How to Tackle 5 Common Challenges in Leading Remote Teams

Building the right remote teams and managing them brings a ton of benefits to employers.

According to this 2018 report from Red Rocket Ventures, they found out that this helps them cut down on their operating expenses and other business costs.

It’s estimated that a company with 100 off-site part-time workers can save up to 1 million USD per year with the right remote work arrangement.

Remote work also gives them the flexibility to hire the best talent anywhere in the world.

The right work-from-home arrangement is also beneficial for employees.

Red Rocket found out that many of their off-site workers are much happier than their in-house staff. They’re able to manage their time more efficiently for completing their work-related responsibilities and domestic duties.

This boost in morale also significantly increases their productivity, which can greatly benefit your business.

Effects of Remote Work Arrangements by Numbers


In 2015, Coso Cloud published a report after they conducted a series of surveys to find out how a remote setup can affect employers and their employees.

Their findings show that: 

  • 77% of off-site workers are more productive than in-house staff.
  • 52% of these remote employees are less likely to file a request for leaves and vacations.
  • 3 out of 10 remote employees say they save an average of $5,240 per year when working at home.

Yet many companies say they also encounter a variety of challenges when managing remote teams.

This 2013 news story reported that household brands like Yahoo! and Best Buy have canceled their remote work contracts because of these issues. 

Was this the right choice? That’s hard to say at this point. 

There are many challenges, so let’s explore some common ones that might hold companies back from embracing remote policies.

5 Common Challenges in Leading Remote Teams

If you’re planning to build and manage your own off-site team for your business, then you should be ready to resolve these remote work problems even before they happen.

1. Communication Issues

Communication between employers and their employees is among the most crucial factors that can make or break a business.

This is usually the key to business success.

It’s important to collect information from your employees. This enables you to know exactly what they’re working on at the moment, along with the time and resources that they still need for accomplishing their current duties.

However, this isn’t an easy task, especially for off-site workers and managers.

Without setting up an efficient off-site work pipeline, you won’t be sure that your remote employees can instantly be informed about urgent changes and events that can affect their work output for the day.

How to Resolve The Issue

Many businesses create a communication platform that’s solely dedicated to their off-site team leaders and workers.

Although emails can work really well as a method to communicate with your remote staff, an internal communication system can make this much more convenient for everyone.

A lot of businesses and their team leaders use Slack to foster better communication among their executives, in-house staff, off-site resources, clients and suppliers.

This is a helpful communication tool — team leaders who handle multiple groups of off-site employees can create particular “workplaces” for each team.

This can organize the communication and collaborative activities of your in-house and off-site resources.

2. Scheduling Difficulties

Creating and instantly applying changes to workforce schedules aren’t as quick and simple as it sounds.

It isn’t straightforward to know the availability of your remote workers, especially when you need immediate resources for urgent situations.

This is among the most challenging remote workforce management drawbacks.

Remember, remote workers are likely to be based across a variety of regions with different time zones.

This makes it much harder to assign workforce schedules and set up team meetings through phone and video conferences.

How to Resolve The Issue

Team leaders need to know where their in-house staff and remote employees are based.

And according to a recent Forbes report, offering flexible hours to Appen’s off-site employees significantly helped them become this year’s top work-from-home employer.

This arrangement allows employees to choose from a list of shift options or work schedules.

Many tools can help you implement this flexible setup.

You can create a poll with various time slots and let your team members choose among those available options.

This makes it more straightforward for you to update your workforce schedules and set team meetings.

3. Dependability Problems and Data Security Concerns

It’s often easier to ensure that in-house employees are working on completing their day-to-day duties and responsibilities for your business.

Your team leaders can instantly monitor their activities as they work and can also coach them to resolve unforeseen problems.

But it isn’t as easy to do these things when you’re handling a remote team.

So optimize your daily, weekly and monthly work output expectations from each of your off-site employees. This means you should know the work output to expect from them after every day, and also at the end of each week or month.

Also, let them know what they’re expected to complete as they fulfill their tasks and obligations for your business.

Meanwhile, another problem is that a remote work arrangement can expose your business to data leaks.

You surely wouldn’t want your competitors to learn about your trade secrets, promotional ideas, customer data and other sensitive details.

These issues are more likely to happen without your knowledge when you build and manage an off-site team.

How to Resolve The Issue

Improve your hiring processes, workforce data management systems and legal documentation.

For example, you can grant sensitive data access privileges and assign confidential business activities to your in-house staff.

Your remote workforce can handle roles that won’t expose your business to these risks.

Also, make sure that your workforce database is kept updated with the latest details of your in-house and off-site employees.

You should know their valid home addresses, contact information and other professional details.

Your legal documentation, contracts and other relevant paperwork should also protect you and your staff against possible breaches, security risks and other liabilities.

4. Monitoring Productivity

It’s often more complicated for executives and managers to accurately monitor the performance of their remote workers than doing the same thing for their in-house staff.

Also, a common notion is that most employees produce higher quality work output and consistently hit deadlines through close supervision.

But this 2019 Forbes report points out that 30% of remote employees produce more work output in less time than when they were working on-site, while 77% of them are more productive when they work from home than at an office.

How to Resolve The Issue

Have an optimized work and communication pipeline for both your in-house staff and off-site employees

Implement processes and systems that can help you track the overall performance and productivity of your resources.

But there are already several ways and tools that you can use to do these things.

For example, you can use ScreenMeter to track the activities of your remote and in-house staff as they do their daily tasks.

This is an application that works on Microsoft Windows, Mac OSX, Linux and Chrome OS.

Also, such software products work even while offline as it creates time and activity logs, which are then automatically uploaded once the machine has an active Internet connection.

5. Language Barriers and Cultural Differences

An advantage of building remote teams is the ability to hire the most suitable talent anywhere in the world.

Another is to promote more diversity throughout your organization.

But language barriers and cultural differences can make it more complicated for your in-house staff and off-site employees to efficiently work together.

This can also make it harder for your team leaders to manage their workers.

How to Resolve The Issue

Ensure that your hiring processes, communication platforms, work pipelines and productivity monitoring systems are all suitable for your business, in-house employees and remote staff.

So carefully select the right employees and also make it a point to know their up-to-date geographic locations and personal details.

Plus, you need to provide them with easily accessible, simple to use communication tools with auto-translation functions.

And to make your on-site and remote employees feel more connected as they work, you’re advised to incorporate team-building strategies into your work pipelines.

Your team leaders should also be trained in analyzing time and work productivity logs.

They’ll be able to use this data for enhancing your task completion targets and collaboration systems to best suit your network of in-house and off-site employees.


All these things can let you benefit from the perks of working with the best professionals in your industry, and also from having more diversity in your organization.

So always keep these drawbacks and solutions in mind as you lead your remote teams to success.

Joe Peters is a Baltimore-based freelance writer and an ultimate techie. When he is not working his magic as a marketing consultant, this incurable tech junkie devours the news on the latest gadgets and binge-watches his favorite TV shows. Follow him on @bmorepeters