#1 The most important question
The most important question comes BEFORE the interview. Oprah says "I approach every interview by asking, "What is my intention? What do I really want to accomplish?"" It's something podcasting trailblazer Pat Flynn puts another way, he says the most important thing to determine in your interview prep isn't what or how but WHY. A clear understanding of the goal that guides your questions and your reactions, that's what will set your interview apart.
A conversational interview is about rapport and compassion. For Oprah the means to a connection from behind the mic is empathy. "You can't accomplish anything if you're judging," says the Supersoul Conversations host. It's an intentional technique - "I'm nonjudgmental in an interview. Out of an interview, there's a whole other side of me!" The goal is to disarm the guest so they speak freely, and for you as an interviewer to search for meaning. "my secret to interviewing: How do I find the common denominator that allows a person to know that I hear them, and that what they say means something to me?"
#3 Detailed preparation
Yesterday I listened to Oprah's interview with Steven Pressfield (if you haven't read his book "War of Art" I highly recommend it!.) Oprah's detailed preparation for the interview was clear. It was clear that she had been working to understand Pressfield's take on the concepts he discussed. Winfrey arrived ready with questions that would allow her to dig deeper into the ideas, and the level of detail was evident in her frequent references to quotes and page numbers. The perfect combination of big-picture thinking and detailed groundwork.
The "why," the empathy and the detailed prep all come together in the conversation. Oprah acts as a translator, helping her audience process the ideas her guest presents through her own lens. Oprah is not afraid to be an active participant in the conversation sharing stories, and ideas of her own to help deepen her audience's understanding and give them additional routes to access the information her guest presents. This is the art of the conversation interviewer: bringing her own stories and comments to the conversation to lead her audience to a better connection with the guest.
Read more about interviewing for podcasts, documentaries, testimonials and oral histories at Interview Lessons.