How to Ask Better Questions

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Asking questions, or should I say, great questions allows you to get great insight and knowledge from others around you, and more particular, to the context of public speaking, it allows you to get the right intuition of your audience as quickly as possible to master them and WOW them.

But, the challenge now is how in the world do you ask great questions?

1. Practice asking questions that you’re not comfortable with (1:05).

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. 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.

2. Ask questions that you believe only that person can answer (3:17).

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. I come up with questions, not because I’m this super genius, but rather I’m super CURIOUS. Every senior exec I talk to keeps telling me stuff I already knew, so how do I get the insights that they aren’t telling me? By asking him about the advice he gives at people at the TOP since they already know the conventional advice, point being if you ask questions they only know the answer to (or very few do), you’ll be on your way to asking better questions since those questions stem from an intense level of curiosity.

3. Be obsessed in detecting inconsistencies in other people’s logic and trying to make them whole for your own benefit (6:40).

This is more of a bonus tip, 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.

As always, if you enjoyed this week’s episode of MT, SUBSCRIBE to the YT channel and SMASH that LIKE button if you enjoyed the video. If there’s anything I can leave you with, is if you know one person that’s trying to refine their ability to ask questions, send them this video and they can master their talk in the process.