2 of the top game changer lessons I learned from Oprah

Libby Moore

Executive Coach, Inspirational Speaker, Adventurer and former Chief of Staff to Oprah Winfrey.

People always ask me what I learned working with Oprah for 11 years. It used to take me a moment to reply because I had learned SO MUCH, it was hard to break it down into one simple answer. After several years of practice, here are 2 of the most important things I learned:

Lesson #1: Stop trying to be “perfect” and simply do your BEST.

My first year in the job, it was action-packed days, with long hours, juggling extremely high responsibilities.

I was managing a big team of assistants, and we were handling, what felt like, a trillion “moving parts” in both her business life and personal life. It was my job to keep everything running smoothly, efficiently and in sync, (without “dropping any balls”).

I made a lot of mistakes in that first year. I heard myself say, many times, “I’m sorry. It won’t happen again.” (And, sometimes it DID happen again!) I was putting so much pressure on myself to get everything “perfectly right.” One time, while on the phone with Oprah, I blurted out in a sarcastic tone, “I’m sorry I’m not perfect.” She said, “Libby, I don’t expect you to be perfect, I expect you to do your best.”

That changed everything for me!

The impossible pursuit of “perfection” was stressing me out, and tripping me up. By giving myself permission to simply do my BEST – I could think clearer, focus better, and therefore do a much better job. It was a game changer!

Lesson #2: Have the COURAGE to speak the TRUTH, even if it means you might get fired.

Most of the time, Oprah and I were aligned and “in sync” in our thinking with regards to various things at work. When she would ask for my input on something business related, I would always carefully consider these 3 things:

  • What was in the best interest for her?
  • What was in the best interest of the company?
  • What was in the best interest of the brand?

In over a decade of working together, there were maybe four or five times where we STRONGLY disagreed with each other on very important issues and decisions.

In some of those circumstances, I had to dig down deep, and muster up a lot of COURAGE to stand in my truth, and stand behind what I believed to be the truth. In a few of those occasions, I was a “lone wolf” in the process. Translation: it felt super uncomfortable! But, I stood by my input. I would say to myself, “if I get fired because of it, then so be it, because I know in my gut, this is the right thing to do.” That courage to stand behind, what I believed to be true, and in the best interest of her/the company, is what laid the cement foundation of our solid relationship. You have to have COURAGE to stand in your truth, and expressing that truth is what lays the foundation for your character and your value to the company.

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