Asking the Right Questions

School is mostly about giving the right answers to questions. Life, in contrast, is mostly about asking the right questions to begin with.

Growing a business while attending university let me see some of the differences between the two worlds as I stepped through them in parallel. More than anything, I feel the biggest difference is the importance of answers versus questions.

I can remember taking a business class where a student presented outside facts, not available in the case. He was dismissed because the facts didn’t fit within the model being analyzed. Reaching the “correct” answer was rewarded, even if the questions asked and models used were broken.

Answers are the Easy Part

Most questions, if you define them well enough, can be answered without too much difficulty. Sure there are those hairy philosophical points that will be debated endlessly. But most questions have attainable answers. Even when they don’t, you can usually make a good first guess.

Good questions are much harder to come by. I often spend twice as long deciding what to write than I spend writing. I’d rather read a poorly written essay about an interesting question than a flawlessly executed one about nothing.

The rewards for being good at asking the right questions are greater too. It’s like a formula:

Results = Question * Answer

Where answers range from 0-100%, and questions range from 0 to infinity. Answering a good question incompletely is worth a lot more than answering a trivial question well.

Answering the Wrong Question Prevents Asking the Right Ones

The situation is more complex because once you’ve come up with an answer to a question, there’s a strong internal pressure to avoid asking a different question. Your mind is already made up, the mental work finished and you have a stake to protect.

The world would probably be a better place if after every opinion, you had to acknowledge, “but it’s more complicated than that.” We’d still have opinions and people would act upon them. But after every opinion is written it would be stamped as a rough draft in the mind, leaving a slight crack open for a different question to be asked.

I’m guilty of this as much as anyone. I’ve written about atheism and vegetarianism, two opinions I feel I’ve arrived at roughly the right answers for. But I still try my best to be open to the possibility that the questions weren’t the right ones to ask in the first place.

What and Why, Not How

People often get too caught up on the how of things. Execution matters, of course. It matters dearly. But it too is a process of asking questions that may not be visible from the start. Knowing how to start a online business that pays all my bills certainly wasn’t an answer I had to start with. But in the process of continually asking what and why, the how fills itself out with enough effort.

How is dependent on the what and why, but unfortunately many people have this backwards. They begin their journeys in life looking at what is feasible, and upon finding little of interest, decide to accept that and move forward.

Everyone I know who has accomplished anything interesting properly focused on asking the right questions first. Even if they couldn’t answer them at first, asking what and why shapes the eventual how.

Even with what and why, it’s the question that matters more than the answer. The what and why will change, not always because you get better answers to the how, but because along the way you start asking better questions.

Asking Better Questions

I don’t think there is any formula for asking better questions. If there were, that too would be an answer instead of a question. But if better questions get better answers, then what delivers better questions?

For me, I feel the best solution is to be surrounded by people who are asking better questions. When your conversations take place with people who embody the status quo, how can you expect anything but the standard answer?

This step is easier than most people realize. When I started this website, I was living in a small town, and I didn’t have many people to think through big ideas with. But I could still read books, so I could expose myself to better questions even if most my friends weren’t asking any.

Another step to asking better questions is to seek people, ideas and situations that break the answers you’ve already arrived at in life.

The cliché about travel is that you leave home to find yourself. When I lived in France for a year, I found the opposite. Instead of finding an identity from confusion, I found I was breaking many of my old assumptions and answers about my life. Perhaps that is more discomforting, but in the end it’s more useful.

  • Stepan

    New goal: Get an infinity on my essays.


  • Wendy Irene

    “surrounded by people who are asking better questions” I thought this was very interesting and it got me thinking. Love that! Have a great week!

  • Nicky Spur

    Nice post.

    You’re dead on about school — I felt it almost countered the important things I learned in life because your trained to find the answer the teacher wants, not use your brain to find your own answer. I also like the idea of using books, new experiences and other activities to surround yourself in an almost pseudo-mastermind circle.

    Sometimes you’ve got to seek the knowledge you want yourself.

  • Stanley Lee


    What are your thoughts about asking the right questions, even if doing so makes you look really stupid or incompetent?


  • Life Exceptional

    Yes you are right about school. It’s also true of the early years of a corporate career when you are expected to answer the questions your boss gives you. After that you are suddenly expected to be able to ask the right questions to those more junior than you. No wonder so many corporations make such stupid mistakes!

  • Praveen

    very profound article , Have you read “Asking Questions” by Bahiyyih Nakhjavani

    very much on the similar lines.

  • Scott Young


    There’s certainly some backlash to asking a different question when the answer has already been given. But that’s the price of nonconformity, and I think the benefits are worth the costs.


  • Alex

    As LessWrong puts it, school is all about memorizing the teacher’s passwords. Oh, and becoming “socialized”.

  • Veron

    This is a great article! Glad i stumbled on your site again, through digging through my google reader.

    Your post reminds me of a quote in the Matrix, where Trinity say…”It is the question that drives us Neo. It is the question that brought you here.” And there’s another part where Morpheos, I believe, refers to the question, as “the splinter in your mind, driving you mad.”

    i think these are the best questions, and they seem to have a life all their own. And the answers they lead you to, also seem imbued with some magnetic force. I’m simply referring to those epiphanic moments, when what you held as truth encounters something you see(answers) as a step to greater understanding. Uncomfortable, almost traumatic, yet very exciting!

    I can identify with the method you mentioned that allows one to ask better questions. I experience these moments through associations. Whether reading, or intentional conversations about the deeper questions in life. Again…really enjoyed this one. :->

  • John Sherry

    Answers questions to yourself is a true goldmine as you always know the answers deep down. Self-enquiry has the key to change our life and make dreams begin. Why ask another what is their truth when yours is waiting inside?

  • Ryan Niessen

    The key to life is definitely asking the right questions, thanks for a very insightful post!

    I like that you clearly explain the benefits, what to avoid, and tangible ways to to ask better questions and attain better results. I find our generation especially to be quite lazy at asking questions, and they’re missing out!

  • Greg

    In my opinion, you can learn more about a person by the questions they ask than the answers they give. Questions create clarity, and clarity is power 😉

    Great stuff as usual.

    – Greg

  • Zainal

    Awesome post,

    The whole time I was reading your post, it reminds of that saying my maths teacher once told my class

    “the best teachers in life aren’t the ones who teaches you how to get the answers, they are the ones who teaches you how to ask questions”

    And, I thought he was just saying this because he couldn’t be bothered to teach us properly. Turned out the old man knew what he was doing.