Dig deeper in conversations with why questions

Dig deeper in conversations with why questions

Most conversations that people have are usually over the surface

Some may want to have a deeper connection with someone yet they don’t know how to do it

People always value deep conversations

Deep conversations is a place where people share more vulnerable parts of themselves with one another

These vulnerable parts are way below the mask, also known as the ‘normal self’, that they present to others in the community

They are not sharing their ‘normal self’. They are sharing more of their ‘real self’ in front of you. The real person behind that mask

By sharing deeper and more ‘real self’ part of you:

  1. you are inviting others to understand you.
  2. you are building a deep strong bond with one another
  3. you are building trust

Trust and understanding are what we need to have a great quality listening sessions or conversations in general

So, how do you exactly invite others to have a deeper conversation?

Before that, let’s take a look at examples of what not to do if you want to have a deep conversation

Take following conversation between a couple for example:

Tom: “Hi Betty, how was your day?”

Betty: “Today was pretty good. Nothing much happened. It’s all the same as before. I find myself staring out the window a lot at work just wondering.”

Tom: “What are you wondering about?”

Betty: “I wonder about what life would be like if I had taken another choice. Maybe as an artist since it’s more of what I love”

Tom: “Oh yeah you always love to draw and dance as your hobby. It’s normal for you to feel that.”

Betty: “I guess so, yeah today was a good day nevertheless”

The problem

Tom had good intentions, it was a nice conversation. You can tell Tom cares about Betty

If Tom truly cares about Betty and wants to take this conversation to the deeper level, then there’s something wrong with this conversation

It lacks depth

This conversation barely scratched the surface and there’s a lot more going on that needs to be uncovered with deep conversation

Betty is subconsciously showing a sign of dissatisfaction at work.

Tom kind of noticed but wasn’t able go deeper into this great opportunity and learn more about Betty

Solution

So now, back to the same question:

How do you exactly invite others to have a deeper conversation?

The answer is once again fairly simple

You invite others to have deep conversations by:

  1. Asking “why” questions repeatedly (3 - 5 times)

The word “why” is a beautiful word in human history

It’s only made up of 3 words yet it has extremely powerful when used correctly in a listening conversation

It invites others to share a deeper reason of what you do or how you feel

When you ask why,

you are asking the reason “behind” something,

you are asking the reason underneath the “surface”

If you ask that question to a person, you are asking others to explain or share deeper part of themselves underneath the surface

Imagine every time when you ask why, you are digging deeper into someone’s heart

The more why questions you ask, the deeper you will go

Let’s go back to the conversation between the couple again but with “why” questions

Tom: “Hi Betty, how was your day?”

Betty: “Today was pretty good. Nothing much happened. It’s all the same as before. I find myself staring out the window a lot at work just wondering.”

Tom: “What are you wondering about?”

Betty: “I wonder about what life would be like if I had taken another choice. Maybe as an artist since it’s more of what I love”

Tom: “Why do you love being an artist?”

Betty: “I love it because I want to be more creative and expressive with myself. I feel more free compared to the boring office job that I have now”

Tom: “Why do you want to be more creative and expressive with yourself?”

Betty: “Because in this office I feel like I have to hold back so much of myself as a manager who is younger than her team members.”

Tom: “Why do you need to hold back?”

Betty: “Because I need to be strong so that others can look up to me and respects me so I can delegate tasks to others better. Sometimes I feel like I am not who I am anymore”

Tom: “Who are you?”

Betty: “I am a soft person who cares about others and value peace and harmony in groups.”

Tom asked the “Why” question 3 times and it made a huge difference

He was able to have a deeper conversation with Betty

Tom learned that even though Betty was a manager who is supposed to be strong in front of others yet deep down inside, she was soft and more vulnerable

Great benefits of deep conversations

After this deep conversation, it is highly likely that Betty will trust Tom more as a boyfriend

Betty was able to share a more vulnerable and secretive part of herself with Tom that she probably normally don’t share with others

As the relationship bonds deepens, Betty will be able to share more of herself with Tom

With deeper conversations, Tom is able to access a deeper part of Betty closer to her heart

With repeated deep conversations, Betty will inevitably fall in love with Tom if she hasn’t already

Deep conversations creates trust between friends and family

Deep conversations creates trust and love between partners

Final remark

If you ever want to build trust and understand the other person, deep conversations are needed

You build deep conversations by asking why questions repeatedly until you cannot ask anymore

With this, you are able to understand a secret part of the other person who they don’t usually share

This understanding will help you build trust between friends, and even love between partners

If you ever want to improve your relationship and strengthen it with someone

Invite them for a deeper conversation by asking why