Oprah Winfrey may just be one of the best interviewers of all time.
Her recent interview with Prince Harry and Meghan Markle proves, once again, her amazing talent for making people open up, asking uncomfortable questions, and having tough conversations.
The fact that the CBS interview averaged more than 17 million viewers around the world and that the press worldwide had all kinds of comments about the show proves the masterpiece interview Oprah delivered.
Whether Meghan avenged the Royal family’s unwelcoming treatment towards her or whether Meghan was actually the Hollywood diva that broke the Royal family apart will be a question that will remain open to public interpretation.
Where there are no doubts, however, is that regardless of your views on Meghan and the Royal family, Oprah’s unique storytelling, curating, and interviewing talent is something that will never stop amazing the world.
How Oprah Leverages Her Star Reputation
Very few people have the celebrity access that Oprah possesses.
Throughout the years, Oprah has been able to make celebrities open up on interviews in an unthinkable way. Through her magical interviewing gifts, Oprah has enabled the public to better understand celebrities’ humane side. The world still remembers how Oprah got Tom Cruise to jump on a couch out of sheer excitement for his new relationship with Katie Holmes, how she influenced Kim Kardashian to open up and showcase to the world her relationship with Kanye West, and, of course, her wholehearted chat with President Barack Obama.
Oprah may have been one of the only people capable of securing what the New York Times called “one of the most anticipated, and most heavily spun, television interviews in recent memory.”
It wasn’t just the fact that Oprah is Prince Harry’s and Meghan’s neighbor in California, or that she was personally invited to their wedding, that made the couple trust her to share their story. It’s more than that. It’s Oprah’s authentic interest in how everything developed. It’s how much she can personally relate to the racism Meghan has been the victim of. It’s her unique capacity to authentically empathize.
Here are perhaps the most powerful lessons Oprah has taught us on having tough conversations – ones that come not only from people’s mind, but directly from their hearts.
1. Have Your Goals and Intentions Clear
Before facing an interview, Oprah not only has her personal goals in mind, but also makes sure that the interviewee’s intentions are also top-of-mind.
In her own words, Oprah has stated that “before I do any interview, I have a conversation with whoever I’m interviewing and ask, ’Tell me what your intention is, and I’ll tell you what my intention is, and we’ll see if we can align those two.”
Having clarity of intentions is not only vital for steering a clear conversation, but also for both parties to be satisfied with what has been shared.
As Oprah stated, “I don’t want you to finish the interview and at the end of the interview say, ‘I wish I had said…’”
2. Paint a Clear Perspective
At the beginning of her interview with Prince Harry and Meghan, Oprah clearly painted the perspective the conversation would be guided by. This is crucial when having honest and tough conversations.
“You don’t know what I’m going to ask, and no subject is off limits, and you are not getting paid for this interview. So, you ready?”
Those words were said even before the interview began. It sends a clear message: the conversation will be authentic, and we’ll let nature guide its course.
It also prepares both parties (and in this case the audience as well) for whatever could come to light during the interview. Both parties have each other’s permission to be vulnerable, to share their innermost thoughts, and explore boundaries that would otherwise feel invasive or delicate.
As a consequence, trust is built within both parties, boosting each other’s willingness to connect.
3. Be Your Most Authentic, Genuine Self
Having tough conversations involves expressing feelings that are sensitive, and oftentimes, suppressed. For Meghan, confessing her battle with depression and anxiety throughout her time as a member of the Royal family must have been hard, especially given how invasive the press had been.
During the interview, Oprah didn’t have a cheat sheet or a list of questions she wanted to cover. Throughout the interview, the conversation flowed naturally because Oprah wasn’t thinking focusing on what question to ask next. Instead, she was actively and empathetically listening to her story.
Having tough conversations requires both listening and speaking. Oprah took it to a whole new level. Her ability to truly listen has enabled her to reach a deep understanding and then help convey that message to the audience.
To master this art, Oprah has shared that she “practices this thing called mindfulness every day, which means really just staying present in the moment. It’s one of the most life-enhancing things I’ve ever done.”
4. Make them Feel Heard
There is nothing more empowering than feeling heard, noticed, and appreciated. And Oprah knows it.
As Brené Brown states, a lack of connection and empathy diminishes trust. Oprah’s empathetic but directional questions gave space for Meghan to openly share her hard-to-digest realities. Realties including her suicidal thoughts, the racist treatment she and her son Archie have been subject to in England, and the overall toxic relationship she had with the Royal family.
By making Meghan feel heard and validated, Oprah assured Meghan that her heart was in the right place and that she was genuinely invested in hearing her story.
Tough conversations, those that unleash our most guarded thoughts, demands this kind of trust and empathy.
5. Make Friends with Silence
Most people feel awkward when a moment of silence takes over a conversation. Oprah, on the other hand, has befriended silence to build momentum.
Silence often signals that someone is either unsure, uncomfortable, or hesitating about sharing more information.
Often, silence during tough conversations elicit people to break it with the first thing that comes to their mind.
Oprah has mastered how to make silence part of her storytelling. She doesn’t rush to cover any pause. Instead, she sits back and waits, giving the other person permission to explore their feelings.
6. Follow Up, Dig Deeper, Don’t Leave Room for Ambiguity
Throughout her interview with Prince Harry and Meghan, Oprah used simple, yet powerful follow up questions such as “Who?” “How so?” “Why?” “So let me get this right…” It was brilliant.
Her follow-up questions enabled Oprah to dig deeper into the heart of what was being shared. It enabled both her and the audience to have a clearer understanding. She didn’t leave room for open interpretation.
For instance, Oprah’s famous firm follow-up question “Were you silent or were you silenced?” made the drama in the story even more enticing.
Regardless of how clear the answer may be, Oprah stills goes a step further to avoid confusion. At one point in the interview, Meghan shared that she lost all her will to live. While most of us would assume that meant her depression took her to considering committing suicide, Oprah made sure no one could interpret something different. She directly asked Meghan whether she was “having suicidal thoughts.”
Oprah’s effective follow-up questions were also seen when Prince Harry joined the interview. When Prince Harry was sharing how them abandoning the Royal family caused issues with his relationship with his brother, Oprah made sure to have a clear perspective by mentioning “You didn’t tell me what the relationship is now…” To what Prince Harry responded, “The relationship is… spaced.”
Why Having Tough Conversations Matter
In the words of Brené Brown, “people are opting out of having tough conversations because they fear looking wrong – choosing our own comfort over hard conversations is the epitome of privilege.”
It’s time for us to have the courage to step out of our comfort zone and embrace tough conversations. They are vital for us to grow and become better, more authentic versions of ourselves. They are not easy, but they are worth it. Beyond the inner growth we can experience from having tough conversations, they allow us to build truthful and honest connections with people.
Conflict is a natural part of life. Conflicts teach us where there’s room for improvement and help us visualize a more perfect future.
By avoiding tough conversations, we are losing out on an opportunity to pave the way for making that future come true.