3 Ways Oprah Showed Us All How To Have High-Stakes Conversations

Learn from the expert communicator herself how to ask uncomfortable questions and get the answers you need.
Oprah Winfrey interviews Prince Harry and Meghan Markle on CBS, March 7, 2021.
Photo by Harpo Productions/Joe Pugliese via Getty Images
Oprah Winfrey interviews Prince Harry and Meghan Markle on CBS, March 7, 2021.

On Sunday, the world was once again reminded that Oprah Winfrey is a gifted orator, master storyteller and expert interviewer. Over two hours of a CBS primetime special, Winfrey’s empathetic yet firm questions to Meghan Markle and Prince Harry about their exit from the British royal family prompted dramatic disclosures about the racist treatment Meghan and her son Archie faced in the U.K. and the toxic relationships between members of the royal family.

You may not be a media mogul who honed her skills over more than 5,000 episodes of a daytime talk show, but there will likely come a time in your job or your life where you will need to have a high-stakes conversation and ask uncomfortable questions.

Here are some techniques just demonstrated by the expert herself:

1. To have a good conversation about hard topics, find areas of alignment.

On Monday’s CBS This Morning show, Winfrey was asked why the Duke and Duchess of Sussex agreed to be interviewed by her when they knew it was unlikely to make their relationship with the British royal family any easier.

“Before I do any interview, I have a conversation with whoever I’m interviewing and ask, ‘Tell me what your intention is, and I will tell you what my intention is, and let’s see if we can align those two,’” Winfrey said. “I don’t want you to finish an interview and at the end of the interview, you say, ‘I wish I had said ... ’”

In other words, Winfrey doesn’t need a “gotcha” moment in which she springs a question on a participant who is not willing to answer in order to have an effective conversation. She does it by seeing where interests intersect and focusing her questions along those paths.

When you are talking with someone and have an eye for a desired outcome, see where your goals and theirs align.

2. The root of conflict is not feeling heard. Give people your full attention when talking.

Winfrey said last year that she has interviewed 37,000 people, and from that experience, she has learned that, above all else, people want to know they are being heard. “I can tell you, in your daily encounters, in your kitchen, in your conference rooms, in your work, in all of your relationships,” Winfrey said, “that is what every person you encounter is looking to know. ‘Did you see me? Do you hear me?’ And every argument is about that.”

Winfrey has said she validates that concern by practicing meditation and working to stay present during her conversations. During her interview with Meghan, viewers could see Winfrey validating the Duchess’ experiences and giving her the power of her full attention.

At one point, when Meghan said concerns had been raised about the possible color of her future child’s skin, Winfrey let out an incredulous and purposeful “What?!?” that conveyed the weight of what Meghan had just revealed. Without rushing or interrupting, Winfrey then asked: “Who is having that conversation with you? ... What?”

She knows the power of pausing, and letting the moment build.

By showing her empathy and her incredulity, Winfrey let the viewer know that this is something that deserves their full attention, too. Doing this with others shows you are an empathetic listener who will give their sensitive story the attention it deserves.

3. If an answer is unsatisfactory, don’t be afraid to follow up.

Throughout the interview, Winfrey asked hard questions of the Sussexes. When they did not fully explain an answer to her satisfaction, Winfrey asked it again, often by reframing the question or asking a follow-up such as, “How so?”

When Meghan explained that she had always advocated for women to use their voices but then she herself was silent, Winfrey followed up by asking if she was “silent” or “silenced” after her marriage to Harry. Meghan then clarified: “The latter.”

When Winfrey first asked Harry to share what was said about his son’s skin tone, he said, “That conversation, I’m never going to share,” but later Winfrey got him to clarify it was centered on the question, “What will the kids look like?” In her appearance on CBS Monday morning, Winfrey clarified that she followed up again off-camera and learned the person who brought up the topic was neither Queen Elizabeth nor her husband, Prince Philip.

Winfrey’s firm persistence is what makes her one of the greatest celebrity interviewers of all time. She knows that to ask a question, you have to keep up with what is and is not being said, and be unafraid to circle back and call it out. You may not be interviewing the Duke and Duchess of Sussex on primetime TV, but the ability to be direct about wanting a clarification is a skill everyone can benefit from.

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