What It Was Like to Work for Oprah: The Biggest Business Lessons Learned

From my first day walking into O, Magazine, it was clear that the space and ambiance was special. We ran the business in the Hearst Tower, and something about the energy and the office felt welcoming to everyone—regardless of status or income within the company.

When I worked at the company from 2007 to 2010, people seemed excited to be a part of what Oprah created. My colleagues were also the best in the business at what they did. Everywhere I turned, I had the smartest people working on a part to make the whole machine go forward.

During my time with Oprah, I learned to stay focused, believe in what you’re selling, show appreciation for your team, let the experts be the experts, and trust my gut.

Don’t be a fan, be focused

Oprah can attract the best to her team. Having worked in the business department, I was exposed to almost everything Oprah touched in our office, including editorial, marketing, advertising, sales and, of course, my team of two business deals coordinating with advertisers and brand partners.

I knew right away that there were intentions in who was being hired. We were excited to be part of Oprah’s team, but we weren’t fans.

To work for Oprah, you had to work. Be aware that you were part of the team inspiring the world with life-changing messages, but it was not your position to get so involved in working for an influential person that you couldn’t do your job. I learned from Oprah that to work for someone like her, be great, but don’t be a fan.

Surround yourself with the best and believe in what you are selling

Oprah was and still is about her business. She surrounds herself with people who protect her. I saw firsthand how anyone who was more concerned about how often they were in the office or when they would be seen would not make it to the final rounds of hiring.

Looking back, it’s crazy that people would ask that in an interview. Oprah taught me that you have to believe in what you’re selling, but not at the expense of letting star power cloud your judgment and skills.

Many of those who worked for Oprah made sacrifices, and along the way, she made us aware that she knew it. Once, I sacrificed Mother’s Day, my day off, to do a fundraising walk for the magazine. I took my mom with me and her positive reaction to my work made me realize that my work was worth the sacrifice.

Show appreciation for your team with thoughtful gestures

Oprah recognized each of our talents throughout the year with thoughtful gestures and gifts for the team. I remember walking into the office and seeing an iPod on my desk. To think about it, every Apple product I owned back then was a gift from O.

In the case of the iPod, everyone had gotten one because of a big quarter that year.

Oprah often left a token of appreciation at our workstation without making a big announcement. Even though I had access to a lot, I was still shocked when the gifts left my desk. These thoughtful gestures motivated me and made me realize that one day when I have my own company, I will do the same.

At the end of every year, we would have a holiday party. We would get a bonus every year I was there. It was a week’s salary from her own money. None of Hearst’s other publications ever received such a sweeping gesture, and I knew that because we were the envy of the media business to have such a giving and high-level boss.

Oh, Oprah Magazine was my first job in the business. Oprah set the tone for giving and I learned to keep doing the same no matter what. Now I live my life in service.

Let the experts be the experts

After three years working for Oprah, one of the biggest things I learned about running a business and bringing people together is to let people you trust to be experts be experts.

I was honored to travel with Oprah around the country every year. Our experts, who you would see on her show and read about in the magazine, would come to our events to inspire, connect and spread to our loyal fans. Dr. Oz, Suze Orman, Dr. Phil, Nate Berkus, Marianne Williamson, Gayle King and many others made the dreams of so many fans come true.

In this selfish me culture in the entertainment industry, and I would say in America in general, it’s rare when you’re a celebrity and a brand to lift others up. Oprah did this perfectly.

She pushed the experts forward and celebrated their findings on various topics for her and the audience. To me, that was genius. Let the experts be the experts. No one knows everything, and seeing her curiosity and ability to let others shine made me realize how special it was to work for her.

Trust your gut

Oprah had and still can elevate experts and allow them to be independent stars. She trusts her gut, which she is publicly open about. I still carry this lesson with me: to lift others up and not worry about their star.

I learned a lot working on the Oprah Empire. I’ve been lucky enough to check out people still in Oprah’s orbit. Relationships are everything to me and my media agency. I smile, realizing that I can trust Oprah for most of how I run my business. Because of her, I’ve been able to live some of my wildest dreams.

Boodie runs ConnectUp Media Agency, advising and managing influencers, royals, wealthy families, non-profits and brands on systemic impact, business strategy, events and partnerships.

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