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

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

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.

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