How to Ask Better Questions

How in the world do you ask great questions? I believe that anyone can learn this skill, so I’m going to show you how to do it. Follow me on Instagram: @masteryourtalk

1. Practice asking questions that you’re not comfortable with. (1:36)

I’ve met very few people in my life that ask extremely high-quality questions and the only commonality between all of these individuals is their high level of comfort in asking very tough questions. Think about that with me. If you take 1000 questions in the world, easy questions, anyone would ask, right? Tell me about yourself, what’s your greatest challenge/strength/weakness? The classics that people EXPECT, but the true masters, or those who want to hone their question asking ability are prepared to ask the questions, no one else is willing to ask. This is exactly how to ask better questions.

Take the Peter Thiel question, he’s the author of the book Zero to One, and in the book, he begins by talking about a question he uses on all his future employees and it goes like this: What is the truth you believe in that most people would disagree with you on? By nature, this question is uncomfortable because it forces others to answer something controversial. Thus, I think that by practising yourself in asking these types of questions, you’ll be able to craft up questions for yourself and develop the resilience of being comfortable with making others uncomfortable with questions. I also believe that the best question askers are so curious that they are willing to ask the questions that others won’t to get the answers they seek, so work that muscle to develop it yourself.

2. Ask questions that you believe only that person can answer. (3:04)

This tip requires some experience with someone to get to this point, but the general rule of thumb, is trying to ask the person something very specific in their lives and why they’ve chosen this path or the thought process behind their decisions. In other words, you want to ask things you’re genuinely curious to know the answer to a specific aspect of who they are. Here’s an example since almost all these types of questions are FOLLOW UP questions. When I started working my new job 2 months ago in consulting, the leader of the entire practice came to speak to us about the company’s vision and where he believes we were heading as a business. It’s pretty much a ONCE in a lifetime opportunity to talk to the man at the top, he talked about consulting, career advice, what would he have done differently, he was hitting all the check marks, but there was 1 thing that I was itching to ask, and 2 weeks into the job, that curiosity got the better of me and I asked him regardless, so when we went for dinner, I had the chance to sit next to me and I said John, I only have one question for you. This is the key on how to ask better questions.

You’ve had all this career success, and your advice was fantastic, but you also said, you were HAPPILY married for 19 years, so what’s your secret? The other consultants looked at me in dismay, and he just laughed hysterically, said it was a great question, and gave him a great answer, the point being here is if I asked him general questions like, what was your greatest challenge a) I wouldn’t have gotten the answers I really wanted and b) I wouldn’t look interesting or impressive at all since everyone else is going to ask him the same thing. Thus, with this insight, it will help us figure out how to ask better questions.

3. Get rid of the fear you have when you ask simple questions. (5:16)

I would say other than just pure genuine curiosity, a lot of my questions as well as the other question askers I know stem from hey, this doesn’t make sense to me, could you explain why you think like this? In other words, this is probably the most fun tip, but that yields the greatest output. Go out with friends that like to argument and learn from each other and just engage in heated debates that are sensible, of course, and I think that’s a great exercise. My FAVORITE hobby is having heated debates with my closest friends on life topics, not necessarily anything controversial by the way, maybe something in the news or your thinking on how a company is ran, it’s really anything that works for you. So, if my friend says something that’s inconsistent with something they said before, I immediately point it out and challenge him on that. Building that resiliency has helped myself and him ask phenomenally better questions and hopefully these insights will help you too. This will help us in how to ask better questions.

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For business or one-on-one public speaking coaching inquiries, you can reach me at [email protected].

Special thanks to Maison Leporem for letting me use the space.
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