How to ask better questions

How to ask better questions

Successful people are not more talented than you and I.

What makes them successful are often uncommon habits and asking bigger questions. The more ridiculous the question, the more profound the answers. For example, billionaire Peter Thiel likes to ask himself this:

“If you have a 10-year plan of how to get [somewhere], you should ask: Why can’t you do this in 6 months?

Questions like these forces us to think outside of the artificial limitations we place in our head systems, societal rules, and standard frameworks we forced unto ourselves.

Allowing us to be aware of our ability to renegotiate our reality.

12 questions for ourselves

On the topic of questions, I’m reminded of Richard Feynman, a Nobel Prize-winning physicist, who once said:

“You have to keep a dozen of your favorite problems constantly present in your mind, although by and large they will lay in a dormant state. Every time you hear or read a new trick or a new result, test it against each of your twelve problems to see whether it helps. Every once in a while, there will be a hit, and people will say, ‘How did he do it? He must be a genius!'”

Every 6 months, I will spend 30 minutes to write down the 12 questions that drive my intellectual curiosities. These can range from investing, health, relationships, and more.

I recommend you to try this out. These 12 questions will hold the keys to your next creative breakthroughs.

Invert, always invert

“All I want to know is where I’m going to die, so I’ll never go there.”
— Charlie T. Munger

This idea was inspired by mathematician Carl Jacobi. He often solved difficult problems by following a simple strategy: “man muss immer umkehren” (or loosely translated, “invert, always invert.”)

During Berkshire’s annual general meeting, Munger explains “Turn a situation or problem upside down. Look at it backward. What happens if all our plans go wrong? Where don’t we want to go, and how do you get there? Instead of looking for success, make a list of how to fail instead — through sloth, envy, resentment, self-pity, entitlement, all the mental habits of self-defeat. Avoid these qualities and you will succeed.”

Inversion is one of my favorite mental models as it forces you to uncover hidden beliefs about the problem you are trying to solve. “Indeed,” says Munger, “many problems can’t be solved forward.

Instead of thinking “what makes a good life?“, invert the question and ask “what makes life miserable?” Ideally, you avoid all those things.

Avoid stupidity is easier than seeking brilliance. Inverting the problem won’t always solve it, but it will help you to avoid trouble. It presents you with easy ways to improve.

How can we use this in practice?

1. Find our role models. Mine can be found here. Find a positive role model and a negative role model. These are the people you can learn from – on what to do and what not to do.

Warren Buffett did a similar exercise with MBA students at Florida University.

Think for a moment that I granted you a right — you can buy 10% of one of your classmate’s earnings for the rest of their lifetime.

You’d probably pick the person who has leadership qualities, who is able to get others to carry out their interests. That would be the person who is generous, honest and gave credit to other people for their own ideas.

And here comes the hooker: In addition to this person, Buffett told the students they had to sell short another one of their classmates and pay 10% of what they do.

You’d think about the person who turned you off, the person who is egotistical, who is greedy, who cuts corners, who is slightly dishonest.

If you see any of those qualities in yourself, you can get rid of them. It’s simply a question of which you decide.

2. Identify your goals and imagine all the obstacles that will prevent you from succeeding. Being aware of these obstacles and doing everything you can to overcome them will significantly raise your chances of success.

Asking questions like Tim Ferriss

If I had only one hour to save the world, I would spend fifty-five minutes defining the problem, and only five minutes finding the solution “. 
Albert Einstein

Most of us have an action bias and jump into tackling problems too fast. If we want to learn from the best in the various fields, good questions would be the map for finding that treasure. To build a world-class network, we need to communicate in a way that earns it.

Tim Ferris is a self-experimenter and bestseller author, best known for The 4-Hour Workweek. Newsweek calls him the “human guinea pig”.  Tim’s mission is to decode human greatness by asking questions. He has interviewed high achievers like Arnold Schwarzenegger, Jamie Fox, Tony Robbins, Seth Godin, Brené Brown, and many more.

The following are Tim’s advice to asking great questions.

1. Study questions of skilled hosts

Listen to podcasts of great hosts to borrow their questions and test them out. Some of my favorite podcasts include The Tim Ferriss Show, The Knowledge Project, and Invest Like the Best.

2. The question can be answered quickly

“A problem well put is half-solved.”
— John Dewey

Can the person answering think of an answer in 5 seconds or less? Time matters to people and questions that are too broad cannot be answered quickly.

Questions like “What is your favorite book?” is a bad question because they probably have read many books and it would take time to decide on one. A better question would be “What is the book that you have gifted the most?” This helps limit the scope drastically and it is much easier to answer.

Much like asking yourself the question “What makes me happy?” These questions are terrible because it is too broad. It would be difficult to define happiness. A better question would be “What makes me feel most relieved after work?”

3. Ask specific questions

Life punishes the vague wish and rewards the specific ask”. 
Tim Ferris

Whether the question is for ourselves or for an expert, it should be as specific as possible. Ask a general, half-hearted question and you will elicit a half-hearted general response. It goes something like this:

Question – “How’s it going?”

Response – “It’s fine. Things are going well.”

Sounds easy and obvious enough. Yet in reality, this happens more often than we would like. From parents asking how their kids are doing at school to superiors asking their employees are coping.

Be specific about what you want to learn. Scope in your questions by providing context, focusing on a specific event or time.

4. Sequence of questions

Proper sequencing is the trick to bring out optimal responses. Good questions in the wrong order get bad responses. You can rise above your peers by putting thought into sequencing, as most people don’t.

Always warm up your interviewee with questions that are easier and less intimidating. Once they are flowing and engaged, proceed to ask the more challenging questions.

Research shows that people are more willing to reveal sensitive information when questions are asked in a decreasing order of intrusiveness.

The Actors Studio hosted by James Lipton is famous for asking high-quality questions. James interviews the most successful actors such as Tom Hanks, Al Pacino, and many more to deconstruct their greatness. This questionnaire was originally used by Bernand Pivot, one of the greatest talk show host:

  • What is your favorite word?
  • What is your least favorite word?
  • What turns you on creatively, spiritually or emotionally?
  • What turns you off?
  • What is your favorite curse word?
  • What sound or noise do you love?
  • What sound or noise do you hate?
  • What profession other than your own would you like to attempt?
  • What profession would you not like to do?
  • If Heaven exists, what would you like to hear God say when you arrive at the Pearly Gates?

James start by asking light-weighted questions and gradually escalate to complex and philosophical questions. If you want to ask those important questions, build up to them.

5. Provide Examples

When asking difficult questions, help your interviewees out by sharing some examples. This will help buy them 30 seconds or so to think about the answer.

For example, when Tim asks his interviewees “What is the most absurd thing that you love?” He would then provide his personal example on why the number 5 by 5 is good luck to him for many reasons.

Tips from Alex Blumberg

Alex Blumberg was featured in Tim’s book, Tools of Titans. Alex is the CEO and co-founder of Gimlet Media, which makes many blockbuster podcasts. Here are his tips on asking questions.

1. Ask the dumb question everybody is afraid to ask

At the center of a story often lies a very basic and dumb question that no one is asking. Alex gave an example of one of the biggest story he ever did on The Giant Pool of Money, was centered on this: “Why are the banks loaning money to people who can’t possibly pay it back?”

Asking the right dumb question is often the smartest thing to do.

2. Using the right questions and prompts

Good questions should draw out stories, not an uninformative yes or no answer. Alex elicit what he calls “authentic moments of emotion” by covering three bases: setting (e.g. where, when, who, what), emotions, and details.

Here are some examples Alex provided in the book – Tools of Titans:

Prompts to Elicit Stories (Most Interviewers Are Weak at This)
“Tell me about a time when . . .”
“Tell me about the day [or moment or time] when . . .”
“Tell me the story of . . . [how you came to major in X, how you met so-and-so, etc.]”
“Tell me about the day you realized ___ . . . ”
“What were the steps that got you to ___ ?”
“Describe the conversation when . . .”

Follow-Up Questions When Something Interesting Comes Up, Perhaps in Passing
“How did that make you feel?”
“What do you make of that?”

General-Use Fishing Lures
“If the old you could see the new you, what would the new you say?”
“You seem very confident now. Was that always the case?”
“If you had to describe the debate in your head about [X decision or event], how would you describe it?”

There is something to learn from everyone

“Empty your mind, be formless, shapeless, like water. If you put water into a cup, it becomes the cup. You put water into a bottle and it becomes the bottle. You put it in a teapot it becomes the teapot. Now, water can flow or it can crash. Be water my friend.”
— Bruce Lee

Last but not least, have an open mind. Strong opinions, loosely held. Have the courage to act on your ideas but have the humility to question what you know.

Challenge yourself to truly listen to people who have differing ideas and opinions than you do. Stay out of echo chambers – an environment where we only hear information or opinions that reflect and reinforce our existing thoughts.

After asking your questions, listen. Assume that the person you are listening to might know something you don’t.

Don’t try to impress people and one-up their response with your reply. Ask follow-up questions and learn.

Milan Kundera, author of The Unbearable Lightness of Being, has said that “The stupidity of people comes from having an answer for everything. The wisdom of the novel comes from having a question for everything.” Substitute “master learner” for “novel,” and you have my philosophy of life. Often, all that stands between you and what you want is a better set of questions.

Thank you for taking the time to read my blog.

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