Challenges of Managing a Remote Team For Your Business And How to Work Around it

Working from home is slowly becoming the new norm.

Many companies are now giving the “work from home” option to various of their departments. And it is estimated by the year 2028, about 73% of all the departments in a typical company will have employees who work from home. (

Let's face it, even nature is contributing to pushing the agenda of working from home. The recent Covid-19 pandemic made us stay in lockdown for months and do our work-related operations from home.

This is clearly the era of “working in an office to working from home” transition and evolution, and we need to embrace it with open arms and be well-prepared to make it work.

While this is the case, it is clear that this evolution brings with it new challenges for anyone who will be managing a remote team. Often, the challenges are more difficult than managing a team you normally work with face to face.

We will be taking a deep look into the most common challenges that you face, as a manager or CEO, when managing a remote team and how you can get everything to work fairly smoothly for your company.

Challenges and Solutions of managing a remote team for your business

 1. Establishing trust 

Trust is one of the greatest foundations in business and life in general.

When it comes to managing a remote team, lack of trust comes in many forms. It begins with the person managing the team and goes to the team itself.

Most managers, especially those who have never done it before, don't have trust and confidence in themselves regarding the ability to manage a remote team.

A study by Harvard shows that almost 40% of the managers and supervisors who participated in the study admitted lacked confidence in themselves. ()

Employees themselves also tend to have trust issues with the colleagues they are collaborating with and this might pose a serious problem for you as the supervisor, CEO, or manager.

Solution: You should develop confidence in yourself and realize that you are more than capable to work with a remote team and still get to achieve your business goals.

Having a strategy for distributing tasks for your employees to do, believing in them, and giving them freedom is what makes for good management. You don't need a degree in managing a remote task force to achieve the goals or fulfill the company's mission.

In the case where you feel there is no cohesion among your team players due to trust, you should figure out ways to build trust amongst them.

Encouraging them to have more interactions on their own through video conferencing or other ways will help them open up more and better relate with each other.

2. Tracking level of productivity

Most managers have a hard time wrapping their heads around the fact that a remote team can be as productive as a team working in an office setting.

They feel like having the people whose work they are overseeing remain within their field of vision, accounts in some way for the high level of output they get at the end of the day.

Managers who like walking around the desks of their employees seeing their progress and helping them in areas they need help with usually don't feel comfortable with the idea of having people working in their home offices where they can't be monitored.

The reality is that there are employees who are quite productive alone at home while there are others who take advantage of the idea of not being monitored physically.

Solution: It is important that you set clear goals, in the short term as well as long term, and let your team know about them. Then you should aim to create a list of tasks that will help you achieve the goals on time.

After that, you should distribute the tasks to your team based on their abilities and skills and allocate everyone enough tasks to do so that you get to achieve the day's, week's, or month's objective.

Tracking their efforts is also a good idea.

You can use progress tracking tools such as Toggl, RescueTime, Time Doctor, and Harvest to help you know how much time each team member is putting into work and you can even use this information for future decisions.

3. Communication

When it comes to connecting with your team, it can prove difficult to maintain a good flow of communication among the employees.

If you are doing it for the first time and you don't have a communication strategy in place, you might have many days of broken communication and this affects the output of the people who you are working with.

You might want to ask someone a question about a particular issue of the work they are on and they might not be available. And since you want to have things run smoothly while they have their freedom, you might have difficulties trying to balance the two.

Solution: Establish a proper communication strategy where the employees or freelance workers can reach out to you and get prompt responses about work when they need them.

Also, make sure you agree on the best time to communicate with every employee based on their daily schedule.

You should also consider using communication tools like Twist or Slack that help with managing your communication with your employees even on projects where collaborations are needed. They are quite handy tools for transparency and efficiency as far communication and productivity are concerned.

4. Maintaining work's culture

You always want your team to uphold the workplace culture even when working at home so that they feel like they are still at work if the team you are with is the same one you were working with physically in the company's building.

If you have gotten new people to join your team, it is your duty to get them acquainted with the company's culture and get them to flow with it, which can be quite daunting.

Most companies tend to have a culture that gives off a good vibe among the employees and even between the manager and the employees, and translating the same energy to people at home is not always easy.

Solution: You should create open communication for all your employees such that they are able to come straight to you when they need anything work-related.

Making the team feel free and “at home” with everyone by setting time aside where you have casual chats and other fun activities virtually also helps. You can have virtual game nights or movie nights or any activity that goes well with your team which you know will be interesting and refreshing.

Sending gift cards and at times company's merchandise fosters the company's culture as well.

5. Securing your business' sensitive information

One thing you should be ready for when you are working with a remote team is giving away sensitive information.

There are times when some employees or freelancers will need to access a certain area of your company that is quite crucial to do serious tasks as part of their work.

Normally, when you are in an office setting, it is easy to give them limited access to maybe the company's servers or systems that have documents or data that shouldn't be accessed just by anyone who feels like it.

But since you are miles away from each other, you might not have the ability to entirely control their activities and the data they will get their hands on.

And you don't know what they might decide to do with it later on especially when you are no longer on good terms.

I have heard cases where some freelancers tried to install viruses in a certain company's software after they were given negative feedback on their work and their contract was terminated.

Other employees have even gone ahead and deleted all the data of a company when they were laid off.

These are all critical challenges you have to deal with.

Solution: Always have several backups of your sensitive data on external drives that can't be accessed by anyone except you.

Also, make sure you limit the data you share with your employees or freelancers.

If they have to access a certain section of the company you know carries huge value to your business, put layers of security on it and categorize and store the data in a way that the workers will access only the exact data they will need and nothing else.

Based on my personal experience with my online business Affiliate Dove, I have also found that regularly changing the password of your sensitive business sections helps a great deal.

Ensure that the encryption of your business systems does not remain the same for a long time. As you add multiple layers of security, also remember to give them new passwords that are so hard to crack now and then.

6. Salary Increase

This mostly applies to the situations where a business owner, supervisor, or manager is working with employees.

Although there are times freelancers you have worked with for years may request a pay increase, employment is what is often affected by this problem.

It is always essential to keep in mind that members of your team are constantly looking for ways to increase their income earning potential and to increase the knowledge and skills in their area of expertise.

Shifting from working in the office to home can make this issue easily clouded by other demanding issues but that doesn't make it any less important.

If you don't put it into consideration, you might lose some of your best employees and in turn, cripple the growth and development of your business.

Solution: You should try to have personal meetings with each employee and discuss their plans and visions in the long term.

Understand what skills they are more interested in gaining, the skills they already have that they want to sharpen, and what they would like to focus on in the near future.

Since the majority of the employees don't feel comfortable raising the topic about a salary increase, you should be the one to initiate it and make them comfortable talking about it.

Also, you should offer remote training and other related forms of training that are in line with their plans, be they video training, online courses, or other training resources.

Research shows that 51% of employees will quit a job if they don't receive the necessary training.

So you have to be aware of this and actively work towards helping them become what they want to be.

7. Building unity among your team members

As earlier mentioned, lack of unity can stem from a lack of trust and openness among your team members.

It can also result from not describing the role of each employee well so that you have two people doing the same thing but on different levels that affect each other's work negatively.

For example, you can have a writer and an editor who both know each other and maybe the writer is lazy and doesn't want to do a lot of work.

So what happens is, once they finish writing, they don't check their work for simple mistakes because they know the editor is there and among their work description is checking articles for mistakes.

Solution: Always explain the tasks to each employee with great accuracy. In the case of the example of the writer and the editor, make the writer understand that they need to read and correct any mistakes in their work before giving it to the editor.

The editor's work is to make deeper improvements to the article, not the basic ones like simple spelling errors.

Also, create an environment where every team member respects the work, ideas, and thoughts of the other members.

You do this by leading by example.

In your meetings, you show concern and pay attention to what everyone is saying and give them good energy. Even if what they are saying may not be the best course of action or the best idea, at least listen to them and treat them well.

8. Language barriers

Almost all companies across the world have people from different corners of the world, who have different native languages.

They are fluent in the native language but they have to use either English or another international language to communicate with others that they may not necessarily be good at.

As you communicate, you find that there are some things they say that you have to take time to understand which in turn slows the progress.

They might also say things that can easily get misinterpreted.

Solution: If they are having serious problems with the language that other people are using, you can get them to do an online course that teaches that language and help them through it where you can.

If they have some grasp of the language, although not perfectly, encourage them to keep using it until they master it.

If they use direct translations from their native language that might across as rude or inappropriate, understand them and don't make them feel bad about it.

9. Rewarding employees' efforts

Some employees give their all to the tasks you allocate them. These are keepers and you want to show that you recognize their work and you are pleased with the extra effort they put in.

However, doing it in a way that encourages them and the other employees can be tricky if you don't approach it well.

Solution: Create reward programs that are aimed at establishing good working habits, not just temporary performances.

Also, reward teamwork. This will enhance unity and trust. You can also decide to give employees the chance to choose their rewards or if you choose them yourself, see that you keep changing them so that it always keeps them excited.

10. Cultural differences

Variety is said to be the spice of life and when you apply this saying to work, you will realize how having a diverse team from different continents, countries, and cities, and who have different personalities, work ethic, lifestyles, and styles of communication can be rewarding.

It makes working together interesting because employees get to learn new things every day and appreciate the diversity, but this also comes with its share of troubles.

There might be negative effects based on the variety which can greatly affect overall performance.

Solution: Create and maintain a certain work habit through encouraging and rewarding your employees.

Also, appreciate those who are different from you and understand how they perceive and do things so that you can work well with them without feeling the need to work with those who are like you, which is favoritism.

Set the pace for equality and show everyone that nothing matters more than good performance and cohesiveness towards the company's goals.

Regardless of where someone is from, how they work or relate with the others, as long as people are working seamlessly and are getting things done, everyone is winning.

11. High tempered and seemingly rude employees

Although on very rare occasions, you will hire a freelancer or employee who might not observe the required work etiquette.

Some people can't take no for an answer and others get angry very easily.

Immediately you show them signs of disagreement or disapproval, they will get infuriated.

Since we all want to lock down income-earning opportunities as fast as possible, you will meet people who will agree to all your requirements to get the job but once you get started working, they start complaining that the work is too much and you are not paying a fair amount.

They might also have problems with other team members as they work together on a project.

Keeping in mind that they are a remote team, you can't really summon them to your office and this can make things hard for both you and the other workers.

Solution: Have a remote conflict management system in place.

This will vary depending on your team, company, and other factors.

Essentially, aim to maintain your respect towards them and encourage others to do the same. Even when insulted, remain reasonable and composed.

If it is a small issue that you or their teammates can solve, do it and continue working together because they might be talented people. And if you continue working together, let them know politely that you like the environment to remain respectful.

If they are not willing to give respect, drop them.

They might end up messing your work and disappointing you in the long term.

If you have given them access to any of your sensitive data, change the password, add more security and make backups before you end the contract so that you protect your business from their rage.

12. Responding to employees' emergency cases

Sometimes, one of your employees will want to approach you with an emergency case hoping to get a salary advance or if it's a freelance worker, some advance payment for the project they are working on.

The problem here usually is, helping someone while protecting yourself or your company from losing money.

See, some freelance workers can make you believe that someone will die if you don't give them the advance. And some of them could be telling the truth while others lying.

Solution: Since you are transacting remotely and there is no way to meet them face to face if they from another country, the best thing here is to use your reason and gut feeling and make the best decision.

You may want to research more about your particular case and the person, make considerations, and consult some people if you can before you make the final choice.

The idea here is to be helpful while keeping in mind that this is a remote situation, you might never see that person again after you send them the money but also you might save a life.

13. Maintaining an official work relationship with employees you know on a personal level

It is a fact that most employments come from recommendations or from people we know personally.

You could be having a friend who knows a friend who's a good fit for your company or could have a friend who is exactly what you need to fill a certain position in your business or the company you work for.

If the job is remote, and you know the team member personally, there are high chances you are going to get tempted to treat them informally.

After all, you are not “in the office”. (pun intended)

If you are not careful, other team members will notice the special treatment you are giving the friend and they will raise concerns.

Maintaining a flexible relationship that is formal when it needs to be, and informal during after-work hours is key but not a walk in the park.

Solution: Set boundaries and stick to them firmly. Let the friend know that you will be treating them like the rest of their team members while working, but after work, you can still hang out as friends.

If for example you have a virtual meeting before you finish the day's work and you have plans with your friend after that, see that you address them the way you address the others and when the meeting is over and you are done for the day, you can now call the friend and follow through with the plans as a friend.

The idea is, the friend's colleagues should not even know or take hints that you are friends. Remain professional during work hours. This calls for great discipline.


In summary, there is no shortage of problems you are going to face when trying to make your remote teamwork cohesively towards achieving the goals of your company.

Immediately after you have solved one problem, another one comes up, and you have to be ready for them, understand why they are surfacing, how they affect your progress, and determine what you can do to overcome them.

The mentioned challenges are what most managers and CEOs face but they are not limited to that. There may be other issues that are specific to your business that you might face as the head.

What you need to do is actively seek advice from other business leaders you trust and look up to, do a lot of research, considerations, and deep thinking, as well as work on creating a personal problem-solving process.

These two go a long way in helping to minimize threatening troubles and remain on the right path to success.


Author Bio

David Oscar is an affiliate marketer who has been working from home and managing a remote team since 2016. He is also the founder of Affiliate Dove, a blog that shares ways to succeed in affiliate marketing. He also enjoys philosophy, programming, and swimming.

Mercy - CBNation

This is a post from a CBNation writer. CBNation is a Business to Business (B2B) Brand focusing on increasing the visibility of and providing resources for CEOs, entrepreneurs and business owners. CBNation consists of blogs(, podcasts ( and videos ( CBNation is proudly powered by Blue 16 Media.

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