• David de Souza

The 80/20 Guide to Becoming a Better Questioner - 29 Mental Models

Updated: Oct 6

School teaches us how to answer questions, but it fails to educate us on how to ask better questions.

Knowing the right question to ask will help you find the answers you are looking for. But questions will also make you more likeable, persuasive and a better leader.

Questions help us to see things from a different perspective and in the words of the great Betrand Russell: "In all affairs it's a healthy thing now and then to hang a question mark on the things you take for granted."

There aren't many books specifically on the subject of questioning but a number of other books on such subjects as interviewing and social skills include sections on questions also. Below is the list of books I used to create this guide:

The Books:

  1. A More Beautiful Question

  2. Ask More

  3. How to Talk To Anyone

  4. The Book of Beautiful Questions

  5. Ask Powerful Questions

  6. Talk to Me

  7. Superhuman Social Skills

  8. How to Talk to Anyone, Anytime, Anywhere

  9. The Coaching Habit

I've studied these books and distilled the core principles from each. I've deleted any overlapping principles to produce the ultimate guide to the 80/20 of becoming a better questioner:

29 Mental models for Questioning:

1. Activation Energy

  • The most important thing, when initially meeting someone, is to put them at ease.

  • Small talk is not about facts or words. It's about music, about melody. Small talk is about putting people at ease. It's about making comforting noises together like cats purring. You must first match your listener's mood'.

  • Jeff Bezos says 'if you have a conviction....even if there is no consensus say: "Look, I know we disagree on this but will you gamble with me on it? Can we disagree and commit?

  • Look for things such as furnishings, mementos or photographs to start a conversation.

  • Ask questions that people will enjoy answering.

  • Make opportunities for people to talk about themselves and their life accomplishments.

  • Pick a topic of conversation that everyone can participate in.

2. Association

  • You can use questions to prime & persuade. The more you think about something the more likely you are to engage in that behavior.

  • Asking someone if they are going to vote will increase the likelihood by 25%.

3. Catalysts

  • The best questions shift perceptions and act as a catalyst for change.

4. Comparative Advantage

  • What does the world need, that you are most uniquely able to provide?

  • Everyone has something interesting to say. Everybody is an expert at something. Ask yourself: What can I learn from this person?

5, Confirmation Bias

  • To be a critical thinker you must be willing to question all angles of an issue, especially the side you are inclined to agree with.

6. Curiosity Instinct

  • Being curious helps you to become open to new information.

  • Curiosity shows you are coming from a place of learning not attacking.

7. Ego

  • There is an inverse relationship between experts and good questioners.

  • The more you think you know, the fewer questions you think you need to ask.

  • To create new ideas and to avoid habitual thinking we must be humble and adventurous to enter a state of mind of "knowing nothing".

  • Questioning works best when we remove our egos and attempt to understand someone's thoughts without judging them.

  • When we listen sympathetically, we think we are listening but we are really listening to how we ourselves feel. We are hearing our own story.

  • "A person's toothache means more to that person than a famine in China which kills a million people."

8. Emotions

  • 'There is a difference between asking a question that provides heat for heat's sake and one that provides heat for light's sake'.

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

8.1 Anger

  • People who are angry, often don't find good listeners. A person who affirms acknowledges, and listens can provide a welcome solace.

9. Fear

  • The 2 most common fears for connecting with people are: 1. Fear of being rejected 2. Fear of looking stupid

  • Once you notice the fear, you can be aware of it and even be thankful for it. You can then decide to lean into it.

10. First Principles Thinking

  • Question the questions

  • Effective listening allows you to ask better follow-up questions.

11. First-Conclusion Bias

  • The questions you first think of are probably the least interesting and ones that have been asked many times before.

  • Preparing (non-cliche questions) will do 2 things: 1. Put the person at ease because they know they are in safe hands. 2. They know that they should tell the truth.

12. Feedback Loops

  • A good question is one that is not too broad and not too narrow.

  • Combine being persistent in asking questions with discretion, asking in a way that puts the person at ease.

  • The sweet spot of questioning: "A question that is hard (and interesting) enough that is worth answering, and easy enough to actually answer it" Edward Witten - Physicist

  • 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?"

13. Identity

  • People and organizations mold themselves to the types of questions they ask. If you ask questions about what can go wrong or who is to blame it will result in people becoming defensive. If you ask questions that are expansive and opportunistic it will lead to growth.

14. Inversion

  • One of the most important questions you should ask is: What should I stop doing?

  • Bad news is good news. If you want to fix a problem you need to look for bad news and not bury your head in the sand. Discovering bad news is the 1st step in diagnostic questioning and understanding and fixing problems.

  • Force your brain from its natural way of thinking by purposely thinking wrong. Think of ideas that don't make any sense and mix them with things that don't go together. "When you force yourself to confront contrary thoughts, you jiggle the synapses in your brain".

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

15. Lateral Thinking/Smart Recombinations

  • To be creative you don't have to have a unique idea. You can simply combine two or more ideas that already exist.

  • Take features from an object and mix them to create something original, surprising or interesting.

  • Think wider than just: "What if we combine A + B". Instead, think about combining A + Z or A +27

  • Everyone uses the front door so there will be a line and it will be busy. Look for side doors for life opportunities.

  • Make your question different and original.

16. Liking

  • Questions show that you are interested and create understanding.

  • If you ask questions you become more likable.

  • Ask your boss for advice: I have a feeling I could be doing my job more effectively. Can you help me understand what areas I should concentrate on?"

17. Narrative Instinct

  • What kinds of questions elicit stories?

  • Notice the stories you like to share about yourself. What question would have allowed that story to be told?

18. Newton's 3rd Law/ Reactance

  • Ask don't sell. Questions are one of the most effective tools for selling. People become defensive when they think you are trying to sell them something. When you ask questions instead you build a relationship.

  • When you say 'why?' or 'why not?' people become defensive and will try and justify themselves.

  • Arguments can increase when we question more.

19. Pareto Principle

  • You only need to know a few great questions to become an excellent questioner. Create a mental toolbox of 3-5 impactful questions. (see the list at the bottom of this page)

  • Jeff Bezos says: "Most decisions should be made with somewhere around 70% of the information you wish you had. If you wait for 90%, in most cases, you're probably being too slow".

20. Paradoxes

  • Paradoxes highlight that humans don't fit neatly into boxes and they are never exactly one way or another. Every conservative has a liberal exception.

  • Highlighting contradictions is a great way of asking tough questions. For example: "John said it happened this way and you said it happened this way. Can you help me understand my confusion behind this?"

21. Reciprocity

  • Notice when people don't ask clarifying questions, it's an indication they are not interested in what you are saying.

22. Resistance

  • If you experience resistance from another person it could be because you are not being empathetic and are only interested in your own needs and desires.

  • Notice the resistance you feel when you want to tell someone they are wrong.

  • Pushing against resistance will only result in defensiveness.

23. Seeing the Front

  • When you are too far removed from an issue you lack complete information, and ask the wrong questions. Contextual inquiry uses on the ground observations, listening and empathy to help formulate a better question.

  • Charities may ask: "How can we get more incubators to developing countries?"

  • The obvious, (but not so good answer) is: "Donate them".

  • Many incubators are donated but end up in 'incubator graveyards'.

  • A better question is: Why aren't hospitals in developing countries using the incubators they have?

  • The answer is because the machines break down and without the knowledge and parts to fix them, they aren't being used.

  • This then led to an even better question: How can we provide incubators that are easy to maintain and fix?

24. Tendency to Minimize Energy Output

  • The brain looks for ways to reduce our mental workload and one way we do that is to accept without questioning.

  • Daniel Kahneman found that "people who face a difficult question, often answer an easier one instead."

  • Ask questions that are cognitively easier to process and don't require translating from your perspective into the other person's. For example if you ask: "Can I take Monday off work?" your boss needs to translate what you said into: "Can I manage without this employee on Monday?" It is better to ask: "Can you manage without me on Monday at work?"

25. Tendency to Want to do Something

  • Question without comment or judgment and let the silence linger. This allows the person to reflect and answer more deeply.

26. Tenses

  • If you ask: "How was your weekend?" it takes people into the past,. creating unconscious resistance.

  • To connect with someone find something that is happening in the moment.

27. The Ikea Effect

  • Instead of asking a question, let people create their own questions. This results in them taking ownership of it.

  • Advice doesn't usually get remembered. By asking a question and the subsequent generating of answers, enhances memorization.

  • Peter Drucker said that his greatest strength was "to be ignorant and ask a few questions". People often expected him to come up with great solutions, but he told clients: "The answers need to be yours."

28. Trust

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

29. Value

  • You can provide value by asking impactful questions.

  • Don't ask questions that aim to impress, ask a question that: informs, entertains or engages.

  • People want to be heard and understood and it provides deep value to them when they are.

37 Tactics for Questioning

1. Activation Energy

  • Make an observation before asking a question (or two).

  • Start a conversation by asking:"What do you make of....."It can't be too broad of a question, for example: What do you make of climate change? It needs to be narrower: What do you make of people who don't believe in climate change?

  • Start by asking safe questions. When the person seems relaxed ask the deeper more probing ones.

  • Be playful: Ask the person if they would be willing to play a little game. Give them a name or a topic and they must give a 1-word answer.

2. Agenda Setting Theory

  • Scan a newspaper or website before going out to ensure that you have something interesting to talk about.

3. Anchoring

  • Ask people to rate something on a scale of 1-10. Assuming they didn't pick 1, ask why they didn't. This will help them to justify their own doubts.

4. Authority

  • Challenge the experts, they owe you an explanation. Ask them: How did they reach their conclusion? Ask for their process. Ask for your options.

  • Appeal to Moral Authority: Evoke a statement from a respected 3rd party. This takes the attack from you as the questioner to someone with expertise, trust or moral authority.

  • Be cautious when questioning your superior. Use this template:"I've been thinking about x and something that I was surprised to learn was Y. It made me wonder, do you think possibility Z could be an option?"

5. Bottlenecks and Constraints

  • We have a tendency to be too narrow in our available options. To overcome this, generate at least 3 options or questions for each decision you make.

  • Encourage people to think deeper and to go beyond the obvious answers by asking "And what else?"

6. Closed-Ended Questions

  • Usually, start with: 1. Is... 2. Do... 3. Does... 4. Where... 5. When... 6. Who...

7. Confrontational Questions

  • Just like a lawyer, know the facts before you ask a question.

  • Start with a comfortable conversation so the person feels at ease and then take the questioning somewhere that they did not expect.

8. Creative Questions/Breakfree of Reason

  • Creative questions embrace crazy ideas and ask people to imagine what could be.

  • Making connections between unrelated questions or ideas is the most effective way to innovate.

9. Curiosity Instinct

  • You can show curiosity (and reduce friction) by asking: 1. "I'm curious/I was wondering about..." 2. "That's fascinating, help me understand more about that."

  • Journalist Mindset: Before going to an event tell yourself: "I am going to go to this event as a journalist, looking for stories about the people I meet."

  • When you introduce someone include some hooks which provide people something to ask questions about.

  • It is guaranteed that someone will ask the two questions: 1. Where are you from? 2. What do you do?

  • Add some hooks to your answer to give people something to work with.

  • Wear something curious or remarkable.

10. Decision Making Questions

  • The advice we give to others is better than the advice that we give ourselves because the advice we give others is based on the single most important factor. When we are thinking for ourselves, we think about every small and inconsequential detail.

  • When making a decision ask your these questions: 1. What are my biases? 2. Why do I believe what I believe? 3. What would I like to be true? The desirability bias 4. What if the opposite were true? (Inversion) 5. What would I advise someone else to do?

11. Diagnostic Questions / First Principle Thinking

  • Diagnostic questions find the root of an issue, they are the foundation from which other questions comes.

  • Start broadly, asking what the problem is, and then narrow down on specifics.

12. Ego

  • Add "for you" to Questions to make them less abstract and more personal.

  • Add "you" to a compliment will amplify it. Compare: "That's a good question" vs "You've asked a good question".