Asking Questions

(This post was originally written in Issue #54 of my newsletter.)


This week I recorded two episodes on alternate days, and it was … exhausting!

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But this is a good thing. Both my guests do fantastic work that I have admired for several years. And they were interesting not only for their art but also for the trajectory of their work and lives. I learned many good things!

I am a curious person with lots of questions. Curiosity drives all my learning, and it also guides all the conversations I have. But a virtual conversation can be a strange thing, especially when it is the first conversation you’re having with someone.

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First conversations often tend to be surface-level conversations. When I listen to podcasts featuring 20-30 minute interviews, I am reminded of how surface-level conversations work. Or how they don’t work.

Every statement is a lie.” - Derrida.

Jacques Derrida, philosopher of Deconstructionalism, explained that every party in a conversation uses words in their own way, with their own ideas about phrase and sentence and context and subtext. Simply put, words mean different things to different people. In fact, any conversation between two people is actually a conversation between four people - the first person speaking to who they think the second person is, and the second person responding to who they think the first person is. We talk past each other. Nothing is heard and nothing is understood. Every statement is a lie.

[When I first read about Derrida, I wrote about how this manifests on social media and real-life political conversations.]

So in my episodes I take the long way around this problem, by asking lots of questions and letting my guests speak without interruption. Every conversation has its own tempo, which is set by the guest, while my job is simply to keep the wheels turning. Good questions are important too. This is what Socrates did, using good questions to peel away the layers behind the rules, laws, and customs, that we take for granted.

Why this? Why not that?

The idea is not to be contrarian, but to arrive at a logical and rational understanding for a certain thing. Asking good questions to delve deeper is an important tool for every host and interviewer also articulated as the “Theory of the 3 Whys”.

This is also the way of philosophy. The founder of phenomenological thought, Edmund Husserl, urged his students to reject all labels, perceptions, metaphors, and inherited ideas, and get to “the things themselves”. It was a process of ‘bracketing’ or suspending biases and judgments, for which he used the ancient Greek word, epoche.

[Read what I previously wrote about existentialism and phenomenology as they apply to SneakyArt.]

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In order to understand a person, therefore, it is worth the effort to get past the metaphors and idioms and biases - the epoche - and get to the things themselves. It can take time, but this is where the magic lies.

In these recent conversations, I think I am better able to tell when I reach that point. I know I’m close the first time that they lean forward to offer an anecdote. When their eyes light up as I formulate my question, I know we’re almost there. And when they add their own stories to my observations, I know we have started hitting the sweet spot. Every podcast conversation is a race to reach this sweet spot, and once there, to stay in the zone.

I didn’t mean to get philosophical about all this! The point was just to share that I’ve had two, long, exhausting, enriching conversations this week. And I’m excited to share them with you soon. There is good stuff in there. Real magic.

Nishant Jain