In tech industry mythology, the San Francisco Bay Area is the unmatched crucible of ideas and execution. Companies like Facebook offer generous salaries and stock awards to lure staff in Silicon Valley’s overheated job market. They pay for some of the nation’s most expensive office space and perks that ensure workers spend a lot of time inside it, such as free commuter shuttles, food, haircuts, and laundry.

Two months of pandemic-mandated working from home now has some tech titans questioning that orthodoxy. Facebook CEO Mark Zuckerberg said in a company videostream last week that remote work will be an option for most new and existing positions; he told the Verge he expects half the company to toil outside a company office in as soon as five years. His announcement came after Twitter CEO Jack Dorsey said that company’s workers don’t have to ever return to the office if they prefer to work elsewhere.

Switching from bums-on-seats to work-from-where-you-like is a challenge for any organization but may be extra tricky for companies incubated in Silicon Valley culture. People who have studied or practiced remote work say leaders like Zuckerberg and their executives will have to tear themselves from their Bay Area roots—in some cases physically—if they are to avoid making their new legions of remote workers second-class employees.

It’s not hard to see why tech companies might want to have a smaller fraction of their workers inside their lavish offices. Raj Choudhury, a Harvard Business School professor who studies the geography of work, says chief financial officers generally love the idea of slashing real estate costs. Tech workers hired outside the Bay Area are generally paid less; Zuckerberg said Facebook will reduce salaries for people who move to cheaper places.

Some may find the trade-off worthwhile if they stand to gain more living space and shorten commutes. Zuckerberg said surveying Facebook workers showed 20 percent were very or extremely interested in working remotely, with another 20 percent somewhat interested.

But adopting remote work has costs less easily tracked on a spreadsheet. One of the biggest is coordinating and managing workers spread across locations and time zones, and able to meet only virtually.

That will be challenging if Facebook and other remote-curious tech companies keep most managers and top executives onsite amid the conference rooms, snack stations, and foosball tables. Choudhury says a hybrid of remote and office work is hard to pull off without disadvantaging people offsite who receive less attention from leadership, while onsite workers can more easily cater to executives and win promotions. “That’s a recipe for disaster,” he says. “To do it well you have to have all or the majority remote, and you have to have managers who are remote.”

Darren Murph, head of remote at GitLab, a software startup with more than 1,200 workers in more than 65 countries but not a single office, agrees. He likens combining traditional offices with a large remote workforce to mixing oil and water. “You’re going to have to work really hard to make sure remote workers don’t feel like a second class,” he says.

Facebook didn’t respond to a request for comment. Zuckerberg said last week that he expects to work outside the office himself more often, but the company seems unlikely to put its Frank Gehry-designed headquarters up for sale or to ask many executives to move out of Silicon Valley’s exclusive neighborhoods.

“I have a hard time believing companies are going to hire senior-level executives remotely unless it’s deeply baked into their culture,” says Adam Bennett, a director with recruiter Robert Half Technology in San Jose. When WIRED asked Google CEO Sundar Pichai if he would adopt a remote work strategy like Facebook’s, he demurred.

Even if companies like Facebook do end up with employees of all levels offsite, more remote workers will place new burdens on managers. “It makes management so much harder,” says Sigal Barsade, a management professor at the Wharton School.