Stephanie's Aviation Origins and Career Rise

On the latest episode of The Leadership Habit Podcast, Jenn DeWall sat down with aviation executive, trailblazer, and author Stephanie Chung to discuss one of the biggest challenges leaders face today: how to lead people who are not like them.

Stephanie is the author of the new book Ally Leadership: How to Lead People Who Are Not Like You, which provides a practical framework for leaders who want to get the best results from diverse teams. In this episode, she shares her philosophy of Ally Leadership and explains why learning how to lead people across differences is not just about diversity, equity, and inclusion—it is about return on investment.

Meet Stephanie Chung

Stephanie Chung began her aviation career working at Boston Logan Airport, parking planes and handling luggage. From there, she rose through the ranks, becoming a top sales executive, then moving into private aviation, where she eventually sold and oversaw the sales of private jets.

Her career milestones include becoming the first Black person in U.S. history to lead a major private aviation company as President of JetSuite. She later became the founding Chief Growth Officer at Wheels Up, helping take the company public—the first private jet company in the United States to do so. Today, she is an international bestselling author, keynote speaker, board member, and coach to Fortune 500 executives.

Stephanie has also been named to the Ebony Power 100 list and recognized as one of the top 500 CEOs by the respected consultancy YPO. Her journey reflects not only professional success but also resilience, courage, and a commitment to helping leaders everywhere learn how to lead people across differences through the practice of Ally Leadership.

Why Leading People Who Are Not Like You Matters

Modern workplaces are changing faster than ever. Stephanie explains that today’s leaders face challenges never seen before. “If you are a leader worth your salt, your job is to make sure that you get the best people in the best position to get the best result. That’s the job of a leader.”

What makes that more challenging now is the sheer range of diversity within the workforce. As Stephanie describes, six generations are now working side by side—from Boomers to Gen Z. Gender dynamics have shifted, and ethnic and cultural diversity is increasing. Organizations are more aware of the contributions from LGBTQ+ professionals and neurodiverse employees.

This variety of backgrounds and perspectives can lead to misunderstandings if leaders rely on a one-size-fits-all approach. But when leaders embrace differences, the benefits are measurable. “Diverse teams are 35% more productive, diverse teams have a 70%… more likely to actually be more innovative, and diverse teams are 36% more profitable.”

The takeaway is clear: learning how to lead people who are not like you is no longer optional. It is a requirement for leaders who want to deliver results.

The Ally Framework

At the heart of Stephanie’s philosophy is her book Ally Leadership: How to Lead People Who Are Not Like You. She defines Ally Leadership as the ability to create trust, curiosity, and action in diverse environments.

The ALLY framework is simple but powerful:

• Ask – Leaders must ask thoughtful questions and avoid assuming they know what their team needs.
• Listen – Active listening is more than waiting for your turn to speak. It requires paying attention to what is said and what is not said.
• Learn – By asking and listening, leaders naturally learn. This learning helps them adapt and grow.
• You Take Action – Learning without action accomplishes nothing. Ally leaders follow through and implement change.

“That’s the secret sauce here to getting the result out of your people”, Stephanie explained.

By practicing Ally Leadership, leaders build stronger relationships, create safe environments for contribution, and encourage teams to innovate.

The EARN System

In addition to the ALLY framework, Stephanie developed the EARN system, a step-by-step approach to building high-performing teams:

• Establish an environment of psychological safety.
• Assure alignment so everyone knows how they contribute to company success.
• Rally the troops around a vision, not just a to-do list.
• Navigate the future by guiding teams through change and challenges. 

Stephanie notes that misalignment is expensive and disengaged employees are costly. The EARN system gives leaders practical tools to align teams and build momentum toward shared goals.

Final Takeaways

Leadership is never easy, but Stephanie believes it does not have to be overly complicated. “When you have to have an honest conversation about it… it’s not as hard or as complicated as people have told you it is. Utilize the talents that you have around you because they too have gifts and talents”.

Her advice is clear: stop trying to do it all yourself. By becoming an ally leader, you can unleash the potential of your entire team.

Where to Find More From Stephanie Chung

• Connect on LinkedIn
• Visit her website: stephaniechung.com
• Buy her book: Ally Leadership: How to Lead People Who Are Not Like You

Listen to the Full Episode

To hear more from Stephanie Chung, including her insights on curiosity in leadership and building psychologically safe teams, listen to the full episode of The Leadership Habit Podcast.

At Crestcom, we believe leadership is a journey, not a destination. That’s why we offer a complimentary leadership skills workshop for organizations that want to sharpen their leadership practices. In just two hours, you will walk away with tools to improve decision-making, build trust, and create accountability across your team.

The post How to Lead People Who Are Not Like You with Stephanie Chung appeared first on Crestcom International.