When and How to Fire Someone
Firing is one of the hardest things founders do. Here's how to know when it's time and how to do it right.
Firing someone is painful. It feels like failure—yours and theirs. But keeping the wrong person is more painful. It’s unfair to them, unfair to the team, and damaging to the company. Learning when and how to make this decision is one of the hardest founder skills.
When Firing Is Necessary
Performance Problems
When someone consistently underperforms:
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Missing goals repeatedly
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Quality of work is poor
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Not improving despite feedback
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Holding back the team
Culture Violations
When someone violates company values:
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Toxic behavior
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Dishonesty
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Treating people badly
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Not aligned with how you work
Culture violations can be worse than performance issues.
Role Mismatch
When the role has evolved beyond them:
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They were right for stage A, not stage B
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Skills don’t match new requirements
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Can’t grow with the role
This happens often in startups.
Attitude Problems
When someone is:
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Constantly negative
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Resisting change
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Undermining decisions
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Creating drama
Energy vampires damage teams.
Signs It’s Time
You’ve Had the Conversation Multiple Times
If you’ve given the same feedback repeatedly:
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They know there’s a problem
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They haven’t changed
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Continuing is prolonging the inevitable
You’re Making Excuses for Them
“They’d be great if only…”
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The market was different
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They had a different manager
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The role was clearer
Stop making excuses. Evaluate them as they are.
The Team Is Suffering
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Good people are frustrated
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Others are picking up slack
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Team morale is affected
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People are leaving because of them
The cost to the team matters.
You’re Relieved When They’re Out
If you feel relief when they’re:
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Sick
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On vacation
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Not in meetings
That’s a signal.
You Wouldn’t Rehire Them
If they resigned today, would you:
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Fight to keep them?
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Feel relieved?
If you wouldn’t hire them again, why are they still here?
Common Mistakes
Waiting Too Long
The most common mistake.
Why founders wait:
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Don’t want to be mean
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Hope they’ll improve
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Fear of confrontation
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Worried about the work
Cost of waiting:
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More damage to the team
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Harder conversation later
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Lost time and opportunity
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Unfair to the person
Fire quickly but fairly.
Avoiding the Real Issue
Hoping they’ll quit:
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Making their life harder
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Giving them bad projects
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Being cold
This is cowardly and unfair. Have the conversation.
Not Documenting
Making decisions without a paper trail.
Why documentation matters:
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Legal protection
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Forces clarity on issues
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Gives them a fair chance
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Creates improvement opportunity
Surprising Them
Firing someone who didn’t know there was a problem.
Fix: No one should be surprised. Feedback first, always.
Public Humiliation
Firing in front of others or sharing details inappropriately.
Fix: Private conversation. Dignified exit.
Before You Fire
Give Real Feedback First
Clear feedback includes:
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Specific behaviors/outcomes
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Impact of those behaviors
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Clear expectations going forward
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Timeline for improvement
Document this conversation.
Create Improvement Opportunity
Performance Improvement Plan (PIP):
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Specific goals
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Clear timeline (30-60 days)
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Regular check-ins
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Documented progress
PIPs aren’t just legal cover—they’re fair.
Make Sure It’s Not You
Ask yourself:
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Did I set clear expectations?
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Did I give them what they needed?
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Is this the wrong role, not wrong person?
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Could they succeed elsewhere in the company?
Sometimes the problem is management, not the person.
Check Your Bias
Ensure it’s fair:
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Would you fire someone else for this?
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Is there any discriminatory factor?
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Are you applying standards consistently?
Get Alignment
Before terminating:
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Discuss with co-founders
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Consult legal if needed
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Review with HR if you have one
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Make sure decision is solid
How to Fire Someone
The Conversation
Preparation:
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Plan what you’ll say
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Have paperwork ready
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Choose private setting
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Schedule appropriately (not Friday afternoon)
The conversation:
1.
Get to the point quickly
2.
Be clear this is a termination, not negotiation
3.
Briefly explain why
4.
Share logistics (last day, severance, etc.)
5.
Allow them to respond
6.
End with dignity
What to say:
“I’ve made the decision to let you go. This is based on [brief reason]. Today is your last day. Here’s what happens next…”
What not to do:
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Don’t debate the decision
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Don’t apologize excessively
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Don’t make it about you
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Don’t give false hope
Be Human
This is hard for them:
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Be compassionate
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Be clear
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Be respectful
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Be brief
You can be kind without being ambiguous.
Logistics
Have answers ready:
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Last day (today or specific date)
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Severance package
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Benefits continuation
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Reference policy
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Equipment return
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Access removal
Severance
Standard practice:
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Some severance is typical
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Usually tied to tenure
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Get release of claims
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Be fair but not excessive
Consult legal on specifics.
Access Removal
Timing matters:
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Remove access during or right after conversation
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IT should be coordinated
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Don’t make it humiliating
After the Firing
Team Communication
What to tell the team:
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“X is no longer with the company”
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Don’t share details
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Don’t badmouth
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Brief, respectful
Answer their questions:
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What happens to the work?
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How will responsibilities shift?
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What does this mean for the team?
Team Morale
Watch for:
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Concerns about their own jobs
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Questions about the decision
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Relief vs. anxiety
Address it:
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If it was performance, team usually knows
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Reassure those not at risk
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Be available for conversations
Your Processing
Firing is hard. After:
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Don’t second-guess the decision
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Learn what you could do better
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Talk to someone you trust
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Move forward
Reference Handling
Decide your policy:
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Confirm employment only?
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Provide honest reference?
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What will you say if asked?
Be consistent.
Special Situations
Firing Friends
Extra hard, but same process:
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They deserved honest feedback earlier
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Friendship shouldn’t protect bad performance
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Preserve dignity
Sometimes friendships survive. Sometimes they don’t.
Firing High Performers
When someone performs but violates culture:
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Keeping them says culture doesn’t matter
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Others are watching
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Short-term loss, long-term gain
Firing Early Employees
When someone was right for early days but not anymore:
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Be grateful for what they did
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Acknowledge the transition
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Treat them generously
Layoffs
When cutting for business reasons, not performance:
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Be honest about the reason
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More generous severance
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Help them land elsewhere
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Communicate clearly to remaining team
Legal Considerations
Document Everything
Paper trail matters:
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Performance feedback
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Improvement plans
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Violation records
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Decision rationale
At-Will Employment
In most US states:
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Can terminate without cause
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But some protections exist
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Discrimination is illegal
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Retaliation is illegal
When to Involve Legal
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Any termination of protected class
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Anyone who has complained of harassment/discrimination
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Any contractual employees
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Uncertain situations
When in doubt, ask a lawyer.
Key Takeaways
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Firing quickly but fairly is a founder skill—waiting too long is the most common mistake
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No one should be surprised: clear feedback and improvement opportunity come first
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Ask yourself: Would I rehire this person? If no, why are they here?
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The conversation: be clear, brief, and human. Don’t debate the decision
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Have logistics ready: severance, last day, access removal, benefits
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Communicate to team: brief, respectful, no details or badmouthing
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High performers who violate culture must go—keeping them says values don’t matter
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Document everything: feedback, expectations, decision rationale
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Consult legal when in doubt, especially with protected classes
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After: don’t second-guess. Learn and move forward
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