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Here you will learn to have more engaging conversations as well as receive more in-depth and heartfelt stories from the fascinating individuals I interview.

Question 1: Why?

Asking why invites others to delve into their motivations and reasons, offering you a glimpse into their world. It encourages them to clarify what they really mean, sometimes to their surprise.

For instance:

“Anything new going on with you lately?”

“I’m starting an Instagram page dedicated entirely to cute animals.” 

“Why cute animals?”

“Whenever I’m feeling down, looking at pictures of cute animals always cheers me up.” 

“Why does it cheer you up?”

“I guess because they represent innocence and joy, which reminds me of my childhood.”

Through why we weave a pathway into deeper understanding, allowing us to uncover more about a person's experiences and perspectives.

Question 2: What’s that like?

A question that fosters empathy, what’s that like is pure curiosity and encourages the sharing of personal experiences and feelings, paving the way for genuine connection.

Continuing the previous exchange:

“What’s it like to feel like a child?”

“It’s freeing. It’s as if the world is full of wonder and possibilities.”

“Why?”

“Life seems hopeful, I haven’t become jaded by failures or disappointments yet.”

What’s that like creates space for the other person to reflect on their thoughts and emotions, why helps narrow down the truth of it all. This leads us to…

Question 3: How does that make you feel?

This one’s a little meta, but adds a deeper layer of reflection and insight.

“How does realizing you’ve lost hope make you feel?” 

“Kinda sad I guess, but also encouraged. I recognize now what’s holding me back.”

“What’s holding you back?”

Boom. You’ve just entered into a deep and meaningful conversation in a very natural and empathetic way. What could’ve ended at “Oh that’s a cool idea for an IG page” at the beginning of the conversation has instead turned into an opportunity for deeper connection.

Bonus: Watch these questions in action!

I met Ralph walking around Soho on a Saturday afternoon. In these chance encounters on the street, I don’t have much time, so I employed why, what and how to quickly distill the reality of his experiences. (I cut out the whys in the edit, but you can see how they lead to greater detail and clarification in the conversation)