Questioning Means Firing

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: 11:18
AW

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.

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