Questioning Means Firing
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A framework for making difficult decisions, particularly around firing employees and handling tough choices in business.
Core Philosophy: "Easy choices, hard life. Hard choices, easy life."
- When you know the right thing to do but delay it, it usually leads to bigger problems
- Making the hard choice immediately leads to better long-term outcomes
- The road to hell is paved with good intentions - trying to "make it work" rarely succeeds
The Firing Decision Framework
- If you're questioning whether to fire someone, you likely should
- You never question firing a superstar employee
- The mere presence of doubt indicates action is needed
Important Caveat (from Shaan):
- Before firing, verify:
- Has the person received clear role expectations?
- Do they understand what "winning" looks like?
- Have they been given 2-3 weeks to improve after clarity?
- Some employees can transform into star performers with proper direction
Decision Making Between Two Options
- When stuck between two choices (A vs B):
- If you can't decide, identify which choice is harder
- Your brain naturally discounts difficult choices
- What appears to be two equal choices often isn't
- The harder choice is usually the better choice
- Your brain applies a "tax" on difficult decisions to avoid short-term pain
- Remove this mental "tax" to see the true value of each option
Implementation Tips
- Make the hard decision immediately when you recognize it
- Don't delay difficult choices hoping things will improve
- Trust your initial instinct when questioning an employee's fit
- Consider if you've provided proper structure before making final decisions
01:21 - 01:37
Full video: 11:18AW
Andrew Wilkinson
Co-founder of Tiny
Wilkinson is the co-founder of Tiny Capital, which owns companies including AeroPress, MetaLab and Dribble. He is also the co-founder and chairman of WeCommerce, a holding company that starts, buys, and invests in the world’s top Shopify businesses.