Workplace Flexibility Isn’t Perfect—Here Are Two of Its Biggest Challenges

As more companies dive headfirst into flexible workplace policies, they’re running up against the learning curves of dispersed teams and remote work. Here are two of the biggest problems they’re trying to solve for.

It’s no secret that a growing number of employees what the ability to work from a location of their choice so badly that they are willing to walk away from their current job for it.

At Upflex, we champion workplace flexibility — but this is not to be confused with permanent work-from-home, which can be isolating and can hurt company culture. Recently, I’ve been party to some very thought-provoking discussions about how to balance these two pillars of the workplace, and whether true and total all-out “work from wherever you want, whenever you want” flexible workplace policies — which are cropping up at companies of all sizes — are compatible with company culture and equity as we know them, in the long term.

Aki Ito’s recent Business Insider pieces, “Employers are waging a war over work from home. WFH is winning,” and “Sick of working from home? These companies are reinventing work for a post-office world” have both given me a lot of food for thought.

Nicholas Bloom, a “work from home expert,” expressed to Ito that while companies with WFH policies will have all manner of acquisition and retention advantages — like a more successful time hiring demographically and gender diverse candidates — especially in the short term, he is trepidatious about where this evolution will carry us a few years from now, and stressed that flexible workplace policies need some amount of structure.

Atlassian was among the earliest companies to establish a truly flexible workplace policy.

1. In the Hybrid Workplace, Time With Teammates Isn’t Guaranteed

If only some people are in the office on only some days, employees aren’t guaranteed to get time with their teammates.

“The thing about remote or hybrid environments is, the water-cooler conversations are much, much, much less available to people — these serendipitous-type of connections,” Tsedal Neeley, Harvard professor of business administration and author of Remote Work Revolution, told Ito. “You’ve got to be intentional and thoughtful and create the conditions and opportunities for people to work well together.”

Indeed, HR departments and company leaders are desperate to get to the bottom of how to unite workers who want to stay dispersed — and how to promote equal buy-in from and attention to workers who are out of office versus those who work on site.  Looking toward a possible future with no centralized workplace at all, some of the solutions being explored include more frequent all-company off-sites, or more frequent work travel in groups.

In short, companies who thought they were going to save a bundle by reducing their real estate footprint have more to divert that previous lease budget to than just a couple-hundred-dollar-stipend to each employee to optimize their home office set-up. (Though some companies have of course taken it far beyond that — Dropbox, for example, replaced the cafeteria, gym classes and on-site cocktails that came with their old office and replaced it with a $7,000-per-year allowance to supply their own amenities.) Ito writes:

Dropbox, one of the first major companies to announce that all its employees would be working from home indefinitely, has redesigned its flagship offices in cities such as San Francisco, Seattle, Austin, and Dublin into “studios,” swapping out individual workstations for couches and large meeting tables. The company will fly remote employees to one of the studios at least once a quarter, so that they get a chance to interact with their teams, kick off new projects, and engage in strategic planning. The studios will also serve as a physical hub for social events, with regional committees organizing local get-togethers. The goal is to create “those moments for connection and belonging that we know are incredibly important,” said Alastair Simpson, who is co-leading Dropbox’s transition to a virtual-first workplace.

Alloy, which has adopted a flexible hybrid model, also plans on paying for its remote employees to come together with their teams at least once a quarter, usually at its New York office. Even though some workers won’t be spending as much time there, the company didn’t wind up saving money on the new office it’s moving into soon. The new headquarters will feature lots of space for collaboration, including conference rooms, high-top tables with stools, and couches, as well as shared desks for remote employees. “We want people to feel welcome in the office, even if they’re remote,” Johnson, the company’s COO, said. “You need to almost over-invest in the office to make it attractive.”

2. Ensuring Equal Buy-In Across Dispersed Teams Is a Tricky Balance  

Another obstacle Ito says companies will need to overcome is the question of location-agnostic equality and influence in the workplace.

“You give people choice [in work location], and they initially think it’s great, but then they realize, ‘Hey, wait, Jimmy’s coming in every day. I’m going to fall behind Jimmy. I better come in too,'” Bloom said to Ito. “And the whole thing collapses, with everyone coming in. It’s like ‘Lord of the Flies’ in the workplace.”

Atlassian an early adopter of truly flexible workplace policy, and when then they acquired remote-friendly tech company Trello in 2017, they integrated one of the Trello team’s workplace practices: If there’s even a single attendee joining a meeting remotely, everyone dials in — no matter whether they are on-site, with coworkers, or working alone off-site — to ensure equal participation and influence all around.

Moving forward, more than two thirds of employees at Atlassian only want to come into the office for part of the week, Ito shared, while the rest split between hopping to work full-time in the office or full-time at home. Ito writes:

Price assured me he’s well aware of the risk that in a workplace where everyone can choose their own schedule, the office becomes “a premium location,” with everyone else relegated to a “second-class citizen.” He also admitted to being “nowhere near” figuring it out. “We’re still experimenting our way through this,” he told me. But that hasn’t stopped Atlassian from letting its workers choose: “We still believe it’s the right thing to do.”

As companies continue to hack experiment their way through, more innovative techniques and strategies will emerge, but it won’t be easy: We’re talking about a total rethink of the workplace as we know it, and only time will tell if we’ve disrupted enough of the old way to make space for something truly better and more productive to generate.