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Art of Leading

The Quality that Box CEO Aaron Levie Values Most in New Hires: Humility

September 23, 2019

Always great to catch up with Aaron and hear how his approach to leadership has evolved. He shared smart insights about making sure Box stays nimble as it scales, and why humility is such an essential trait for building a high-performing culture.

Q. How have you grown as a leader since founding Box in 2005? 

A. When we were a very small operation, maybe 50 or 100 employees, I could have my hands in everything. Obviously, that approach doesn’t scale as we’ve grown to 2,000 employees. I’ve had to figure out the right ways to get involved in the business.

What’s interesting, though, is that the fundamentals are almost exactly the same. It’s about people. It’s about teams. It’s about collaboration. It’s about building a culture where you can be nimble, you can debate and have dissent. That’s fundamental to how we execute, but then how do you build the systems that let you scale that to 2,000 employees?

More of my job is to figure how to build a business where we have teams of five or ten people, just as we were when we only had 50 or 100 employees, but now that there’s going to be 400 or 500 of those teams. How do we make sure we’re able to all be aligned with the same set of goals and building a culture that is aligned to our values?

It all fundamentally starts with your core management team. Do you live by your values as a team? How does that core team define the culture, make decisions and collaborate, and how effective is that core team? That tends to ripple down throughout the organization.

Then my job is to plant a flag of where we’re going, show people how we’re going to get there, and then ideally let everyone else figure out how do they ladder up to that and what they need to do to align to that vision.

Q. Let’s talk about your leadership team. How do you make sure your team acts like a real team? 

A. We spend about four hours every Monday together as a leadership team, partly on tactical issues, partly on more strategic topics. With all the different functions coming together, we spend a lot of time just talking about the business, like what are the head winds? What are the tail winds? What’s going well? What’s not going well? What functions need support? What problems are people dealing with?

    “You have to create an environment of vulnerability.”

You have to create an environment of vulnerability, where people can be honest, with a high degree of candor, so you don’t feel like there are too many issues festering among individuals, and that you can surface them and address them. Then you have to be as execution-oriented as possible, by making decisions and moving things forward.

Q. Creating that culture of vulnerability and candor on teams is difficult. How do you make it real?

A. The best way possible way is to model it yourself. So the less defensive that I can be when we’re talking about an issue – or especially an issue I caused – the better. Sometimes I have a hard time doing that. If I think I’m right about something, then it’s hard to fess up sometimes and admit that I made a mistake with a decision or we didn’t move fast enough on an issue.

Second, you have to encourage as safe of an environment as possible, where people can bring up their issues or mistakes without getting pounced on or having their credibility damaged as a result. Easier said than done, but being able to create an environment where people can bring up mistakes and issues without fear of some kind of downstream consequence is really important.

Q. How has the way you’ve hired evolved over the years? 

A. One big struggle when you’re scaling is that there is a certain percentage of people who’ve done the job that you need to scale into, but they’ve done it in an environment that looks completely different from yours. And maybe they weren’t the ones who personally scaled it.

You’re constantly trying to filter for what type of person is going to work at our specific moment in the journey. Even if they have all sorts of experience, how are they going to enter our environment, take things forward and scale things even further? It’s always tricky.

Q. What’s the most important quality you’re looking for?

A. The single trait that I care more about than anything else is a high degree of humility. If you’re going to have an environment that is agile, that’s collaborative, where people take risks and they move quickly, the ability to have an ego-free environment is so important.

We’re going to deal with a lot of challenges, and if we have people who are going to mask those challenges, or not be able to actually address them because they’re just over-confident or have too much ego, we can never succeed as a business, especially in any kind of rapidly changing environment. And frankly people just don’t like working with those kinds of people.

Q. Let’s go deeper on this challenge of how you keep the company feeling small in terms of culture as it gets bigger. How do you operationalize that?

A. Our job as an organization and as a leadership team is to create an environment where those small teams have the ability to make decisions without a lot of check-ins across other parts of the business, with as few dependencies as possible.

And obviously, you need really strong leaders driving those teams. You have to have people who are execution-oriented, with a bias toward action, and where you create an environment where it’s safe for them to be able to take risks, to move quickly, where it’s celebrated when you do move quickly, and where, if something doesn’t turn out as planned, you don’t instantly get fired. Instead, you want to learn from those moments through post-mortems so we can continue to scale.

    “A lot of our work around culture is about trying to inspire an understanding that one of our greatest competitive advantages is our speed.”

A lot of our work around culture is about trying to inspire an understanding that one of our greatest competitive advantages is our speed. The moment we start instituting a lot of processes, bureaucracy and reviewing a strategy 15 times before we make a decision, we have no competitive advantage as a company.

Q. What is your best advice to aspiring entrepreneurs?

A. Your founding team matters more than any other factor in getting a company off the ground. So make sure you’re starting with a team you trust and that you can be in the trenches with, because it’s going to be lots and lots of sleepless nights, and weeks, and months, and quarters, and years of stuff not working and pivoting constantly.

The second one is really make sure that what you’re building is tied to very long-term trends and tail winds. When we started, we had four major, macro tail winds, which is rare, but shows you the degree to which you want to be riding tail winds. We had mobility, cloud, much faster browsers and way cheaper storage and computing as these massive tailwinds. Without maybe even one of those we might not be here as a company. I see a lot of companies that start that don’t have those kinds of gusts of wind behind them.

And make sure you’re doing something you’re incredibly passionate about. Way too many companies get started to optimize something, like buying pet food online. You might build a business that generates revenue and is even successful, but you might find yourself in three, five or ten years just not caring that much. A lot of businesses get started because of a particular kind of bubble environment. I think that’s a disaster.

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