CEO Rapidfire: DataStax CEO Chet Kapoor On Mastering The Art Of The No-Look Pass

Welcome to CEO Rapidfire, fast-paced questions with today’s most successful founders and CEOs. Be sure to look for these special Q&A editions of my newsletter, where I’ll share insights from the amazing leaders in my network.

Today in CEO Rapidfire, I’m talking with Chet Kapoor, Chairman and Chief Executive Officer at DataStax in Santa Clara, California. Chet’s a fantastic leader who started out at Steve Jobs’ post-Apple company, NeXT, and has been in leadership at other illustrious tech companies like Google, IBM and BEA Systems. 

His leadership principles are relentlessly human-centered. He likes to quote the adage by Warren Bennis and James O’Toole: “Real leaders, in a phrase, move the human heart.”

When Chet was the Chairman and CEO of the cross-cloud API management platform Apigee, he was instrumental in growing the company into a prominent technology provider for digital businesses. Apigee went public and was bought by Google for a reported $625 million in 2016.

He’s now CEO of DataStax, a real-time AI company, that provides a platform for managing and storing large amounts of data using the Apache Cassandra database management system. Under his leadership, the company has worked to make it easier for organizations to manage and extract value from their data in real time using AI.

But for all his success, he’s quick to point out that failure is an inevitable part of the journey. As he mentions below, “Obsessing about the last shot is not what champions do. They practice. They pivot. And they define success as the team winning.”

He’s an inspirational leader, and I’m excited to share his thoughts this week.

The one secret to succeeding as a leader, in 5 words or less: Believe. Inspire. Execute.

What was the most exciting “minute” of your leadership journey? It’s happening right now. (It sounds cheesy, but it’s true.) DataStax just acquired a machine-learning company and did a rebrand that represents our new mandate to deliver Real-Time AI for everyone. We’ve got a world-class team, awesome enterprise and developer partners relying on our product stack to power their real-time apps, and passionate open-source communities driving innovation. 

One truth you wish you knew about leadership before starting? As you go through your career, the list of failures will far exceed the list of successes. When you miss a shot, spend some time thinking about why you missed and then move on, QUICKLY. Obsessing about the last shot is not what champions do. They practice. They pivot. And they define success as the team winning. 

If you had to battle a giant, what weapon would you use? A GREAT bottle of Pinot. Who doesn’t love a great wine?

Your worst mistake as a leader (and what you learned from it): I make mistakes all the time. One of the biggest throughout my career has been putting off people-related decisions. We all want to see the best in others and believe that people can change. But the reality is if someone is not a fit for the role, you have to take action. Do yourself and the other person a favor by making a decision as quickly and respectfully as possible. 

Top 3 websites, blogs, or podcasts you can’t imagine your day without: Reid Hoffman’s podcast Masters of Scale – it’s super insightful and fun. Sam Harris’s meditation app, Waking Up. And I’ve been having a blast with ChatGPT lately. 

What popular leadership advice do you disagree with? The notion of hierarchy or titles – it’s so ancient. Of course, each individual should know their role and responsibilities. But a title alone does not define your value. I always remind people that value is in the impact you make, how you work with your team and inspire others.

One life hack you can’t live without: Breathe. It sounds simple, but breathing can take you through any moment or experience in life – good or bad.

One soft skill that you’ve realized is supremely important: Having hard conversations. It’s okay to disagree, and it’s also okay to escalate. If you don’t fix issues internally, they will end up impacting your customers. So it’s really important to take the time to listen, discuss, and then commit wholly to a solution.

The one thing that makes a good leader great is: A deep sense of belief in something far bigger than themselves or their job. You have to believe in a mission to the core of your being and then inspire your team to achieve more than what they ever thought was possible. And finally, you have to go off and execute like crazy. 

Your secret to building a great team is: Master the “No-Look Pass.” This is the magic moment in sports where one player gives their teammate the ball without even a glance in their direction – and that person goes off and scores. How do you make this happen in an organization? 

1. Hire world-class leaders. 

2. Practice a lot together.

3. Define success by the team winning.

The key to navigating hypergrowth is: Execution. You can have the best strategy and world-class talent, but if you can’t deliver, none of it matters.

Every leader must read: The Little Kingdom by Michael Moritz. It tells the story of two Steves who built a company called Apple, and it’s what inspired me to get into tech. Other favorites are Consolations by David Whyte (a collection of short, thought-provoking essays) and Sacred Hoops by Phil Jackson. 

What are you most excited about at work right now? Solving hard problems with smart people while having fun. 

Your one “non-negotiable” in business (or life) is: Whatever you do or whatever you’re trying to achieve, make sure your intentions are pure. Don’t do it because you want money or recognition. Do it because you love it, believe in it, and have a desire to serve others.

Thank you, Chet Kapoor, for sharing your leadership thoughts this week. To learn more, follow Chet on LinkedIn or check out Datastax.   

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