When Inexperience Is Your Biggest Advantage

When Inexperience Is Your Biggest Advantage

Spencer Rascoff Technology executive (Zillow Group CEO)

For my latest Office Hours podcast, I connected with Aaron Levie, CEO of Box, an enterprise-focused cloud storage company used by big names like GE and AstraZeneca. Aaron and a couple of his high school friends founded Box in 2005 around the same time we started Zillow in Seattle. Interestingly, our team considered doing something similar before deciding to focus on real estate. Had we gone into cloud storage as well, we wouldn’t have Zillow… and Aaron and I probably wouldn’t have had such a candid and friendly conversation.

Aaron and I have a lot in common. At 10 years my junior, Aaron knows what it’s like to be a young CEO; he cut his teeth on the C-suite at the same age I was when co-founding Hotwire. Being a young executive has huge implications on your leadership style; in fact, it almost dictates how you behave. As a 23-year-old leading 40- and 50-year-olds, you absolutely cannot tell people what to do. You’ll be met with a, “Punk, what do you know?” response. But you still need to lead these people, and I found as a young leader that I could only do so through two-way communication, transparent decision-making and always, always communicating the “why” behind any effort.

This leadership style isn’t just important for young leaders; it’s important for all leaders as the future of work continues to evolve. In addition to being a young CEO, Aaron leads a company that is all about changing the way information is shared across organizations. He believes how companies communicate internally will be what makes or breaks their future: “No industry is exempt from disruption,” says Aaron, “which means companies need to have the shortest distance between the person with an idea and the person who can make a decision.” That exchange needs great technology like Box, but it also needs the open communication channels and an environment where new ideas, perspective and even dissent can come from all levels.

Beyond leadership, inexperience brings another huge advantage on the ideas front. I mentioned that our founding team explored the idea of doing a file-sharing startup, but what I failed to mention was why we didn’t. Our team, having originated from Microsoft and Expedia and being in the Seattle area, discarded the idea because we thought the behemoths like Microsoft and Amazon would eventually create the same service and give it away for free, and we wouldn’t be able to compete. We had played in this industry; we were jaded and cautious. Aaron wasn’t. He was a junior in college who, along with a few of his friends, saw an opportunity to solve a problem and dove right in.
The founders of Box didn’t think of what Microsoft would or could do, and that was their advantage. Aaron put this well in our conversation: “Silicon Valley – and tech innovation in general – thrives on a set of people every couple years who know nothing about history coming in and saying, ‘What’s Microsoft? What’s Google? We are trying to solve a problem.’” When you have a lot of experience, those questions are unavoidable.  

Lastly, inexperience pretty much requires you to take big swings if you want to make a mark quickly – whether that means disrupting an industry or just bringing something new to a company. Aaron recalled that one of the most valuable pieces of advice he’s ever received was from Box’s first investor, Mark Cuban; he told them not to hedge their bets, that they couldn’t “kind of disrupt” if they wanted to be successful. They had to go all in.

We also had the advantage of inexperience when we founded Zillow. None of us knew anything about real estate beyond how frustrating it was to find information when trying to buy or sell a home. We had a very clear problem we were trying to solve, and so we didn’t just “kind of” disrupt access to real estate information; we turned on the lights – giant floodlights. We believed it was best for the consumer to know and access as much information as the professional when it came to making one of the biggest financial investments of their lives, and we didn’t consider that it hadn’t been done before or might be met with industry pushback. By going all in, we created something that truly addressed a problem and opened the doors for a whole set of innovation around the entire lifecycle of homeownership, and the industry has since evolved to embrace this transparency because it is ultimately best for the consumer.

“Inexperience” isn’t typically seen as desirable in the workplace – but I think organizations should make sure they are introducing enough inexperience, whether by bringing in executives from different industries, reorganizing team structures or ensuring their summer interns feel they can contribute. New voices and new perspectives may sometimes be rooted in naïveté, but that’s not necessarily a bad thing. Sometimes, like in the case of Box, inexperience has huge payoffs.

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