How to ask good questions at events

I just finished watching a video of a talk given by Peter Thiel at Stanford, and the Q&A at the end is littered with long and rambling non-questions. It was a waste of time to watch.

Most people suck at asking questions during live events. But that’s not their fault! It’s actually hard to do, and most people have very little practice.

Since I’ve hosted conferences for 15 years, I think I’m ok at it. Here’s my cheat sheet for doing a great job.

1. Recognize that the most impressive and memorable thing you can do for the room and for the speaker is ask a curious and concise question. If you want to impress everyone, be quick.

2. State your name, and nothing else about you unless your question has to do with it.

3. Write your question on your phone before you ask it. Even if you don’t read it verbatim, it will help you ask concisely.

4. There is a category of question which amounts to: “what do you think of this idea?” This is a tricky one because you feel compelled to over-explain the idea. But people are remarkably good at understanding an idea from a short description, and if the speaker doesn’t recognize it they will ask you to elaborate. So always try to describe the idea in one sentence, then just ask: “what do you think of this idea?”

5. Ask a question that you genuinely want to hear the speaker respond to.

6. Most questions get long because you feel you need to provide context. Try skipping the context and just asking the question — see what happens.

7. Some questions get long because you want to take the opportunity to make a point to the room that you think is important in the context of the topic. That’s not a good use of the Q&A mic, and is way less effective than you think. Much better to ask the speaker the “mic drop” stumper of a question that makes your point for you.

Let’s say you just watched a talk by author Malcolm Gladwell about his book Outliers.

Good question: “Hi, I’m Jason Preston. What’s the most interesting piece of research you discovered but left out of the book?”

Bad question: “Hi, I’m Jason Preston. Thanks so much for being here and giving a talk. I really loved your book, and it’s such a great opportunity to hear your thoughts on all these things. I’m a VC at Alsop Louie and the co-founder of the community and conference called Dent — we named it after the Steve Jobs quote about putting a Dent in the Universe. You know, I’ve talked to a lot of entrepreneurs and a lot of interesting people as we put the conference together every year, and we have to figure out which people we want to invite as speakers and what we want to have them talk about. I’m sure it’s a little similar when you’re writing a book, especially the kinds of books that you write. So when we figure out these topics, we always learn a bunch of cool stuff for the speakers that never makes it on stage. Is it the same with your book? Make you could talk about if that’s right for you and if so a little bit about what didn’t make it into the book.”

Good question: “Hi, I’m Jason Preston. Thanks for being here. I think that 10,000 hours of practice isn’t a good rule of thumb because some things have more difficult feedback loops. What do you think of that criticism?”

Bad question: “Hi there. Thanks so much for coming to give a talk on your book. It’s really, it’s been a meaningful book for me. I’m Jason Preston, I’m a VC at Alsop Louie, and co-founder of a conference called Dent, like putting a dent in the universe. So you have this idea in your book about 10,000 hours and how if you practice something in a certain way, I think you call it deliberate practice, then 10,000 hours of deliberate practice is about how much you need to do in order to get really good at it. And I know, you’re talking about a kind of approximate number, but I think you’re over simplifying it. So there’s this idea that you can divide things into learning environments called “wicked” and “kind” and kind environments are like chess or spelling bees or any of the examples you use in your book, because they give you feedback. But if you’re trying to get good at something in a wicked environment it could be really tricky, need a different kind of practice or whatever.”

There you have it. Seven principles and two examples. Go forth and be impressive.