An Entrepreneur’s Challenges of Managing Remote Workers

An Entrepreneur's Challenges of Managing Remote Workers

An entrepreneur who has started a company in the 21st century simply cannot ignore the possibility of running a team of people who work remotely. In fact, he or she might decide to keep the entire company running remotely, at least in the early days. This allows the entrepreneur in question to cut down on the costs of opening an actual, physical office. It also helps him or she find experts from around the world who might better fit his or her needs, or who might be willing to work for less money than someone from the entrepreneur‘s area.

And while having remote employees can be a great thing, managing them provides a whole set of very particular problems and challenges.


The most obvious challenge of every remote working setup is communication. When you work in an office, you do not really think about it but spend a day or two working from home and you will soon find out how isolated you can feel without being physically present at the office. You start feeling left out and you never can quite get everything right.

Now imagine an entire company or team working like that.

Communication can be a huge problem for remote teams, even with today’s incredible communication tools. Not being able to see other people can cause a whole array of problems, both work-related ones and personal. Problems can arise from something as silly as a misunderstanding that would have been avoided easily in person.

Also, there is always a chance that someone will be left out of something they should have had access to simply because of an oversight. This kind of thing happens all the time.

It is, therefore, essential that you as the entrepreneur in charge come up with ways to facilitate people’s communication. Do video meetings every morning. Encourage people to use video or at least audio for important communication. Use Wrike or a more remote team-friendly Wrike alternative to ensure people are on the same page when it comes to various projects.


Another huge challenge for entrepreneurs whose employees are (mostly) remote is establishing a company culture. Every company needs its own culture and the problem is that, for the most part, culture is born from everyday little interactions between employees. When you have an office, these everyday interactions are common and natural.

In a remote work environment, people can often feel isolated and interpersonal relationships can be somewhat lacking. In such an environment, a company culture will always feel somewhat sterile or incomplete.

The good news is that you can do something about this. You should organize regular informal meetups online where people will be able to talk about whatever they want. You should also encourage one-on-one talks between your employees. You can even take this a step forward and have your employees spend an entire workday in constant audio communication with another member of the company.

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If it is doable, you should also organize actual meetups where the entire company will get together in person and spend a day or two getting to know each other.

This can go a long way towards building a company culture that will help keep the company together even during rough times.


Even the most hardworking of people sometimes feel like not working or, at least, working to the T, not really applying themselves. For more “average” people, the lure of slacking off is even more pronounced.

When you run a company that operates remotely, it is easier to start bunking off work than it is when your employees are in the office with you.

For some reason, accountability in remote companies and teams still has to catch up with the more traditional companies and teams. This is a peculiar thing to notice, but it is really easy to notice. For some reason, people are less likely to work hard when they do not share an office.

Once again, there are remedies to this.

For one, you need to make it very clear that your company is as serious as any other and that people have responsibilities and tasks that they have to complete. If they do not, they will experience repercussions. This may sound harsh, but with remote companies, things like this have to be emphasized more often than in more traditional companies with offices.

You may also consider promoting some of your employees to team leaders and if you choose to do so, hand out promotions to people who have good organizational skills and who know how to get others to work. Maybe later when your company builds up a culture of accountability, you can finally start promoting more creative types.

Until then, stick with structure.

Closing Word

These are only the major challenges that entrepreneurs face when running remote teams and entire companies. There are much more and you will be encountering them on a regular basis should you decide to go remote.

Still, it can be a great way to keep your company afloat and growing.

You only need to handle it the right way and we hope this article helped.