Cortney Stapleton, Chief Strategy & Business Officer at Highwire PR and former CEO of The Bliss Group, joins Taking the Lead to share the leadership philosophies that have shaped her career. From mentorship and defining leadership tenets to navigating doubt and leading through her agency’s acquisition, Stapleton offers a candid look at what it takes to lead with clarity, confidence, and purpose.

Here are excerpts from the full interview:

Who are the three leaders who’ve most influenced you, and why?

The first leader is John Bliss. John founded The Bliss Group in 1975. He was fair, he was honest, and he was kind. He was a show-don’t-tell leader. He was the first person in my career who really said, “Go do it. I’m not going to put anyone over you. I’m not going to limit your potential. I want you to just go and do.” I think he was the first person who saw my leadership potential and had confidence in me. That translated into the confidence I brought into leadership at a very young age.

The second person was Jerry Walsh, who was my first real boss in public relations. He taught me that age didn’t matter. If I knew the media and what was interesting, I always had something to say in the room, even in my early 20s. I embodied that in my leadership style going forward, which was go and do. You can do anything. It doesn’t matter how old you are.

And then the last person who influenced me was really a team. When I first became CEO, I launched with an executive leadership team, the first created at Bliss. It was those people I really credit for helping me become the leader I am. And of course, my longtime partner, Michael Roth, who really influenced me as a leader. I like to say he’s my coach and I’m his when it comes to leadership. Having somebody who’s completely honest with you and sees your flaws and your strengths is important.

What are the three tenets of leadership that have guided your career?

The first tenet is about giving people opportunity and seeing what they’ll do with it.

The second is about understanding your leadership gaps, your weaknesses as well as your strengths, being open about them, and surrounding yourself with leaders who can complement you and fill those gaps. You make each other better leaders together, and it creates a more complete leadership package. It’s probably one of the hardest things for leaders to accept and then actually do.

The third is always be learning and always be teaching. Everyone focuses on always learning, but it’s just as important to teach. You never truly master something until you teach it. You should always be teaching someone something and always be learning from others. When you open yourself to both sides equally, that’s when you become a great leader.

All leaders, if they’re being honest, have doubts. What was a moment when you had the deepest doubt about your leadership skills, and how did you get through it?

If I’m being really honest, I originally didn’t want to be the CEO of The Bliss Group. I was the owner and co-owned it with Michael Roth, but I didn’t feel like I was after CEO. To me, it always felt like a power play, and I wasn’t after power. I was after influence. I wanted to be influential in the team’s lives and the clients’ lives and focus on that.

I overcame that because I realized I was already doing the job. As John Bliss always said, “You get the title or the promotion when you’re doing the job above you.” I remember looking at Michael one day and he said, “You’re already the CEO, so why don’t you just take the title?” And I thought, “You’re right!”

It was important at that moment in the evolution of the agency to take the title, work with the executive leadership team, and embody that for Bliss. I’m really happy I did it and proud of the work we did.

The Bliss Group recently was acquired by Highwire. What are you doing as a leader to make this as smooth as possible and to reassure team members?

I’ve tried to be as transparent as possible with our teams, clients, and everyone. I’m a pretty transparent leader as it is, and I felt like we had to be in this situation. We built Bliss on being smart and kind, and I intend to bring that to Highwire.

When we started talking with Highwire about culture and values, there was a lot of alignment. We’d say something and they’d say, “Us too,” and vice versa. From the very first conversation, we talked deeply about culture, and that made both sides feel really good.

There are a lot of similarities in how both organizations operate. Both are meritocracies, both promote from within, and both focus on developing talent. This combination gives people more opportunity to grow, evolve, and reinvent. It was about growth, not consolidation. The cultural alignment was core to why we did this.

You’re a founding member of Exponent Women. What’s your counsel to newly minted women leaders to embrace their power?

Know what you’re good at. There’s a point in a leader’s journey where you have to focus on your highest and best. What’s the skill that’s unique to you? Own that, embody it, and know when to focus on it. Then you can shift into learning, teaching, and reinventing at other times.

Don’t shy away from your natural tendencies. People often think what got me here won’t get me there, but I’d argue it might, if you really lean into it.

And when you get feedback, work with it. Don’t take it as defeat. I always treated it as a challenge. I’d internalize it and turn it into grit. I wasn’t going to fail. That kind of internal grit is something every new leader needs to build and embody.

You started your career working with Vermont Department of Environmental Conservation and NYPIRG. What leadership lessons did you learn that you still tap today?

One of the biggest lessons I learned was about asking questions. I never want to be the smartest person in the room, but I do want to ask good, meaningful questions about where we’re going and why.

I also learned the importance of making connections. Being a connector, talking to people about what they’re doing, what challenges they’re facing, and understanding what matters to them is something I still carry with me as a leader.

What’s something surprising about you that we wouldn’t know from your LinkedIn profile or Highwire agency bio?

I’m a pretty big kid with my kids. I have a lot of fun with them. Whether it’s sports, Anime Con, Disney, museums, I’m in. I go with them, I dress up, and I support everything they’re into.

We take full advantage of being in New York City. We’re tourists on the weekends sometimes and have been since they were young. It’s probably a little different from my work persona, but I love it and I want them to have those memories.

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Ken Jacobs, PCC, CPC, ELI-MP, is a sought-after executive coach helping PR and communications leaders, agency owners, and senior executives lead with confidence, inspire their teams, and drive lasting business growth. As principal of Jacobs Consulting & Executive Coaching, he draws on more than 25 years in agency leadership. To the leaders who shape the PR world, Ken is a trusted partner in unlocking their full leadership potential. Connect with him at www.jacobscomm.com, [email protected], on LinkedIn, or on Instagram.