Leadership Development Inside and Outside of the Box

Evan Wittenberg, Senior Vice President of People at Box, discusses how to develop talent and create a winning culture in a rapidly growing environment

Evan Wittenberg has earned a black belt in full contact Japanese karate, however, his certificate reads that he has just “mastered the basics and is ready to begin learning the true meaning of the way.” Wittenberg, Senior Vice President of People at Box and a karate veteran of more than 25 years, says he believes this is a good way of thinking about development. Though most people prefer immediate gratification, he thinks about the long term and entire lifespan of his policies and projects. At Box, he leads a team that finds, develops, and retains the company’s world-class talent.

Wittenberg was originally approached by Box to work on leadership development, but the more interesting challenge was to run the entire people organization. With previous experience at Google and HP, he says, “I had come to develop an expertise in the leadership development space but I hadn’t stretched myself in terms of new challenges for a few years, so I wanted to take on a bigger role, with different responsibilities in different areas.” Furthermore, he explains that while the culture at Box had developed organically and the people were amazing, the company’s explosive growth dictated a need to focus overall on the people space. He says not only was leadership development only a piece of what was needed, it alone wasn’t enough of a challenge for him, so he wanted to “do the whole job.”

A Wharton School M.B.A. graduate, Wittenberg says that one of the primary reasons he wanted to go to business school was to be able to understand and speak in terms that would persuade C level executives to invest in talent. He was convinced of this when he worked on the merger of New York Hospital, Cornell Medical Center, and Columbia Presbyterian Medical Center before going to business school; he found that as a consultant he was able to meet with the CEO almost anytime he needed, but when he switched to the client side and joined the organization, it was harder to get those meetings. “I was still the same person but it was harder to get the CEO on the phone once the call was coming from inside the building, if you will,” he says. At the same time, he was also frustrated with some layoffs the hospital was doing and spent a lot of time fighting against it. But “then I realized, this switch flipped in my head, and I understood I should be focusing on the survivors and helping them be more effective, more capable now that the person on either side of them was gone.” He explains that shifting his focus this way helped empower him to spend his energy where he could really make a difference in the organization.

When he graduated from Wharton he stayed on to work there, taking over the Graduate Leadership Program and the Wharton Leadership Ventures, both of which prepared him for his later roles with Google, HP, and Box. He explains that technology companies are unique in that they are less tied to “best practices” than businesses in traditional industries, where companies are sometimes reticent to try new approaches unless their competitors are already using them. “And technology companies, at least the ones I’ve been in, don’t think that way. They ask questions like: what is some new idea that has some research behind it that might work? They find it and say ‘let’s try it. If it fails, so be it; we’ll learn fast,’” he explains. At Box they say “Take risks, fail fast, and GSD, which stands for Get Shit Done.” Wittenberg says, “Whatever it is, let’s try stuff that might work and let’s see if it does and let’s learn if it doesn’t, and we can change on the fly.”

At Google, Wittenberg was brought in to create a global leadership development function for the company. The scale of this project was quite different from the leadership program at Wharton because the growth at Google “was so explosive.” When he started with the company, there were about 7,000 people there; when he left 4 years later there were 24,000 people, “and that is a crazy scaling challenge,” he says. He and his team created a program called the Advanced Leadership Lab and they created it as a kind of work in process, knowing they might encounter new issues each time they ran it. “We wanted to design something that was a rough scaffolding with some guide wires, but where the experience was more of a ‘create your own adventure’ and ‘go where the energy in the room is and where the need is.’ And that program that we created essentially hasn’t changed and they’re now on the thirtieth or fortieth session.”

Doing The Hard Stuff

Wittenberg’s advice to young professionals is to follow your passions and be willing to do the hard stuff. While he has this attitude now, he admits he probably wouldn’t have been able to advise this as a younger man, explaining that his twenties were mostly about discovering what he did not like as opposed to what he did. He says what he learned through a multitude of experiences is, “the through line for me was all about helping people meet their full potential.” He continues, “At the end of my twenties I realized that I’m good at the qualitative side of some of this stuff; I understand why giving people tools and some empowerment helps the organization long term, and I had this vision that I wanted to help create environments where anybody from the janitor to the CEO could have a good idea and see it through to help the organization.  But my quantitative skills were not nearly as strong” Going to Wharton was one of the hard things he did that really enabled him to build a more diverse skill set and accomplish these goals.

At Box the culture is very strong which is something Wittenberg wanted to maintain, while also being able to scale and use metrics and data to analyze this company culture. One project he discusses is Project Moneyball, used to assess Box’s hiring and employee character. Wittenberg wanted to make sure they weren’t passing on people who might be very successful at Box, and to make sure they weren’t getting too homogenous as an organization. He references James Surowiecki’s book, The Wisdom of Crowds, and explains, “The idea is that a heterogeneous crowd will come up with better solutions if you crowd source the answers and sum them, better solutions than even experts. But it doesn’t work if that crowd is homogeneous.” For Project Moneyball they looked at typical hiring data (like undergraduate institution, GPA, etc.) and vetted it against performance ratings over time, but they also included something new: psychometric factors, things like introversion versus extroversion. Interestingly, they did not find that extroverts make the best salespeople, like one would think. “We found that the best salespeople at Box were actually what we call ambiverts, which are people in between extroversion and introversion.” Introverts sometimes did not do as well working with people, but extroverts were not always the best salespeople either, because they might be too social and find it hard to sit down and do the individual work on things like contracts and background research. The findings from this research are used to make sure Box is hiring the best people in the world for each role.

Another way they keep people happy at Box is in maintaining a transparent culture, and one way they accomplish this is with their all-hands lunch meetings. When Wittenberg joined the company, this forum was already in place, but he pushed the question and answer portion of the meeting because, as he explained, they had grown so much that people needed to be able to ask the executive team questions since they weren’t all working in the same room or floor anymore. He admits the first time they did this “it was like crickets, nobody asked a question.” But this has changed and they’ve even added some technology to the Q&A; people can text in questions which some are more comfortable doing. Wittenberg explains, “It matters less what the answer is when somebody asks a hard question than the fact that you answer it honestly and openly. The answer might be ‘we really screwed that up and we’ll do better next time’; the answer could be ‘I don’t know, I’ll get back to you on that’; or the answer could be ‘here’s what it is, here’s why we did it, here’s why it makes sense.’ The answer is less important than the open, honest ability to hear feedback.” ♦

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Leadership Versus Management

“There is a funny analogy for the two: A good manager will make sure that the trees in the forest all get cut down and shipped to the right location. A good leader will get in an airplane or climb up a tree and make sure you’re in the right forest first.”

“Management is a positional role that somebody has assigned, and leadership can be that but needn’t be hierarchical. Leadership is about taking ownership, accountability, responsibility, making hard decisions, stepping up, giving good feedback, showing the way, guiding, giving vision; that’s leadership. Managing is about making sure people are empowered and supported to get the right work done, in the right way, at the right time.”

“I want everybody to be a leader. And that requires taking accountability, and that’s hard. Sometimes people don’t want to take accountability; it’s easier to run the other way. Our COO says, ‘I want the kind of people who run towards fires, not away from them.’”

“Most companies wait until somebody is an executive to start developing their leadership skills, and I think that’s ridiculous. The research shows that it takes 10,000 hours to become an expert in something, so why would you wait until somebody is a director or a VP? Do that right out of college and maybe by the time they’re actually required to have these skills, they’ll have them. And along the way, they’re going to do all kinds of great things that you may never see, but will help the company be better.”