How to Ask Good Questions


You ever felt stuck in a dead conversation?

A conversation where you felt like you were doing all the listening…

While the other person was not returning the same favor?


Those conversations are the worst.

And those are the conversations that can tarnish likability.


The problem with many people nowadays is that they are quick to talk but slow to listen.

In the most interconnected era of all time, social skills are plummeting.


But that does not have to be the case for you.

You can’t always control someone else’s behavior…

But you can always control yours.


The beauty of social skills is that it’s all about training your mind to do less, not more.

1 correct question asked beats 10 statements said.

That’s a powerful mindset to condition yourself into.


In this blog, we are going to be discussing how to ask good questions.

A question that makes others feel like they were being listened too.

Let’s begin.


What is A Question?


I am all about breaking things into the fundamentals.

So let’s do that in terms of humans.


Humans are information systems.

We process life via information & create perceptions around that.


There are 4 parts of the information system that we call a human:

Input – Information acquisition.

Process – Apply rules to information.

Memory – Store information.

Output – Information sharing.


A question is when you are outputting information from a fellow human.

You are extracting information to build more situational context.


In tv shows, we notice that the officers interrogating the criminals are asking questions.

They are outputting information from the information system (criminal) in order to gain more context (guilty or not).


So that is all a question is:

When you are outputting information from a human.

Got it?





What Makes a Good Question?


‘So what makes a good question bro?’

Hm… can’t really answer that in a concrete manner.


Because a good question depends on the context.

Let me explain.


You are asking questions all the time.

Especially on the internet.

So let’s use an analogy with the internet to help you understand what a good question is.


If you desired to eat a meatloaf, what kind of question will you ask google?

‘How do I cook a meatloaf?’


So in the context of your desires, this was a good question.


But what if you asked something like:

-What is the best school for engineer?

‘That would be a silly question!’


‘Because it does not match my desire.’



Therefore, one thing you want to get out of your mind is thinking that there are ‘perfect’ questions.

This has you becoming ego focused.

And has you exiting the present moment.


This is when you hear something your ego deems a good question & you just hold on to it.

That’s when you wait for the other person to shut up so you can ask this ‘perfect’ question.

Only problem? He or she has transitioned points, while you are still stuck in the past.



There is no such thing as the perfect question.

However, there are questions that are optimal based on the situation.

And in order for you to understand what is optimal, you need to be actively listening.


As you are actively listening, the other person will drop things called hooks.




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The Importance of Hooks


Hooks are portions of a conversation that you can expand from.

Individuals can drop hooks consciously and/or subconsciously.

Other times, they don’t drop any hook at all, but it’s creativity on your end that can build a hook.


Let’s go thru a few examples.


Example of a conscious hook:

“I just got promoted.”


With proper judgment, we can understand that this statement is meaningful to the contributor.

Someone does not get promoted every day.


This is why a solid question will be ‘Dope! What’s the new job entail?’

Something like that.

This is a case of the contributor giving you a hook to expand on hoping that you pick up the clues.


The socially unintelligent individual misses the hook and makes the conversation about themselves.

‘Oh, yea I remember that one time I got promoted…blah blah blah.’


Example of a subconscious hook:

“I just got back from work, been having a long day. And now I am ready to watch the movie with you.”


For subconscious hooks, you want to notice changes in tonality or message content.

Can you spot the potential hook from that statement?

‘ I don’t know.’

It’s: been having a long day.


You can ask the question ‘why have you been having a long day’ and go onto a brand new conversation from there.

This question matched the context of the conversation & is deemed appropriate.


Other times, there will be no conscious or subconscious hooks from the other person.

‘So what do I do in those cases?’

Get creative.

‘And how do I do that?’

By going from surface to depth.


Drill Down Questions


If you think about it, any friend we have was once a stranger.

The process of turning a stranger into a friend is a:

Formal to informal transition.


At first, we are super stiff with the person.

Asking surface-level questions.

-What do you do?

-What do you study?

-Where are you from? 


Those are normal questions for someone that you are initially meeting.

But as the rapport is gradually building, you want to add depth to your questions.

Depth questions are more personalized.



‘You mentioned you’re working on a business. Have you always wanted to do that since growing up?’


This is an in-depth question.

Which requires thought, but can help the person know you better.


In-depth questions require guts & judgment.

Guts because going deeper can mean require entering uncharted territory.

And judgment because some people are private & don’t like going that deep.


This is where your creativity comes in to play.

You need to go on a case by case basis to decide if this person is a better fit for a surface level question or in-depth one.

That’s what keeps social skills fun & dynamic.



Leveling Up your Questions


The beauty of questions is that you can always experiment.

Questions that work with one party does not always work with other parties.


But ultimately, you want to realize there is no such thing as the perfect question.

Instead, good questions are situational based.

So if you want to ask better questions, then maintain awareness of the social situations.


From there, look out for hooks.

Whether it’s conscious or subconscious from the other person’s end.

Look out for out of normal tonality and/or subject matter from the general theme of the conversation.


If you don’t have that, then create your own hooks!

This requires you to create surface level to in-depth (more personal questions) based on your judgment.


Remember this, my friend, one right question beats a lot of statements bragging.

Be present.

Be charismatic.

And build your network from inside out.


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