Many years ago, when I was still in my early twenties, a friend of mine called to say thanks. A conference I recently helped him organise went really well and he appreciated my help a great deal. Doing events which included presidents and politicians, professors from the top universities and movie stars, he was and still is one of the most connected and powerful people I ever considered a friend and a mentor.


I had been helping him for several years and have never asked for anything in return, when he called and told me: “Andrey, I appreciate your help and would like to pay you back. If I could be your goldfish and help you in any way you wish – what would that be?”

It was not the question that struck me at that moment, but an understanding of the magnitude of my friend’s potential, and the realization that he was not joking. So I thanked him for his generous offer and asked for a day to think about it. That night, I could not sleep. The next time we talked, I thanked my friend for his offer and refused to take it, as his question alone had had such an impact on me that I couldn’t possibly ask for more.

What happened was, I realised I never asked myself what I really wanted to do, nor what would I do if I had no limitations. I knew just by looking at the world around me that pretty much anything in life is possible, but now it became clear that without knowing what you want, you can never make any progress in that direction.

The following weekend I spent asking myself the same question, this time with a notebook in front of me. I made a list of things I would like to accomplish and, surprisingly, pretty much everything from that initial list I completed in roughly 3 years.

But that is not the point of this story. The point of the story is actually in the side-effect, and I’m not talking about dreams or goals. What I’m really talking about is asking questions.

Questions are always the first step in understanding something, the first step in increasing our self-awareness. Without questioning, everything we learn just piles up in our brain uselessly.

You know how, if you’ve ever read the same book several times, you get different insights each time you read it? That’s because at each specific moment those insights were a part of your questioning stack.

Throughout my teaching experience, my best-performing students are always the ones with the most questions. Their minds are open and they notice anything and everything which does not fit into their life perspective – like a 3-year-old who is constantly in questioning mode.

Here are 3 exciting facts about questioning that can help you in your everyday life:

  1. Insights and ideas come to life only after formulating a question. I call it idea-fueling. When you have a question on your mind, your brain will put energy and focus into solving it. Part of our attention automatically shifts onto things related to that subject, which helps connect facts into a single picture and leads you to your answer. It’s like finally deciding on the model of the car you want to buy – you start seeing that model everywhere!
  2. Every question has a purpose. This is important to remember both when you question yourself and when other people are questioning you. Understanding the purpose of the question can dramatically help in answering the question.
  3. A question can tell more about the person asking it than about the person answering it. This is partially because the right question not only gives an understanding of the answer but also gives a purpose, which can be even more powerful; and also because finding the right question can be as hard as answering it.

Asking the right question is always the best way to connect with someone you want to start a relationship with. The right question shows your interest in the subject and the person responding, your respect (otherwise you would not want to know the answer anyway), and your level of preparation and awareness.

Want to learn the art of questioning? Start asking yourself the 3 most important questions in your life every day. Open a notebook and write what​ you​ would​ like to ask the smartest person on the planet if you get stuck in an elevator with them.​​


Andrey Shtylenko