5 Challenges of Working Remotely & Ways to Tackle Them

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Nowadays more and more companies are incorporating flex time and integrating digital nomads and remote workers to their workforce. As reported by Global Workplace Analytics, telecommuting, also known as remote work, has grown 103% since 2005 with a 6.5 percent increase in 2014 alone! Some even project that 50% of people will work remotely by 2020.

This trend is especially true for the software industry. Many companies such as GitLab, Mozilla, Zapier, InVision, Buffer, Clevertech and Canonical are comprised of teams who do most of their working from home. This makes a lot of sense, after all. A stable internet connection and headsets are really all you need in order to work from home.

Nevertheless, working remotely poses some challenges as well; I know this first hand. Though my home is located close to the office, my team is distributed across four cities and I tend to work from home regularly. To learn more about the issues that can arise while working remotely, I turned to the #remote channel of one of my favorite Slack communities, Women In Tech. We discussed the challenges of working remotely as well as ways to overcome them.

Here’s a list of the top 5 challenges remote workers typically encounter:

Challenge #1 Bonding with your team

When you work in an office next to your teammates, some bonding is bound to happen. More than likely you’ll spend several minutes each day talking about each other’s personal lives and sharing opinions about work related topics as well. Getting to know each other on a personal level definitely increases the level of trust and rapport of a team. Unfortunately, this is something that is harder to achieve when working remotely or on a distributed team.

With a remote team, opportunities to bond on a personal level with teammates won’t just present themselves, you have to make them happen.

How to tackle it:

  • Start the conversation

In her post “Remote Work in Review”, Kim Moir, Release Engineer at Mozilla, gives the following advice: “Talk about stuff not directly related to code with your coworkers so you have some rapport for them as people outside the context of work.” Finding shared interests might take a while, but you can always crack some jokes to break the ice.

  • Meet up with your team in person on a regular basis

This is a great way to get to know your teammates. In Kim’s words, “when you know them as people, you are more willing to help each other and feel more cohesive as a team.” So, leverage company retreats to bond with them, or set aside a few days each year to visit the office.

Challenge #2 Getting feedback

When working remotely, feedback is not immediate and in many cases you don’t get any at all. Without feedback employees feel uncertain about their performance and don’t know what they’re doing right or in which areas they need to improve.

How to tackle it:

  • Ask for feedback constantly

Don’t wait for your team to give you feedback, ask them for it every once in awhile. It can be hard at first, but they will appreciate your desire to improve.

You can also have 1-on-1s with your boss to have an in depth talk about your performance.

  • Have retrospectives

Even if you’re not a developer, retrospective meetings are a great way to analyze what went well, what went wrong and what needs to improve. Suggest implementing retrospective meetings every week or two, and you’ll receive constant feedback. Here’s a post on how to make the most out of retrospectives.

Challenge #3 Time zone differences

This comment really stood out when we discussed this particular challenge:

“If you work in a different time zone it makes it a bit problematic. You submit a PR and would like to discuss it right away, but you can’t do it because the other person already finished his day.”

If the time difference is just of a few hours, it’s not too big of a deal. The real problem starts when your workday doesn’t overlap much with your coworkers’. In such cases communicating in real-time is rarely achieved.

Disconnecting can also be challenging in this situation, especially when you see that your teammates are still working.

How to tackle it:

  • Define time slots for meetings and calls

Discuss a time for meetings that work for all of you, especially for dailies and standups, so no one in particular has to sacrifice their personal time to attend.

Use timezone converters to know when it’s acceptable to contact your teammates or schedule meetings with them. Here’s the one I always use.

  • Write it down!

Don’t wait until your team is connected to ask them what you need. Leave all your comments in your chat for them to tackle when they start their day. You can also use tools to schedule emails to be sent at an appropriate time for your co-workers without disturbing them when they’re off the clock. I recommend this one.

Challenge #4 Focusing and avoiding distractions

When working from home it can be tempting to watch Netflix or read a book when you should be working. There’s no one there to tell you you should, so you have to be very self directed and motivated.

For people with kids or family who stay at home it can be tricky to focus solely on working. Constant interruptions and urgent chores can prevent you from being as productive as you would like to be. Also, finding a quiet place to take calls and have meetings can be quite challenging.

How to tackle it:

  • Setting work hours and a workspace

Focusing on work gets easier when you eliminate, or at least minimize, the potential distractions around you. Leaving your personal devices far away from the workstation is a must. Also, it’s a good idea to make a list of all the tasks you should finish before taking a break, or use Pomodoro to know when it’s time to take breaks.

Challenge #5 Separating work time from personal time

This challenge is completely the opposite from the one above. When working remotely there is no rigid schedule, so you might find yourself working from dusk till dawn if you’re not careful. Disconnecting can be tough, but not doing so can lead to a burnout.

How to tackle it:

  • Set work hours and alarms

You don’t have to follow a strict schedule every day, but alarms help you visualize your workday and when you’re past the eight-hour workday.

Another thing that’s also great for setting work boundaries: external factors.

“I find that having a dog really helps. She makes me stick to a schedule, and I have to stop working to take her for walks.” — Morgan Kay, Wordpress developer at Range.

Spouses, kids and significant others can also play the role of alarms. Their arrivals and or requests let you know it’s time to logout. External factors are really good for setting work boundaries, just find one and use it as your cue to stop working.

  • Log off during your lunch hours

Mark your lunch hours in your calendar to make sure no one schedules meetings for that time and use the reminders as an excuse to log off and enjoy your lunch. As tempting as it may be to rush through a couple of tasks while eating, you won’t be as productive as you think and you won’t give yourself a chance to replenish your energy.

  • Have different devices for work and for personal use

Morgan goes even further and recommends having a separate laptop for work and for personal use. “One of the best things I ever did for work/life boundaries was buy a separate laptop for gaming and fun stuff.”

Kim also has two computers, and she does not use her work laptop when she’s off the clock. “Then I’m not tempted to log in and start working on personal time.” — Kim Maida, Technical writer engineer at Auth0.

In the end, it’s not important which methods you choose to tackle this challenge, the key is making sure you’re not putting your personal life at stake due to not being able to disconnect.

Benefits of working remotely

We already explored some of the many challenges of working remotely, but it’s also important to mention its pros. Here are a few that were mentioned during my chat with the gals:

  • Flexible schedule
  • No dress code (aka working in pajamas)
  • Having total control over your work environment
  • Being able to work on the road — you can travel as long as you have wi-fi. With remote work you’re not limited by geography.
  • Being able to live anywhere! Being able to relocate as needed.
  • Avoiding long commutes to the office
  • More time with family and pets. Perfect for people with babies and children.
  • Choice of workspace: home, coffee shops, outdoors with wifi or hotspot, coworking space.
  • Great for people with chronic illness and other special health needs.


Remote work can be less challenging when you use the right tools. Here are the ones the gals recommended:

  • Slack, HipChat
  • Screenhero
  • Shared issue tracking: Bugzilla/ Github, Trello, JIRA
  • Google Docs
  • Google Hangouts, Skype
  • Tmate

There are lots of useful tools out there for distributed teams, it’s just a matter of trying them out and deciding which ones work best for your team. For instance, at my company most teams use Google Hangouts for video calls and Skype to chat, but my team only uses Slack for the latter. We also use Confluence to keep the documentation of our projects and PlanningWith.Cards to estimate on our backlogs by playing Planning Poker.

Ready to tackle the challenges of working remotely?

Here’s a list of sites dedicated to posting remote job offers:

Let me know what other challenges you’ve faced when working remotely or on a distributed team, as well as the tools that you use to stay connected. :)

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