• David de Souza

'Ask More' Summary



My biggest takeaway from this book was the idea of projecting moral authority by evoking a statement from a respected 3rd party. Doing so takes the attack from you as the questioner to someone with expertise, trust or moral authority.

Want to dig deeper than the core principles? Check out my notes in Roam Research and see how the principles from this book connect with other books I've read.




Core Principles:


I have summarized 'Ask More', distilling the book into 19 core principles:

  1. Start by asking safe questions. When the person seems relaxed, ask the deeper, more probing questions.

  2. Be Playful: Ask a person if they would be willing to play a game: you'll give them a name or a topic, and they must give a 1-word answer.

  3. 'How' questions trigger explanations, background and stories.

  4. Some of the best questions don't have question marks: 1. Tell me more. 2. Please explain that to me. 3. Go on.

  5. When others talk, do you convert what you hear into a reference about you or a similar experience you had?

  6. People remember how you make them feel not what you say.

  7. Making connections between unrelated questions, problems or ideas is the most effective way to innovation.

  8. Project moral authority by evoking a statement from a respected 3rd party. This takes the attack from you as the questioner to someone with expertise, trust or moral authority.

  9. Ask people questions that you (and they) already know the answer to. Get into a comfortable dialogue so that they feel at ease and then take the questioning somewhere that they had no anticipated.

  10. Be respectful, charismatic but yet forceful and skeptical when asking questions. For example: Mr. President. You seem so sincere in your quest for peace. Why don't you do something to demonstrate that to Israel? Perhaps you could open some direct human contact with Israel. Why not allow an exchange of journalists, or athletes or scholars?"

  11. System 1 questions are easy for people to answer, they do not require much thinking. System 2 involves thinking and can make people defensive.

  12. People who are angry, don't usually find others who listen. A person who affirms acknowledges and listens can provide a welcome solace.

  13. Ask without comment or judgment and then allow the silence to linger. This allows the person to reflect and answer more deeply.

  14. Listen beyond words.

  15. The more you can show genuine curiosity, the more people will open up and trust you.

  16. Ask people about what shaped them and what adversities they faced.

  17. Bad news is good news. If you want to fix a problem you need to look for it and not bury your head in the sand.

  18. Challenge the experts. They owe you an explanation as to what's going on. Ask them: 1. How did they reach their conclusion? 2. What was their process? 3. What are your options? 4. How would they feel if their mother was in the same position?


Let me know how these summaries can be improved? Contact me via Email (david@thisdomain.co) or on Twitter.



The 80/20 of Worldly Wisdom: