I fire this person?”
It’s that simple.
When you have a Good-But-Not-Great VP of Sales, you’re not lying awake at night wondering if they should go. You’re thinking about how to scale them. You see the progress. Bookings are up since they started. They’ve hired some solid reps. Maybe they struggle with enterprise deals but crush the mid-market. You can work with that.
The internal dialogue is completely different:
- “Sarah is doing well, but I think she needs help with enterprise sales”
- vs. “I don’t know if Sarah is working out”
See the difference? One is about optimization. The other is about survival.
If you’re genuinely thinking “Should I fire this person?” it means they’ve crossed the line from “good but needs development” to “this isn’t working.” Your subconscious has already done the math and concluded they’re not viable long-term.
The One Exception (Maybe)
The only time you don’t fire immediately is if you literally cannot function without them and you have zero bench. But even then, you’re making a plan to replace them within 90 days. You’re not hoping they get better. You’re executing a transition.
And honestly? Even this exception usually backfires. I’ve watched companies keep their “okay but not great” VP of Sales because they were scared to go back to founder-led sales. Revenue stayed flat for 18 months while the VP burned through budget and hired a team that couldn’t sell. When they finally made the change, revenue immediately accelerated.
How to Actually Do It
Move fast. The longer you wait, the more expensive it gets. The person you’re questioning knows you’re questioning them. They’re already checked out or defensive. End the uncertainty.
Be honest but kind. “This isn’t working out, and we both know it. Let’s figure out a transition that works for everyone.” Don’t make up excuses. Don’t blame the market or timing. Just acknowledge reality.
Have a plan. Know who’s covering their responsibilities, even if temporarily. Know your hiring timeline. Know your budget impact.
Trust your instincts. The moment you think “Should I fire this person?” the answer is yes. Your gut is protecting your business, your team, and honestly, that person too. Nobody wants to stay somewhere they’re not succeeding.
The Real Question
The question isn’t “Should I fire this person?”
The question is “Why haven’t I fired them already?”
Every day you wait is another day of:
- Burning cash on underperformance
- Demoralizing your best people
- Missing opportunities with mediocre execution
- Avoiding the tough conversation that needs to happen
Stop avoiding it.
Figure it out today.
