How the Future Works. Brian Elliott

Why Flexible Work Works

      “The workplace will now be wherever work happens, and the workweek will be whenever work happens best for each person.”¹ That was how Dropbox CEO, Drew Houston, described the company's flexible work strategy, announced in October 2020, which was a clear break from how they'd worked in the past. Dropbox had largely been an office-centric culture, and they'd invested a lot in creating what Chief People Officer, Melanie Collins, describes as “the most delightful work environment we possibly could.” Their office spaces, which are located around the globe from San Francisco to Sydney, Australia, included things like state-of-the-art gyms and world-renowned cafeterias featuring their own signature roasted coffee blend. Office space was such a big part of their culture that pre-pandemic only three percent of its people didn't work out of one. When the COVID-19 pandemic hit and those offices had to close, the vast majority of Dropbox employees were displaced.

      Much like what happened at Slack, as the pandemic forced them to pivot, Dropbox leaders were surprised to find that productivity and performance didn't really miss a beat. That caused them to rethink what they'd been doing and accelerated their conversation around the merits and possibilities of flexible work. The pandemic forced more flexibility on companies, of course, but the question for Dropbox quickly became: How could it work over the long-term? What would a flexible work strategy look like if it were dictated, not by circumstances, but by design?

The answer wasn't obvious. Dropbox began by forming a team, co-led by Collins and Alastair Simpson, their Vice President of Design, with representatives from different parts of the company—design, tech, HR—to really study the issue. They took their time and kept an open mind as they looked internally at how their people were responding, as well as externally to benchmark dozens of companies. “We considered everything on the spectrum from full-time to no-time at the office,” Collins explains.

      Among the models they rejected was the typical hybrid one—where some people work remotely and others continue to come to the office as usual. This is, perhaps, the model most people think of first, but Dropbox decided it wasn't right for them—the main reason being, as Collins explained, because it “creates two very different employee experiences that could result in issues with inclusion, or disparities with respect to performance or career trajectory depending on whether you are in the office or remote.”

      Instead the team came up with a strategy that makes flexible work the primary experience for all employees. But when the concept was proposed to their leadership team, it was far from an immediate win. There were questions and pushback. Houston, in particular, wanted more detail. It sounded good in theory, but he wanted to be able to picture what a “day in the life” would look like for employees.

As we mentioned earlier, Houston now describes the workplace as being “wherever work happens,” and the workweek as “whenever work happens.” So, how do you balance those notions with the very real need for team members to connect and collaborate with one another? Instead of the traditional 9-to-5 expectations, the team asked what people really needed to collaborate effectively with one another while balancing individual needs for focus time. The flexible work proposal included the concept of “core collaboration hours”—four-hour windows of time each day when employees would be accessible to one another to do these very things, leaving the rest of their schedule open to get individual, focused work done when it suited them (see Figure 1). That concept raised concerns, like: “How will I be able to meet with people in different timezones?” and “How will I condense eight hours of meetings into just four?”

The team had to come up with answers. Core collaboration hours needed to be aligned to time zones, for example: a window of 9:00 a.m. to 1:00 p.m. on the West Coast synched with noon to 4:00 p.m. on the East Coast, which meant that everyone could collaborate during a reasonable timeframe but still allowed flexibility in the schedule so people could have lunch with a family member or pick up a kid from soccer practice.