How do you ask good questions?

I love Tyler Cowen’s work, even though I’m not that into Economics. But Tyler has a knack for simplifying concepts and asking questions that make everything he writes easy to understand. You should check out his daily (sometimes several times a day) blog for fresh insights on culture, economics, and beyond.

Today, one of his fans asked him the question that I’ve been pondering for years now.

The Question

Do you have an instinctual knack for posing high-quality questions, or is there a conscious method when you engage with ideas.

Are you aware of any interesting articles/books exploring the nature of questions and how to improve asking questions. Lots written about answering questions; very little, so far as I can tell, about asking questions.

And here’s Tyler’s response:

I have a few tips for asking better questions:

  1. Highly specific questions are better on average.
  2. It is often better to preface a question with a confession of some sort or with information from yourself. That sets a standard for the respondent. Set that standard high!
  3. Demonstrate credibly that you are truly listening and that you care about the answer.
  4. With any possible question, ask yourself in advance: can the person being asked the question respond too easily in a vague and not very useful way? “Why did you write a book about Napoleon? Well, let me tell you, French history always fascinated me.” etc. If that is the kind of slop you might get back in response, try making the question more pointed or more specific.
  5. High-status people get better answers than do low-status people. So be high status. Or at least credibly pretend to be high status.
  6. I have enjoyed Gregory Stock’s The Book of Questions.
  7. You might say, “listen to other interviewers.” Well, maybe, but perhaps not too much? They will encourage you, by default, to ask the same questions that everyone else does. And too many of the sources available to you are mega-famous people who are getting by using their fame to boost the significance of their questions. (Anything Oprah might ask me would be interesting per se.) So use this standard tip sparingly and with caution.
  8. Any questions about all this?

See, I told you, Tyler’s at a different level. You must check out and subscribe to his blog (no affiliation, of course!) Marginal Revolution right now!

Asking questions comes naturally to me because I’m super-curious by nature. I don’t have hard questions but a few standard ones, including:

  1. What’s happening?
  2. What’s on your mind?
  3. And what else?

I think the power is in the follow-up questions, which, at least for me, can never be scripted; else, it comes across as unauthentic. Following up with questions also reassures the speaker that you’re closely leaning into what they’re saying, and that makes the whole conversation just magical.

Try it and let me know how it went.

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