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Employer’s Guide to Managing Remote Workers 

Employer’s Guide to Managing Remote Workers 

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Remote work is becoming the new normal with innovative ways of managing remote workers. While traditional office environments still reign supreme for now, a younger workforce is coming to expect remote work more and more. This, in turn, has forced many employers to incorporate at least part-time remote work into their contracts. 

A 2019 study showed that 99% of people would like to work remotely at least some of the time. With cramped subway commutes and rush hour traffic to contend with, it’s no wonder that most people would rather just work from home. Employers increasingly cave into the demands of a younger workforce. Therefore, remote work is now becoming more and more common, seeing a 400% increase since 2010. 

The 2020 coronavirus outbreak forced many companies to adopt a remote work strategy with very little notice, meaning that employers had to quickly learn how to manage remote employees effectively. 

remote work challenges for managers

Switching to remote work might sound like a breeze, but it actually presents its own problems. 

In this guide, we’ll discuss the key challenges that arise when managing remote workers, as well as simple strategies that you can implement quickly to avert them. We’ll try to be as concise as possible and get straight to the point. We’ll also introduce some useful software to help you manage your remote staff. 

Don't forget to check out the guideline for remote employees to understand your people

While this guide has been written under the backdrop of the global coronavirus lockdown, the information within it is relevant to anyone who wants to learn how to excel at managing remote workers - pandemic or no pandemic!  

Key challenges of managing remote workers

Managing remote workers - whether they’re salaried staff or freelance contractors - comes with a unique set of challenges that you wouldn’t have to deal with in a traditional office environment. You’re also now managing a staff who have their own challenges relating to productivity, mental health, and a sense of belonging within the company culture. Here are four key macro challenges that often arise when managing remote workers. 

You might also like: Tips to Manage Remote Employees.  


This is by far the biggest challenge when switching to remote work. You’ll notice as we go through this guide that many other problems stem from a lack of clear communication and the solutions are generally vice-versa. Gone are the days when you could simply turn your chair around and have a word with your employees. 

Getting the right information to the right employees is much more challenging when you don’t have them all gathered under one roof. But the solution to this problem is fairly simple, as we’ll see later. 

In order to sustain effective communication with remote workers, you’ll need to get your head around telecommunications software. Being tech-savvy is important in any case. It’s absolutely essential when managing remote workers. 

boss potato meeting remote communication challenges

This image went viral after a boss accidentally turned herself into a potato during a conference call and couldn’t figure out how to revert the changes. The price of not being tech-savvy. 

Getting work done is a lot more difficult when you have a fully-stocked fridge within 20 meters of your desk and no manager to ensure you’re not procrastinating on YouTube. It’s absolutely essential that work-from-home policies are implemented quickly and rigorously to ensure that your employees keep up their momentum. Setting KPIs and making frequent drop-ins will have to become the new norm. 

You’ll need to learn to measure productivity in a different way. Quite simply, you can’t just count desk-time as productivity. This is actually a good thing as it takes the focus away from how much time your employees give to you and instead puts it on actual output.  


As remote work becomes more common, the research to go with it becomes more thorough. While some people might associate remote work with sandy beaches and morning lie-ins, the reality can look more like loneliness and anxiety about one’s future in a company. 
More than 50% of remote workers report feeling disconnected from their in-office colleagues. Another 19% report that loneliness is their biggest challenge when working remotely. Employers will have to recognize the problems that remote work will bring to their employees and actively try to mitigate them to ensure continued productivity and morale.

biggest struggle working remotely 2019

Remote workers report a variety of problems,  many of which are mental health-related, according to’s State of Remote Work Report 2019


Another key challenge thing to consider is maintaining the trust of your employees. This is especially relevant for freelance contractors. Remote workers tend to feel more disconnected from their company, which produces uncertainty about how valued they are within it. Your employees need to be able to trust their management when working remotely. 

This issue is a double-edged sword, however. As an employer, you’ll also have to learn how to trust your employees when they’re not in the office.

Employer’s guide on how to succeed in managing remote workers

Now that we’ve covered the key challenges that managing remote workers will bring to the table, we’ll dive into the simple solutions for each one.


Managing a remote team is a lot like having a long-distance relationship: It’s only ever as strong as the effort that you put into communication. The key thing to take away here is that you’ll need to set up more effective communications within your company.

You cannot just use email and Skype to communicate. The right information will need to be available to the right employees as and when they need it, and frequent video calls will have to be made by all employees. As a result invest in a good webcam.

Make use of telecommunications effectively 

You’re already using telecommunications software every day. Facebook Messenger, Skype, WhatsApp - these all fall under the umbrella of telecommunications. That being said, none of them are effective at managing larger teams. 

You’ll need to look into platforms like Slack, which allows you to set up channels with different team members to chat and answer questions. You can also use Slack to delegate tasks and measure progress with roadmaps. Other software like Trello, Jira, and Asana is also ideal for managing remote workers. 

Your telecommunications software will underpin your ability to communicate and organize effectively. This will, in turn, go a long way towards solving other problems that you might face when managing remote employees.

remote work guide for employers communication

Conference calls are the remote manager’s best tool for effective communication.

Schedule frequent conference calls 

You may have noticed that Zoom has become hugely popular since the outbreak of the coronavirus. Zoom is an effective software to use when it comes to making remote conference calls with your team. Once you get the hang of it, remote conference calling is pretty much the same as any regular meeting. 

You should make sure that your management staff is having frequent calls with their respective teams and reporting progress to you. Having one-on-one video calls with your employees is also a great way to get them motivated and make them feel more valued in the company.

Make sure the right information is available 

Your employees need to be able to access the information they need to complete the tasks that are delegated to them. Your use of team management platforms like Jira and Trello will make this much easier, as will making effective use of Google/One Drive.

Once everyone is on the same page with this software, you’ll find that managing remote employees is sometimes even easier than it is in an office!


Believe it or not, 77% of remote employees say that they’re actually more productive at home. This could be attributed to employees feeling the need to demonstrate their value more when they’re less ‘attached’ to the company.

Still, productivity won’t just happen if you’re not actively fostering it. Also, you don’t want your employees to fall into the 23% who don’t feel more productive when working from home!

Set KPIs

One simple way to keep your employees on track is to set KPIs. This is likely something that you already do. Therefore, it shouldn’t come as much of a shock to the system. For freelance contractors, a simple deadline for an article or project should suffice, while milestones for larger projects should also be reported. 

So long as you have an effective system of reporting completed work (such as a roadmap or spreadsheet), then measuring KPIs shouldn’t be too difficult.

remote work guide for employers productivity

Balancing productivity at work with home life can present challenges for some. 

Focus on goals, not desk-time

How much time is Jannet from HR spending on Facebook? Probably a lot. The truth is that your employees spend a lot of their time distracted from the task at hand. This isn’t something that you can really control, either. The most recent neurological research suggests that humans are practically incapable of focussing deeply for longer than 4-hours in a day. 

The trick to increasing workers’ productivity is to stop focusing on how much time they spend sitting at their desks and start measuring their output instead. Are they reaching their goals? Working from home tends to involve more time spent in ‘deep focus’ as there aren’t people around to distract you. This is good for entering flow states, where you get the most work done. However, it’s dangerous to spend too much time in this state - you risk burning out much quicker.

Delegate tasks effectively 

Your employees’ productivity has as much to do with your management as it does your employees themselves. If the management can’t delegate tasks quickly and effectively, then employees will be stuck without anything to do and they’ll quickly get restless. 

You need to become super-effective at delegating work in an efficient manner to ensure that you’re not getting swamped by employees asking what to do next. Having a clear hierarchy within your staff helps with this as well.


Sun Tzu said: “Treat your men as you would your own beloved sons. And they will follow you into the deepest valley.” As an employer managing remote workers, you must keep morale high to ensure that productivity doesn’t sink.

Schedule frequent drop-ins with individual employees 

We’ve already established the importance of conference calling when managing remote workers. Now we want you to understand how important the one-to-ones are. As the boss, you carry a lot of weight.
Simply calling your workers one by one and having a five-minute check-in with them. “How are you settling in? Is there anything you’re struggling with? How are you managing the transition to remote work?” This kind of attention has a compounding effect. It’ll make your employees feel more valued and secure within the company, which will improve their morale and productivity.

remote call one on one morale

One-to-ones are a great way to make remote employees feel valued.

Foster an open and fun remote company culture

Without those little Friday afternoon parties and after-work drinks, it can be difficult to hang on to company culture. Take steps towards preserving your company culture by setting up a non-work related channel on your communication platforms. 

You can organize an informal chat with your staff on Fridays - maybe even encourage them to crack open a beer. You could host a virtual pizza party or send the occasional joke around. There are many ways to hold onto company culture when working remotely and doing so can have a strong effect on morale.

Get the team together at least once per year 

If you’re only temporarily working remotely due to the coronavirus outbreak, then this tip doesn’t apply to you so much. If, however, you have permanently remote staff or you’re routinely working with the same freelance contractors, then try to get everyone in the same room at least once per year to keep the relationships going strong.


The final hurdle you’ll experience when it comes to managing remote workers is trust. Another way of putting this would be to say that it’s difficult to give your employees a sense of certainty when they’re working remotely. A lot of remote workers - especially freelancers - don’t enjoy the same contractual privileges as their in-office counterparts. In times of trouble, they’re often the first to go. Building up a sense of trust and certainty between you and your remote employees is essential for maintaining morale.

Ensure employees know where they stand 

Your employees need to know exactly what their role is and how valued they are in the company. This is especially true with remote freelance contractors. They should have a clear and honest understanding of how much work they will be expected to produce and how long the contract will last. If not, then they could come to rely on your company too much and then be taken by surprise when the project suddenly comes to a halt.

Remote worker with dog managing remote workers

Making sure your employees follow clear guidelines at home will help keep them on track. 

Establish clear work-from-home policies 

Make sure that you have clear expectations about the work your remote employees produce. It’s imperative that they feel that they’re operating within set parameters even when outside the office. This will help them to feel more attached to the company, rather than like they’re simply working within a void while reporting to you once a week.

Understand your employees’ troubles and work with them on solving them 

You already know that your remote employees will experience unique difficulties that your in-office staff wouldn’t necessarily share. You need to let them know that you understand these difficulties. Moreover, you’re willing to help overcome them. This will show your employees that you’re on their side and that they can approach you when the going gets rough. In short, your workers do look up to you when they’re having trouble. By showing that you’re a reliable person to turn to, they’ll place much more loyalty in your management.

Useful tools for managing remote employees 

A builder is only as good as his tools. Frankly, your management is the same. Here are some great tools that you can use to better manage remote employees.

  • Slack: Great for team communication and delegating tasks.
  • Trello: Simple and effective project management tool.
  • Financial Cents: An accounting project management software. Perfect for streamlining accounting processes.
  • Jira: Essentially a ramped-up version of Trello. 
  • Asana: Another great project management tool. 
  • Zoom: Perfect for making group conference calls. 
  • Google Hangouts: Another great tool for conference calling. 
  • Every Time Zone: Allows you to clearly see all your employee’s time zones. 
  • ScreenHero: Allows your programmers to code together remotely. Also great for designers. 
  • Skitch: Image processing and annotation - great for showing exactly what you mean visually to someone.  
  • Conclusion 

    If this guide has shown you anything, then it should demonstrate that remote work doesn’t have to be too complicated and that it can actually make monitoring productivity even easier than in a traditional office environment. 

    You need to lay the groundwork to establish solid communication channels and an efficient project organization system. Once this is established, you can focus more on your individual employees and keeping their morale and trust in you high. Good luck.


    Billy Gray
    eCommerce Growth Advocates
    eCommerce growth enthusiasts from Boost who love spending time digging eCommerce trends, building strategies and learning new things.
    eCommerce growth enthusiasts from Boost who love spending time digging eCommerce trends, building strategies and learning new things.