We believe that distributed work is great for many reasons, and will eventually replace most traditional office environments. But an important part of treating distributed work seriously is discussing its downsides and the hurdles it presents to teams and individuals. To better understand the concerns around the distributed work model, Matt recently spoke with venture capitalist Arianna Simpson, a vocal skeptic of remote work.
It’s difficult to know what kinds of statements are going to make a big splash on social media. Brands spend untold resources trying to learn how to “start a conversation,” but usually the tweets that go viral are offhand remarks that were never conceived as definitive statements.
Such was the case with venture capitalist Arianna Simpson’s “tweet heard ‘round the world,” as she calls it. She set out to share a casual thought with her audience, but something about her perspective touched a nerve:
The tweet racked up almost 4,800 likes and generated hundreds of retweets and comments, with people arguing for or against the merits of the remote-work model.
It turns out that Arianna’s views on the optimal workplace are more complex. Twitter rewards concise, direct statements, and doesn’t leave much room for nuance. When speaking about the tweet, she shares a few qualifiers. For one, she didn’t mean it as a personal attack on anyone, though it seems like some folks took it this way.
“I was referring to… traditional, venture backable, early-stage tech startups,” she says. In other words, the kinds of companies she’s interested in working with in her role as a VC. Simpson is an early-stage investor with over 50 companies in her portfolio, many of which focus on developing blockchain tools and platforms. Before that, she was a project manager at BitGo, a blockchain-security company that first commercialized multi-signature cryptocurrency wallets. Prior to that, she worked on Facebook’s Global Marketing Solutions team and ran sales at the Y Combinator-backed Shoptiques.
Simpson first became interested in the blockchain in 2013, when she took a trip to Zimbabwe. At the time, the country was recovering from a protracted period of severe hyperinflation, which caused financial distress and material suffering for wide swaths of the population. She wondered: if the people of Zimbabwe could have accessed a cryptocurrency like Bitcoin, perhaps they might have been able to bypass their government’s bad economic policies and mitigate the ensuing disaster. She began heavily researching blockchain technology, convinced that it would be the next big thing.
Simpson’s enthusiasm for the blockchain — a decentralized system that substitutes complex mathematics for centralized control — seems to be at odds with her skepticism toward distributed teams. After all, decentralization is built into the technology itself, and many blockchain companies rely on a workforce spread all over the world.
Her caution is grounded in her experience across several successful tech companies, which comes with a strong understanding of the kinds of work environments that succeed — and of the ones that do not. VCs meets with hundreds of companies with the goal of partnering with the ones who show the most promise. They possesses a keen ability to recognize when teams lack motivation, coordination, or shared goals. Any company considering a distributed model would do well to take Simpson’s criticisms seriously.
Shared mission, camaraderie, and connectedness
Simpson believes that distributed teams suffer from a number of critical flaws. One of them is the difficulty of sustaining a strong sense of shared mission. She feels that co-located teams are better able to mobilize their members’ passion toward a common goal. This vision of the office is one of late-night coding and pizza sessions, where employees grind through the long hours and push themselves to the limit.
One thing I’ve noticed about startups that end up being very successful is often there is this strong sense of shared mission and shared energy, and that I find very difficult to replicate if you have people in different locations because you don’t have the same sense of camaraderie, the same sense of “You know what, this sucks but we’re gonna stay here until 10 PM and pound it out until we’re done ’cause we’ve gotta get this release out,” or whatever it is. So that is a really difficult intangible that’s hard to replicate if you have people in different time zones or different locations. It’s hard to muster up the same level of enthusiasm.
“And I think that’s why,” continues Simpson, “especially at the beginning of a working relationship, I think it’s really helpful to spend time in person. Now that may or may not always be possible but it does really help set the tone for how you will be perceiving interactions with that person.”
In addition to shared mission, sometimes camaraderie can be difficult to sustain on distributed teams. When we don’t have regular face-to-face communication, we often revert to a baseline of formality. It’s difficult to replicate the camaraderie that can come from shared lunches and happy hours. These are often moments where colleagues become friends.
That’s not to say that distributed teams can never have shared mission and camaraderie. It simply means that managers need to take special care to ensure remote team members feel connected, that their passions are aligned, and that there are opportunities for team members to bond.
An intentional team-building strategy can help accomplish this. Some companies (like Automattic) have regular meetups, where employees travel to a fun destination to spend time getting to know one another and working on projects in one shared physical space. [Editor’s note from Matt: I’m actually at one of these right now with our designers in Scottsdale, Arizona.] Another tactic is to encourage regular one-on-one, unstructured video chat sessions. This gives team members a chance to extend the work context and interact with one another not just as coworkers, but as colleagues too — the equivalent to sharing a coffee in the breakroom.
In companies operating with a hybrid model (some employees are co-located, while others are remote), a common mission and camaraderie are both crucial. But hybrid teams need something more to cultivate a sense of belonging. That requires codified team policies that ensure distributed employees aren’t treated like second-class citizens. Simpson explains how the disconnect can occur:
I’ve seen that happen a lot, where the employees who are not in the main office often end up getting passed over for promotions or they just feel really disconnected, and so often have higher churn, and end up deciding to leave because they’re in a silo. Everybody wants to feel connected to their team and to their work, and it’s hard to maintain that connection if you’re not on the same physical playing field as most of the team.
The facts on remote-employee churn are up for debate, but Simpson brings up a very real concern for managers of distributed teams. Remote workers can feel overlooked during meetings when the folks at HQ are sharing inside jokes to which they aren’t privy. Some distributed companies explicitly discourage this in their employee handbooks. Regular employee reviews and casual check-ins from management can go a long way to ameliorate any sense of disconnect that remote workers can feel from time to time.
Another way to avoid such concerns is to go 100% distributed. It’s easier to feel connected when you know that everyone else has the same relationship to their coworkers that you do.
Logistical complexity and knowledge density
Simpson’s hesitation with remote work doesn’t stem exclusively from the way it might make some employees feel. There are logistical issues as well. It isn’t always easy to corral a large team of people who live in a variety of cities, and this problem is magnified when workers are located in different time zones, or when they speak different languages.
I’ve seen companies — sometimes they’re small, they’re 15 or 20 people, and they have eight time zones. And I honestly don’t know how you manage to get anything done, because even just internal scheduling can become such a time suck and such an added complex issue that really shouldn’t be one, that it can easily become a drain on resources and time.
Our conversation with Upwork CEO Stephane Kasriel hints at a potential solution to the time-zone problem. He believes that companies and societies in general will move toward vertical social arrangements. Workers located in countries that share longitudes will increasingly become natural colleagues due to the ease of scheduling compared to workers located along a latitude.
Another benefit of co-location is that many of the best workers are drawn to hub cities where they have easy access to a wide range of employers. This phenomenon is amplified by network effects and the presence of universities that feed these companies with newly trained workers and fund research partnerships with them.
According to this view, there is a reason why the San Francisco Bay Area became Silicon Valley: if you want to work for and learn from the smartest minds in tech, you need to be in a major tech hub. Simpson explains that she gained a lot of understanding on blockchain technology from her own self-directed learning online, but there was a point where she needed to learn from other folks who knew more about it. “Everything I’ve learned in that category has been through a combination of reading stuff online, but also learning from peers,” she says. “And that’s true both if you’re an operator and if you’re an investor. And the highest concentration of that is going to be where? Probably the Bay Area.”
It’s true that lots of smart, trained techies tend to gather in hub cities like San Francisco, Los Angeles, and New York. But does it have to be this way? Perhaps the benefits Simpson describes could be spread around more widely if smart, trained tech workers didn’t feel like they had to leave their hometowns for a handful of cities. Perhaps mid-size cities and rural regions throughout the country and around the globe could become gathering places for folks interested in tech if enough people could sustain fruitful careers there. Replicating the Silicon Valley environment is a gargantuan task which many cities have tried — and at which many have failed. But maybe the missing pieces are only now starting to fall into place — new communications and productivity tools and a new willingness from founders and investors to experiment with distributed teams.
The indignities of the open floor plan
Simpson admits that working from an office isn’t always ideal. She explains that when she was at Facebook, she worked along the main walkway, so anytime an employee needed to get from one part of the office to another, they had to pass her desk. This was in the early days of the company, when only around 300 people worked there. So she knew a lot of them, and many naturally wanted to stop for a friendly chat, which ate into her productivity.
So then what I started doing was barricading myself. I was booking conference rooms, which technically you weren’t supposed to do, but whoops, to just go in there and work. So that’s where I realized — okay, actually what I like is having other people around and the ability to go and talk to my colleague if I need to, be present in meetings, and all these sorts of things — but also an independent workspace where I can just be alone and think — that’s where my preference on that emerged personally.
Simpson gets at one of the frustrations many people have with the modern office. An environment that’s supposedly designed for productivity can actually make us less productive.
The open-plan concept was envisioned as a work environment that would encourage spontaneous social interaction. Communal spaces were thought to facilitate such interactions better than traditional offices with cubicles — to say nothing of private offices with walls and doors. Privacy and concentration were thought to be worth sacrificing for the perceived rewards of greater collaboration.
That was the goal, but the results of the open-plan revolution have left many feeling as though they wish they could revert to a traditional office setup with more private spaces. The Harvard Business School funded a study, released last year, which confirmed some of our doubts about open-plan design.
“In short,” the study’s intro reads, “rather than prompting increasingly vibrant face-to-face collaboration, open architecture appeared to trigger a natural human response to socially withdraw from officemates and interact instead over email and IM.” This was the first study of its kind to track the impacts of the open-plan office using objective measuring tools such as electronic badges and microphones.
Simpson’s personal experience highlights a different problem — the kind of social interaction that open plans do encourage is not always the kind of social interaction you want.
I think having people come and interrupt you every 25 seconds, as is often the case in open floor plans, is definitely not the most productive situation. So the model I’ve seen work well, or the model I lean towards, is having an office where people are working from, but having private offices or spaces where people can plug in their headphones and just do work alone while still being in the same place as, hopefully, all of their colleagues.
One thing is clear — there is no perfect work environment. Whether you believe that the traditional office is indispensable, or you’ve fully embraced the distributed model, it’s important to recognize how different models work in different scenarios. There’s no one-size-fits-all solution. Companies who remain faithful to traditional work arrangements can experiment with a hybrid model, and hybrid companies can experiment with a fully distributed model by allowing their co-located employees to have temporary stretches of remote employment. If it doesn’t work, there’s always a cubicle with an Aeron knockoff waiting for them back at the office.
For more, read this episode’s transcript.
Remote work should be a natural part of most organizations today, but it probably shouldn’t be “yes or no”. Social interactions with coworkers are important, and those are much stronger in a face to face situation than a Slack conversation. To make remote work actually work I think we need some real face time, and we need people to learn how to use collaboration tools so that they tools don’t get in the way of the flow of ideas. If people could spend a day or two in the office a week for meetings and informal socializing over work, and the other days working from wherever they like using technology everybody knows how to use, I think we would be both happier and more efficient. We would also contribute to reducing carbon emissions by reducing the amount of people commuting every day. That should be a win-win but I still think it would require a big change in management culture for many organizations, especially those who are stuck in a mindset where productivity is measured by attendance and time sheets.