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Dropbox CEO Seizes the Opportunity to Rethink the Workplace

August 2021

As Dropbox CEO Drew Houston sees it, the COVID-19 pandemic has offered a once-in-a-lifetime opportunity for organizations to rethink the future of the workplace.

“There are challenges to working remotely, but there are a lot of things to like about it, too, like the flexibility,” Houston said. “The key question is: How do we retain all the things that are great about working remotely, but bring back the things that are good about the in-person experience?”

More than a year after the pandemic started, Spencer Stuart’s Jason Baumgarten sat down with Houston for a virtual interview, where they discussed leadership during the pandemic, as well as the pandemic’s lasting impact on the workplace. The interview below has been edited for brevity.

Tell us a little bit about how COVID-19 impacted Dropbox’s workplace, and how that change will carry forward post-pandemic.

Going through something with so much uncertainty, we had to shift to a new mode, and then over time that enabled us to become a lot more adaptable — to grow that muscle of resilience and adaptability. Moving overnight to remote work was one of the biggest changes to knowledge work, maybe since that term was invented 60 years ago. We realized that this was kind of a once-in-a-lifetime opportunity to rethink how we operate, to rethink the role of the office, to rethink the work week.

There are challenges to working remotely if you are working out of your living space, but there are a lot of things to like about it too, like the flexibility. Very quickly we saw that it worked better than we might have expected early on.

One silver lining from the pandemic is the ability to work from anywhere. It’s convenient not spending hours every day commuting, and to have more choices about where to live. It's good for companies, because they can unlock more pools of talent beyond their immediate geographic area. It’s good for society overall if it opens up more job opportunities to more people.

On the other hand, we all miss is the in-person experience. What we’ve been living in the pandemic is a lockdown, virtual, remote-only model. Looking ahead, there's an opportunity to be a lot more intentional about that experience. I think you can get a lot of the sense of community, cultivate relationships, and build culture without having to spend 100% of your time in an office.

So then, the question is, how do we retain everything that’s great about working remotely, while bringing back the good things about the in-person experience? If we can get the best of both worlds, then I think ultimately this will be a good thing.

What are you doing at Dropbox to create this “new” hybrid experience?

The thing every company has to avoid is creating a hybrid model that brings the worst of both worlds. Something like, you have to go back to the office three days a week, so you need to live close. You're still commuting, just a little bit less, but you’ve lost the flexibility you had while working remotely. And then when you're in the office, half the desks are empty, because half the people are working remotely. Not only are you in a big open office, but everybody is now talking on video to remote employees and it’s not a great experience.

At Dropbox, we're calling our model Virtual First, where remote work outside the traditional office is the primary experience for all Dropboxers. We’ve reimagined our office space to create what we call Dropbox Studios, convening spaces for in-person collaboration without individual desks. It was a fundamental shift for us as a company. We decided we want to have the flexibility and freedom of remote work while retaining meaningful human and in-person interactions. I think a lot of what helps people perform at their best is when they can focus, and being able to work remotely is good for that. Then when we really think about connecting, how can you build on-site events that make the in-person experience a lot more meaningful?


Is your sense that the model will morph to using your physical space to bring people together in a much less frequent, more curated way? Is virtual going to become the default?

I think a number of different models will emerge, but I think hybrid will be the midpoint. I think there will also be variation depending on people's preferences and roles. Some roles might be more conducive to working much more remotely. Other cross-functional roles might need a lot more connection that is harder to get remotely. I think the truth is, no one really knows exactly how this is going to work. In that kind of environment, similar to when the pandemic started, what you want is adaptability and the ability to iterate more often, rather than trying to throw a bullseye on the first throw.

One interesting thing from the standpoint of being at work is that technology used to be a sidecar to the office experience. The office was the primary experience, and you'd be on your phone or computer, with maybe one video meeting a day. Your day was confined to a designated physical space. And then in lockdown, it was completely the opposite. Work was done entirely out of your screen, there was no in-person experience. Down the line, I think the two experiences will be on more even footing. There’s more room for a combined experience that plays to the strengths of both spaces. I just don't think we had that canvas to paint on until the pandemic, because we had been so fixated on a physical mode that was inherited from an industrial-era factory orientation.

Was there anything that helped you keep employees engaged during the pandemic?

We amped up the frequency of communication, trying to help provide some of that stability and connectedness, especially as things first started to hit. But there are also the rituals in the office from eating together, or happy hours, or just running into folks in the hallway that we eventually tried to create in a virtual environment, even if they’re imperfect. For example, our Dropboxers at Home program included company leaders who joined a video call during their normal morning routine — so sometimes they would be making coffee — and you'd have an open meeting that anyone could join and just kind of talk. I think we've all had an interesting glimpse into people's humanity during this virtual period, and this was a good example of turning the pandemic into an opportunity.

Social elements like that helped, and more broadly we put programs and practices in place to help people maintain a sustainable pace. We encouraged employees to have a window during the day where everybody schedules their meetings — called core collaboration hours — so that on the early and later side of that window, you can have time for more focused work. We tried to defragment the day so that you don't have a meeting and then 30 minutes, and then another meeting and another short meeting — or worse, 10 straight 30-minute meetings back to-back.

Tell us a little bit about your personal journey as a leader through this year. What have you learned? What personal adjustments did you make in 2020?

In this rethinking of how we work, I thought a lot about my own role. Where do I really contribute? What do I want to spend time on?

Personally, I've been spending more time coding, going deep on the technology and prototyping a bunch of things myself. Coding was something I didn't have as much of a chance to do during normal life. I also created a president structure, promoting an executive into that role. It is a dramatic change for the organization, but it is one that created alignment while allowing me to focus more on longer-term important issues for the company.

This year was an opportunity to ask those fundamental questions about how I spend my time and what our principles as a company are, and then make changes that would otherwise be really easy to put off or be too disruptive.