What are the challenges of working remotely?

In 2017, IBM decided to withdraw its immensely popular work-from-home policy and ask its remote workers in IT, procurement, and Watson-related departments to “co-locate” in one of six U.S. cities in a bid to foster more in-person collaboration.

When a pro-remote company that has embraced remote work culture for decades then, starting from the early 1980s, decides to call its employees back onsite, it was a matter as a concern not just to its employees, but to quite a lot of eyeballs.

We completely stand by our belief that remote is the future of work, but we’ll be completely blunt and say this too:

Not every company is built to work remotely.

Does that mean they cannot manage to make it work? Of course not!

“Technology now allows people to connect anytime, anywhere, to anyone in the world, from almost any device. This is dramatically changing the way people work. Especially, when facilitating 24×7 collaboration with colleagues who are dispersed across time zones, countries, and continents. Dell is a global technology leader, so our team members should be able to take advantage of the flexible work opportunities that our own products and services create.” – Dell report

The 2019 State of Remote Work report showed that 62% of the respondents worked remotely at any frequency.

It has several undisputed advantages too – cost savings, increased productivity, improved employee satisfaction, reduced attrition, and enhanced talent recruitment and retention.

However, not every company is convinced of the benefits due to the challenges involved in managing a virtual workforce. So coming back to cases like IBM…

Not Every Company Endorses Remote Working Benefits

Why so?

It may not work for them, maybe it didn’t too.

Previously, Yahoo’s Marissa Meyer had shut down the company’s work-from-home options, drawing swift and negative backlash from all quarters. Other companies, like Bank of America, Honeywell and Best Buy also abandoned their remote work initiatives.

The reasons these companies gave for stopping remote working options were to improve productivity and increase collaboration by encouraging face-to-face engagement.

Source: Omnis Group

No one denies that there are challenging aspects to remote work.

Any kind of work comes with its fair share of challenges, it may just be worth your efforts to overcome those. In fact, some companies have turned those around to give them that extra edge too. Here’s how.

Challenge 1: Communication

Source: Time Doctor’s

Most of the work is done via email, calls, or chat making sure of the time and clear communication.

A survey by Zogby Analytics showed that the two major challenges of working remotely in the United States are:

  1. Failure to share information on time (39%).
  2. Lack of adequate information sharing by the management (38%)


Managers should take care to avoid falling into the “out of sight, out of mind” trap. If remote workers are located in different time zones, coordination and scheduling meetings become significant hurdles ineffective communication.

Choose the right tools to communicate effectively.

Beyond the phone and email, there are a number of tools to streamline day-to-day operations.

Slack is a popular instant messaging option to quickly check in on team members, Dropbox and Google Spreadsheets can be used for real-time collaboration on documents, Zoom is often used for video conferencing, Calendly is useful for scheduling meetings, and Trello is a popular project management tool- to name just one tool each.

You can read the list of remote work management tools to pick what works best for your work purposes – communication, workflow collaboration, meetings, project management, product issues, and bugs, etc.

Managers can choose which tools are most useful for their remote teams and train their workers to use them effectively. An executive at Collage.com says, “As we’ve grown, we’ve had to focus more on how we communicate to ensure nothing falls through the cracks. Our team loves email and thinks it is a great – and underappreciated – communication tool, but we also now use systems like JIRA to stay on top of critical issues and ensure they are fixed.”

Build a culture of communication in the organization.

Managers can lead by example by prioritizing clear communication, and holding regular check-ins with the team and communicating updates promptly. If team members are present across different countries and time zones, address language and time barriers directly. Provide guidelines about how appropriate language and tone should be used.

Getting the entire team to meet once a year is important to foster engagement and bonding between team members.

Hire people suited for remote work.

Just like not every company is ready to go remote, not everybody is equipped to work remotely either. It may help to hire a person who has experience working remotely, can effectively communicate on calls and through writing, and works proactively.

As Automattic Inc. mentioned, “If this is the first time someone has worked remotely, they may not anticipate that they may have feelings of isolation. We pair people with a mentor in a similar time zone when they first join, so they have a designated person to chat with if they have questions about how we operate, or if they just want to chat. We provide a $250/month (USD) co-working allowance if Automatticians would like to work with others on a regular basis.”

Employers Speak

When companies were asked if they have remote communication protocols in place, these are some of the responses:


“We try to avoid too many emails, instead of using Trello to communicate, Skype for IM, Jing for training, etc. On weekdays, due to the time zones, we like to see responses within the day.”


“There aren’t rigid rules in place for our communication. For example, we do not expect replies on Slack or email within any particular time frame. We encourage daily huddles for team-based projects via videoconferencing.”

GitHub Inc.:

“It depends on the team. I don’t know of any teams in our company that mandate response times for internal communication, but plenty of teams have set up regular schedules for video calls, stand-ups, and patterns of communication to help make sure the whole team stays on the same page over time.”

Challenge 2: Tracking Productivity

Source: Funding Societies Blog

When asked what challenges were encountered while building a remote team, an executive at AgileBits said, “Managing without micro-managing. It’s important for our team to be able to allocate their time in a way that works for them, but it’s also important for our work to get done in a timely manner.”

Managers worry about the myriad distractions present for the remote worker and whether they will get their jobs done on time. While most telecommuters take initiative, others don’t have the necessary drive and discipline and take advantage of the fact that their boss cannot look over their shoulder. On the other hand, some remote workers may burn out due to their failure to set boundaries.


Ensure accountability

Managers can ensure that their remote team members are doing their work properly by setting clear expectations and having regular check-ins. With the usage of project management tools or time tracking tools like Toggl and Harvest, managers can get status updates about work done by remote workers. Certain tools can help keep the team productive – Cold Turkey to block distracting websites,- Coffitivity to provide ambient noise, and Google Drive to synchronize all documents.

Develop processes

Remote workers are often at risk of burnout from working at all hours and forgetting to set boundaries. Managers must encourage team members to keep regular office hours and be observant of the signs of burnout—a drop in output quality, erratic or moody behavior, and emails being sent at odd hours. Regular one-on-one meetings with team members help managers provide the necessary support, while also holding the worker accountable for his/her performance and evaluating the workload.

Employers Speak


“It’s not always easy to collaborate on projects when working remotely. Collaboration is different when you can just stop by someone’s desk. To address this, some sort of online project management tool is necessary. In marketing, we use Trello. Our development team uses Sprintly for iteration planning and tracking. Making sure the priorities are clearly defined and well-organized helps keep our distributed team on track.”


“One of the biggest challenges of running a remote company for me personally has been to remember to have a life outside of work. I often get asked the question, “How do you make sure your employees are working eight hours each day?” It’s counter-intuitive, but I find that the opposite is true. I really have to emphasize the importance of setting boundaries with my team, so they don’t burn out.”

Challenge 3: Trust

Source: Buffer Open

An important ingredient of a successful remote working arrangement is trust, and it runs both ways. Managers must trust the remote worker enough to assume that he/she is getting work done without the need to constantly check-in. Conversely, the remote worker must trust the manager to be available to help solve issues and provide guidance.

However, the remote worker must earn the manager’s trust over time. Sometimes, it is difficult to determine if someone’s personality is a good fit for telecommuting unless they’re working on the job.


Encourage regular videoconferencing sessions:

Help your team members become familiar with one another. Be sure to send out a message that you’re approachable and available to help them out or give the required support.

Communicate clearly your expectations as a manager:

Your team needs to know that they are working towards a shared goal.

Remote workers should know where they belong and who their reporting manager is. An executive at Automattic Inc. (the team behind WordPress) says, “When Automattic first started, everyone, reported to Matt (Mullenweg, their founder). When we reached about 50 people, we divided into teams. The teams have evolved over time. We’re open to experimentation with our organization structure because we want to continue to have as little hierarchy and bureaucracy as possible.”

Employers Speak

When asked how companies foster communication and build culture, they said:

American Express:

“Broadly speaking, our culture is based on the Relationship Care approach to service. An ethos that says service is a people business driven by the power of human interaction. To that end, all of our employees receive constant coaching on how to connect with customers and deepen loyalty. While the form factor may be slightly different – virtual side-by-sides as opposed to in-person coaching – the approach is the same.”


“I’ve found that the little things really make a difference. Acknowledging birthdays and work anniversaries on Yammer. We practice that style of communication by providing opportunities for regular check-ins with managers and HR, as well as platforms and norms for easy one-off discussions. Finally, we train our managers to be compassionate and flexible with their teams and to get creative, when necessary, to meet business goals.”

Stack Overflow:

“We have remote social hangouts every Friday. Everyone is invited to hop onto a video call to hang out with their coworkers with a beverage of their choice. We also have a program Stack Roulette that matches you with 2 people from different locations. Usually, the departments in the company to get to know coworkers you otherwise wouldn’t.”

The Bottom Line: “Go all in.”

As 10up Inc., an entirely remote company, says, “Go all in, if you’re going to make the leap. In order to select and build the tools, systems, habits, and culture that really enable remote working, everyone has to feel both the pain and benefits – especially the company’s leadership.”

Satabdi Mukherjee

About Satabdi Mukherjee

Satabdi Mukherjee is an HR tech writer who shares engaging and informative pieces about trending recruitment topics and advances in recruitment technology. She enjoys keeping up with innovations in the HR community.

View all posts by Satabdi Mukherjee

Leave a Reply