“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.
A genius moment comes from them asking questions all of the time. Over the years, their pattern recognition has gotten better. That only comes from firsthand experience.
3. Asking a question you literally know the answer to is usually counterproductive.
Asking for confirmation is good. Asking someone to tell a story or raise a point that you’ve heard them mention before is also good. But if the intention might be for other people to learn, or to sound smart, or to mask an ulterior motive, or simply to have a chance to raise your hand out of fear of not being heard, it’s very possible it will backfire and waste the other person’s, or any listeners’ time. Don’t ask questions you don’t need the answer to.
4. Shut up when other people are asking questions or when someone is answering your question.
5. Ask short questions.
Talk for two or three phrases at most, even if you’re setting context. If the answerer needs clarification, they’ll ask.
6. A bad question might lead your brain to the good question.
A question, even if it’s phrased poorly, might lead you to realize the better way of phrasing it. If it’s a high stakes situation, you could hedge it, “I’m sure there’s a better way of phrasing this question, but…”
7. Asking questions synchronously is ideal.
Some people are more comfortable answering questions on email, but whether it’s in-person or on the phone, generally synchronous conversations are better—there’s more opportunity to investigate, rephrase, or correct misunderstanding, follow up with questions in real-time, etc. And nobody skips your questions, delays, misses deadlines, etc… You can always follow up on email or conduct further research yourself.
8. Some answers don’t need a question—just listen.
For example, “How can I help you?” or, “What can I do to support you?” is one of those types of low effort questions. Instead of asking them, show people you care and, I dunno, have actually listened by suggesting or anticipating some of the ways you can support. Then, use that as a way to gauge other ways you can support. It’s a little more resource intensive, but it’s much less generic and builds trust.
9. People need to trust you before they can answer some questions honestly.
Speaking of trust… Not everyone can or will give you an answer to a hard question without it. This is one of the greatest challenges in business. Finding a business problem is one thing, but a personal problem might require years of acquaintance or friendship. Properly understanding a business problem means understanding the business and personal interests, so it’s best to figure both out.
10. If you’re doing an interview, spend at least a couple of hours on research.
Repetitive questions with repetitive answers bug people, especially if they do a lot of interviews. Don’t ask someone, “What’s your inspiration?” but maybe a variation, “What kind of music are you listening to today?” or something. Be bold with the question, own it, and challenge it. You are throwing a baseball, they are choosing to catch it—they will not catch it if you don’t throw with conviction.
Don’t overthink it.
There are some great general questions that have gotten a bit annoyingly repetitive (the Peter Thiel one comes to mind), but overall, the fundamentals of questions are pretty straightforward. If you need to know something, ask. If you’re not sure, ask. If you don’t need to know, don’t ask. If you need to clarify or confirm, ask.
Follow these rules, and at worst, you’ll learn a lot. Tweak them to your specific needs and contexts as well—maybe your boss never leaves time in meetings for questions, so you need to dial up #8 (finding answers without questions).
Have fun learning!
You can ask books questions, too…
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