Strategic Question Framework

A collection of powerful strategic questions used by successful entrepreneurs Tim Ferriss and Shaan Puri to improve decision-making and unlock potential.

Core Strategic Questions

• "What would this look like if it was easy?"

  • Forces simplification of complex problems
  • Helps identify unnecessary complications
  • Leads to more elegant solutions

• "What's my theoretical maximum?"

  • Identifies true upper limits of performance
  • Helps cut through limiting beliefs
  • Example: Testing true maximum push notification response rates (50% vs assumed 10-15%)

• "What silly story am I telling myself?"

  • Identifies self-imposed limitations
  • Helps recognize false narratives
  • Similar to addressing fears by making them ridiculous
  • Most uncomfortable question but often most needed

Unfair Advantage Assessment

• "When have you seen me at my best?"
• "What do you see me do that is easier for me than others?"
• Ask friends these questions to identify blind spots
• Look for activities where you have natural momentum

Additional Power Questions

• "What would make this worth 10x the price?"

  • Forces creative problem-solving
  • Leads to unique value propositions
  • Example: Delivering event value in first two hours

• "Don't believe everything you think"

  • Questions internal assumptions
  • Challenges default thinking patterns
  • Helps identify cognitive biases

Implementation Guidelines

• Use questions as "pickaxes for the brain"
• Keep a swipe file of powerful questions
• Questions should make you slightly uncomfortable
• Focus on questions that challenge assumptions
• Look for questions that reveal hidden opportunities
• Use questions to reframe problems into opportunities