hiring remote workers


In this post, we outline the 10 most common mistakes people tend to make when they are hiring remote freelancers. At FreeeUp, we’ve personally found great success using online contractors. Before our founders started FreeeUp, they were running e-commerce businesses using mostly remote freelancers, and taking in millions in sales each year. However, we do know that not everyone has had the same experiences we have. Maybe you’ve found the hiring part overwhelming, or had difficulty onboarding freelancers when they were far away.

Typically, we’ve found that when people have had a bad experience, it is often because they are falling into some of the same basic pitfalls. These pitfalls are fortunately pretty easy to avoid once you know how to recognize them. If you want to use remote contractors to achieve great success, we recommend avoiding the following mistakes below.

Mistake #1: Not knowing exactly what you want to outsource

Sometimes people get so excited about outsourcing (cheaper rates! a more flexible schedule!) that they forget to ask themselves exactly what they are outsourcing for. This should be the first step in any process for hiring remote freelancers. Know which tasks you want to outsource before you start talking to candidates. Make a detailed list of what you would like to offload. Ideally, we recommend starting with relatively straightforward and repetitive tasks, such as inventory management for your online store. These are perfect to assign to remote contractors.

Mistake #2: Not having an organized interview process

Interviewing is often where many people get bogged down in the hiring process. There are a vast number of candidates to be found online, which is both a blessing and a curse. If you have an organized process, you’ll save a lot of time. When reviewing candidates on sites like Upwork, know your automatic red flags so you can work through your host of options more quickly. Some of your red flags will be individual to your company or the position, but we suggest you watch of for the following red flags in general:

– Poor English skills
– Negative reviews
– Not enough hours worked online
– Bad response times

Once you schedule an interview, prepare a list of the standard questions in advance, with the most important (such as the candidates schedule) listed first. That way, you can know immediately if there’s going to be a big problem. If there is, you don’t need to keep asking questions and filling up your time. Instead, you can politely end the interview then and there.

If you’d prefer to keep your number of interviews to a minimum, we’d like to make a shameless plug for our own marketplace, FreeeUp. We’ll assign you a qualified contractor based on the needs you tell us. You’ll then get a chance to talk to them and decide for sure whether you want to hire. Sometimes, you might end up passing on the first person, and interviewing one or two more candidates we offer you, but we’ve found most of our clients find a great fit the first time, eliminating the need for exhausting searches and interviews.

Mistake #3: Going for the cheapest option when hiring remote freelancers

This is such an easy trap to fall into. Let’s say you find a couple candidates online who are only charging $3 an hour for a certain task, while most of the others are charging $6-$7. The difference in rate can be intoxicating. Imagine how that might affect your bottom line. However, the very cheapest candidates are often the very worst. They typically come with many of the red flags mentioned above, including poor communication skills and a lack of experience. Instead, if you need a deal, take a look at more of the “middle of the road” options. You can still usually find something quite reasonable, but you won’t be scraping the bottom of the barrel.

Mistake #4: Not setting clear expectations in the beginning

Never hold freelancers to a standard you haven’t made clear. This promotes resentment and a lack of loyalty. Instead, start setting clear expectations as early as the interview. Let them know what you need in terms of schedule, updates, communication, etc.

Mistake #5: Not diversifying contractors across your business operations

Let’s say you’ve hired an amazing online freelancer. You couldn’t be more pleased with how they are handling their tasks. So you give them even more tasks, from every department at your company. Why shouldn’t you, since they are handling everything so well?

The problem with this is you now have one person doing essential tasks for every single department. If this person left, your company would be hit extremely hard. Instead, try hiring more than one freelancer, rather than letting just one person be responsible for everything across the board.

Mistake #6: Failing to properly set up online freelancers

After hiring remote freelancers, you need to take the time to onboard them. And here’s an important caveat: you should set them up even if they are experienced in the field you are hiring in. If you make sure they understand your company’s culture and methodologies, you’ll reduce miscommunication down the line. You should also provide all new freelancers with onboarding guides that outline the specific processes they should follow, step by step.

One thing we’ve found useful is using chat to onboard new freelancers, rather than getting on a call. This way, the new freelancer has a log of everything you’ve discussed together. If you are using overseas freelancers, this can also help with language barrier issues when it comes to accents and phrasing.

In addition to these tips, we recommend using a tool like TeamViewer to view their screen as you onboard them. There’s always a potential for miscommunication when collaborating online. If you can view their screen, you can be sure they are correctly performing the tasks you are explaining.

Mistake #7: Not preparing backups in your free time

This mistake is closely related to Mistake #5. You always want to be at a place where your business runs well, even if someone goes on vacation or leaves unexpectedly. That’s why you should consider getting other online contractors up to sped on each other’s tasks. This way, you never have to face an emergency. Let’s say you hired a freelancer named Peter who gets too sick to work. If he isn’t available, you can have Mindy take over, since you’ve already caught her up on Peter’s day to day tasks.

Mistake #8: Not fully integrating online freelancers

In our extensive experience with hiring remote freelancers, we’ve found that across the board, these are the three things they value the most:

1. Consistent work
2. Competitive rates
3. Being a part of a growing group

Far too often, companies treat remote contractors as a foreign satellite, and not a true part of their organization. However, if you take the time to make freelancers feel at home, you’ll reap the rewards. Tell new freelancers about the history of your company, your ideals, and your goals for growth. Validate their work and give them bonuses when appropriate. You’ll find that you create fiercely loyal freelancers, even if they are not full-time. If they feel that they are a part of something, it will show in their work.

Mistake #9: Not listening to their ideas and asking for feedback

Schedule one-on-ones with online freelancers. Ask them what they think about what they are doing, how they are being managed, and how the company is doing in general. They may have unexpected insights for you, as they can see things you can’t when they are working in the trenches every day, so to speak. They may also suggest great ways to improve processes and more quickly carry out tasks. But you’ll never know if you don’t ask.

Mistake #10: Not allowing  online freelancersto grow with you

Remote contractors are just like any other freelancers: they want opportunities for growth and advancement. This doesn’t change just because they don’t come into your physical office. When you hire a new freelancer, ask them about their future. What do they want out of this relationship? Where do they see themselves in five years? This will give you a good—but not perfect—idea of their ambitions and expectations.

Then, keep an eye on their drive as you continue down the line. Promotions not only promote loyalty, they also make your life easier. If you have a standout member in customer service for example, make them an associate manager. They can prepare reports and stats for you, instead of you doing all of that work yourself.

This list of mistakes may seem a little bit intimidating. Remember, you don’t need to be perfect at everything to still have a great experience hiring remote freelancers. Instead, use these guidelines as overall goals to shoot for.

If you want more information on successfully hiring remote freelancers, we strongly encourage you to check out our ebook on the subject. It’s jam packed with detailed advice, including step by step checklists for choosing what to outsource, conducting great interviews, and setting clear expectations.


Emily Bell


Emily Bell has worked in digital marketing for seven years, tackling projects for a wide variety of tech and PR companies, as well as a few of Amazon’s top third-party sellers. Her work has appeared in Entrepreneur, Influencive, Addicted2Success, Forbes, and around the web.



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4 thoughts on “10 Most Common Mistakes of Hiring Remote Freelancers

  1. It can be so frustrating as a freelancer when clients lowball after you’ve already set your rates. And no offense, but they sometimes think that because they Googled your country they know how much you should be paid. It’s not really accurate or fair.

    1. Hey Amy, this can sometimes happen. That’s why it’s important to be firm as well as polite. This is a top guideline at FreeeUp, where freelancers are also free to set their rates to whatever they want and only negotiate a project rate if they are willing and before they are hired.

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