Some Questions I Rely On For Life-Enriching Conversations

Two things I enjoy: traveling and having one/one conversations. Ideally, I’d be doing both at the same time but the former requires planning, money, and time. I’ve come to realize that through one/one conversations, I can still do the traveling, albeit in a different form.

Conversations are a doorway for me to enter a person’s world. It’s like I’m taking a deep dive into a world of their own. Letting go of my own world, I enter theirs and immerse myself into a different worldview. It’s an enriching experience because through the conversations, I come to realize two things: how we can be looking at the same world we inhibit so differently and also how despite the differences, deep down we have the same universal needs that bind us together as humans.

To have life-enriching conversations, I have relied on two things: asking questions and listening with intent.

Here are a few questions I’ve come to rely on:

– What have you been thinking about lately?
– What experiences have shaped you as a person?
– What do you look forward to in life?
– What do you want your life to be about?
– What’s something useful you’ve learnt in the past year or two that has made your life better?
– What doesn’t make sense to you anymore?
– What is the best compliment anybody could give you?
– If everyone in the world was just like you, in what ways would the world be- better and worse?
– What worries you?
– How do you deal with frustration?
– In what ways are you trying to become a better version of yourself?
– What would you like people to understand about you?
– Who are you willing to disappoint? (More on this here)
– What has taken you a long time to accept?
– What makes life worth living?
– What’s something people could learn from you that would genuinely make their lives better?
– What are you trying to learn-unlearn-relearn?

It’s perhaps because of questions like these (and genuine intent to listen and learn), I’ve been incredibly fortunate to have met some wonderful people in the last one and half years and cultivated what I believe to be life-long friendships with them.
What are your go-to questions to travel the depth of the other person’s world?

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