Interviewing in a conversational way

What I find especially difficult in interviewing guests for my podcast is making it truly conversational, yet also deliver insights to the listeners. 

When a guest is speaking, making a split second decision: ask a contextual question or a pre-planned one? 

Go further and did deeper hoping to uncover an insight or settle for a surface level answer?

Really listen to what a guest is saying instead of thinking where to take the conversation next?

Interviewing is a skill. It’s learnable. And I need to improve on it. 

Sergey Ross