How to Lead with Authenticity

Libby Moore, former Chief of Staff to Oprah Winfrey, sat down with ASAP to share her advice on leadership and being authentic at work and in life.

Recorded at APC 2024 and produced by the American Society of Administrative Professionals - ASAP. Learn more and submit a listener question at asaporg.com/podcast.

Leah Warwick: Hi, everyone. I'm Leah Warwick, and you're listening to "The Admin Edge." Our guest today, Libby Moore, was a keynote speaker at APC 2024. Libby has worked as a personal assistant to Maury Povich, an executive assistant to Jann Wenner at Rolling Stone, and chief of staff to Oprah Winfrey. Now let's listen in to ASAP Advisory Board Member Nakia Whittaker-Woody talking with Libby about themes from her keynote on how to lead with authenticity in your life and career.

Nakia: Hi. I'm Nakia Whittaker-Woody and my guest today is Libby Moore, executive coach and former chief of staff to Oprah Winfrey. Welcome to the podcast, Libby.

Libby Moore: Thank you. It's so nice to be here with you, Nakita.

Nakia: I know. I'm so excited. When I heard that, I was like, hmm, interesting. Interesting.

00:01:00

What is the most significant lesson you learned as chief of staff to Oprah? 

Libby Moore: Yeah. The number one would be to be yourself, to be your authentic self with all people at all times, in all situations – to the best of your ability, I would add – is the number one most powerful thing you can do. Being yourself, being in your – as were talking about earlier, your authentic intelligence, the original, the OG AI: authentic intelligence.

Nakia: How did that shape your leadership style? And how can we, as administrative professionals, lead authentically in our own roles?

00:01:44                     

Libby Moore: Great question. I would say when I took that position I really was way in over my head. I had only managed one person in my whole life, which was a driver to Maury Povich, and maybe the driver to Jann Wenner. I had not managed anybody else. So I step into this role and I'm managing – I think it was three people when I started, and then it grew to five people, plus security, aviation team, house managers, and on and on and on. So I was way in over my head. But I asked a lot of questions. That was being authentic, not pretending like I knew everything, and really leaning into the team, who was excellent. I did that job for about 11 years because of an incredible team, who are really, really good at what they do – and better than me, by the way, smarter and better and more skilled than I was at that job. So leaning into the team, asking questions, saying, "I don't know." Or, "Angelique, you're really good at this. What about you do this?" So really delegating to people.

00:02:48

And being myself, just saying, "I don't know. I don't know what this is." 

Nakia: Yeah, having a great team is amazing.

Libby Moore: It's the only way to be successful.

Nakia: Okay, in leadership we all face challenges. How can we better understand and embrace the personal struggles as opportunities for authentic growth?

Libby Moore: Ooh, good question. In the coaching I do with people, every single – and tell me if I'm off base on this. I think this is the answer. This is what's coming up. When I coach people, we always start with the three deep breaths, slow exhales, as we just did, and I ask: What are the top three best things happening in your life right now, personal or professional? They tell me.

Number two: What are three things you're grateful for? As they pop in. Don't think about it. Whatever pops in, in the order that they come. And then number three: What are your top three challenges? They'll boom, boom, boom. They pop up like that, because you're not thinking it. It's just popping up. And then I have them look at those challenges. It's real. It's real life. That's a problem. That's a challenge. 

00:03:53

Now we're going to flip it over, look at it through a different lens, different perspective, and see: How is this here? This is here as an opportunity for you to heal something from your past, for you to grow, for you to expand, so take a deep breath, slow exhale. How could this be an opportunity for you? Boom. Pops up. And then we go into: What are three action steps to move toward that opportunity? 

Nakia: I like that. It's a play on the SWOT. I love that.

Libby Moore: Exactly.

Nakia: Okay, authenticity in leadership often requires vulnerability. As administrative professionals, how do you find the balance between being open and maintaining the professionalism? You can have that schmooze with your friend, but when it comes time to be at work, how do you find that balance?

00:04:44                     

Libby Moore: It's not black and white. It really isn't because I feel like, at 58, I grew up in an era where it was like: You do not bring anything to work. You do not talk about work. When I started working with Oprah at 34, her personal life is her work life, and her work life is her personal life, so it gave me space to be more myself. But having said that, I'm clear – I'm a professional – on what is okay to share with my team or coworkers, or her for that matter, when I was working with her, and what isn't okay, which is too much.

I really didn't share that much with her about my personal life. I mean, we worked together for 11 years. We traveled all the time. She knew a lot about my personal life, but I was very edited about what I shared and didn't share, and when I shared it. I think the vulnerability is huge, and it's essential to being a strong leader. 

Nakia: Yes, I definitely agree. I know myself, I self-advocate for myself and I tell my team immediately when we start working that I have ADHD and that I require a certain amount of things from them. That helps me be vulnerable, but it also gives them the opportunity to support me better so that I can support them better. So I definitely believe that finding the balance is important. I don't tell everybody on the way, but I do tell my team right away. And then, as I feel the need, I share it with everyone else.

00:06:11                     

Libby Moore: I love that. I want to say, a good friend of mine, who had a very high-level job at a big publishing house for years, she's dyslexic. She never told anyone. And then she started telling people and they were like, "Why didn't you just tell us?" And it took off so much pressure from her. And by the way, ADD – I know you said ADHD. ADD, I believe, should be rebranded into "attention to dynamic discoveries." We just need to learn how to manage all of those interesting discoveries coming in.

Nakia: Yes, yes, because there are a lot. [laughter]

Libby Moore: That's right.

Nakia: Okay, so we have a question from our viewers: "In situations where company culture doesn't fully align with your personal values, [how] do you stay authentic while still being effective?"

00:06:58                     

Libby Moore: Excellent question. Number one: The thing – when I was working at Harpo Productions, Oprah's company, and with her specifically, I didn't feel like there were company values that I was not in alignment with, but there were certainly things that would come up. Or she would ask for people's opinion: "What do you think about this," as it relates to a show or something else? And I would always give my honest answer. One time everybody was agreeing on one and I was saying something different, I thought: No, that is not in your best interest or the best interest of the company. And everyone was like, no, no, no, it is. Because it was about ratings. And I thought, this might get you great ratings, but it is not the right thing for you, Oprah Winfrey, to do, or this company, or this brand. It just isn't.

00:07:48

And I remember feeling like, she might fire me over this. But I thought, I don't care. I have to look at myself in the mirror and I have to be true to myself. And ultimately she appreciated that. That's all I'm going to say about that specific thing. But because I was honest and I always told her the truth, in particular, which I felt was in alignment with her best self, she appreciated that, and it made our relationship stronger. 

Nakia: Do you have any advice on how you would implement that in your role? So being vulnerable, but allowing yourself to have that boundary of my personal values versus the office?

Libby Moore: I would go into the deep breaths, slow exhales, always, to clear, get out of your head and your ego and your mind, which is going to give you 150,000 things. You go into the deep breaths, slow exhales, and ask yourself: What is the best thing for me to do in this situation? And it will pop up immediately. And if it doesn't come immediately, you wait until it does come. That's what I would do. You go internally into your gut, your intuition, higher consciousness, inner wisdom, and you access that through the deep breaths, slow exhales.

00:09:07                     

Nakia: That is a really great thing. So I want to say thank you very much for joining us on "The Admin Edge" today. And Libby, where can our listeners find you?

Libby Moore: Libbymoore.com is my website. It's easy-breezy.

Nakia: Love it.

Libby Moore: Thank you so much for having me. I appreciate it.

Nakia: Thank you. It was nice to meet you.

Libby Moore: Nice to meet you, too.

[music playing]

Leah Warwick: Thank you for listening to "The Admin Edge," produced by the American Society of Administrative Professionals, original music and audio editing by Warwick Productions, with video and audio production at our events by 5Tool Productions. If you like this podcast, please leave us a nice review, five stars, and subscribe. If you'd like to submit a listener question, you may do so on our website at ASAPorg.com/podcast.