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Remote Workers

How to Transition Your Team to Remote Work

How to Transition Your Team to Remote Work
Image credit: Tom Werner | Getty Images
Guest Writer
Co-Founder and CEO of Gain
6 min read
Opinions expressed by Entrepreneur contributors are their own.

The number of organizations that offer flexible or completely remote work options increased by 40 percent over the past five years. Companies transitioning to remote work stand to benefit greatly when it comes to hiring top talent and keeping their employees happy. However, taking away the office and sending off employees to work remotely is not an easy undertaking. It requires significant planning and preparation.

Related: A Remote Workforce Keeps Your Business Agile

Here’s what to keep in mind for a successful transition to remote work.

Define remote work policies.

According to Upwork, the majority of hiring managers said they have the resources to hire remote employees, but they don’t have the necessary procedures in place. Before transitioning a team to remote work, it’s important to outline expectations, share them with everyone on the team, and update them regularly.

These policies will depend on the team size and needs, however, a general remote policy should outline:

  • Availability -- Does the team need to be online during specific business hours or will they be able to set their own schedules?
  • Tools -- Which tools will the team use to communicate and collaborate effectively?
  • Data management -- Which tools will the team use to organize and share documents and information securely?
  • Productivity -- How will the team track progress on projects and measure results?

Update hiring policies.

Going remote brings a whole new set of challenges to the hiring process as well. Whether a company is building a remote workforce from scratch or transitioning to hiring remote employees only, managers will need to revise any hiring strategies to reflect remote work expectations and responsibilities. For instance, it may be more important to focus on a candidate’s soft skills -- such as self-motivation and communication skills -- to ensure they’ll be an appropriate addition to the team.

Have the right tools ready.

Team collaboration and communication can become messy and disconnected quickly if managers aren’t careful. Therefore, it’s important to have all the tools in place to support remote workers before making the switch.


When working remotely, teams will need a way to communicate with each other painlessly. Email is not always the best option, so remote teams should opt for communication tools such as Slack, HipChat or Skype to stay connected. All of these tools offer real-time messaging, video call options and the ability to organize conversations by channel, project or topic.

Project management.

Organization will be key for teams working remotely. It’s a good idea to set up a cloud-based project management tool so that everyone can access the files and information they need at any time. These tools also offer ways to organize projects between different departments and set deadline reminders. A few of the most popular project management tools for remote teams include Trello and Basecamp. For document and file sharing and management, Google Drive, DropBox and Box are popular options.

Related: Is Remote Work Making Open Plan Office a Relic?


How do remote managers know if their remote employees are really working? Nowadays, most remote teams assess their employees based on the number of tasks completed and whether or not they are meeting their goals, rather than the number of hours they clock in each day. However, it can still be challenging to keep everyone on task. If productivity begins to slip, time-tracking tools such as Toggl, Tick and Timesheets can be used to monitor projects or simply assess how long tasks are actually taking to complete to make improvements.


Going remote means many team members will be tapping into WiFi networks at cafes, coworking spaces, libraries and other public spaces to do their work. Therefore, it’s important to have an information security policy in place before transitioning to remote work. Remote teams should create secure passwords with tools like LastPass and update them frequently. Sensitive information should be stored in a secure cloud storage platform like Box, and a virtual private network (VPN) like VyprVPN is recommended when connecting to public networks.

Prepare managers.

A successful transition to remote work also depends heavily on well-prepared managers or team leaders. For many managers, the process can quickly become overwhelming, so it’s important to train and prepare them well. The first step is to make sure managers have the right tools (such as those mentioned above), so they can be available for their employees, answer any questions, offer feedback, and most importantly, keep projects on track.

Have a meeting place.

Going remote allows teams to eliminate the expenses that come with an office space, such as rent and utilities. However, it still may be necessary to have a physical place for the occasional team or client meeting. In most cities, there are temporary office spaces that teams can rent by the hour or day. These services can range from lavish meeting rooms that can impress clients to creative and comfortable spaces for in-person brainstorming or collaboration sessions.


Maintain company culture.

A positive company culture is fundamental for employee engagement. In fact, according to Gallup’s 2017 State of the American Workplace report, company culture was among the top five reasons why employees leave their jobs for positions with other companies.  

Many teams fear that by going remote, company culture will suffer. However, this couldn’t be further from the truth so long as team leaders make an effort to maintain it. With some creativity, teams can maintain a strong company culture. For example, with the money saved from eliminating an office space, teams can travel and meet each other quarterly or annually.

In addition to a team retreat, there are lots of ways to maintain a company culture digitally. For instance, regular video conferencing, rewards for accomplishments (such as gift cards), and having a place for team members to chat casually (such as a Slack channel or Whatsapp group) can help bring employees together.

Trust and let go.

About 35 percent of employees admitted they would leave their current job for one that offered remote work. Additionally, 90 percent of people who currently work remotely say they plan to continue doing so for the rest of their career. The demand for remote work isn’t going away, and team leaders that don’t trust their employees will find transitioning to remote work difficult.

There will be challenges along the way and managers won’t be able to control everything all of the time, so it’s important to let employees find their own solutions to challenges that arise when necessary and suggest how to improve things moving forward.

With the right planning and preparation, teams can transition to remote work successfully.

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