Real Time With Remote Workers

With 930 employees spread across 68 countries and not a single company office for any of them to report to, Automattic CEO Matt Mullenweg may well be the world’s biggest advocate of the remote workforce phenomenon. But even he acknowledges the inherent difficulties of managing globally dispersed employees working in isolation.

With 930 employees spread across 68 countries and not a single company office for any of them to report to, Automattic CEO Matt Mullenweg may well be the world’s biggest advocate of the remote workforce phenomenon. As the creator of the web publishing platform WordPress and CEO of a $1.6 billion web development company, he’s also got the technical wherewithal to bridge thousand-mile gaps electronically, enabling his army of Automatticians to collaborate and connect digitally. Yet, even Mullenweg acknowledges the inherent difficulties of managing globally dispersed employees working in isolation.

“There’s a level of trust that can be built when you share a meal together that has not been replicated online,” he says. “You can get 80 to 90 percent of the way there, quite close… but periodic engagement in person definitely helps.”

While few companies have made the jump to Automattic’s entirely virtual model, many are grappling with managing workforces spread across a network of offices or that encompass home-based employees. In fact, in a recent survey by Upwork, hiring managers predicted that within the next few years, over one-third (38 percent) of their employees will spend most of their time working remotely.

At national healthcare provider network First Choice Health, approximately 30 percent of the company’s 200 employees already telecommute on a permanent, full-time basis. The arrangement began as a retention effort when the company relocated and commuting to its Seattle office became untenable for many employees, explains CEO Jaja Okigwe, who adopted a remote-worker friendly model by necessity rather than intent.

“If there were a place we could relocate that would pull more people in, that would be awesome,” he says. “I actually prefer human-to-human, real-time interaction, because I think that just helps people understand where you are and where you’re going and also builds a connection for them to provide feedback. When you have a remote workforce, you don’t hear what’s going on, it’s not like you’re gonna bump into them walking down the hall.”

HQ vs Off-Site Venues

While periodic face-to-face meetings often play a crucial role in engaging and aligning remote workers, approaches differ. Automattic, which jettisoned its corporate office entirely in 2016, encourages small teams of 5–10 to gather at a central location for Meetups several times a year and provides a stipend for that purpose.

The company also brings its entire workforce together for an annual Grand Meetup, a week-long event that Mullenweg describes as “a really cool family reunion” featuring keynote speakers, skill-building sessions, team meetings and opportunities to socialize. “It’s about three things, clarity, communication and alignment, making sure everyone has a clear idea of the mission and how they connect to it and getting us all talking with one another,” he explains.

First Choice’s Okigwe prefers to bring remote workers to headquarters, where it maintains “hotel cubes” and virtual machines so visiting employees can log in to seamlessly access their projects, on a quarterly basis. “Without that intentional investment in face-to-face interaction, we’re just training a remote workforce that could be pilfered by somebody else,” he says. “If they don’t have a connection with you and what you’re trying to do, then it’s just a paycheck, and there are a lot of other organizations where they can get that.”

Getting the ROI

However you go about it, any employee gathering represents a significant investment of time, energy and money. “It won’t be an inexpensive endeavor, so it’s critically important to make sure you get the return you want from the expense of bringing these people together,” says Scott Graf, global president of the business travel management company BCD Meetings & Events. These six steps can help companies pave the way for a successful remote worker meeting:

Know your who and why: “Ask yourself, ‘What is my objective, which of my virtual employees should be present and why?’” suggests Graf. “That will help you determine where and how long it should be, who should be invited and the content you need to develop.”

Follow the 80/20 rule. An agenda packed with back-to-back, information-rich sessions is likely to backfire, overwhelming attendees, says Graf, who advises an itinerary that devotes 80 percent of total time to pursuing meeting objectives and 20 percent to giving participants opportunities to exercise, take a walk or catch up with colleagues.

Give them mingle material. “If your goal is to facilitate peer-to-peer engagement, don’t just leave people to mill about a reception,” says Danielle Bishop, president of HB Hospitality, a community of independent luxury resorts hotels and meeting planners. “Add an interactive component that will bring them together and give them something to talk about.” Bishop incorporates a range of ice-breaking activities into sessions, from having flamingo ambassadors on site to holding activities like tomahawk tossing.

Mandate digital detox. Armed with iPhones, it’s all too easy for telecommuters to retreat to a corner—and their comfort zone. “We don’t even use apps at our events,” says Bishop, “because we don’t want people looking down at their phones. We want them connecting.” If confiscating devices is too aggressive, “smartphone sleeping bags” can help remind people to limit their phone use.

Game the seating situation. Let’s face it, given the choice, people will gravitate to sit with friends and acquaintances—so Automattic doesn’t offer a choice. “Almost all of our dinners have assigned seating,” says Mullenweg. “We have a database that tracks whether people have met before, and at each dinner we try to seat you with three to five people you haven’t met before. Since we’re a tech company we have a lot of more introverted people, so it’s a great way to meet people you wouldn’t normally meet.”

Ultimately, Mullenweg, whose enthusiasm led him to share Automattic’s journey to becoming what he dubs a “fully distributed” company at, sees office-lessness as not only manageable but preferable—and the employment model of the future. “I think a distributed workforce is the most effective way to grow a company,” he says in a video posted on his blog. “The key is that you have to approach it consciously.”


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