The Art of Asking Good Questions

Two hunters are out in the jungle when suddenly one of them collapses. His pulse is gone and his eyes are glazed. The other guy yanks out his cell phone and calls the emergency services.

He gasps, “My friend is dead! What should I do?”

The operator says “Calm down, sir. I can help. First, let’s make sure if he’s really dead.”

After few moments of silence, the operator hears a loud gunshot. Back on the phone, the guy says “OK, now what?”

The hunter was dumb but given the high adrenalin and panicky situation, the operator’s question wasn’t brilliant either, was it?

There’s some truth to the saying – the quality of your questions determine the quality of solutions. Computer programmers know this very well. They call it GIGO, i.e., garbage in garbage out.

Good question begets good answer. Bad question leads to bad answer.

With the Internet, world’s information is available at your fingertips. You can find anything about everything. Google isn’t just a search engine. It’s a verb.

Don’t know something? “Google it.”

Wouldn’t you agree that the quality of the search results in Google largely depends on what keywords you type in the search box? No matter how intelligent the searching algorithm is, what you ask from Google matters. That’s why Google search isn’t just about finding what you are looking for but also discovering that you weren’t asking the right question in the first place.

In fact, the best way to learn anything is by following a trail of good questions. It’s not the soundness of answers but the sharpness of queries that determine the quality of learning.

Mother nature doesn’t tell you how many holes there are on the roulette table, writes Nassim Taleb in his remarkable book Fooled By Randomness, “Nor does she deliver problems in a textbook way. In a real world, one has to guess the problem more than the solution.”

Socratic Questioning

Socrates, the Greek philosopher and one of the founders of Western philosophy, devised a method called Socratic Questioning.

Socratic questioning is disciplined questioning that can be used to pursue thought in many directions and for many purposes, including: to explore complex ideas, to get to the truth of things, to open up issues and problems, to uncover assumptions, to analyze concepts, to distinguish what we know from what we don’t know, to follow out logical implications of thought, or to control the discussion. The key to distinguishing Socratic questioning from questioning per se is that Socratic questioning is systematic, disciplined, and deep, and usually focuses on fundamental concepts, principles, theories, issues, or problems. (Source: Wikipedia)

To put it in another way, Socratic Questioning is a systematic way to think about problems. It’s a brainstorming tool.

When two individuals with opposing viewpoints get into a discussion by asking and answering questions, it stimulates critical thinking. In a healthy debate, each person plays the role of a Devil’s Advocate. Each would poke loopholes in other’s logic. That’s how ideas take shape.

You can practice the Socratic method even alone. Professor Bakshi, in his immensely educating post Playing Socratic Solitaire on A Gal Called NIMBY, writes –

Charlie Munger started using these Socratic devices in a variation he called Socratic Solitaire, because, instead of a dialogue with someone else, his method involves solitary play. Munger used to display Socratic Solitaire at shareholder meetings of Wesco Corporation. He would start by asking a series of questions. Then he would answer them himself. Back and forth. Question and Answer. He would do this for a while. And he would enthrall the audience by displaying the breadth and the depth of his multidisciplinary mind.

A Socratic Solitaire is a fantastic tool for self-inquiry. The only thing that can trip you while using Socratic Solitaire is when you get stuck in the wrong questions.


There are some lessons which are too complicated to be learned by searching google, reading books or even self-inquiry. There comes the point where you need another human being – a mentor, a guide or a super-thinker – who can answer your questions. You seek to learn from these people either because they are more knowledgeable or simply ahead of you in the game of thinking.

As the superficial knowledge has become cheaper and ubiquitous, these super-thinkers have become more valuable and their time more scarce. You get access to them when you deserve it. These people like answering questions for people who can learn from the answers. By definition, these super-thinkers are smart enough to tell how much thought and effort you’ve put into solving a problem.

Every year in Berkshire Hathaway’s annual meet in Omaha, Warren Buffett and Charlie Munger spend six to seven hours answering questions from shareholders. Buffett, in his 2017 letter to investors, wrote –

..our hope is that the analysts and journalists will ask questions that add to our owners’ understanding and knowledge of their investment. Neither Charlie nor I will get so much as a clue about the questions headed our way. Some will be tough, for sure, and that’s the way we like it.

Super-thinkers like Buffett and Munger like hard problems and it’s easier to get them involved by asking stimulating questions. If they didn’t, they wouldn’t be where they are.

So when you meet the super-thinkers make sure you’ve come prepared and are asking good questions.

Good Question Vs Bad Question

So what makes a good question? Let’s use Charlie Munger’s inversion trick and stand the question on its head, i.e., let’s first investigate what’s a bad question.

Have you heard the saying – “There’s no such thing as a stupid question.”? Well, the sayings aren’t always right.

A question may not be entirely stupid, but there are some which are pretty much useless. These are questions people ask when there is little chance that they will learn something from the answer.

Let’s talk about few examples.

The first type is what I call the sponge questions. These come with the intention of soaking up the answer with no interest in learning how that answer was developed. People who ask sponge questions don’t give enough independent thought to their queries. These lazy sponges are unwilling to do homework before raising the question. It’s an act of intellectual dishonesty. Answering such question is a huge time sink for the time could have been spent on another question asked by someone more worthy of an answer.

Then there are questions which are based on faulty assumptions. Ignorance emanating from wrong assumptions is still pardonable but what’s inexcusable is being closed-minded about those assumptions.

And finally, there are questions which aren’t just bad but outright ugly because the seeker isn’t even looking for an answer. These aren’t questions. They are statements disguised as questions. They are intended to impress others by showcasing the seeker’s depth of knowledge. They are meant to stoke the ego. The seeker isn’t asking because he has a question, he’s asking because he has to ask something to register his presence.

Tim Hanson, in his wonderful article The Questions That Matter, writes –

Back in college, I had a professor who cut off any question that began with the phrase “Don’t you think,” explaining that no real question could begin with that phrase…“Don’t you think” questions are dangerous everywhere because they are fueled by bias.”

Okay. Now that we have a fair idea of how a bad question looks like, we’re well on our way to finding good questions.

Let’s talk about few traits of a good question.

First, a good question leads to the discovery of the more relevant question. A good question doesn’t necessarily lead you to an answer. It refines your thoughts and helps you formulate the better question.

Second, a good question makes it clear that the questioner is willing to participate in the process of developing the solution. It exhibits problem-solving intelligence rather than passively waiting for an answer to drop from above.

So how do you construct right questions?

A good question is rooted in humility. There’s no assumption about entitlement to the answer. It’s the attitude – being alert, thoughtful, observant, and willing to be an active partner in developing a solution- that matters. An attitude that contributes rather than merely demanding. This attitude leads to competence – the ability to ask a crisp, incisive, and thought-provoking question. The questioner deserves the answer because he’s earned it by having the right attitude and right competence.

So take the time to prepare your question. Think it through.

I hope I haven’t made a complete villain out of bad questions for they are the stepping stones to good questions. A good question is the product of a self-inquiry involving lots of bad questions but slowly, by deliberate practice, one becomes better in filtering out the bad ones. In that sense, stupid questions get the ball rolling.

So I’ll take the liberty of rephrasing the aphorism – “There’s no such thing as a stupid question if one doesn’t stop the inquiry there.”

Are You Ready for the Answer?

In the science fiction comedy novel The Hitchhiker’s Guide to Galaxy, humans build a supercomputer called Deep Thought. They ask Deep Thought to find out the answer to the ultimate question of life, the universe, and everything. The supercomputer gives an estimate of 7.5 million years to calculate the answer. After seven and a half millions year, the humans return to the supercomputer and wait for it to deliver the answer.

Deep Thought tells them that the answer is 42. Nobody likes that answer because nobody understands what 42 means.

Two observations stick out from this story.

First, humans wanted a precise answer to an abstract question. It was a bad question. They hadn’t thought through the question as deeply as they should have.

Second, the human understanding was inadequate to make sense of the answer. How could a solution, that took 7.5 million years for Deep Thought to calculate, be understood by humans in few minutes?

So what do you do if you don’t understand the answer?

A farmer has to prepare the soil before the seeds can turn into saplings. Similarly, the work that you do before asking the question makes the mind fertile enough for useful insights to germinate. Exercising the brain before asking the question creates the space for the answer. Investing sufficient time to grapple with the question prepares the mind to absorb the answer. This is where Socratic Solitaire helps.

Writing down your thoughts is the most powerful tool for crystallizing thinking and decision making. People who don’t have a habit of writing down their questions are usually sloppy thinkers. Expressing your question clearly and well is important. If you can’t be bothered to do that, you don’t deserve an answer. The question doesn’t have to be in flawless, stiff and formal language but it has to be precise. There has to be some indication that you’re thinking and paying attention.

Steve Wynn, CEO of a hotel and casino company, was once asked by an analyst to expound on how stable the economic situation in Macau (a gambling hub) would be over the next few months and a question about go-forward 90-day market share. At that time it was a company with an enterprise value of more than $20 billion and revenues of more than $5 billion and plans to open a massive new resort in Macau in just a few years time. Wynn replied –

It’s hard to give you — to quantify this. I know we try all the time, but to tell you the truth, Robin, it’s sort of a waste of time for all of us…It’s the kind of super detail that seems to matter on these kinds of calls, but really amounts to nothing in the long run.

The analyst made a fool of himself and blew away his opportunity to learn something useful from Steve. This example is from Hanson’s article.

Good questions are the foundations for developing a deep understanding. They provide food for thought, something substantial for the mind to chew on. Good questions reveal problems that might have gone unnoticed in the past.

A good question is nothing less than a gift.

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