Expedia CEO Shares the Critical Traits to Develop by Age 30 Dara Khosrowshahi discusses his views on the vital leadership qualities to develop as a young professional.

By Sina Chehrazi Edited by Dan Bova

Opinions expressed by Entrepreneur contributors are their own.

Bloomberg | Getty Images
Dara Khosrowshahi, chief executive officer of Expedia Inc.

Dara Khosrowshahi was born in Tehran, Iran, in May of 1969. Less than a decade later, Khosrowshahi and his family would emigrate to the United States in the wake of the Iranian Revolution.

"We sure didn't feel like refugees, but in hindsight I guess we were -- my father and mother left everything behind to come here -- to be safe and give their boys a chance to rebuild a life," Khosrowshahi wrote recently in a company memo. "I remember my father taking us to meeting with lawyers, interviews with immigration officers, doing everything he could to get us that treasured Green Card -- and the happiness, the sense of relief, when he finally did -- we knew that we were welcome now, and we would be welcome tomorrow."

The 9-year-old immigrant would eventually become CEO of one of the world's largest travel companies, expanding Expedia's presence to over 60 countries across the globe. Despite the company's ascent deeper and deeper into the Fortune 500, Khosrowshahi has kept the company's envied culture intact. Expedia has been consistently named one of Fortune's Most Admired Companies, Forbes' Most Innovative Companies and ranked No. 1 on Glassdoor's Best Places to Work in the UK.

Related: 22 Qualities That Make a Great Leader

Looking back, Khosrowshahi shares his views on the different skills, personality traits and critical life practices that entrepreneurs and future executives should aim to develop by age 30.

From a substantive leadership and skills perspective, what were the key talents that you developed during your 20s?

Khosrowshahi: When I was in my 20s, I learned not only how to work hard, but about the importance of focus. I started in investment banking at Allen & Company in 1991. It was the go-go days of media mergers and we were incredibly busy with one deal after another. Unlike typical investment banking groups, even in the midst of merger mania, we didn't have a formal face-time culture -- and I felt empowered by that.

You should identify specific takeaways from your first few roles as a young professional that will prove relevant for a lifetime. Early on, I learned the importance of being acutely focused on my goals -- and the importance of fostering a culture that avoids unnecessary restrictions.

Related: 11 Steps to Starting a Successful Business in Your 20s

From an emotional and human perspective, what do you think were the vital qualities that you developed during your 20s?

I learned how critical flexibility is. Learning to cope with endless demands on your time --- at a young age -- will both position and prepare you for advancement and growth. As you move up, business problems become non-linear and systems less predictable. A uniform approach just won't cut it so you have to approach problems differently, with flexibility.

I remember a task I was given by Herbert Allen early on in my career. He was worried about certain financial products becoming a ticking time bomb. As you would within a startup, I was given the job of researching the subject and reporting back to him personally, with little guidance or direction. That's how the day-to-day works at many early companies, and it's a work setting you should become comfortable with. As I mentioned, the farther you move up, the tasks at hand often lack any structured precedence or linear roadmaps.

When you were in your 20s, what did you reflect on/think about most often? How did you come to understand your strengths and weaknesses?

Maybe it had something to do with my family having lost a lot when we emigrated from Iran to the U.S., but when I first began my career, I was a bit "Wall Street-obsessed" when it came to being financially successful. In the longer run, Expedia would teach me that passion and mission are much stronger motivators than money.

Related: 10 Entrepreneurs Share the Best Advice They've Ever Received

If you could go back and make one decision differently, what would it be?

If I could go back and make one decision differently, I'd travel more, but you knew I'd say that!

In what ways is serving as a leader of a company different than what people might assume?

Many people think that leadership is solely about communication -- presenting, making speeches, motivating. Being a good communicator is certainly important, but I've found that one of the most important skills for a leader is being a good listener. The higher up in the chain of command you are, the harder it is to really know what's going on, so you have to discover the right information out of your people. You have to be great at reading body language and asking questions. You have to engender trust to get to the real stuff. Leaders who are disconnected with reality are the ones who fail.

Looking back, if you could tell your 30-year-old self one thing or share one piece of guidance, what would it be?

If I could give my 30-year-old self one piece of advice, without a doubt it would be that it's ok to fail. When I was younger, I was so afraid of being wrong, of being late, of being rejected. I was afraid of failing. But, the thing is, failure is so important in life, not only in terms of learning, but also in taking risks -- both in your business and your personal life.

Believe me, it's not fun to fail, but when it happens, you get up, you dust yourself off and you move on. A life without a fundamental fear of failure is way more fun than a life spent ducking for cover.

Sina Chehrazi

I chronicle entrepreneurs and businesses that millennials admire

Sina Chehrazi chronicles the backstories of the founders and companies that millennials admire. He studied at Georgetown Law and Georgetown Business School. He is headquartered in both San Francisco, Calif., and Washington, D.C.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Editor's Pick

Business News

JPMorgan Shuts Down Internal Message Board Comments After Employees React to Return-to-Office Mandate

Employees were given the option to leave comments about the RTO mandate with their first and last names on display — and they did not hold back.

Innovation

4 Ways Market Leaders Use Innovation to Foster Business Growth

Forward-thinkers constantly strive to diversify and streamline their products and services, turning novelties into commodities desired by many.

Franchise

The 10 Best Franchises to Open in 2018

Here's everything you need to know about the startup costs, training and investment opportunities from the top 10 companies in our Franchise 500.

Business News

'Nothing More Powerful': How to Transform Companies From Within as an 'Intrapreneur,' According to a Microsoft Office and Yahoo! Shopping Cofounder

Elizabeth Funk wrote the first code for Yahoo! Shopping on her own, based on skills she acquired from an "HTML for Dummies" book.

Business Ideas

70 Small Business Ideas to Start in 2025

We put together a list of the best, most profitable small business ideas for entrepreneurs to pursue in 2025.

Growing a Business

How Meta Generated $32 Billion in Ad Revenue Last Quarter — and How You Can Create Million-Dollar Weekends Using the Same Strategies

Meta's staggering $32 billion quarterly ad revenue isn't just about size; it's about strategy, systems and execution as well.