The Human Part That Can't Be Automated: On Leadership, Connection, and Showing Up

Join Molly Baker for a conversation on what it really means to lead, why vulnerability is the skill most people spend years avoiding, and how a single, terrifying moment changed the way this week's guest thinks about the relationship between work and life. She shares how a background in theater and two decades of running organizations led her to build a leadership development company helping people bring more of themselves into how they lead. Together, they explore why leadership is a verb not a title, how to read a room in under 30 minutes, and why the experiences that shaped us outside of work might be the most powerful tools we have inside of it.

MB (Molly Baker): Without telling us who you are, what is top of mind for you professionally right now?

CC (Christine Courtney): I just came from somewhere. I won't say where, but I will say I'm amazed at how boring and unconnected work has become at so many places. COVID happened, and all of a sudden everybody went to their corners and got on Zoom. Then we came back to work, or maybe we didn't, we're still remote. But either way, we have somehow not evolved to the next phase of work. You see people come to a building, but they still all go to their separate corners, go on meetings, and everybody's just head down in their phones. So I find that top of mind right now.

MB: How does that change? What do you think needs to happen?

CC: Everyone's focused so much on AI as being the next revolution in work, and I actually think it is. But it is not how we are going to evolve. We as humans still have to do the work of evolving, and that is still going to be human to human. We'll use AI as a great tool, but how are we making it so that we connect more? That we actually bring so much of what makes us fun and unique into all parts of our life.

MB: Brag about yourself. What are you really good at?

CC: I think I'm good at discerning situations. Going into a room and reading it pretty quickly. Reading people pretty quickly, figuring out what's going on with them without a lot of words from them. When I was little, if I would come home from school complaining about a girl at school, my mother would play this game with me where she would say, well, what do you think they're thinking right now? I was so frustrated at first. And then I started to do it. So now I blame her, because I really do go very quickly to what is somebody thinking, what's going on for them. Which can be very annoying when I do it with my daughter or with my staff. But it does help me to very quickly move to, wait a minute, what's going on with somebody else here? And I think I also have a lot of energy, so I'm good at energizing a room pretty quickly.

MB: How do you read people quickly? Are you watching body language? What are the tells?

CC: Because I've been doing it so long, it's really hard to break it down. But I think one is I'm really good at watching and listening to people. I can go in and work with a bunch of folks and pretty easily have a real good sense of who they are. I do think it is body language. But I also key in very quickly to what lights somebody up. If I see a strong reaction one way or another, I pretty much can feel that and go, okay, we're going in there, like a sonar missile.

MB: What do you think has been the most pivotal moment in your career?

CC: I might be in it right now, and I think it's really hard to know when you're in a pivotal moment when it's happening. But I'll share what I've always thought it to be. About 15 years ago, my daughter and my mother were in a pretty bad accident. I was at work as I always was. My mother picked my daughter up from pre-K, she was almost four, and they got hit by a school bus. They're fine now. But I got a call at work from my mom in the middle of the street in Brooklyn, screaming. I could hear my daughter screaming. I was weirdly calmed by it because I knew she was alive.

She was crushed underneath the wheel of the bus for a little while until they reversed it. She was relatively fine in a few weeks, and now she's a hundred percent fine. But in those moments, you think everything is about to change and life will never be the same.

What was interesting is that before that moment, everything for me was, here's my work life and here's my home life. I was good at both, and the two never really met. But when I was at the hospital, who showed up more than anyone I ever expected, besides my husband, was my work friends and colleagues. I got the most amazing cards. They immediately came with clothes, makeup, food. They made things for my daughter. Every day there was somebody there. And I thought to myself, what am I doing spending this life so separate, when in fact these are the people that are defining who I am and what I go through? From that day, I started to look at things very differently. These are who we spend our days with. And when it comes down to it, they're also the people that showed up in tragedy. So I started to think, I need to blend these two lives a little bit more.

Since then, I've worked with people for over 20 years. We've grown up together. We used to go out in our twenties and now we've seen each other through children, colleges, divorces, illnesses, deaths. How wonderful to have that experience.

MB: Has that shaped how you've built your business?

CC: Yes. I'm very committed to the folks I've worked with. And the reality is, the more people I talk to, while they may not have had a dramatic experience, at the end of the day we spend more than eight hours a day with each other. What are we doing if we're not building relationships?

MB: How do you define leadership today?

CC: It's such a loaded word. When I started working, we ran a lot of programs with students. And whenever we said that word, the examples were always Martin Luther King or Abraham Lincoln, people that feel so foreign to us. Or there's a lot of judgment around it, like, I don't want to be that because a leader is this in my mind.

So I think it's about defining it as a verb. That's why I like to say, how are you stepping into your leadership? Because it makes it about you, not just about how a leader is supposed to be. How are you literally stepping in? How are you going, okay, let me be a little courageous here and use more of my voice, more of my creativity, more of my ideas? Leadership should be more verb and less like a specific person.

MB: What relationship has been most impactful on you professionally?

CC: When I started working, I would've said the kids we serve. Then when I stepped out of classrooms and was running businesses, I thought it was the people I worked with. They were my new kids. And then I had actual kids, and then it became the kids. And now that my kids are pretending to be adults, I appreciate the relationships in my life that allow me to act like a kid too, with my friends.

But I think overall, the one relationship that has stayed the course of time by choice is the one with my husband. My kids are now in college and are less a part of our daily life, which is such a change. You look at your husband and go, oh right, we didn't just get married to have kids. We got married later in life and had kids pretty much right away. So now we're redefining our roles. I'm loving this new, handsomer, more silver husband I have. And enjoying, oh, this is actually the long-term relationship of my life. When you have little kids, they become the priority for both of you. So this is kind of a new thing I'm really enjoying.

MB: Tell us who you are and what you do.

CC: I'm Christine Courtney and I run a leadership development company that goes into businesses and helps create more spark in people's lives and businesses. Energizes what's happening, makes people work together, redefines leadership, helps people step up and step in, and know how to bring more fun and meaningful connection into their work.

MB: What kinds of things do you do?

CC: Today I just came from doing leadership and management training for brand new leaders getting their first direct reports at a pretty big company in the FinTech world. I also do offsites for companies and speaking engagements with CEOs around how to supercharge the performance of their people.

I have a book coming out in the fall. The idea is that we all have these experiences we love. For you, it might have been running or sports. For me it was theater. But there are these seven core things that most people do some version of. And if we as leaders know this about everyone on our team, we can use those things to supercharge a meeting, engage performance, and see more potential in people.

I had a new leader I was working with who said, I'm not the direct manager of these guys, but my boss wants me to influence them. How do I do it if I'm not their boss? So I asked him, did you play hockey growing up? And he lit up immediately. I said, you were a captain, right? Same thing here. You can't decide if he gets a raise, but you can say, hey, why are you late? Or how can I help you? And I saw it click. That thing he'd been struggling with immediately made sense because I was talking his vocabulary. If we investigate a little more and find out those core experiences, we can actually supercharge performance and see more potential in people.

MB: What led you to start this company?

CC: I think it's the perfect version of all the things I've done my whole life. I was an actor for years, and then I became a teaching artist, doing work in the most under-resourced schools in Philadelphia and New York. From that, I started running that company, which is called the Leadership Program. I learned how to be a boss and a leader from scratch, through experience, and by messing up a billion times.

Then I thought, I need to try this with other businesses besides my own. We started getting work from teachers and principals, and they loved the workshops and started telling everyone they knew. That triad of things, understanding how the brain works, the performance and energy aspect, and having actually managed people ourselves, made me realize I was supposed to have been doing this my whole life.

MB: What do you find to be the most challenging part about helping others grow in their leadership?

CC: There is a real earnestness in people who want to be good leaders. They're curious, conscientious, driven. But what's magical or special about you as a person often comes with a lot of vulnerability and awkwardness that people don't want to share.

For me, it took a while to realize I wanted to be polished and perfect for way too long. And I see that in a lot of the folks I work with. I just want to say, if you can relax and be more of you, you're actually going to be great. I find that if I can get folks to loosen up and enjoy themselves, more of who they actually are comes out. And that's where you see their real leadership.

MB: Leadership is so personal. You can't just master a toolkit and call it done.

CC: You're so right. You have to be willing to do that work. And I can't tell you how many places I work with where people say, can we just get to the part where you tell me how to be a good boss? And I'm like, uh-oh. That's not really how it works. So many leaders don't realize that's the part that comes with it. It's truly humbling. Not fake humbling. When people win an award and say, I'm humbled by this. No, you're not. You're proud. Just say you're proud. Humbling is when you mess up and learn from it.

MB: How do you help someone identify what they're really good at?

CC: Some of it is just listening to them talk and hearing what they put forward. But I also use an assessment called the Six Types of Working Genius, which I love because it's quick, about ten minutes, and gives people ways in which they light up at work related to core skills. When people recognize, oh yeah, I'm good at invention, I'm good at coming up with ideas, or I'm really good at tenacity, give me the ball and let me take it across the finish line, it gives them freedom to be open and honest about that. It's kind of like your opening question of brag about yourself. When someone is able to do that, you go, great. Let's do more of that.

MB: If someone is stepping into a leadership role for the first time, what work needs to happen first?

CC: I think it is about looking at yourself first. And I don't think many people do it. Leadership is in relationship, so you can only practice alone so much. If you don't have a direct report yet, start developing more influence. Ask yourself, can I practice my leadership by having more influence on the people around me? Can I ask to lead a meeting? Even at home, if I have little kids, am I thinking about dinner time as a leadership moment, not just something to get through? The more we practice in relationship, in our everyday relationships, the more that will serve us when we have a much bigger team to lead.

MB: What's one thing you wish you knew earlier in your career?

CC: I wish I knew the power of vulnerability. For years I was trying really hard to be perfect. One year I went to a conference and a lot of people were getting up on stage, and there was this tension of, I want you to realize how good I am, here's the research. And then this guy got up, Jeffrey Canada, who started the Harlem Children's Zone. So accomplished, really changing the world. And he gets up there and tells everybody all his mistakes. Here's everything I messed up on. And everyone was laughing and relating. I loved him and his work more than any of the other speakers.

So I made a decision. Every time I get up in front of my company or anyone else, I'm going to share a mistake or something I don't do well. And it was not easy. But the tenor of my all hands meetings changed immediately. I would get so much more from those moments where I said, I don't know, guys, this is where I'm struggling right now. It was such a difference.

MB: Did you think at 21 you'd be doing what you're doing now?

CC: Never. I was going to be an actor. I went to a very big high school in Texas, over 1,500 in my graduating class. I was the theater queen of that department. People asked where I was going to college and I was going to New York, to Tisch at NYU. That was all I had planned. No other schools, no backup.

My NYU letter came and it said, call us. No one else had gotten a letter like that. So I left class, went to the payphone in the hallway, gathered all my coins, and called NYU from school. They said, you're great, but we'd like to put you in our school of teaching and nursing. I was furious. I said absolutely not and hung up. And had no other plan.

Sometime soon after, a man came from a school in Philadelphia called the University of the Arts. My theater teacher asked me to give him a tour. He said, why don't you audition for us, even today after school if you want? I thought, what else am I going to do? So I did, and thank God I got in. I went to the University of the Arts in Philly and I loved it.

But I think back to that version of me, so indignant that I would not be a teacher. And that's exactly what I do now. That person at NYU saw in me who I am now, when I wasn't ready to see it yet. Sometimes we know it about someone before they know it themselves. You just have to wait for them to get there.

Find Christine on Linkedin or visit the The Leadership Program website!

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