My philosophy of interviewing

After I do Conversations with Tyler interviews, I receive emails telling me I should have “stuck it to person X,” rather than “letting them off the hook,” etc.  “How could you not refute them on that topic!”  And so on.  Just to be clear, here is my underlying attitude behind the series:

1. Appreciation is an underappreciated art and skill.  These interviews are most of all about appreciation.

2. I hope to teach people how to learn from other people.

2a. For one thing, you can learn from what the interviewed person says, whether or not you agree with it.  In fact, you do better if you don’t focus on whether or not you agree with it.

2b. You also can learn something through a better understanding of how the person built his or her career into a success, and usually I ask something explicitly along these lines.  The broader conversation is implicitly all about this, of course.

2c. You also can learn something about how I try to learn from these people.  And that is the part of the conversation I have the most control over.  I am trying to teach the art of learning, and that art involves less rather than more contradicting and gainsaying.

3. Follow-up questions are overrated.

4. You want the interviewed person to be maximally open and relaxed, to bring out a steady stream of their best content.

5. If I leave a topic hanging, perhaps it is because I want you, the listener, to think more about it.

6. The best follow-up questions don’t sound like follow-up questions at all.

As I said to Ed Luce before my conversation with him: “You know, most famous people are used to someone trying to make them look bad.  They actually should be more nervous about someone trying to make them look really good.”


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