Seven leadership lessons, as told by a CEO

Be curious

I love to learn. In any given conversation, I ask questions to understand the idea, the context surrounding that idea, why we want to do this, what our options are and so on. As a leader, the more questions you ask, the more you can learn from others and expand the diversity of your thinking.

Seeking new experiences is also part of being curious. For example, after completing my education and a year of working in India, I moved to Europe and worked in 10 or 12 different countries. When an opportunity came up to work for a company in California, I didn’t hesitate to move there. As part of my new role, I was leading large engineering teams across the country, and I decided to get an MBA to learn more about general business management. Once I completed that, I felt I should apply my knowledge and broaden my experience by working for a startup, so I looked for opportunities to do just that.

Stay flexible

To be a leader, you must be flexible and willing to adapt to new experiences and situations. When I first joined my company, for instance, I was like a fish out of water. After 25 years of working in Microsoft Windows, I had to learn a whole new set of tools to adapt to the organization’s Apple environment. There was also no office or room to run meetings, so I used to go for a walk to take my phone calls and hold daily meetings with the engineers in the hallway.

Work hard

I credit my father for instilling a strong work ethic in me. I remember him starting his day by 6 a.m. and finishing around 11 p.m. I think that’s one reason I started taking work so seriously at an early age: because he inspired that sense of discipline in me. This has helped me as an entrepreneur because when leading, sometimes you must make personal sacrifices. To help you stay motivated to do so, envision how completing the task will impact your business, and measure progress along the way.

Protect personal pursuits

At the same time, it’s easy for your life to become unbalanced if you’re only focused on work. There’s an old proverb that says, “All work and no play makes Jack a dull boy.” One thing I’m passionate about in my personal life is hiking and, for a long time, I was inconsistent about doing it. However, in the past 10 years, it became part of me, and I go on hikes every week now. Find an activity outside of work that interests you, and incorporate it into your schedule. For example, I plan the week in such a way that if something interrupts my hike on one day, I’ll go on the next day, but I won’t miss it even when I’m traveling. It’s important to be as disciplined in your personal pursuits as you are in your work.

Go outside your job title

As I mentioned previously, I tend to be curious about everything around me, but not just what’s in my job description. As a technology leader, I started out learning about my company’s product and platform. But working at a startup gives you a unique opportunity to try on different hats. One of my first projects, for example, allowed me to get more involved with other areas, including operations, client services, nonprofits and more. This diverse experience factored into the board’s decision to select me as the next CEO because other candidates were more specialized in only one area of the business.

Help everyone

One motto I live by is to help everyone. As a leader, it’s important to show that you care about the people around you and set aside time to get to know who they are outside of work. Listen to your team to see if they need any help, and make sure they know you’re available. This is something I practice in my own business, and as a result, I’ve found people are more inclined to ask for my help or input. And that opens the door to more new learning.

Fail fast and move on

Sometimes, there’s a tendency in business to make decisions as if your life depends on it, but that can lead to analysis paralysis and loss of innovation. For 95% of the decisions to be made, I’ve found you can often move forward based on the information you have at the moment. As Jeff Bezos once wrote in a letter to shareholders, most business decisions are changeable and reversible. If you’ve made a suboptimal decision, “you don’t have to live with the consequences for that long,” he said. “You can reopen the door and go back through.” I’ve found you often learn the most from bad decisions. Plus, you could have a perfect plan and still not be ready for when the unexpected happens, as Covid-19 has taught us this past year.

If I were to offer a parting piece of advice, it would be this: Enjoy all your experiences. Whether they are fun or tough, your experiences as a leader present an opportunity to learn something new or do something better — as long as you are curious, flexible and not afraid of failure.

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