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10 Question Commandments

The Art of Asking Good Questions

Herbert Lui

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Image: Changing the Letter by Joseph Edward Southall (1908)/Birmingham Museums Trust

“1, 2, 3, 4, 5, 6, 7, 8, 9…”

I’ve professionally asked questions for years. Clients pay me thousands of dollars to ask the questions I do. I’ve also asked recording artists who I do interviews with. I got good enough that A$AP Ferg told me our interview was the best one he’d ever done.

Questions are, still, a tricky business. A lot of questions vary by context — so while these principles hold up generally, there are some specific situations in which it won’t apply. Trust your judgment! Here are some things I learned along the way:

1. A question doesn’t have to be a reflection of you.

This frees you up to allow yourself to ask stupid questions, which is a big part of asking questions and investigating. I’ve lost count of the number of times I’ve been in situations where somebody else asked a question we were all thinking, or, the number of times I’ve heard someone tell me a story like that. People with fixed mindsets or playing high stakes, finite, games might take issue with this point, but I think it’s good general advice.

2. Anyone who consistently asks good questions has probably already asked all the stupid questions.

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