My Reflections from Zoom’s Fireside Chat with Jay Chaudhry, CEO of Zscaler

My Reflections from Zoom’s Fireside Chat with Jay Chaudhry, CEO of Zscaler

I recently had the pleasure of speaking with my friend Jay Chaudhry, entrepreneur, security expert, and co-founder and CEO of Zscaler, as part of Zoom’s Guest Speaker series. As the founder of multiple companies, including AirDefense, CoreHarbor, and SecureIT, and a world-renowned security expert, Jay shared some of the insights that he has gained during his life and career. 

Many of his points about leadership, attracting top talent, and making tough decisions were very inspiring! It’s no wonder he has built so many successful products and companies over the years, even during the pandemic.

Jay was also kind enough to share some insights from his personal life, including his beginnings in the small village of Panoh, India, and how he made the transition from software engineering to eventually using his life savings to start his first company. Jay also explained how he stays dedicated to self-improvement and what drives him on a daily basis, giving me an inspiring look into how Jay models his life and built his companies.

Here are some of my key takeaways from our discussion: 

Encourage your employees to try new things — and not be afraid to fail

Many business leaders struggle to build a strong company culture where employees feel empowered and satisfied, but Jay seems to have it down. When I asked him about how he does this, he gave me a valuable piece of advice: 

“Encouraging employees to try new things — and actually fail — is a good thing. If you’ve never failed, if you’ve never made mistakes, then you’re playing too safe and you’ll never do anything truly outstanding.”

Jay explained that organizations must build an environment where employees can innovate and take advantage of new opportunities to develop themselves. Failure can happen in these environments, but they also create happier, more productive employees, which creates happier customers. 

Choosing leaders who can scale with your business is critical to success

Over the course of his long career, Jay has made lots of tough decisions. I was curious about how some of those difficult decisions have impacted his career. He responded: “The biggest decision that a CEO has to make is that the leaders you select are the right leaders to scale with the company,” he said.

Jay explained that hiring leaders that are a good fit for your goals and objectives will have the greatest impact. He also said that the decision to move leaders out of their positions is very difficult, but having the right leaders who can adapt and grow with the company is fundamental to success. 

Keep the ‘ABCs’ out of your organization

Many of the world’s greatest business leaders, athletes, artists, and thinkers follow daily routines and habits. Jay is no different. When I asked him about his daily routine, he shared his love of daily exercise, good food, and time with his family. 

But Jay also offered valuable advice as he spoke about the importance of being self-confident and self-critical at the same time. Jay explained that you must have the confidence to experiment, but you also need the ability to look critically at what you’ve done so you don’t become arrogant. 

“As I drive my business, I follow this philosophy we have at Zscaler: ‘Keep ABC out of the company — A for arrogance, B for bureaucracy, and C for complacency.” With this mindset, you can create an atmosphere where employees are confident, eager to learn, and give their best effort. 

Build a ‘brain trust’ of friends 

Whenever I have the unique opportunity to speak with someone as successful, experienced, and wise as Jay, I’m always curious if they have any lessons about what they would’ve done differently over the course of their life.

When I asked Jay this question, he spoke about how grateful he was for his life and how he had already exceeded what he thought was possible. But he also gave me a great piece of advice that everyone can use: “Putting together a brain trust of great friends who inspire each other is the most important thing for me. If I could do it all over again, I would probably have started working on that brain trust sooner than later.” 

Jay explained that he didn’t recognize the value of that group of friends until later in life. He added that you can do anything if you have the right team in place, and having that inspiring group of friends is a big part of that. 

Communication starts at the top

Communicating company objectives, goals, and visions to employees needs careful planning and a good strategy. I was curious about how Jay communicates his company objectives and messaging to employees, and he offered advice that will stay with me. 

Jay explained you have to start by explaining the basics of what you’re trying to achieve to employees. Then leaders at different levels of the organization can explain how specific tasks and targets tie into those goals. 

“If my goals are defined at a 40,000-foot level across the company, then my head of engineering needs to take that down to the 20,000-foot level for the managers underneath him, and so forth until that work is complete,” he said. 

My sincere thanks to Jay for joining our team for this fun and enlightening discussion, and for permitting me to share my learnings with you all. Thank you, Jay!

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