The GOATs of Interview: How Oprah Winfrey and Howard Stern Get People to Open Up

Interviewing is one of the most effective ways to get to know something about someone in a formal setting. The script is simple: question and answer. It seems straightforward: take a skilled interviewer, ask the right questions, follow intriguing conversational leads, and facilitate an insightful conversation.

Leading an interview is both a dance and a balancing act, and in thinking about what makes for a truly great interview, two of the greatest help us understand how to get the most out of one’s interview guests. Long-time television host, actress, and producer Oprah Winfrey and long-term radio host and self-appointed “king of all media” Howard Stern are arguably better than anyone at extracting information from guests using very different techniques. While the two have seemingly opposite styles and delivery approaches, both share the qualities of great conversationalists. So, what makes them so effective?

Oprah Wants You to Feel Human.

Oprah Winfrey makes her subjects, rather than her questions, her focal point as she digs deep at emotional and at times gut-wrenching topics. According to Insider, the one question Oprah has asked each of her over 70,000 guests she’s interviewed prior to getting into the meat of the discussion is “What is your intention?”

The power of such a simple question was seen in the backlash faced by A Million Little Pieces author James Frey. Frey wrote a purported autobiography promoted on Oprah’s beloved book club, and it was later discovered that Frey’s accounts of his life-long struggle with alcoholism were made up. Oprah invited him onto his show and confronted his insincerity, never allowing him to falter or change the subject – making for not only great television, but a fantastic interview.

Oprah was relentless. She went straight into the story behind Frey’s false book, citing that she does not know what is true from what is false, providing him with a platform to explain himself. Oprah remained authentic with how she felt, telling viewers that she was “Standing here on behalf of the reader who is pissed [off].” She said that during her career, she’s always tried to “maintain a position of non-judgment, and being able to find a thread of light a way in, to see that person as a human being, and look at them with some sense of compassion.” While she certainly did not give this grace to James Frey, her authenticity is what makes her so exceptional at what she does.

When she covered the prevalence of racism in Georgia’s Forsyth County, just six months into the Oprah Winfrey Show, she asked outwardly-racist people why they hold their views. She riled up Tom Cruise so much that his infamous appearance has been a meme for quite some time. In 1999, she was the first to interview Whitney Houston in seven years and asked “What do you love that people say about you?” – a question that is sure to open any interview subject up and make them feel more comfortable speaking about themselves and their experiences.

Howard Stern Wants You in the Zone.

Stern is often criticized for going places that interviewers – for the most part –  don’t because they seem taboo. He’s been pegged as uncouth, crossing the line, and sometimes gross. Anyone who has listened to his show sees these characteristics in action – they’re central to his interviewing technique. On ABC’s 20/20 in May of 1991, when reporter John Stossel told Stern “People despise you,” Stern replied, “What I do is out there, but I know it kicks ass when I get on that radio and it makes people laugh.” His stream-of-consciousness interview style allows his guests to really open up and reveal things that they normally might not broadcast. He prodded Madonna to reveal her relationship with Tupac Shakur. He created the atmosphere that enabled Paul McCartney to definitively blame the split of the Beatles on John Lennon. Describing to ABC’s Stossel what makes good radio, he says “…there’s something great about that – tension – and it’s real.”

Stern is also exceptional at meeting people on their level and asking questions in such a way that shows he’s a conversationalist, rather than an interviewer. He told Katie Couric how he does it: like Oprah, one element to Stern’s style is his ability to make people feel comfortable enough to “slip into this sort of hypnotic kind of experience right where we really think we’re alone…and I’m naturally curious I mean I am fast first of all you look fantastic…Like what are you doing to look so good…” See what happened there?

Great Interviewers Make Us Feel Part of the Conversation.

If there’s one thing to learn from both expert interviewers, it’s that you must forge a connection with whomever you’re speaking to. If your subjects don’t feel like they’re being heard, or if the interview comes off as transactional, the conversation that unfolds will be inauthentic and forced. Take a page out of Winfrey’s and Stern’s books during your next interview and truly connect with your interview subjects to get the most out of the conversation.

 

This article was written by Avenue Group Content Strategist Chelsea Catherman.