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On March 8, in the early days of the global COVID-19 pandemic, Stack Overflow, the world’s largest online community for software developers and technologists, announced that its nearly 250-employee workforce would be going all-remote. It was a dramatic change, says CEO Prashanth Chandrasekar (MBA 2008) (pictured above right), but the company already had a strong remote-work ethos, with 40 percent of its employees working remotely and a globally distributed workforce with offices in New York, Austin, London, and Munich. Fittingly, Chandrasekar was abroad when he made the call with his team. “I think the decision drove a tremendous amount of confidence,” he says. He saw many of his peers in the tech industry scrambling; Stack Overflow, in contrast, was inherently prepared for the transition.
Lumry Family Associate Professor Prithwiraj “Raj” Choudhury has been studying remote-work models for years, focusing on what he calls “the geography of work” in organizations as diverse as the US Patent Office and open-source collaboration platform GitLab. In this conversation, he and Chandrasekar discuss the strategic benefits of remote work, the ways companies have tried to replicate office culture in the digital world, and the movement’s wider implications for how and where we organize ourselves.
Prashanth, you said in a March announcement about Stack Overflow going all-remote that the most important factor was the health and safety of your workers. But when did you start seeing the strategic benefits of remote work?
Prashanth Chandrasekar: There’s actually been, in some ways, a rise in productivity because people are able to focus and be very efficient with their time. We have not seen any kind of drop in output. The only place where there’s been more stress has been the inability for folks to be able to manage their personal family lives with kids studying at home. Not everybody has a setup where partners are able to split the work.
But outside of that, there’s the benefits of lower stress levels with no traveling. There is more balance in people’s lives because they are actually able to put deliberate markers around their days and weeks once they get past the change curve of, "I’m actually working 100 percent remote."
Raj Choudhury: When I think about the benefits, I think about the benefits to the company and the benefits to the worker. For the company, the biggest immediate benefit—which gets all CFOs excited—is the real estate savings. If folks are working from home and in fact working from anywhere, you don’t need that expensive real estate, especially for a company in New York or Silicon Valley. The second strategic benefit is hiring. Think about all the talent that is being left behind because they can’t migrate to the US due to the current immigration system. I have done research on military spouses, and they can’t have any continuity in their careers unless they work for an all-remote company. But also I’ve studied how productivity changes, which is the third leg. I found that in the US Patent Office, causally, not correlationally, they saw a 4.4 percent increase in productivity.
Now, what are the benefits to the worker? The first is what Prashanth said: the ability to manage time, the ability to manage your workplace, to have a better connection with your family. The second thing, especially in a work-from-anywhere model, is that people now have the flexibility to leave New York and leave the Valley and go to places where the cost of living is much cheaper. I think from both the company’s perspective and the workers’ perspective, this could be a win-win. Some CFOs and workers will see that and that will make this a more permanent phenomenon or a trend.
The companies that view this as a strategic opportunity to cut real estate costs, to improve hiring, to get people with more diverse skills—those are the companies that will emerge as winners from this. I feel that’s the big lesson. Instead of just focusing on whether or not productivity will dip in the next six months, I think the conversation of the C-suite should be, “How do we make remote work more strategic and long-term, and what does that mean in terms of how we communicate, socialize, and hire?”
Stack Overflow CEO Prashanth Chandrasekar on how he encourages his remote teams to separate from work
During the pandemic, firms have been forced into this model. Why wouldn’t people do this before? Was a lack of trust driving an aversion to this?
RC: Trust was definitely part of it. It’s also the habits that people have. Some managers would like to see people face-to-face or just see a hallway full of people that are working for them, right? This is fear of shirking—that my folks will shirk or not respond to me immediately.
As human beings, we’ve been tuned for synchronous communication. We ask a question, we want an answer right now. But in a work-from-anywhere model, as Prashanth said, people are spread all over the world, they’re working in different time zones, so you have to trust that they’re going to wake up and respond to you at the first available opportunity. But just letting go is hard, I guess.
PC: I couldn’t agree more. It has actually been very eye-opening: As long as you are enabling your employees to succeed with overall goals and giving them direction, there are other ways in which you can make sure that progress is happening. You don’t need to physically have face time to make sure that work is getting done. In fact, in some ways that could be counterproductive, because you’re not necessarily operating with your most authentic self by just doing it for the sake of doing it.
I think there’s going to be a cultural shift as companies transition to enabling employees to succeed and trusting them to do the right work—and hiring the right people to make sure that happens—versus a micromanaging sort of culture, which is more traditional in top-down organizations.
What are the experiences that are hard to replace in remote work? And how can companies replace those with digital experiences?
RC: In terms of the work getting done or sharing information related to work, one model has been to codify everything. I’ll give you the example of GitLab. They have something called the “one handbook" policy. What that means is that they write down everything so there’s no uncertainty. It’s as simple as just having a Google doc open constantly and filling it up in real time, so that when someone wakes up in London, and someone else wakes up in Delhi, they know exactly what the third person in the US has done. So, there’s no need to shoulder-tap. There’s no need to even have a Zoom call. You can just read that asynchronously.
But I think there’s a second element of shoulder-tapping that relates to socialization and informal discussions. The model there has been to informally mix people randomly to create these water-cooler moments. I was on a panel recently and a woman was mentioning how, during the COVID crisis, [her company] has had folks doing virtual DJ sessions. They’ve had virtual sessions where parents offer support for [co-workers’] kids’ homework. We are only bound by our creativity there.
PC: From a work standpoint and in terms of the cultural elements, Raj’s examples are very relevant to how we’ve thought about this. For the asynchronous work, we’ve used our own SaaS product, Stack Overflow for Teams, which allows us to break down silos, store evergreen knowledge internally and share information on the latest products. Go-to-market, customer success, finance, legal—all these teams are really gravitating toward these internal knowledge bases.
From a cultural standpoint, we have translated a lot of what we have historically done in our physical offices in New York City, London, Austin, and Munich. It has been a tradition for many years for everybody to have lunch together, and there are things like happy hours and team get-togethers. Now we have Zoom lunches so people have an opportunity to eat lunch together. We have “bev bashes,” as in beverage bashes, on a weekly basis on Fridays. I do a bev bash every other week with my own leadership team where we don’t talk about anything with regard to work—it’s mostly us coming together as a team and really understanding one other. Even our Slack channels have things like break rooms to replicate water cooler chat. We’ve got fitness channels—and I’m in that, challenging my direct leadership team to say, "Hey, let’s all do 100 pushups, 100 situps a day to stay fit throughout this period."
Raj, I also wonder if you think that this will impact the way we think about career longevity?
RC: In the US Patent Office, we found that the older or more experienced workers, when given flexibility, moved to Florida. And they were actually more productive after they moved. I thought that was interesting given the aging workforce problem we have. It could help people extend their careers by even five years by letting them choose where they want to go to retire.
I’ve also started some work with millennials and this phenomenon of digital nomads. These are workers who just travel around the world and work. There was a company called Remote Year that moved these people around the world while they were working for Google or Facebook.
PC: Right before I started at Stack Overflow, I was at Rackspace, and we actually leveraged the Remote Year program. We were able to retain some really excellent talent because of the flexibility that we provided, and they were highly productive. As technical folks who are operating completely online, pushing code or writing code and pushing it into production, everybody is able to stay coordinated through online code repositories or knowledge repositories like the kind we offer. That was very powerful to see. But we obviously did not have a premonition that we were going to accelerate to this level of coordination based on this pandemic.
Let’s consider the wider implications of this movement. The UN says by 2050, 68 percent of the world’s population will move into cities. So there’s a global trend towards urbanization. Does an effective remote work movement redefine that? How can this impact how we organize ourselves in general or in society?
RC: I’m personally just fascinated by that possibility. Given the fact that, at least anecdotally, some companies are starting to encourage work-from-anywhere, the bottom line implication is that it could trigger a de-urbanization or de-agglomeration from the large cities, and could lead to a reverse brain drain toward our smaller towns. But it doesn’t have to be only Middle America where people are returning to, and they can return to these places for multiple reasons. It could be the cost of living. It could be, "I want to be with my aging parents." My parents live in Calcutta, India. I wish I could live with them. My dad is 80 years old. Some folks would like to choose locations based on climate or their hobbies, right? And there could be second-order effects in terms of climate outcomes and traffic outcomes. So, I think if this becomes a phenomenon there could be a lot of very, very positive changes.
PC: In the tech ecosystem, I think there’s been a long-standing point of view that Silicon Valley is the heart of the tech industry in the United States. Then similarly, of course, there are places like Beijing in China and other places like Bangalore in India. But to Raj’s point, if this persists, you can only imagine that the gravity that exists in Silicon Valley is only going to disperse to other regions that also have some critical mass—like Austin, Texas, or other cities like Boston. So I believe there will be long-standing implications on the centers of power in the tech ecosystem.
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