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How to Ask Better Questions

Steli and Hiten talk about the art of asking better questions, why it one of the most important skills in business, and how questions is the best way to understand or gain deeper insights about almost anything or anyone.

Updated on June 13

Key Smash Notes In This Episode


Ask questions, and ask the right questions, don't assume you know the answers.

If you don't get the information and context, you will end up having to guess what your customer wants, and that never leads to the best results.

If you ask a question, and you don't get enough details in the answer, then dig deeper, and ask more questions.

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Say you said that you bought a house last week.

What did you buy it with? Was it money? What money? What currency? US dollars or maybe Euros. What if it was something else? It could be equity in a company or something else.

Who did you buy this house from? Was it from the owner, or was it from the police department, or maybe it was from an ex convict?

When hearing the original sentence, your brain might have added a lot of contextual information relevant to you (for example, US dollar, a brand new house). But that information was never provided.

That's why it is crucial to ask a lot of question, and get all the details.

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Here is an example. You are a founder selling a product, and your prospect is asking you to send them three proposals, what does it mean?

They are not giving you enough context to understand their real needs. Why three, what are you they going to do with those proposals, what are they trying to accomplish, and who are going to look at those. Are they going to compare them with your competitors. ..etc?

Just doing the proposals is not going to make you successful until you understand in details what those proposals are going to do for the prospects, then you can craft just the right ones.

To get the details, you have to ask questions, dig in, and listen to everything you are told. Only then will you know enough to sell what you've got.


If you are a business person, simply by asking the right questions you can understand your team better. For example, you would know why your engineers make decisions the way they do, and choose some options while you choose the others. Listening and asking questions will make your whole organization better.


Just ask yourself who is the best listener you know, who is the person that asks the best questions? Spend more time with that person, and when you interact with that person, try to understand how that person is interacting and communicating with you versus just communicating with them.

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Here is one example. If you're looking for advice or help with something, don't ask people what they did in your situation, just ask them what you should do. Otherwise, you are wasting their time.

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