Trust your instincts, master the skills: Career advice from Oprah Winfrey’s former Chief of Staff

Supporting Oprah required absolute discretion and timing. How did you decide when to speak up—and when silence was the more strategic option?

When I was paying attention, listening to my gut instincts, and ‘reading the room,’ the best timing was very clear. After working together for a certain amount of time I learned her natural rhythms, making the requirements in my role easier to navigate. If you are not sure, take three deep breaths and slow exhales and internally ask yourself the question, “is now a good time?” The answer will come immediately. Go with that.

As EA roles become more senior, what technical or operational skills should EAs be prioritising today to stay relevant?

The obvious answer is that you need a strong understanding and use of tech, including AI. Equally important is accessing what I refer to as the original AI – your Authentic Intelligence. The more you lead from your ‘higher consciousness’, the more you will stand out in this ever-increasing artificial world.

Many EAs are now managing projects, stakeholders and budgets. What skills helped you transition from a support role to a true operational partner?

1. Honesty. I was always forthcoming with my opinions and insights, even if they went against those of the Leadership Team.
2. Delegate. Delegate. Delegate.
3. Listen to your gut instinct, your intuition. It will never steer you wrong.
4. Build strong relationships and be an excellent listener and communicator.

How can EAs add more value through how they filter, frame and present information to leaders?

You have to be very discerning about what information to share, and how to share it. One of my filters was; Is this in Oprah’s best interest, is it in the best interest of the company and is it in the best interest of the brand? Stick to the facts, and keep your emotions out of it.

The Golden Rule: It’s not what you say, but how you say it.

For EAs aspiring to Chief of Staff or leadership-adjacent roles, what capabilities make the biggest difference?

Speak up and share creative solutions to existing problems or challenges. Bring your positive attitude and vibe into the office, people want to be around that energy! Be an excellent listener, and be kind to
people. Don’t become a ‘corporate speak-robot.’ Be yourself, and bring your unique gifts and visionary ideas to the table.

For more senior EA leadership lessons, you can find Libby on linkedin.com/in/libby-moore