Never thought I’d see the day: WFH Wall Street

It was my first job out of school, just before the 2008 financial crisis. If you’ve seen the movie The Big Short, I had basically the same position as the guy sent to gently reject “Brownfield Fund” in the building lobby.

When I wasn’t busy turning down unwanted business, I was making pitchbooks, engaging with traders, or seeing clients. I spent the majority of my twenties in that world, which remained mostly unchanged during that time.

Office life feels foreign to many of us these days. But on Wall Street, it’s an institution. In-person chatter, whether in an elevator, trading floor, or golf course, are as integral to the business culture as the business itself. It’s been that way for decades.

So even though I knew it wasn’t for me, leaving the industry and all that came with it was more difficult than I’d expected. It became part of my identity, whether I liked it or not. Hence the tears.

Tech companies, on the other hand, are in constant motion. I’ve worked at Dropbox for almost seven years—just longer than my finance tenure—but the days of riding scooters around the office feel like five jobs ago. Transitioning to remote work hasn’t been the easiest, but Dropboxers are accustomed to change. That adaptability and progressive mentality are so ingrained in our culture, that going Virtual First feels in many ways like a natural step for the company.

While tech is perpetually focused on what’s next and new, Wall Street—in my estimation—acknowledges the inevitability of change and does adjust; but if they had it their way, they’d be pretty ok with the status quo. Change isn’t met with the same level of enthusiasm or even acceptance.

As it turns out, the disruptive force of the pandemic can’t be ignored by any institution. In these uncertain times, tech is busy imagining new work models, treating the current status quo during shelter in place as a way station en route to a fundamentally redesigned work future. But there are industries for which the present shift to remote work itself feels like a futuristic, previously inconceivable state. And that’s arguably a bigger transformation.

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“It all happened really quickly,” a source in the business tells me. “I insisted on working from home—I think it was the Wednesday that second week of March. By the following Tuesday, we were all told to stay home.”

“We were generally later than the technology firms on working from home,” another source says. “Everyone made sure to have their remote access just as a precaution. Then the firm started to put employees on different floors to have some distancing. But once New York became obviously highly infected, they sent everyone home in mid-March.”

Simultaneously, the markets were crashing. Unlike the job I transitioned to, where writing articles and even editing video can be done on any laptop, lifting and shifting market-driven financial work to a home office is more challenging. On a hectic trading floor, work happens across multiple giant screens that look like they belong on a spaceship. Information flows so fluidly in what Cal Newport calls “hyperactive highline workflow,” that it’s hard to know where one conversation ends and the next begins. During the transition, employees relied mostly on institutional knowledge and phone calls to get through the period of chaos. “It was probably the craziest month of my life,” a source says.

The markets did stabilize and New York City’s outbreak was tragic, but eventually contained. By early summer though, it became apparent that remote work would be the new normal and firms needed to adapt for the long haul.

Think of traders as engineers at tech companies: they’re closest to the money—analogous to the product in tech—so they get whatever they need. “Traders got at-home setups, with Bloomberg terminals and up to six screens. They also get their phone turrets, call forwarding, and now they use big Zoom meetings so you can ‘see’ the whole floor. People stay on mute until they want to shout something out. The nature of the trading floor is free-flowing, real-time information exchange and they’ve been able to mimic that pretty well.”

Others aren’t quite as convinced on the efficacy of a virtual trading floor. “Something that banks take very seriously on the trading floor is the floor plan,” a source says. “Every time you rearrange the seating on the floor, that affects people, and that affects careers, and it affects performance. It doesn't seem like it's a big deal, but it is, and I don’t just mean who gets to sit by the window. By being able to sit by certain people, you learn valuable information. Many conversations happen on a trading floor where two people are talking, other people can hear it, and they chime in. And that's how the creative process really takes hold. Little pieces of information that may not even seem relevant in the moment can lead to trades and opportunities.”

“On a communal Zoom or group chat, people just aren’t as forthcoming,” the source continues. “You’re broadcasting something to a bigger group of people, so it isn’t as natural.”

That sentiment is corroborated by our survey with The Economist Intelligence Unit (EIU), which shows that spontaneous interactions with colleagues have declined sharply during remote work. While Wall Street traders aren’t stereotypical “creatives,” they do draw inspiration from one another and that energy can get lost in a virtual setting.

When it comes to individual productivity at home, sources are echoing our EIU survey findings that they’re both more focused and working longer hours, and that the lack of commute is a boon. “We’ve proven we can be productive,” a source says. “People are starting to talk about how they might modify the workplace next year, with plexiglass and masks and all that. But I’d much rather just keep working remotely and I think we’d all be better off for it. I’m actually able to focus pretty well working from home.”

“We’ve conducted internal surveys and people are feeling like we work longer because when something pops up after dinner, it feels more natural to just address it,” the source continues. “If the kids are doing homework or just messing around, I'll hop on my desk and keep working. The work day has changed. It certainly feels like we’re working more, even though it's not one contiguous block.”

The source refers to dinner time, which in normal times could mean taking a client out. With those engagements off the calendar and travel restricted, client-facing employees all of a sudden have a lot more time on their hands. There is a downside, though. “As much as you try to establish a rapport on the phone, it's much easier to do in person. I'd say there's been a direct correlation between meetings that we've done with people we know, face to face, and the amount of business that we've done.”

Business impact aside, that time gained is a positive, further compounded by not needing to commute. “Much of our firm commutes from outside of New York City, so you're freeing up 20% of the day in some cases. I’d agree that we’re working more, but we have more time overall,” a source says.

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The average age on Wall Street is higher than in an industry like tech, and our EIU study states that baby boomers working remotely are showing less engagement with work, feeling more disconnected from colleagues, and are more likely to perceive remote collaboration tools as ineffective. “We still have a lot of old-schoolers,” a source says. “A lot of them are more tech-savvy than you’d think. But they miss the office.”

According to multiple sources at different firms, employees are slowly starting to go back into the office. They follow rotations, only allowing a certain capacity at a time, geared towards teammates working on the same deals or clients. For smaller firms, like many hedge funds, traders have gone back to their office desk command centers, with an analyst in a conference room on the other end of the floor. Some executives and senior managers are going in multiple days a week.

Which brings us to a topic that brought me much anxiety during my tenure: face time. I paid so much attention to when I came in or left for the day, relative to my manager. For everyone to be remote now blows my mind. “Managers have been forced to trust their teams more,” a source says. “But things like client engagements are being tracked, so they’re still keeping tabs on results.”

“The reality is face time still matters, whether people want to admit it or not,” the source continues. “We’re a traditional industry, and I’d imagine that’s still part of the culture in law or consulting, too. Senior people value face time, and when they start going in, that does send a message. But when you start to think about things like hallways and crowded elevators, just to conform to the traditional views of what it looks like to ‘work hard,’ it doesn’t make a whole lot of sense when we’ve shown we can stay productive working remotely. So I don’t know what’s going to happen.”

Another source feels that firms are doing their part to not pressure people. “It’s a no-shame environment if you want to stay at home.”

In a similar vein to the way Dropbox is approaching individual work at home and team-based work at a Dropbox Studio, one source sees room for both scenarios. “You can do a lot of the process-driven work at home. Maybe people can work at home a few days a week, with very little impact on productivity, and then they're still seeing people when it’s important to be in the same place. So maybe a hybrid model develops some more acceptance.”

Whatever happens going forward, a lot has already changed. I can only imagine how unnatural this all has felt for many industry veterans who’ve been doing things a certain way for decades. It was jarring for me—a 27-year-old who’d only been in the industry for six years and chose to leave—to walk away from that office.

Tech’s blueprint is still young by comparison, and SaaS inherently scales digitally. Dropbox’s Virtual First approach is an internal strategy, but it also reflects our mission externally to facilitate more effective virtual work for our customers. But for service-oriented industries that prioritize in-person engagement, a virtual-first mindset flies in the face of many core business values.

So after the pandemic is over, maybe Wall Street will go back to the way things were. The business has survived and there have been some silver linings with remote work—but overall it’s been a mixed bag. Either way, the industry, its leaders, and employees deserve credit for adapting so quickly to such a dramatic shift in the way they operate.

I’m not quite moved to tears, but have to say I’m impressed.