challenges faced by remote workers


We’re experiencing a massive generational shift, one in which more people than ever are working remotely.

In fact, 68% of millennials looking for work said an option to work remotely would greatly increase their interest in specific positions. But how can you as a business owner meet the demands of a remote worker who has chosen this path for greater flexibility?

If you run a business that relies on remote freelancers, here’s the news: Online freelancers will bring with them their own specific set of challenges that you and the worker need to overcome. Doing so will enhance your relationship with freelancers, which in turn will boost their productivity and the overall growth of your company.

Moreover, it also means that you won’t lose a standout candidate who is a huge asset.

And because it’s expected that more than half the American workforce will be working remotely by 2020, it’s really important that you start addressing the issues ASAP. In this article, we identify the biggest challenges faced by remote freelancers – and we’ll show you how to fix them.

Completing Projects

What is the main aim when you task a worker with a project? You want them to complete it to a high standard, and within a reasonable timeframe that suits you.

When a worker is remote, however, completing a project on time becomes a bit harder.

For a start, a remote worker probably isn’t working for just you. Chances are, they’ve got a few clients. As such, you may not be their number one priority all of the time. So while you think it’s perfectly okay for you to request more changes to a document they thought had been checked off the list already, they might already be away working on another project. This means you might have to wait before they can get around to it.

This sort of thing slows down the progress of a project, and can extend its completion time.

You might also find that some remote freelancers are slow at responding to messages. You fire off an email at 4pm your time, but – because they’re busy on other projects or they always take Wednesdays off (just because they can – the perks of being a remote worker) – they don’t get back to you until noon your time the next day.

To make sure that communication is good, and that a project gets completed within a reasonable time – and, indeed, completed, full stop – it’s a good idea to use a project management app.

A project management app, such as Teamwork or Trello, ensures that everyone knows what is expected of them throughout a particular week. You don’t need to waste time sending follow-up emails to make sure a worker got your last one because everything will be updated on the app. You can check in on freelancers, and it will also improve their accountability. It gives the worker a sense of belonging, too, increasing their motivation to want to complete a project to a high standard.

Working Too Much

The are many benefits of working remotely. A remote worker essentially gets to decide when they will work, and they can choose who they want to work for. They have a lot of control.

However, the flipside to this is that sometimes a remote worker doesn’t know when to say No to a project. After it’s too late, they’re working on five projects at the same time that are demanding their constant attention. One client has just asked for a revision, as has another – and another.

Eventually, stress sets in. This is bad for the worker, and it’s bad for you.

To make sure a remote worker doesn’t burn out, you need to ask the right questions from the beginning and set boundaries:

  • How much work can you complete for us each month?
  • What’s your weekly schedule usually like?
  • What are your expectations from this project?

Inexperienced remote freelancers might have difficulty managing their time, so it’s really important that you make them aware that you don’t want them to take on more than they can handle. It will only result in shoddy work and possibly resentment on their part.

Also, be reasonable with your deadlines. Don’t make the timeframe too aggressive. Give them some breathing space.

Technology Issues

A remote worker is practically useless to you if they don’t have access to the right technology to complete a task thoroughly.

Indeed, not having the right software can be the prime reason why a task takes too long to get completed – or doesn’t get completed at all.

If a remote worker who otherwise seems like the standout candidate for a role within your organization doesn’t have the technology needed to work for you, you can either cut your losses and let them go, or you can invest in company tech that you “loan” out to remote freelancers.

The second option is the better one. By investing in the right technology, you’re investing in your company and its future growth. You’re also investing in the worker who, if they’re the standout candidate, will pay you back with some awesome work.


Ever been on a Skype call with a remote worker, only for it to be interrupted by their children needing something from them?

Or perhaps you hired a remote worker who seemed like the right choice, but whose work for you has constantly been disrupted by their home life. You shouldn’t be surprised, as 45% of said their partners often distracted them.

To minimize the damage caused by interruptions to work low, hold freelancers accountable, make them more visible – and ultimately encourage them to treat this like “proper” office-based work where interruptions won’t be tolerated.

Top tip: Organize monthly Skype calls with remote freelancers weeks in advance, and at a time that works for everyone involved. This will also benefit productivity, as 87% feel more connected and informed through the use of video conferencing.

Communication Hiccups

What do you need to harness more than anything from a remote worker?

The answer isn’t talent. The answer is motivation.

Bad communication is an awful motivator. If you can’t communicate properly with a remote worker, you could weaken their motivation, which in turn will destroy their productivity.

Communication is everything where online freelancers are concerned, and yet it can be so hard to get right for those of us who are not the best at the written word, for example, communicating via emails. Our constructive criticism can be misinterpreted as us shouting at a remote worker, which could cause them to quit.

A remote worker requires constructive feedback. Give them praise, appreciation and encouragement every now and then when they’ve done something good.

Stay in touch with them. An absent “boss” is a boss who looks like they don’t care. And this can be very damaging for morale.

Time Zone Differences

Fixing this one means you and the remote worker will have to do a bit of adjusting, but it’s easy to do.

Time zones can make completing a project a little bit harder, as a worker won’t always be available when you want them to be. Whether you are organizing a one-on-one meeting with a worker or talking to all of them, the answer is to add everyone to a group chat in Skype or use a tool like Calendly.

This tool automatically detects your invitees’ time zones and adjusts the calendar accordingly when they are picking a time to meet, so that everyone is on the same page.

Worker Trust

If you and a remote worker plan to be in this for the long haul, it’s important that you build up trust. Without it, the relationship between the two of you won’t be productive.

When a worker trusts their client, it improves their desire to want to work for them. It motivates them to perform at an outstanding level. They feel that they can ask you questions (which is super important for a task getting competed successfully) and also raise concerns.

Divided Company Culture

In Who: The A-Method For Hiring, Geoff Smart and Randy Street stressed the importance of a collaborative culture – and everyone subscribing to it. If a worker is an amazing candidate but doesn’t buy into your culture, they shouldn’t be working for you. It just won’t end well.

How do you integrate remote freelancers with your company’s culture? How do you make sure they share your values, your work ethic, communication style et cetera?

This is probably the toughest challenge of all. The best time to resolve it is before you make the hire. Ask yourself a few questions before the interview process:

  • What is your culture?
  • What do you expect from freelancers?
  • Do you promote respect and not aggression?
  • Do you have ideals and ethics?

Then, create a series of questions that will give you the right insights into each candidate so that you know whether or not they fit in with your company’s culture.

You Can Overcome the Challenges Faced by Remote Freelancers

There are obstacles to overcome when hiring remote freelancers, but they’re totally worth it. Freed from soul-sapping morning commutes – remote freelancers are more productive, they save you money on office space, and they save money on travel costs, lunch costs etc., which boosts their happiness and subsequently yours. Plus, you only have to use them when you need them.

But perhaps the biggest benefit of all is that you have access to worldwide talent. FreeeUp knows a thing or two about that. They’ve gathered together the top 1% of online freelancers in the world for you to take your pick from. They’ve already done the vetting for you – all you need to do is choose your next All-Star.

Then, go through this list again to keep remote freelancers happy and on track!


Michelle Deery Ecommerce Writer


Michelle Deery is a member of Heroic Search in Tulsa. She specializes in writing about all things eCommerce including development, strategy and pricing.



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2 thoughts on “Greatest Challenges Faced By Remote Freelancers (and How You Can Fix Them)

  1. Getting organized as a business owner is key to making sure that hires have a balanced work load. You can’t expect them to be productive if the boss is all over the place.

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