• David de Souza

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

Updated: Nov 8, 2020

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".

  • Instead of saying: "I can't find the train station' ask them: "Do you know the way to the train station?"

  • 'Your name is the least interesting thing about who you are, and yet it's disproportionately flattering when someone remembers it.'It is easy to forget someone's name when they first introduce themselves. Ask again a few minutes later, it will help you to remember and the person will be flattered.

13. Empathy

  • Notice the emotions the person is feeling and redirect it back as a question. For example: "What I hear you saying is that you are angry with me because I haven't appreciated the lengths you've gone to in trying to win over our Latin American customers. Those efforts have caused you a lot of sleepless nights, time away from the family, and marital problems. Is that right?

  • To be empathetic try to reflect back how they see the world with no judgment or ideas of your own.

  • Listen for the subtle words, references, or phrases that people mention, it is likely they want to talk more about those things. Listen beyond just words.

  • Use Active Listening to ask to follow up questions.

  • Validate people and make them feel heard.

  • If you have trouble being empathetic, start by describing how they see the world: "It sounds like you believe...."

14. Experimentation

  • When you experiment by going off-script with interview questions: 'go with the rip current but never lose sight of the shore'.

  • Write interview questions down but don't be too rigid. Be ready to ask a follow-up question based on the response.

  • Instead of asking: "What went wrong?" say: "Take me through what happened: what went well, what was problematic and what lessons can we learn?"

15. Fear

  • Ask yourself: Which decision will make a better story in 5 years?

  • Steven Levitt conducted a study using people who were in the process of making a difficult decision. These people agreed to use a coin flip to decide if they would go ahead with their decision, if it landed heads they would say "yes". 6 months later he found that the "yes/heads" people were significantly happier than the "no/tails" people. The conclusion is that when left to our devices we are too risk-averse and say no too often. Instead of using a coin, use a weighted question: If I am usually better off saying yes to bold opportunities, why wouldn't I say yes to this one?

  • Ask "courageous questions" to help give you confidence and clarity to move forward.

  • To avoid the fear of silence always have a question in reserve.

16. Friction

  • "Out of curiosity" reduces the abruptness of a question and makes it easier on both you and the person answering.

17. 'How' Questions

  • Trigger explanations and background.

  • Encourage stories.

18. Identity

  • Instead of asking either feeling or thinking based question, ask a question that allows the person to identify as either a "feeler" or a "thinker". For example: 1. How are you taking the news? 2. How did you react?

19. Interest Gauging Questions

  • Help you to determine if you will connect with a person. It will show if they follow current events and their level of interest in the subject. For example: "Everybody seems to have an opinion on 'abc'. What's yours?"

20. Juxtaposition Questions

  • Based on the game "would you rather..." where you think of 2 unrelated topics

  • Follow up by asking: How are they similar/different?

21. Legacy Questions

  • Ask: How do you want to be remembered?

  • Legacy questions will highliht what is important to them.

  • It will show you their values.

22. Liking

  • Share vulnerabilities gradually.

  • Ask follow up questions to dig deeper.

  • Don't say: "I like your tattoo say "You must get comments about your tattoo all the time".

23. Mission Questions

  • Where do your skills and interest intersect? What would you like to change in the world?

  • Instead of giving a talk or presentation ask questions to prompt and engage the audience: What have you heard about the project? How do you think it might help the community?

  • Instead of having a mission statement, companies (and people) should think about having a 'mission question'. "It tells the outside world, "This is what we're striving for - we know we're not there yet, but we're on a journey." It acknowledges room for possibility, change, and adaptability. A company that is arrogant and claims to have figured things out doesn't sound as impressive as one that is striving to answer an ambitious question.

24. Momentum

  • Questions that start momentum: 1. How can I stop being a perfectionist and lower the bar? 2. What if I begin anywhere?

25. Multiple by Zero

  • "But" has the effect of negating anything that was said before it. Use "and" instead of but".

26. Open-Ended Questions

  • Open-ended questions are a springboard for opinions and stories.

  • Open-ended questions start with: 1. How... 2. Why... 3. What...

  • Be careful with 'why' questions, they can often produce defensiveness and scripted responses.

  • Don't ask an open-ended question that is too open-ended, it will in meaningless answers. For example: asking someone "What was it like to live in the Arctic" will provide a vague answer of "cold. To get a better answer, ask: "How did you get food?" "How did people go on dates?"

27. Newton's Third Law

  • Repeat back a few words that the person has said in the form of a question. For example: 1. Can I try and explain what I think your position is- and then you can do the same for me? Because until we can accurately present one another's arguments, we do not know what the other is saying". 2. Just to make sure I am understanding, are you saying....

28. Questionstorming

  • Brainstorming and connective inquiry happens best in informal, relaxed settings. In practice, it usually, happens in a meeting room under pressure.

  • Both adults and children think more creatively when they focus on questionstorming as questions are judged less harshly than answers.

  • During a questionstorming session, the group thinks of 50 questions about a specific problem. The team is then asked to try and think of a better version of the question by opening questions that are too closed and closing questions that are too open.

  • How might we....." is the best way to structure questionstorming questions.

  • Often people ask "How can we do this?" or "How should we do this?" but "can" and "should" brings with it judgment. Using "might" defers judgment.

29. Resistance

  • You are more likely to be challenged or ignored when you approach people with answers. When you come with a question, people can't resist advising or helping you.

  • Question those that you disagree with in an open, curious way.

  • Ask: Why might they see the issue this way? Why do I see it differently? What assumptions are we each operating under?

  • To overcome resistance: Leave the content (what is being talked about) and pivot to a place of process (how it is being talked about). "Wait a moment. Let's leave this topic for a moment and talk about what got us so worked up now"

30. Signal Vs Noise

  • "When you get a long Email reply with: There's a lot going on here. What's the real challenge for you do you think?"

31. System 1 vs System 2

  • System 1 questions don't require much thinking, they are easy to answer and don't put us on our back feet. System 1 questions can be triggered by asking opinions or ideas, for example: How long is too long to keep Christmas decorations up?

  • System 2 is felt during moments of complex and unfamiliar questioning. When System 2 questions are asked people become on alert and we aren't at ease.

  • Avoid cliche questions, such as: "How's it going?" or "Are you busy"? Instead ask: "What is the most exciting thing you are working on"? Or "What are you looking forward to?"

  • You must create enough rapport to allow the tough questions to be asked. Place any tough questions about 2/3rd of the way through your questioning.

  • Prewarn when a tough question is coming: I want to ask you about something which is interesting but which is perhaps painful to you..." or "I am sorry if this seems offensive..."

32. The Awe Question:

  • "And what else?"

  • In 71% of decisions, the choices are binary, yes or no. Having 1 extra option (doing something else), reduced failures by 30%.

33. The Kickstart Question:

  • "What's on your mind?"

  • After asking this question use: 'The 3P Framework' to focus further: 1. Projects: Ask what projects the person is working on what challenges they face? 2. People: Any issues with people they are working with? 3. Patterns: Patterns of life and behavior that the person would like to change.

34. The Noah Adam Question Technique:

  • How did you think it was going to work out before it happened?

  • Follow up with: How did it really work out?

35. The Question Formula Technique:

  • Create as many questions as you can on a chosen topic (for example: Can torture ever be justified?), using the following rules: 1. Write each question. 2. Don't debate or try to answer the question. 3. Think of more questions. 4. Change open-ended questions to closed-ended ones (and vice versa). This shows how a question can be narrowed or broadened in scope and shows how asking a question in different ways can send you in different directions. Why is torture effective? > Is torture effective? 6. Prioritize questions by ranking the top 3 in order of importance. 7. Decide on how to act on the top 3 questions. 8. Reflect on what you have learned.

36. Value

  • Make people feel valued and increase their engagement by asking:: "David, you always have an interesting perspective, what do you think?"

37. 'What if' Questions

  • 'What if?' questions are a fail-safe way to start a conversation or to pick one up during a lull.

  • You can always create a 'What if?' question from current news or on the current topic of conversation.

  • A good 'What if?' question, like any question, is one that resonates with everyone, one that can cut through generations, education, and sociological and economic lines.

  • "What if COVID continues, do you think the stock market will take a hit?"

6 Memory Aids For Questioning

1. Friend or Foe

  • There are 4 variables that your brain questions to determine, whether a situation is safe or a threat. (TERA):

  • Tribe: Your brain is asking: Is this person part of my tribe?

  • Expectation: Do I know what is going to happen (in the future?)

  • Rank: Your brain is asking: Is this person more important than me?

  • Autonomy: Your brain is asking: Do I have a choice in this situation?

2 Improving Your Questions (SCANS)

  • Sharpen your question

  • Close your question

  • Add a "Why?" to the end of your question.

  • Open your question

  • Neutralize it

  • Soften your question

3. Over Talkers: 1. Stopping them: "Can I pause you there". 2. Complimenting them genuinely: Thank you for sharing" 3. Reflecting on what you heard: "I heard you say..." 4. Inviting others to respond: "Let's see how others respond to what you just said"

4. Reflective Listening:

  • Verbatim - Mirror back exactly what the person said. Best for clarification and when emotions are high.

  • Translation - Use synonyms to translate what the person said.

  • Unstated Feelings - Express what you think the person is feeling.

  • Connecting the Dots - Connect to a different theme or idea. Best used when people are self-reflecting or ready to explore.

  • When using reflective listening, end by saying: "Did I get that right?"

5. Universal Needs:

  • Manfred Max-Neef Rosenberg states that there are 9 universal needs. Try and translate what need the person wants when they ask a question. (CRAP IF UPS): 1. Creation 2. Recreation 3. Affection 4. Participation 5. Identity 6. Freedom 7. Understanding 8. Protection 9. Subsistence

18 Impactful Questions

  • How would you like things to be different in your life?

  • What shaped you to be the person who you are?

  • What setbacks and adversity did you encounter?

  • What is the most exciting thing you are working on?

  • What are you looking forward to?

  • What are you proud of?

  • What was the highlight of your year?

  • What's the strangest (or most interesting thing) about where you grew up?

  • What did you want to be when you were younger?

  • What are some jokes/family songs/recipes that stand out to you?

  • What do the stories that have been passed down to you mean?

  • What were some of the greatest accomplishments of your ancestors?

  • What traditions did your family pass down? How did they get started?

  • What first got you interested in.....

  • What is your favorite unimportant thing to do?

  • How would you life have been different if....

  • If you were a contestant on jeopardy/Mastermind what would be your specialist subject?

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