Breaking Leadership Barriers with Stephanie Chung

In this episode, we sit down with Stephanie Chung, a trailblazing executive in the aviation industry, a leadership speaker, and the author of Ally Leadership: How to Lead People Who Are Not Like You. Stephanie’s leadership journey is one of resilience, adaptability, and breaking barriers, and in this conversation, she shares how her upbringing, career, and personal experiences shaped the leader she is today.

From growing up as a military brat and learning to navigate constant change to becoming an executive in private aviation—an industry where very few people looked like her—Stephanie’s insights are invaluable for leaders looking to grow in their own journey.

Growing Up as a Military Brat: Learning Adaptability

Stephanie’s father was a Master Sergeant in the U.S. Air Force, which meant moving every two years and constantly being the “new kid.” While challenging, this experience gave her an incredible gift—the ability to quickly adapt to new environments, build relationships, and embrace change.

I still think of myself as a professional new kid. When you’re always the new person, you learn how to read the room, understand different perspectives, and adapt your communication. That’s been my superpower in leadership.

This level of constant transition can prepare leaders for today’s fast-paced, ever-changing work environment, where adaptability is a crucial skill.

Takeaway: How can you embrace change in your leadership? What past experiences have helped you become more adaptable?

Breaking Barriers in Aviation: The Power of Representation

Stephanie knew she wanted to be in aviation from an early age, but the lack of representation made it hard to see what was possible.

Whenever I would see aviation depicted—TV, movies, magazines—if you were a man, you were a pilot. If you were a woman, you were a flight attendant. And none of them looked like me.

Despite this, she started her career loading luggage and parking planes at Boston Logan Airport before an executive saw her potential and encouraged her to move into sales. That moment changed everything, leading her to a successful career in private aviation, where she eventually became a top executive.

We don’t always see what’s possible for ourselves until someone else opens the door. Leaders have a responsibility to do that for others.

Takeaway: Who in your organization might need encouragement to step into a new opportunity?

The Influence of Military Culture on Leadership

Growing up surrounded by soldiers, Stephanie was shaped by the values of discipline, accountability, and excellence. She shared how those lessons directly influenced the way she leads today.

I grew up seeing cause and effect. In the military, if you mess up, it’s not just you—it impacts your whole unit. That shaped how I lead teams. We either win together or we lose together.

This mindset creates strong team cultures when leaders set high expectations and foster accountability. Leaders who build that sense of shared responsibility can break barriers and create teams that perform at a much higher level.

Takeaway: How does your leadership reflect a culture of accountability and shared success?

Overcoming Challenges and Finding Purpose

Stephanie also opened up about personal challenges that shifted her perspective on leadership. One of the most powerful moments in our conversation was when she reflected on her experience with breast cancer and the way it changed her outlook.

Going through something like that gives you a new level of clarity. You start asking, ‘Why am I here? What am I supposed to do with this life?’

You emerge from these challenges with an awakening—you want to extend your impact, help others, and use your leadership for something bigger. This moment in the conversation was a powerful reminder of why leadership is about more than just business—it’s about impact.

Takeaway: How has adversity shaped the way you lead? What impact do you want your leadership to have beyond the workplace?

Key Takeaways for Leaders

As you reflect on breaking barriers in your own life and leadership, here are a few key questions to consider with your team:

1. How has your background shaped your leadership style? Think about the lessons and experiences that have influenced the way you lead today.
2. Who around you needs encouragement or an opportunity to grow? Like Stephanie’s mentor saw something in her, great leaders create space for others to succeed.
3. How do you foster a culture of shared accountability? Strong teams win together and lose together—are you reinforcing that in your leadership?

Leadership is a journey—one shaped by experiences, challenges, and the people we meet along the way.