📖 Oprah Winfrey's superpower

How the talk show host and media mogul developed her ability to connect with others

Welcome to Origin Stories. In this newsletter, we review the stories of successful people to unpack the skills they cultivated before they turned 30 that prepared them for success.

This newsletter will provide you with the what (what skills set them apart), the how (how they developed these skills at a young age) and - most importantly - how you can develop these skills, too.

- JR

Our last post covered the story of Oprah Winfrey, a media mogul, actress, talk show host and television producer. She is best known for The Oprah Winfrey Show, the record-setting talk show that ran for 25 years. In 2011, Oprah launched her cable channel OWN. Her net worth is estimated by Forbes to be roughly $2.5 billion.

For Oprah's origin story, click here.

The superpower Oprah developed at an early age: empathy, her ability to connect with others.

Skill

Oprah's ability to connect with others is priceless. In an interview at Stanford, Oprah shared the secret of her success: Empathy. Compassion, a willingness to understand and connect. "The secret to that show, is that people could see themselves in me."

Empathy is often misunderstood and confused with sympathy, which is feeling compassion for somebody. But empathy is about putting yourself in someone else’s shoes and seeing things from their perspective.

Amy Blaschka, Forbes

Cultivating connection with others

Oprah is famous for her ability to quickly build rapport with her guests and audience. She does this by being true to herself and asking thoughtful and probing questions that draw out implications and feelings, fostering deeper connections.

"After conversing with everyone from homemakers and schoolteachers to corporate leaders and politicians, I know one thing for sure: Great communication begins with connection. What makes us different from one another is so much less important than what makes us alike—we all long for acceptance and significance. When we recognize those needs in ourselves, we can better understand them in others, and that's when we can set aside our judgments and just hear."

Applying This Skill

Oprah's ability may be priceless, but for anyone in business, a similar skill is worth millions. In her post What Oprah knows for sure about communicating, Oprah shares a story illustrating the power of communication in the business world.

"A few years back, my production team and I were interviewing a candidate for our staff. Once we got beyond the first few conversations, we began negotiating a salary—and each time we offered an amount, he countered with an even higher one. That seemed reasonable until, after about the fifth round, he asked for an exorbitant wage that far exceeded the market rate.

That was my cue to stop the negotiation and ask, "What do you really want?" This is what he told me: "I want you to want me at your company as much as I want to be there." I did—and once I assured him of that, it freed us to go back to negotiating a fair salary. I realized he was saying the same thing we're all saying to the people in our lives: "I want to know that you value me.""

Communication is like a dance. "One person takes a step forward, the other takes one back. Even one misstep can land both on the floor in a tangle of confusion. That's the perfect moment to rise to your feet and get clear about the next move—to gently say to the other dancer, "What do you really want here?"

At first, you might notice a little squirming, a lot of throat clearing, maybe some silence. But if you stay quiet long enough to get the real answer, I guarantee it will be some variation of the need that job candidate expressed to me that day."

Building your skill

Want to improve your connection with others? To acquire this power, Oprah says she doesn't just see herself in another person or try to walk in their shoes, but she practices empathy and compassion when she feels with them. When her heart beats with theirs.

Next time you're listening to a friend or relative tell a story, listen as if it's the only thing in the world. As if it's your story. Be curious. Ask questions. Feel the story as if it was your own.

By listening without judging and sharing your own problems with the other person, you can put them at ease. We're so quick to jump in with examples of our lives, in an effort to connect with others. But we don't need to. Listening and being interested in them is enough. Talk less. Listen more.

While listening, you don't have to think of what you'll say next. From Oprah: "Listening made me feel like an expert, a master strategist. But that description must come with a caveat. I didn't exert power over my companion or wrongly take something from her. If anything, I felt masterful because I was able to give more to her and to myself."

Want a concrete plan for this month? Try a listening campaign.

Listening Campaign

Want to cultivate your own ability? To acquire this power, Oprah says to try a listening campaign.

When with others, focus on their stories and opinions while staying quiet about your own. Ask questions that you're genuinely interested in. Rather than the dry "How's work", ask if their life is what they expected. Ask about the most interesting thing to happen to them in the last year. It doesn't matter what you ask, it's how and why you've asked it.

In early 2000s Oprah tried a listening campaign. "What if I stopped shooting off words like buckshot and started really listening? For a weekend, I decided to open my ears by closing my mouth—well, sort of."

I couldn't fathom getting through a day without saying something, so I opted for modified silence. I sent myself on a listening campaign. Given that I'd been doing a lot of talking at work, I was ready for the lessons a little listening could teach me.

Oprah acts as though her guests are the only people in the world. She maintains strong eye contact, faces towards the person, and leans into conversations. By giving the other person her complete attention, she makes them feel heard, and more importantly, it makes them feel like what they have to say is important. In return, it leads them to speak more candidly.

But keep it simple. This is the genius in Oprah's listening campaign. There isn't a huge list of rules. Just spend one weekend listening deeply to anyone you're speaking with. And see how much more enjoyable conversations become.

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