How to Become World Class at Asking Questions


Answers form our world and our beliefs, but they are always proceeded by questions. We focus on getting the answers we want, but forget to probe if we have the right questions. Intelligent questioning is one of most effective ways to influence both others and ourselves, yet it’s a skill not taught for most of us in any formal way. Through my own pursuit for asking better questions, I uncovered some ideas that can work as ladders on the pursuit for world class questioning.

Ingredients of a Great Question

Before we can start improving our skills at creating great questions, it’s worth defining what makes up a good question. It’s like trying to become a better musician before clarifying what does great music sounds, look, and feel like. When someone says “that’s a good question..” and truly mean it, what do they actually portray?  While the effectiveness of a question is highly dependant on the context and the attempted goal of asking it, I’d suggest there are at least the three factors that make a question universally better, present in varying levels depending on the type of questions.


Firstly, a great question takes you off guard and makes you think deeper that you normally do. You remember that feeling when you think to yourself, ‘hm, I haven’t thought of that..’ or ‘I wasn’t expecting that!’.  This rules out most yes or no questions (not all of them) and paves the floor for new angles. By definition, a surprising question will evoke a non-prepared answer getting you closer to the truth. When they’re expecting to hear ‘so, how do you know the groom?’, ask instead ‘what’s the most fun memory you’ve shared with the groom?’ Coming from an unexpected angle makes you stand out among the herd that’s asking the very things you expect.


Some of the best questions make you listen harder and peak your curiosity. ‘Ooh, I want to know that too’, is the typical reaction to something that really interests us, and often comes with being able to relate. Arguably one of the best interviewers in the world, Cal Fussman, teaches that it’s best to start your interview from the heart instead of the brain. When interviewing Soviet era leader Gorbachev, instead of asking about Perestroika he asked “What’s the most important thing your father taught you?”Ask about beliefs and emotions, instead of the obvious. Don’t just ask what they do, the why is always a lot more interesting.


The effectiveness of practically any question is highly dependent on the intensity of thinking it evokes – regardless of whether it’s posed towards yourself or someone else. This highlights the importance of challenging the status quo and upheaving the hard held assumptions. Whether you’re trying to persuade someone in a sales meeting or educating children in a class room you want the question to pierce a new way of thinking into its audience’s brain. Doing this often contains elements of surprise and depth, but also purposeful contradiction on the norms.


Habits and beliefs to asking better questions

The components of a good question above give us a pretty nice idea of what does a master of questioning look and sound like. Yet telling you that you need to ask more surprising, deep, and challenging questions isn’t very helpful by itself – we still need a roadmap to get there. There certainly isn’t a single route to mastering this fine art but below are some practices and beliefs that I’ve found helpful on the journey.


Discard the obvious, embrace the absurd

“If at first the idea is not absurd, then there is no hope for it.”
Albert Einstein

The first question that comes to your mind is bound to be the most obvious one, so discard it and use it as a platform instead. What’s the follow up, or the consequence? Why did that come first? Is there a different angle you’re not looking at? Jumping into the deep end of the pool will involve more thinking and empower you to look at things for new angles.

For truly unique ways of looking at things, you need to dive into the rabbit hole from Alice in the wonderland and embrace the absurd, which goes hand in hand with creative thinking. Personally I think all humans are inherently creative, the pool is just hidden deeper in some people behind the curtain of what’s appropriate. Throughout the history mankind has masterfully created norms and taboos that allow us to function as a society – but also severely limit our thinking (and questions) to a narrow set that are judged safe by those around us.

Go wild, act weird, and ask the unexpected.


Master your subject

“If people knew how hard I had to work to gain my mastery, it would not seem so wonderful at all.”
Michelangelo Buonarroti

Every great discovery in science has led to an array of new questions to answer. Standing on the shoulders of giants to see farther really means that you’re able to understand the underlying body of knowledge. How can you you ask unique questions if you don’t know which questions have already been asked a thousand times?

As an example, if you’re going to interview someone for an article, asking great questions requires deep understanding of your subject. What have others already asked them, what information is available, what stories are there hidden you can ask about, why did they make the choices they made? The same is true when you’re asking your teacher something during a lecture. To be able to articulate a truly through provoking question, you need to really understand what has been taught and read between the lines.

Wander the miracles of life

“Not all those who wander are lost.”
J.R.R. Tolkien, The Fellowship of the Ring

Everything around you is a miracle, once you open your eyes to it. Look at the curiosity of a child and learn from that innocence. Stop and think about how crazy it is that we’re a bunch of particles in collision with other particles all bound by an invisible force of gravity and moving thousands of miles per second throughout space we know very little of.By practicing curiosity you’ll naturally become a better at asking questions since you’ll be more interested in everything.  You’ll want to delve beyond the surface, know how things work and why.

Finally, open your mind to the idea that everyone you ever meet has a story to tell. Think about all the tales and stories untold, beautiful moments and sad memories. All the questions that are looking to be asked by the curious. Being authentically interested in another makes them feel that they matter.

What’s a better gift you can ever offer?


5 responses to “How to Become World Class at Asking Questions”

  1. […] as a one-off event, I try to imagine what are the implications five years ahead. In the spirit of better questions some examples could be: ‘Am I the kind of person who wakes up early, full of energy?’ […]


  2. One thing that I would add, that is essential to asking good questions, and it goes with “Master your subject” is active listening. Without listening we can’t know what ask, and it is often the follow-up questions that allow us to get to know others deeper and more intimately than those initial questions.


  3. Asking the questions that stir up emotions to reflect the Aha moment or a sense of ponderment (not sure if that is a word), of wonder, causing the Hmmm. I wonder about…


  4. […] How to Become World Class at Asking Questions (Patrick Obolgogiani) […]


  5. […] empower people to find new ways of thinking, the more independent you’ll find them becoming. Powerful questions are the key to unlocking new depths people might otherwise not […]


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