11 Challenges of Managing Remote Employees (with Solutions!)

frustrated manager in front of his computer screen

Updated: 5/18/2023

Are you a manager of remote employees? Whether you’re a seasoned veteran or new to the game, managing a team of remote workers can both a challenging and rewarding experience. With the rise of remote work and the pandemic accelerating this trend, it’s becoming more important than ever for managers to learn how to navigate the unique challenges of remote work. From communication breakdowns to the potential for distractions and interruptions, there are many factors to consider when managing a remote team. Let’s look at some of them…

1. Communication

Making sure remote employees are communicating is difficult, to say the least. When you’re not in the same location as your team, it can be difficult to understand tone and nonverbal cues. For example, a sarcastic comment made over a messaging app can easily be misinterpreted as rude or unprofessional.

But let’s be real, communication challenges can lead to some pretty hilarious misunderstandings. Like the time I was on a video conference call with a remote employee who had a strong accent. I thought they said they were “happy” with their workload, but they actually said they were “unhappy” with it. I spent the rest of the call trying to come up with solutions to lighten their workload, only to find out later that they were actually satisfied with it. Fail!

It’s moments like these that make me appreciate the importance of clear communication. But it’s not just about avoiding misunderstandings – good communication is essential for building trust, establishing expectations, and keeping everyone on the same page.


There are two standout tactics that I’ve found to be more effective than others: showing vulnerability in your own communication as a manager, and establishing regular check-ins with your team.

First up, vulnerability. It’s almost guaranteed: showing openness and being vulnerable allows others to be comfortable doing that as well. It’s almost like it gives employees a type of “permission” to do the same. Obviously, you want to do this in a professional way, but showing vulnerability will certainly make employees feel more comfortable communicating important things in the future than they otherwise would.

Next, regular check-ins. This is something I had to learn the hard way. Several years ago I hired a new project manager to help our team keep things on track (PM is not my strong suit!). The very first things he instituted was regular check-ins with each team member. It had an instant effect. The team members were far more open in those check-ins vs when we were all on calls together. Which makes sense, as the one-on-ones were more personal and dug into any issues that were specific to that individual employee.

Lastly, make sure to be mindful of different time zones and schedules when communicating with remote employees. Consider scheduling meetings and check-ins during a time that works well for everyone, or using messaging apps that allow for asynchronous communication. Marginalizing someone because of their time zone (whether on purpose or not) is an easy way to alienate them. Unfortunately, I’ve also experienced this as well.

2. Team Building

Team building with remote employees can feel like trying to herd cats – difficult and often chaotic. Without regular face-to-face interaction, it can be hard to build a cohesive sense of team and establish trust between team members. Add different time zones, languages, and cultural differences into the mix, and you’ve got yourself a real challenge.

Unlike traditional office environments, remote teams may never meet in person, which can make it difficult to form a cohesive sense of team and establish trust between team members. This problem can be even bigger when team members are located in different countries and speak different languages.

However, team building is essential for creating a positive work environment and achieving team goals. A strong sense of team can lead to increased productivity, improved communication, and higher job satisfaction among employees.

But don’t worry, team building with remote employees doesn’t have to be a total disaster. In fact, with a little creativity and a lot of patience, it can actually be pretty fun (see the post on virtual events!). Imagine trying to teach your coworkers how to salsa dance over a Zoom call – hilarious, right?


This is easy: schedule regular virtual team-building activities. And no, I don’t mean yet another boring PowerPoint presentation. Get creative and plan something fun like a virtual escape room or a team cooking challenge. These activities provide a fun and relaxed environment where team members can get to know each other on a personal level.

Managers can also take the time to schedule one-on-one meetings with each remote employee. Sure, it’s not quite the same as grabbing a coffee together, but it’s still an opportunity to connect on a personal level. Ask them about their hobbies, their favorite TV shows, or their dream vacation spot. This not only helps to build rapport, but also shows employees that they are valued and supported.

3. Time Management

Time management is crucial when managing remote employees, but it can be a real headache. When you’re not in the same place as your team, it can be tough to know when employees are working and how much they’ve accomplished.

It’s like trying to keep tabs on a teenager who’s supposed to be studying in their room. You have no idea if they’re actually working on their homework or playing video games. Except, in this case, your employees aren’t just procrastinating – they’re potentially wasting your company’s time and money.


To avoid this scenario, it’s important to set clear expectations for work hours and establish a system for tracking hours worked. Encourage employees to take regular breaks to avoid burnout, but also make sure they’re logging in the hours they promised to work.

One way to do this is to utilize project management tools like Asana to keep track of progress and hold employees accountable. These tools can help you see what tasks are being worked on, how much time is being spent on each task, and where employees may be struggling.

Make sure everyone on the team understands what’s expected of them and when. This can help keep everyone on track and ensure that work is being completed on time. But don’t forget to give your employees a little trust and freedom too. Remember, just because you can’t physically see them working doesn’t mean they’re automatically slacking off! Give them the benefit of the doubt and trust that they’ll get the job done.

4. Training and Development

Training and development can be difficult when managing remote employees. Here are some examples of problems that likely seem familiar:

Structure? What structure?: Working from home can be like living on a big, comfy couch – it’s so cozy and inviting that you never want to leave. But as a remote manager, you need to make sure your team doesn’t get too comfortable. Without the structure of an office environment, your team may struggle to stay focused and productive.


The obvious place to start is online training resources. From webinars to online courses, there are plenty of resources available to help employees develop new skills and knowledge. Plus, it’s a great opportunity to show your employees that you care about their growth and development.

Another strategy is to establish a system for virtual mentorship. Pair your remote employees with a mentor who can provide guidance and support. This not only helps to build relationships and trust, but also allows for more personalized training and development.

But let’s be real, sometimes training and development can be a bit of a snooze-fest. It’s important to keep things engaging and fun to keep employees motivated and excited about learning. Try incorporating interactive activities and games into your training sessions. For example, use a virtual whiteboard to brainstorm ideas or have employees participate in a virtual scavenger hunt to learn about the company’s products or services.

5. Cybersecurity

When managing remote employees, cybersecurity is a serious concern that can’t be ignored. Think of it as akin to trying to protect your house from burglars when you’re not there – it can be tricky and nerve-wracking.

Unlike working in a traditional office environment, remote employees may not have the same level of cybersecurity protection. They may be using their own personal devices, connecting to unsecured networks, and accessing company information from public spaces. This lack of protection can make remote workers vulnerable to cyber-attacks and data breaches. Hackers may try to steal sensitive information, install malware, or compromise company systems.


To protect your remote employees and company data, it’s essential to establish clear cybersecurity policies and provide training on safe online practices. This can include using strong passwords, avoiding public Wi-Fi networks, and regularly updating software and antivirus programs. Think of it as creating a digital moat around your company’s data.

But even with the best protection in place, there’s always a risk of cyber-attacks. That’s why it’s crucial to communicate regularly with your team about potential threats and provide guidance on how to avoid them. A company I work for has regular cybersecurity meetings every quarter, for example. It’s common to go over new potential threats, and even run “drills” that replicate real-world scenarios we might encounter (i.e., phishing threats).

6. Technology Issues

Tech can be both a blessing and a curse, especially when it comes to managing remote teams. There are a host of tech issues that can arise, making it challenging for managers to keep everything running smoothly.

Connectivity problems are a common culprit here. When employees are working remotely, they’re often reliant on their home internet connection, which can be unpredictable at best. If their internet goes down, or their laptop freezes, it can disrupt their work and create a headache for managers.

What’s more, remote teams often use a variety of software tools to communicate and collaborate, and not all of them play nicely with each other. Remote workers often access company data from their personal devices, which can create security vulnerabilities.


Providing employees with the necessary equipment, such as routers and reliable laptops, and setting expectations around internet reliability can go a long way in preventing disruptions. Managers can also encourage employees to have backup plans in place, such as using their mobile phones as hotspots, to ensure that work can continue even if their home internet goes down.

In terms of software compatibility issues, managers can ensure that their team members are trained on the software tools they’ll be using, and that everyone is using the same versions. Managers can also encourage their team members to share any software issues they encounter, so they can be addressed as quickly as possible.

Finally, when it comes to security, managers can ensure that their team members are using secure networks and devices. This can include setting up virtual private networks (VPNs) and providing guidance on password management. Years ago, I worked on a team that used a team-wide LastPass account to make sure that all passwords were secure and uniform, no matter who was using it. A policy like this may be useful for you as well.

7. Burnout and Stress

As a remote manager, it’s crucial to recognize and address issues of burnout and stress among your team. Working remotely can be isolating and can take a toll on mental health, which is why it’s so important to prioritize employee well-being.

I know from personal experience how isolating it can be to work alone. That’s why I’m a big advocate for coworking spaces, which can provide a sense of community and support. The pandemic only made this issue worse, as many of us were forced to work from home for extended periods of time. It was a difficult time for everyone, and and highlighted how essential it is to show empathy and support for your team.


It’s important to encourage breaks and to take time off, and to lead by example in taking care of your own mental health. This can include access to mental health support, wellness programs, networking events, memberships to coworking spaces, and even things like virtual yoga classes. If you’re in the States, Anytime Fitness even has a calculator that helps you judge how much your membership might cost.

As a manager, it’s important to make sure that your team members know about these resources and feel comfortable using them.

Ah, the fun and exciting world of remote work legalities. No one likes dealing with taxes and employment laws, but unfortunately, it’s a necessary evil when it comes to managing remote teams. When you have employees working in multiple different countries, it can get complicated quickly. Laws are constantly changing, which can make things even more confusing.

Employment law requirements are a good example of this. Different states and countries have different rules around things like minimum wage, overtime pay, and employment contracts. And unfortunately, something seems to change with every election cycle.

To make matters even more complicated, some governments themselves don’t even know how to handle remote workers! It’s a relatively new phenomenon, and there are still many gray areas when it comes to the legal and regulatory landscape. For example, what state regulates taxes for a remote worker: the state they reside in, or where the company HQ is? It can be a headache.


To address legal and regulatory issues related to remote work, managers need to be proactive and take specific actions to ensure compliance with relevant laws and regulations. Here are three actionable points that managers can take to navigate this complex landscape:

  1. Work with legal and accounting professionals: To ensure compliance with tax and employment laws, it’s important to work with professionals who specialize in these areas. They can help you navigate the complex landscape of regulations and ensure that your remote team members are being treated fairly.
  2. Keep up with regulatory changes: As laws and regulations related to remote work continue to evolve, it’s important to stay up-to-date. This can involve subscribing to industry newsletters, attending conferences and webinars, and networking with other managers in the field.

9. Celebrating Successes and Milestones

Finding ways to celebrate successes and milestones when employees are not physically present isn’t easy, but it’s an important part of keeping remote teams motivated and engaged. Whether it’s a big project milestone or a personal achievement, recognizing and celebrating successes can help remote employees feel appreciated and valued.

For example, let’s say a remote employee has successfully completed a difficult project ahead of schedule. Normally, the team would gather in person to congratulate and celebrate, but that’s not an option in a remote work setting. So how can managers address this challenge?


One solution is to hold virtual celebrations. This could include a video conference call with the team, complete with virtual confetti and balloons. Another idea is to send a care package or gift card to the employee to celebrate their accomplishment. These small gestures can go a long way in making remote employees feel recognized and appreciated.

Another option is to create a virtual “wall of fame” where successes and achievements can be posted and celebrated. This could be a shared document or a dedicated section of the company intranet. Employees could share their successes and accomplishments, and the team could add comments and congratulations.

And of course, no celebration is complete without a little bit of humor. Maybe it’s a virtual dance party, a silly meme or GIF, or just some playful banter between team members. Whatever it is, adding a bit of humor and lightheartedness can help make virtual celebrations feel more personal and fun.

10. Benefits and Compensation

Ensuring that remote employees receive benefits can be a thorny issue for managers, as designing a remote benefits program is much more difficult than designing one for in-house employees who are all in the same city. When working with remote employees, managers must consider a variety of factors, such as the different legal and regulatory requirements in different locations, as well as the specific cultural needs and preferences of individual employees.

While in-house employees may value benefits such as onsite gyms or free lunches, these perks may not be as relevant or appealing to remote employees. Remote workers are often working from their homes or other remote locations and are not able to access these types of amenities. Big companies used to have all sorts of employee perks on site (think hairdresser, gym, therapist, etc), but that just doesn’t make sense in the new hybrid age.

Another challenge is ensuring that benefits packages comply with the different legal and regulatory requirements in different locations. For example, some countries require employers to provide certain benefits or contribute to a specific type of retirement plan.


To address these problems, managers may need to work with legal and HR professionals to ensure that benefits packages are compliant with relevant laws and regulations. They may also need to be flexible and willing to adjust benefits packages based on the needs and preferences of individual employees.

Another related solution is to simply provide home office stipends, which can help remote workers create a productive and comfortable work environment at home. This can include providing equipment such as ergonomic chairs, high-quality headsets, or dual monitors to enhance productivity and reduce the risk of physical discomfort or injury. You may not be able to provide every single amenity that you want, but sometimes cold hard cash works just as well 🙂

11. Dealing with Distractions

Working from home can be a potential minefield of distractions for your employees, such as noisy neighbors, barking dogs, or even the allure of a Netflix binge. One minute you’re in a virtual meeting with your team, and the next thing you know, your colleague, Simon, is caught up in a heated argument between his cat and his dog.

To make matters worse, remote workers may be juggling personal responsibilities, such as childcare or household chores, which can lead to further distractions and interruptions throughout the workday. It can be challenging for them to stay focused and productive when their attention is being pulled in multiple directions.


As a remote manager, you need to be able to understand and empathize with the potential for distractions and interruptions. Suggestions for a team member in this situation can include setting aside a designated workspace, creating a schedule that allows for breaks and personal obligations, and communicating clear expectations about availability and responsiveness during work hours.

Additionally, managers can provide resources and tools to help remote workers stay focused and minimize distractions, such as noise-cancelling headphones or time management apps. Finding ways to inject humor and fun into remote work can also be helpful, such as having virtual office parties or encouraging employees to share funny distractions they’ve encountered during the workday. This might make work more engaging than some of the possible distractions!


Managing remote employees comes with a unique set of challenges, but with the right strategies and tools, it can be a rewarding experience for both managers and employees. From communication and team building to time management and cybersecurity, there are many factors to consider when managing a remote team.

Whether it’s dealing with distractions, navigating legal and regulatory issues, or finding new ways to celebrate successes, remote managers must be prepared to adapt to a constantly changing landscape. So, let’s raise a virtual glass to all the remote managers out there – may your Wi-Fi be strong, your video calls be clear, and your jokes be appreciated (even if they only get a virtual laugh).

Founder : Wherever I May Work | Website | Other Posts

Jared has worked remotely for 15 years in various marketing capacities, and has managed hundreds of marketing campaigns along the way. He has held freelance, agency, and in-house positions for companies large and small.

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