Future Failure Exercise

A mental exercise for identifying key business risks by imagining a future conversation about what caused your project to fail.

The "12 Month Failure" Exercise

• Imagine meeting a friend for beer in 12 months
• They ask "What happened with that project?"
• Envision explaining what went wrong
• This framing helps identify:
  • Riskiest assumptions being made
  • Dangerous paths that cut off options
  • Situations leaving you "one move from failure"

Why This Method Works

• More effective than directly asking "What's your biggest risk?"
• Creates psychological safety to explore failure scenarios
• Forces concrete visualization of specific failure points
• Helps validate key assumptions early

The "Why The F*** Aren't You" Game

• Objective outsider perspective of your business
• Questions obvious gaps or questionable decisions
• Examples:
  • Why aren't you hiring for time-consuming tasks?
  • Why aren't you attending key industry events?
  • Why are you doing X when you should be doing Y?

Implementation

• Make a list of 3 key items from each exercise
• Take immediate action to correct identified issues
• Use as ongoing framework to identify blind spots
• Regular check-in to ensure staying on track

The framework combines both exercises to proactively identify and address potential failure points before they become actual problems.