5 Mistakes Companies Make When Transitioning to Remote Work

5 Mistakes Companies Make When Transitioning to Remote Work

Soon after she became CEO of Yahoo in mid-2013, Marissa Mayer caused quite a stir in the tech industry when she eliminated remote work from the company. Many in the industry defended her philosophy that interaction is critical to innovation and teamwork—more specifically, the kinds of conversations and hallway chats that are unique to face-to-face work environments. It’s one of the mistakes companies make.

This act spurred a lively debate about whether or not web-based companies should indeed expect employees to gather in an office day in and day out when work can technically be completed anywhere. From its supporters’ perspective, remote work has its share of advantages for both employers and employees, ranging from environmental to cultural to financial.

Fast forward to 2016. Work flexibility has become a growing professional dialogue and, for some, a foundation upon which to build a company. (There’s even a national conference, TRaD Works, at which remote work experts and professionals convened in June.)

Just as with any major change, however, growing pains exist for those who inadvertently overlook challenges.

Here are five big mistakes companies make when transitioning to remote work:

1.     Moving Forward Without Buy-In

This isn’t a decision to be made in a leadership silo. Not all organizations are run democratically—but even if yours is among those with top-down decision making, it’s perhaps even more critical to explore your colleagues’ perspectives and potential concerns prior to instituting a flexible work environment. Their opinions may not sway the decision to go remote, but having the opportunity to be heard can help you build consensus for the idea, and could help you dodge obstacles that might arise out of blind spots.

Ask your employees: What would you like most about a flexible work environment? Conversely, what are your biggest worries or concerns? How can we as an organization alleviate or minimize those to ensure that you feel both comfortable and productive?

“Always begin with the end in mind. Starting with your strategy, ask yourself what you want your product and organization to achieve. If remote work ultimately lines up with your vision and goals, then it might be worth investigating further.”

Brian de Haaff, Co-founder & CEO of Aha

2.     Underestimating Cultural Issues

Don’t assume that company culture sans office and water cooler will be a rosy experience. When individuals or teams are spread across cities, regions, or time zones, the culture of an organization can make or break a firm. These are the invaluable intangibles: the principles leadership upholds and propagates, how individuals interact with one another, the acknowledgement of employees’ accomplishments and their lives outside of work, and the emphasis on some professional priorities over others.

Companies that start out remotely often start with a deliberate focus on building a robust company culture. (See Buffer’s post on articulating their company values from the very beginning, for example.) For those organizations that are switching from office-based to distributed work, the sense of urgency needs to be just as present. You have a lot to lose, but much that can be gained if you start off on the right foot.

“Having fun is a really essential part of the Formstack culture. We rely pretty heavily on weekly team meetings, fun IM chats and, of course, gifs and memes to nurture our remote culture at Formstack. We have a Talent Department that plans “Formstack Fun” events for both our local and remote team members. Some past events have included a lip sync competition, team video lunches and poster competitions.”

Chris Byers, CEO of Formstack

3.     Believing Communication Will Be Organic

Make no mistake: great communication takes work, and it won’t happen as naturally as it did when everyone was working in one spot. To their detriment, companies with brick-and-mortar audiences can take this for granted. A deliberate focus on communication will soften the initial transition to remote work, and it’ll be paramount to your continued success.

Technology offers a bevy of options for flexible work. Empowering employees and teams to choose their preferred modes of communicating—whether by video chat, instant messaging, email, or conference calls—will go a long way in setting a collaborative atmosphere.

“Whether your team is distributed or local, it is so important to implement the right tools for clear communication, visibility and context setting. Having everyone sit in the same room won’t necessarily solve the communication challenge for you.”

Keith Valory, CEO of Plex

“Without the luxury of seeing colleagues each day, it can, at times, take longer to identify issues.  For this reason, managers need to see engagement and communication as key priorities for their team.”

Claire O’Connell, Director, People & Culture at Canonical

4.     Emphasizing Savings, Downplaying Costs

Never forget that your balance sheet includes both savings AND costs. If you’re eliminating fixed costs in the form of office space or other real estate, other costs may likely arise.

For example, many remote firms hold semi-annual or annual face-to-face company retreats; are you prepared to invest in travel and associated expenses for your team? Hiring also can become a costlier process if you don’t have specific filters in place to find the best candidates. Remote positions tend to attract a lot of applicants, but if you aren’t equipped to select those who are truly prepared to flourish in this setting, your hiring process will be longer with stops and starts. It’s also worth noting that shipping and handling expenses will be an initial burden for any company making the transition to fully remote work.

Last but not least, you’ll have to find solutions (mostly technological) to offset the opportunity costs—missing those spur-of-the-moment hallway chats and critical meetings that Mayer has been keen to preserve.

“The biggest challenge has been hiring; primarily making the false assumption at the start that any talented employee would make a great remote employee. It’s simply not true, and remote work is a skill that you need to look for when you hire.”

Alex Turnbull, Founder and CEO of Groove

5.     Neglecting Governance and Protocol

Disregard the fact that flexibility should go hand-in-hand with new policies and procedures, and you’ll soon be regretting it. A change in work environment requires leadership and direction; how will employees navigate these unchartered waters without a (company) compass? When and where people will work, how secure their networks are, what tools they need to use, and what legitimate time off looks like—and how much is allotted—are items worthy of consideration before moving to a remote work environment.

Here are some tips on establishing a remote work policy:

  • Determine what working hours will or won’t be mandatory, depending on the goals for each role or department;
  • Explain how employees should categorize and request vacation or sick time, how it’s earned, and how much is permitted;
  • Set expectations between employees and managers, and offer suggestions for how each reporting structure can be best positioned for success;
  • Lay out parameters regarding security requirements, including equipment, device, and software types, tech updates, password or document encryption, and other standards to ensure your sensitive data remains safe;
  • Establish HR policies for onboarding (now a new frontier when done remotely), employee review processes, and conflict resolution.

“We went remote about a year ago, and we put a lot of thinking into it. We laid out the pros and cons, talked to our team members and did some research. Once we started going remotely, we had a lot of questions about staying productive remotely, maintaining a company culture and managing a distributed team and we all learned together to make it work.”

Alari Aho, CEO and Founder of Toggl


By Kristi DePaul | June 16, 2016 | Categories: Why Go Remote


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