How to Win in Business

Oprah succeeded thanks to master communication skills—here are 10 tips to improve yours

Oprah Winfrey
Photo by Jemal Countess

Being able to hold a meaningful dialogue with a friend, colleague, boss or potential business partner is an invaluable talent and one which most people don't spend much time cultivating, says Celeste Headlee, a public radio broadcaster, in her wildly popular TED Talk.

"I came to realize that conversational competence might be the single most overlooked skill we fail to teach," says Headlee.

"Kids spend hours each day engaging with ideas and each other through screens, but rarely do they have an opportunity to hone their interpersonal communications skills. It might sound like a funny question, but we have to ask ourselves: Is there any 21st-century skill more important than being able to sustain coherent, confident conversation?"

According to New York Times bestselling author Cheryl Strayed, that is the genius of billionaire media mogul Oprah Winfrey: She has never lost her passion for listening to and learning from people.

When Winfrey picked Strayed's bestselling memoir "Wild" for her eponymous book club, she catapulted the author to mainstream success. And Strayed was impressed by the mogul's communication skills when they met.

"The thing that struck me — and this is why Oprah is successful — the look on her face and what I could see in her eyes is her vulnerability," Strayed told author Tim Ferriss in Austin at the South by Southwest Conferences and Festivals.

"I was meeting Oprah and I wanted her to like me. And Oprah was meeting me and she wanted me to like her. It wasn't like meeting the queen, even though, for the record, she is a queen, but she didn't act like one. She was still this incredibly humble human who was really looking to have an authentic interaction with me and I thought, this is what has driven her success."

Cheryl Strayed and Tim Ferriss speaking at SXSW in Austin.
Photo by Jim Bennett

"The thing that makes her get up and do that work that she does every day is that genuine desire to connect with people and be vulnerable and to be open to what is going to happen next," says Strayed. "And that kind of curiosity has driven her to these great heights.

"I think that some people, they forget that thing that got them to where they are. And to me, the mark of success is staying open in that whole way."

Some people, they forget that thing that got them to where they are. To me, the mark of success is staying open.
Cheryl Strayed
New York Times bestselling author

While the following 10 tips, which Headlee lays out in her TED Talk, won't necessarily turn you into the next Oprah, they will help you become a better communicator.

1. Don't multitask. "If you want to get out of the conversation, get out of the conversation, but don't be half in it and half out of it," says Headlee.

2. Don't pontificate. A conversation isn't a forum where you should expect to express your opinion unchallenged.

3. Use open-ended questions. A question that can be answered with "yes" or "no" will be.

4. Go with the flow. Don't force a conversation to go where you expected it to. Adapt.

5. It's okay to say you don't know. Don't pretend you're an expert when you're not.

6. Don't equate your experience with the other person's. "If they're talking about having lost a family member, don't start talking about the time you lost a family member. If they're talking about the trouble they're having at work, don't tell them about how much you hate your job," says Headlee. "It's not the same. It is never the same. All experiences are individual. And, more importantly, it is not about you. You don't need to take that moment to prove how amazing you are or how much you've suffered."

7. Don't repeat yourself. "It's really boring," says Headlee.

8. Don't get lost in the details. People often don't care.

9. Listen. "Listen. I cannot tell you how many really important people have said that listening is perhaps the most, the number one most important skill that you could develop," says Headlee. "Buddha said, and I'm paraphrasing, 'If your mouth is open, you're not learning.' And Calvin Coolidge said, 'No man ever listened his way out of a job.'"

10. Be brief. A good conversation doesn't have to last all day.

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