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People walk through the financial district in Downtown Toronto.Adetona omokanye/The Globe and Mail

It is now not uncommon, in the world of human resources management, for companies to hire an executive whose sole focus is managing a remote workforce. After all, for many workers, times have changed — they’ve proven, over the last two and a half years, that they can work from anywhere, and they like that flexibility. But whether or not working away from the office will become the predominant way that white-collar workers do their jobs remains to be seen. Recently, companies have begun pushing back, traversing that fine line between mandating that workers return to their desks, and risking the loss of talent.

We spoke to four chief remote officers — all of whom have managed thousands of employees working out of their homes for at least two years — about the challenges they have faced, but also why and how they intend to continue letting their employees work remotely. Here are three takeaways:

Face-to-face interactions are key

“It’s not advisable to build a company where no one sees anyone,” says Darren Murph, the Head of Remote for San Francisco-based tech company Gitlab Inc., which has operated as a fully remote company for 17 years. According to Mr. Murph, the company’s approximately 1,600 employees love the flexibility they get from working remotely, but also crave in-person interactions. “Gitlab made it a priority to have strong in-person strategies by being intentional about organizing get-togethers,” he said. The company also covers the cost of employees booking a co-working space, if they want to work in less isolation.

Katya Laviolette, Chief People Officer at the fully remote Toronto-based tech company 1Password, said that one of the biggest challenges in managing her 900-person workforce is having employees glued to their screens and not getting to know their colleagues in a substantial way. “The social element is critical,” she says. “That doesn’t mean we force employees back into the office on certain days. It just means we organize off-site meetings and social events regularly.”

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A hybrid work environment is the worst of both worlds

Companies that have embraced remote working are critical of what is now a common way of functioning for knowledge-economy workers — spending some days in the office, and the rest of the week at home.

Mr. Murph believes that this type of hybrid work will create a two-tiered environment — those who have access to more in-office time and therefore more networking and potential for promotions, and those who don’t. “It is the toughest system of working for HR professionals to manage,” he said, adding that intentional strategies would need to be put into place to counteract the imbalance.

Paul McKinlay, the vice-president of communications and remote working at Dundalk, Ireland-based Cimpress, the parent company of Vista, said that, as of August 2020, his company has allowed employees to work remotely as much as they like. Among Cimpress‘s 14,000 employees around the world – many of whom work in manufacturing plants – Mr. McKinlay manages about 2,500 who can work from home. “I think having employees come into the office twice a week … takes away 90 per cent of the benefit of working remotely,” he says. “You can’t work and travel, you can’t relocate to a place where your family lives, you can’t take your kid to school every day.”

For Cimpress, says Mr. McKinlay, productivity is what matters the most: “We don’t care how and where you do your work, just do your work.”

Document everything and give every remote worker access

One of Mr. Murph’s main tasks as head of remote for Gitlab is ensuring that everything about the way the company is run is documented, and that every employee has access to that information. “When you’re remote, you cannot rely on osmosis or implicit knowledge,” he explains. “People are not physically around each other to pick up on context.”

Another upside of writing everything down, says Mr. Murph, is that everyone has equal access to the information, which creates a more widespread sense of belonging to the company and understanding of its values.

In a remote environment, ensuring equity in access to information among employees is one of the biggest challenges, but is critical to operating without hiccups, said Kristina Johnson, the Chief People Officer at Okta, Inc., the San Francisco-based tech giant.

Okta, which employs roughly 5,000 people, operates as a hybrid workplace. “You have to think about equity all the time. When you’re on-boarding new employees, for example, if some members of the team are in a conference room and the new employee is on Zoom, make sure the conference room folk log on to Zoom as well,” suggests Ms. Johnson. “These little things make a difference.”


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