Ollie Boarding Question Method

The Ollie Boarding technique is a strategic questioning method developed by the Ollie brothers that combines genuine curiosity with relentless detailed inquiries to extract valuable information from conversations.

Core Elements of the Technique

• Maintains constant flow of questions while showing genuine interest
• Never makes people feel judged for their answers
• Focuses on getting detailed operational insights
• Combines genuine curiosity with strategic information gathering

Key Tactics

• Uses open-ended questions

  • Starts with "How do you think about..." instead of direct metrics
  • Allows people to openly share their thought process
  • Gets people to subconsciously reveal more information

• Shows high engagement

  • Maintains eye contact
  • Doesn't look at phone
  • Gives positive reinforcement through nodding
  • Uses phrases like "that makes total sense" and "got it"

• Handles "wrong" answers strategically

  • Responds with "amazing" instead of judgment
  • Quickly moves to next question
  • Never makes people feel bad about responses
  • Keeps information flowing by avoiding negative reactions

Results of the Technique

• Gets people to divulge detailed business information

  • Financial metrics
  • Operational processes
  • Strategic decisions
  • Company challenges

• Creates comfortable environment for sharing

  • People feel heard and respected
  • Builds trust quickly
  • Makes subjects want to share more

• Generates actionable insights

  • Identifies business opportunities
  • Reveals operational inefficiencies
  • Highlights competitive advantages
  • Uncovers market dynamics

Key Principles

• Information flows one way - mostly asking questions vs sharing
• Genuine curiosity drives deeper insights
• Non-judgmental responses keep people talking
• Strategic progression of questions reveals full picture
• Focus on operational details vs surface level information