20 min read

Top 15 Remote Work Challenges and How to Overcome Them

Top 15 Remote Work Challenges and How to Overcome Them

No long commute, no managers or co-workers distracting you, and more time for your personal life. There's no doubt, remote work has benefits, but it's not without challenges.

Ask anyone who works remotely: It's not all smooth sailing. Yes, it's never been easier to find to find a remote job or attract remote employees. That doesn't mean it isn't important to understand the most common remote work challenges.

At Himalayas, we're massive proponents of remote work but we also understand the challenges and the need for workers to have remote work skills. Whether you're thinking about working remotely, currently a remote worker, or about hiring remote employees, read on to learn about the most common challenges and how to overcome them.

Woman working with two kids in background

1. Overworking and not being able to unplug

A common myth associated with remote workers is that they're slacking off. But in reality, the opposite tends to be true: remote workers are more likely to overwork.

According to Buffer's State of Remote Work report, not being able to unplug is the biggest challenge remote workers face. While a flexible schedule and no commute saves time and money, it also means no separation between home and work.

This lack of separation can lead to longer work hours than you would work in an office environment, and is compounded when you work in a remote team spread across time zones.

New team members often experience this most acutely, particularly those who are new to remote work. When you haven't built trust with your team, it's easy to overcompensate by always being online.

Pair this with the limited social interaction most of us have had due to the coronavirus pandemic and you've got a recipe for burnout.

How to avoid overworking when remote working:

  • Set your working hours in your calendar: This makes it easy for team members to see when you are and aren't working. When work is over, get out of your home office for the day. Learn how to set working hours in Google Calendar here.
  • Set reminders to take breaks: Setting a recurring daily reminder to take a walk, make lunch, or just get outside for a few minutes is a great way to reduce burnout.
  • Be clear when you're unavailable: Set your status in Slack as offline, mute notifications until tomorrow, and turn off your computer.
  • Create physical boundaries between work and life: If you have a dedicated home office, one of the best things you can leave the room after work. If you don't, leave your laptop in another room once work has finished. And don't work from your bed...
  • Turn off notifications outside work hours: It's easy to reply to one message to unblock a colleague, but it's just as easy for one message to spiral into ten then twenty, and the next thing you know you're working again. Make it easy to unplug by turning off notifications.
  • Work at a remote company that values down time: The best remote companies establish a company culture of reasonable expectations and don't expect people to work too much. Sure, every now and then there's need for additional hours but most of the time work should be seen as a marathon not a sprint.
Zoom call

2. Difficulties with collaboration and communication

Collaborating and communicating effectively is one of the most common challenges for remote team members. In REMOTE: Office Not Required, Basecamp founders Jason Fried and David Heinemeier Hansson outline why:

When the bulk of your communication happens via email and the like, it doesn't take much for bad blood to develop unless everyone is making their best effort to the contrary. Small misunderstandings that could have been nipped in the bud with the wink of an eye or a certain tone of voice can quickly snowball into drama.

Communication issues are already abundant in a traditional office environment and compounded further if some of the team works in the office and others don't.

If you work from home while everyone else is in the office, you miss out on impromptu discussions and ad-hoc meetings. This can lead to fear of missing out and you feeling paranoid that others are making decisions without you. And you're probably right. Unless the company culture is inclusive for remote workers.

How to collaborate and communication effectively in a remote work environment:

  • Over-communicate: The best solution is to over-communicate, particularly if real-time communication is challenging. Clarify misunderstandings as soon as possible and be proactive.
  • Ask good questions: While there's no such thing as a stupid question, there are unproductive questions that could have been phrased better for the recipient. When working remotely, invest time upfront when asking questions. Aim to give people sufficient context, identify places where you've made assumptions, and preempt any questions they might have. There's nothing worse than asking a question, waiting a few hours for a response, and getting back another question because you provide enough context.
  • Emphasize writing: Most remote teams rely on written documentation and async collaboration rather than real-time video conferencing. This reduces the burden on team members in other time zones to be available.
  • Default to transparency: Working in public is the best way to ensure everyone is on the same page. Give people access to as much as possible so they can look for information themselves. Always communicate in public unless it's sensitive or personal. You never know who else needs to be aware of what you're working on.
  • Record everything: If you do have a meeting, record it, and share it with whoever wasn't able to make it. Recordings makes it easier for people to sign off without fear of missing out.
  • Default to action: Asking for permission takes time, particularly in a distributed team. It's essential continue working when possible instead of waiting for permission and if you can unblock a colleague who is offline, do it!
Man working at table

3. Loneliness

Hell might be other people, but isolation sure isn't heaven. Even the most introverted people need social interaction. Humans aren't designed for solitude.

Loneliness is one of the most common issues with remote work that has only been accentuated by the COVID pandemic. If you live alone, it's hard to not feel isolated. Even with Internet access, video conferencing, and tools like Slack, it's still possible to develop cabin fever from being alone in your house for too long.

Working in an office is filled with impromptu moments that break up your day, many of which are unwanted distractions. Other moments, like grabbing lunch with colleagues, are a great way to break up the day.

This issue can be felt acutely when working asynchronously.

How to overcome remote work loneliness:

  • Remember that social interaction doesn't have to come from co-workers: We're not saying you shouldn't be friends with your colleagues, you should! Just remember that you also have your spouse, children, family, friends, or neighbors to hang out with!
  • Work out of a co-working space: Co-working spaces are a great way to get the social benefits of an office without the distraction of working closely with your colleagues. Many remote companies offer co-working stipends for this exact reason.
  • Play a sport: Not only will playing a sport get you out of the house and interacting with people, it'll also make you healthier, happier, and more productive when you are working.
  • Wander out in the real world: Everywhere, no matter how small, offers social activities to keep you sane, whether it's playing chess in the park, finding a pickup game of basketball, or volunteering on your lunch break.
  • Play video games: Videos games are a great way to get social interaction without leaving the house and may even teach you some skills that are applicable to working remotely.
Two people working at desk

4. Distractions at home

For some, working from home can be lonely. For others, it's filled with distraction. Yes, working from home means you avoid co-workers dropping by your desk unannounced but it does nothing to stop your family members.

Whether it's your partner distracting you, a delivery person needing your signature, or the fire alarm going off, distractions are everywhere. Working remotely can be particularly difficult if you have young kids at home who can't understand why mom or dad can't play.

It's impossible to avoid all interruptions and interruptions can be a good thing, particularly if you're already working too much!

How to deal with interruptions at home:

  • Be clear about what interruptions are and aren't okay: Set boundaries with your family and help them understand can wait until you're having a break. We also recommend setting up clear breaks in your day so people know when you're available.
  • Let people know when you're in deep work: Close the door, tell your family not to interrupt you for a few hours, and put on headphones.
  • Explain why it's important for you to focus: Let everyone know that each time they distract you it takes you 20+ minutes to get back to work, making it harder for you to get your job done.
  • Invest in childcare: This is a personal decision but employing a nanny or sending the kids to childcare can dramatically improve your ability to focus while working from home.
  • Train your kids and significant other to occupy themselves: If you respond to every interruption, you signal to your kids or significant other that interrupting you is fine.
  • Keep consistent work hours: Not only will this help maintain a healthy work-life balance, it lets everyone know when you're available.
  • If all else fails, escape: If you can't work productively from home, invest in a co-working membership or head to the library or cafe for a few hours.
Man tired working at computer

5. Staying motivated, time management, and prioritizing work

Remote workers need to be self-motivated and experts at time management. Unlike in-office employees, we don't have anyone constantly watching us work or managing our time.

While commuting has its downsides, it does make it easier to stick to a schedule. If you have a more flexible schedule, work asynchronously, and have a manager in a different part of the world, it can be even harder.

Not to mention the temptation to watch TV, scroll the web, or do a few household chores to put off starting a difficult task at work.

How to stay motivated and get important work done:

  • Focus on deep work: Deep work is the ability to focus without distraction on cognitively demanding tasks. It's a skill that allows you to quickly master complicated information and produce better results in less time. Instead of working for a few minutes then scrolling social media, block out a few hours to focus.
  • Eat the frog: Mark Twain once said, “If it's your job to eat a frog, it's best to do it first thing in the morning. And If it's your job to eat two frogs, it's best to eat the biggest one first.” In other words, identify the most important thing and do it first then worry about whatever is next.
  • Limit the number of things you do each day: This might seem counterintuitive but it's much better to do one important thing than ten small tasks that don't move the needle. If everything is important, nothing is.
  • Leverage tools: If you don't have the self-control to get off social media, install something on your computer and phone to block it. If spending $50 on a SaaS product saves you 30 hours a month, buy it.
  • Manage your energy: If you're struggling to work, take a break. If you're tired, take a nap. It's often easier to stop than try to force yourself to work. After all, one of the reasons you work remotely is to have more control over your time, so take advantage of it.
  • Focus on output, not hours worked: Remote companies should focus on results as opposed to hours. Fundamentally, this requires organizational trust. You need to believe that your colleagues will do the right thing.
Woman in video call

6. Being in a different time zone than teammates

Time zone differences compound collaboration and communication difficulties even further. It's not uncommon to be waking up as your teammate is going to bed. You can't rely on them to answer your questions quickly and if you send a message outside their working hours, you're making it harder to unplug.

A lot of the tips we outlined in how to collaborate and communicate effectively in a remote work environment will also apply when collaborating across time zones, so re-read those too.

How to collaborate across time zones:

  • Be flexible: When you work with people in different time zones, you need to think about when to send a message and learn not to reply to every notification when you're not working.
  • Consider having overlap with your team: Jason Fried and David Heinemeier Hansson, the co-founders of Basecamp, recommend teams have a four-hour overlap: Working remotely, if it is to be successful, usually requires some overlap with the hours your coworkers are putting in...we've found that we need a good four hours of overlap to avoid collaboration delays and feel like a team.
  • Learn to work asynchronously: If you don't have overlap or work in a globally distributed team then you'll need to work asynchronously like GitLab. The benefit of async work is that your company operates on a 24-hour clock instead of eight hours. Asynchronous communication challenges the traditional modes of workplace communication but can be more efficient and effective while ensuring team members have work-life balance.
  • Make the most of the synchronous time you have: If you do need to get together in real-time, make the most of it. Invest the time into writing an agenda ahead of time, take notes about the meeting and any decisions made, record the video for those that can't attend, and most importantly try to make it fun!
Woman frustrated with computer

7. Technology problems

Technology is not a panacea. Internet can be flaky, software can have bugs, and technology can grind to a halt. When you rely on computers and the Internet for everything, you're relying on technology that is far from perfect. Computers can break, Internet can disconnect, and it can take a few hours or even a few days to find a replacement.

This isn't too difficult if you live and work in a first world country, but becomes harder if you're a digital nomad who travels and works at the same time. Public Wi-Fi can be spotty and even if you have a decent Internet connection, video conferencing software can still be a source of frustration.

How to mitigate technology issues:

  • Have a backup plan: Invest in a mobile hot spot or a mobile plan with generous data allowances for times when your Internet fails. It could even be as simple as relying on text or voice only when Internet is spotty. Likewise, a backup computer or even your phone can tide you over if your computer needs to be replaced.
  • Invest in quality software: If you're a remote worker, you rely on software to do your job. Like any craftsperson, you should invest in your tools. At Himalayas, we use best-in-class software like Linear, Discord, Figma, and 1Password to stay productive.
  • Be flexible and work asynchronously: If the team isn't reliant on being in contact constantly to get work done, temporary technology issues become less of a pain. Everyone can keep working until you're back online rather than worrying about whether you'll be able to connect to the meeting.
Man working at table

8. Unhealthy or sedentary lifestyle

Knowledge workers tend to live a more sedentary lifestyle than blue-collar workers, no matter where their office is. However, when you're working from home it can be even easier to slip into bad habits.

Your fridge is only a few steps away and inversely, without co-workers to remind you to eat, it can be easy to forget lunch. You also miss out on any incident exercise you might get from walking to the office or train station.

How to stay healthy while working from home:

  • Set up your environment for success: If you know that you'll plow through a box of cookies if they're in the cupboard, don't buy them. The added friction of having to go to the shops can dramatically reduce your chances of indulging.
  • Make it easy to exercise: Invest in a home gym, join a group fitness class, or add a fake 30-minute commute in the form of a walk around the neighborhood before and after work.
  • Start with exercise that is ridiculously small: The best way to make exercise a habit is to start with something that is so easy that you can do it when you're running low on willpower. Make it so easy you can't say no.
  • Focus on habits, not results: Rather than saying you want to maintain a certain weight, gain muscle, or lose weight, focus on the habit of exercise and eating healthy instead.
Notion knowledge base screenshot
Notion is a great tool for building an internal knowledge bases

9. Lack of work structure

One of the biggest challenges of remote working is the lack of work structure. With everyone operating in different time zones with differing deadlines, tasks, communication styles, and priorities it can be hard to know what is going on.

This is why it's so important for remote companies to provide their employees with a clear understanding of what they value, what is important, and what isn't. Otherwise working on a flexible schedule can be stress-inducing.

How to add structure to a remote work environment:

  • Develop an internal knowledge base: Notion is a great way to connect your team, projects, and docs while working remotely. It works well because it's customizable and can work in the way you want it to.
  • Create an employee handbook: An employee handbook is an informative guide that outlines company culture, rules and policies, best practices, and everything else a new hire would want to know on their first day.
  • Invest in onboarding: Onboarding can be difficult when you're remote because it involves more self-learning and you're not physically with your new co-workers. Your onboarding should focus on: the organization, any technical skills the person needs to learn, and social interaction with colleagues. Read our guide on remote onboarding.
  • Leverage project management tools: While tools won't solve all your problems, there are many great tools that are designed to help your team assign tasks and track progress. A few we like are Trello, Productboard, Linear, and Basecamp.
Woman in interview

10. You're not as visible so career advance can take extra work

Career advancement is particularly challenging if you work from home while the majority of your teamwork from the office. You're simply not as visible to your manager so career advancement will take more work.

This is accentuated if your manager doesn't have experience managing a remote team, as they may assume you're not working as hard as your in-office teammates.

You need to take control of your own career advancement and constantly explain, prove, and justify that your performance is there.

How to advance your career while working remotely:

  • Work for a remote-focused company: A simple way to avoid getting passed up for promotions while working remotely is to work somewhere where everyone or the majority is working remotely. Look at companies like Zapier, 10up, Arkency, Articulate, Stripe, Spotify, Shopify, Automattic, or Buffer.
  • Learn to communicate your worth: Write a monthly metrics update and share it in Slack or write a product requirements document that specs out a new feature that you think is worth building. This will not only help you get promoted but teach you how to communicate metrics, an important skill for your career.
  • Meet with your manager and tell them about your career goals: Tell your manager that you want to level up and get them to explain what you need to do to advance to the next level. Put your hand up for important projects and think through how you can maximize your impact.
  • Don't only rely on work to upskill you: Read books like High Output Management and 7 Powers to learn more about management and strategy, take online courses, and do your part to become more valuable.
Zoom call

11. Language and cultural differences

One of the biggest benefits of working in a remote team is that your colleagues are spread all over the world and will likely be from a mix of language and cultural backgrounds. This diversity can help you make better products, reach into new markets, and expand how you see the world. But it also has its challenges.

The obvious challenge is varying levels of language proficiency, but there are also subtle cultural differences that need to be understood. The way people work and what they expect from a workplace tends on where they grew up and where they live. Social conventions are real if you don't understand them, it can make remote work difficult.

How to solve language and cultural differences:

  • Be aware people may be working in their second language: Everyone needs to understand that a person's language ability shouldn't be critiqued or made fun of. If you're a native speaker, be aware that misunderstandings will happen. Do your best to write and speak clearly, and use simple words. This makes it easier for non-native speakers to understand you.
  • Communicate by writing: If you need to communicate important information to non-native speakers, do it in writing. When you talk, people only have one chance to understand everything unless you record it. Even if you record it, reading is often still easier. When you read, you can go at your own pace, re-read bits multiple times if necessary, and look up any words you're not familiar with.
  • Instill a strong company culture: One of the best ways to overcome cultural differences is set a strong and unique company culture that clearly articulates how your team works together. This will help people from different cultures come together and understand how they should communicate with each other when at work.
  • Encourage open and honest conversation: It's easy to offend people from different cultures with an off-hand comment about religion, politics, or culture. Do your best to promote tolerance and understanding across all topics by encouraging everyone to be honest with each other when something offends them.
  • Learn about other cultures: Ask your teammates to teach you about their culture, see if there is any TV shows you could watch, books you could read, or better yet go and visit them in person in their country! Best of all, you'll have a knowledgeable and local tour guide.
Woman in meeting

12. Building and maintaining trust

Trust issues can arise among remote teams when you can't physically see what everyone is doing. This is particularly true if team members have never met each other face-to-face.

There are a number of tools you can use to deal with these issues – for example, Donut helps connect teams serendipitously for virtual coffee, peer learning, DEI discussions, and more.

The best thing you can do is develop a nurture a set of common values, objectives, and methods that are essential for the existence of trust. One way to do this is by articulating them, the more important way is to lead by example.

If your behavior is in line with the values you proses, you'll foster the development of a strong company culture.

How to build and maintain trust in a remote team:

  • Get to know each other: Organize one-on-ones with everyone on the team and ideally, organize a company-wide retreat where people from different teams can hang out and get to know each other in person.
  • Be responsive and reliable: While you need to set boundaries around work, you also need to be there for your team when they need you. Do your best to respond to team members and get your part of projects done on time.
  • Promote transparency: Be transparent with what you're working on, whether it's working, and whether you need a helping hand to push it along. This will not only help you but help people who could benefit from your work.
  • Create shared goals: When people have shared goals and understand what they're working toward, it's easier to build and maintain trust. If you don't know where you're going, you can't expect to get there.
  • Avoid micromanagement: There's nothing worse than a manager who is constantly messaging you to see what you're doing. People choose to work remotely to get away from this type of behavior. Not only does it ruin productivity but it breaks trust and lowers morale.
Two people in meeting

13. Learning, mentorship, and tribal knowledge can be harder to come by

Remote work generally makes informal information sharing harder. As a remote worker, it's harder to get help quickly, and it takes more work to initiate the conversation. But it's critical to do if you're blocked or don't understand something.

It's also hard to pass on tribal knowledge. For context, organizations tend to establish unspoken norms, rules of behavior, and ways of doing things that can be difficult to get a grasp on if you're working remotely as it is generally learned through observation and osmosis.

This doesn't mean learning, development, and mentorship is impossible in a remote environment. In fact, remote companies may have an advantage in some respects as they need to create programs that can scale across cultures, time zones, and teams. It's also more inclusive as people can learn in environments that are most comfortable for them.

How to promote learning, mentorship, and knowledge transfer when working remotely:

  • Be proactive about establishing and documenting communication norms and tribal knowledge: You can't rely on informal information sharing when working remotely. You need to be deliberate and document everything so new employees can get up to speed quickly.
  • Set aside time for learning, development, and mentorship: While asynchronous work is fantastic, it takes more deliberate effort to upskill the team asynchronously. It's crucial to support the growth of remote workers just as you would with in-office colleagues.
  • Encourage informal discussions: While informal conversations can seem tangential, nonessential, or unrelated to work, the opposite is true. Interacting with your colleagues as people is essential to getting real work done.
  • Invest in your team: Provide each remote employee with a budget to invest in their learning and development. This is not only good for the company but good for the employee. It's a great way to attract talented remote workers.
Desk setup at night

14. Information security risks

Security is an often overlooked challenge of working remotely. Even if your remote team does everything right, there is still a risk that a third-party exposes you or your customer's data. Not to mention the risk of man-in-the-middle attacks on public Wi-Fi networks...

There's a lot companies can do at the infrastructure level and individual level to keep data secure, but the truth is confidential information is only as secure as the weakest link which is often the employee.

How to reduce information security risk while working remotely:

  • Have a secure office: Physical security shouldn't go out the window when you're working from home. Laptops can be stolen from your home office or the cafe. Keep your workspace secure.
  • Keep devices up-to-date: Ensure all devices are up-to-date as soon as possible, ideally via automatic updates. This reduces the risk of attackers taking advantage of known vulnerabilities in operating systems.
  • Keep software up-to-date: Most modern software will check for and apply security patches automatically. Likewise, consider using hosted SaaS applications over installable software as it will always be up-to-date.
  • Enable automatic locking: Make sure your devices lock if they haven't been used for a specific amount of time, such as 30 seconds for your phone and five minutes for your laptop.
  • Use strong passwords and invest in a password manager: Make sure you avoid passwords that are easy to guess. A simple way to avoid this is to invest in a password manager like 1Password.
  • Enable two-factor authentication: Two-factor authentication can dramatically reduce the risk of successful phishing emails and malware infections because even if the attacker is able to get your password, they are unable to log in because they do not have the second piece of evidence.
Trio in meeting

15. Unnecessary or too many meetings

One common mistake newly remote managers make is trying to overcompensate for remote work by scheduling more meetings. While meetings can bring a team together for knowledge sharing and decision-making, they can also break up people's workdays and make it harder to find flow.

Research shows it can take 20+ minutes to resume deep concentration after an interruption. So not only do you lose time in the meeting, you also lose time before and after by fragmenting work sessions. A calendar full of meetings is a sure-fire way to decrease productivity.

How to avoid unnecessary meetings when working remotely:

  • No meetings without an agenda: If a meeting doesn't have an agenda then it shouldn't be a meeting. Force people to think through what they want to discuss ahead of time and only call meetings as a last resort.
  • Limit the number of internal meeting hours per week: Not only will this save time and encourage deep work, but it'll also make the meetings you do have more valuable and efficient. Attendees will be more engaged, alert, and motivated to use their time wisely.
  • Encourage asynchronous communication: This is particularly important if you are working at an all-remote company with team members in different time zones who may have to compromise on meeting times. Rely on writing things down to facilitate work without meetings. This will also help reduce the feeling of missing out if you can't attend meetings.