The Benefits and Challenges of Managing Remote Teams

11/20/2019 7 min read
Michelle Labbe
Michelle Labbe VP of People at Toptal, with more than two decades of experience in talent leadership roles, including executive positions at Rent the Runway, Deloitte, Accenture, and ICR.
The Benefits and Challenges of Managing Remote Teams

In a 2017 story reported in The Economist’s Workplace Evolution, a worldwide cyberattack was stopped by a 22-year-old from his bedroom in his parents’ house in southwest England; the report writes, “The days when people needed to go into the office to do even complex international work have long gone.”

The history of remote work is extensive, arguably beginning in 1973 when The Telecommunications-Transportation Tradeoff was published by physicist Jack Nilles, who worked remotely on a NASA telecommunications system. Ten years later the Internet was born, and the concept of remote work has been gaining traction ever since. According to Global Workplace Analytics, 4.7 million employees (3.4% of the workforce) now work from home at least half the time. Remote work has grown 159% since 2005, more than 11 times faster than the rest of the workforce and nearly 50 times faster than the self-employed population.

Remote work has special implications for human resources. A developer writing code (or a concerned citizen interrupting a global cyberattack) requires hardware, software, and a reliable internet connection to work effectively. Human resources, however, has always been about people, including creating a high-performing company culture, ensuring employee wellness, and increasing employee engagement. How, then, can someone successfully lead a group of people if they never – or rarely – meet in person?

I had never heard of a fully remote HR role until last year when Toptal approached me to become their VP of People. I immediately realized that working from home would enable me to spend more time with my son, who was a senior in high school, and my mother, who lives in Florida.

In addition to increased flexibility, the benefits of a fully remote workforce quickly became clear:

Greater team connectedness. This was an unexpected benefit, but remote work has made me closer to my team. Video technology like Zoom gives us the ability to speak face to face, rather than relying on the phone or email. While people can meet face to face in an office, the reality is that people aren’t always in their office, or their office is three floors above, or they’re traveling. Video conferencing lets team members into our homes, where we learn more about their personal side, see their home office, and often meet their pets.

Increases the search parameters. Hiring the right talent in today’s job market is tough. Early in 2019, The Washington Post reported 6.6 million job openings in the United States. According to a recent ManpowerGroup Talent Shortage survey, 72.8% of employers find it difficult to locate skilled candidates locally. Expanding the search parameters beyond the local area helps to alleviate these issues.

Remote workers have fewer distractions. Fortune reports that distraction at work, a majority (68%) of which comes from colleagues, causes employees to lose three to five hours of productivity each day. However, according to Forbes, 77% of remote workers say they are more productive and put in more hours than their in-house peers.

I’ve also found that being remote allows for greater confidentiality. HR is responsible for a range of delicate issues: for example, an employee’s physical health or job performance. In the past, if someone walked into my office and shut the door, it was obvious to those around my office that person wanted a private conversation with me or had been asked to come into my office for a private conversation. That doesn’t mean others could hear or had access to what we discussed, but those folks who are prone to gossip now had some fodder. Working from home, however, gives us increased privacy. There are no coworkers around to overhear our video call or know that it ever took place.

Of course, there are challenges when managing a remote workforce, including hiring and retaining talent capable of remote work and creating an engaging company culture without a physical location to regularly meet.

The Hiring and Retention Challenge

Not every person is right for remote work, and not every remote worker is right for every organization. For example, remote work might be difficult for someone straight out of college if they’ve never worked in an office before. Working in a traditional office allows entry-level workers to observe professional behavior and receive the guidance of more experienced coworkers.

A vigorous recruiting process will help ensure a company hires the right people. This includes multiple interviews and assessments to gauge whether the remote worker really knows their field and if they have the self-discipline to remain productive. The worker will need to actively participate in meetings and respond quickly in communication channels to show they are engaged and paying attention.

Other important aspects to consider when hiring remote workers include:

  • Accurate job descriptions. The job description should clearly outline their role, how the employee will fit into the organization, expectations, and what they will learn while on the job. The clearer the description, the more likely the organization is to find qualified candidates. At Toptal, we include responsibilities and expectations for the first week, month, 90 days, six months, and 12 months. We spend a lot of time on our job descriptions because we want people to understand the work the role entails, and also what they will be learning and how they will be contributing. Without being on-site there’s potential for a new employee to get off-track, even unintentionally.
  • Quarterly goals. In addition to their role, candidates should know the goals for the position and how they tie directly to their team goals and overall company goals. A remote candidate should know their deliverables for each quarter and that they will be held accountable. At Toptal, we outline exactly how each individual’s quarterly and annual goals track to the team and company’s quarterly and annual goals. Clear goals help create a team culture. Even though we don’t all see each other in office hallways or lunchrooms, every person understands their work is valued and critical to the success of the company.

Creating Culture in a Remote Team

According to a McKinsey article, a company’s culture separates the highest-performing organizations from the rest. Their research suggests companies with “top quartile cultures (as measured by their Organizational Health Index) post a return to shareholders 60 percent higher than median companies and 200 percent higher than those in the bottom quartile.”

In other words, culture matters. Remote companies, however, have to be purposeful in creating culture. Without a physical breakroom or water cooler, companies with a remote workforce must rely on technology to create virtual breakrooms and encourage conversations, including:

  • Instant-messaging channels such as Slack, Microsoft Teams, and Google Hangouts: These chatrooms allow for enhanced communication beyond traditional email. For example, at Toptal, we’ve created channels around interests such as pet lovers, gardening, cooking, book clubs, fantasy football leagues, fitness challenges – almost any interest you can imagine. We also use a “donut channel” where the app matches two people who wouldn’t ordinarily work together to have what they call “coffee and donut” conversations. Even though they might be across the world, we work hard to enable human connections.
  • Calendar of community events. Our workforce is spread across 100 countries. Rather than focus on distance between colleagues, we find reasons to get together. We share the locations of all team members and create local community events around the world every month so that those near one another have the opportunity to meet in person.
  • Pulse survey. This is a short question offered to the workers every other month. We ask: “How do you rate your happiness at work?” and “Would you recommend this organization to others to work?” People rate the answers with a number. In some organizations, pulse surveys are anonymous. However, transparency is part of our culture, so we do attach names to feedback, which allows me to follow up with the person and learn more.

Enabling Technology

It’s also critical to provide remote workers with the right tools and technology. Although each organization will differ on the specific products, there are several categories of tools and technology to consider:

  • Communication technology includes web conferencing tools like Zoom,, or BlueJeans, and instant-messaging apps like Slack and Microsoft Teams, in addition to traditional tools like email and smartphones.
  • File-sharing platforms, such as Dropbox and Google Drive, allow employees to share files, sync files across devices, store information in the cloud, and collaborate with team members.
  • Project management programs, including Trello and Asana, help team members collaborate on projects, meet goals and deadlines, and manage resources.
  • Time-tracking tools, like Everhour and Toggl, record time employees spend on specific projects or tasks.
  • Secure data access software, including IBM Guardium and BitLocker, secures data so that only approved parties have access to sensitive information. This includes programs for virtual private networks, electronic signing, locked PDFs, "read" timestamps, and secure messaging.
  • Data backup and recovery, such as Carbonite and iDrive, backs up data to a secure location and restores data lost due to software or hardware failure.
  • Malware protection, including McAfee and Symantec Norton, protects a computer from malicious software such as Trojans, viruses, worms, ransomware, spyware, and bots.
  • Home office includes laptops, tablets, printers, and headsets, as well as any software routinely used by the organization.

Not every company is ready to manage a remote workforce. According to Toptal’s 2019 State of the Remote Workforce Report, companies are most concerned with the productivity of remote team members, the ability to coordinate projects, and reduced team efficiency and productivity. IBM was famously a pioneer of remote work. According to Quartz, “By 2009, when remote work was still, for most, a novelty, 40% of IBM’s 386,000 global employees already worked at home (the company noted that it had reduced its office space by 78 million square feet and saved about $100 million in the US annually as a result).” Yet, in 2017, the company called some of its remote workforce back to the office. They’re not alone: Amazon and Google continue to invest billions in brick-and-mortar headquarters.

Toptal was launched in 2009 as a 100% remote company. Remote work has always been a part of our culture and company DNA. Companies with traditional offices who are implementing or expanding their remote workforce, however, have to manage the transition. Change is difficult, especially the larger and older the company is. There are simply more processes and people to adapt.

When implementing or expanding a remote workforce program, begin slowly. Offer workers the option to work from home a few days a week. Most employees will shine, proving to those who feel uncertain about the efficacy of remote workers that they have little to fear. It also provides an easier transition for employees who may have never worked from home to learn the best way to achieve goals when not commuting to the office each day.

In my experience with fully distributed teams, everybody naturally reaches out to others, even without a lot of structure. When we all know where the boat’s going and we’re all rowing in the same direction, it works well.

Michelle Labbe
Michelle Labbe VP of People at Toptal, with more than two decades of experience in talent leadership roles, including executive positions at Rent the Runway, Deloitte, Accenture, and ICR.