managing remote workers

A Common Misconception of Managing Remote Freelancers

Have you ever hired a remote freelancer, set up them to perform their task, then stopped communicating with them?

You probably ended up with a poor online hiring experience where frustration kicked in because the freelancer was not fully completing the task that you had assigned to them.

It’s a common misconception in managing remote freelancers that there is less need to actively manage once the individual has been taught their initial task. I’m not sure why, but managers feel a disconnect when the hire is remote and they aren’t able to see them every day.

Rightfully so! It’s definitely more difficult to develop a relationship with a freelancer that is hundreds of miles away from your office and who you only talk to through chat. But that doesn’t mean that all is lost!

There Is Still Hope

At FreeeUp, we’ve been going through this unique method of management for the past 4 years. We’ve learned from our mistakes and we’ve generated a list of secrets that can help you effectively manage remote freelancers.

Give them a read and let us know what other tips you have picked up along the way in the comments section. We’ll keep the article updated as we get feedback from the community.

5 Secrets of Managing Remote Freelancers

managing remote workersSecret #1: Tell Them About You

Developing a relationship with someone new takes time and effort. When you first meet someone, you ask them a slue of questions about their home, their family, their hobbies, their work, their motivations, and much much more. Over time, you begin to develop an understanding of that person and you feel more comfortable asking questions, raising concerns, and working through problems together.

Similar to any other relationship, you need to take the time to get to know the remote freelancers that you are hiring for your company. It doesn’t have to be hour long conversations either. Simply make it a habit to spend 20-30 minutes when you first hire a new remote freelancer to share stories and gain a deeper understanding of each other.

The more interest that you show and the more that a remote freelancer knows about you and the company, the harder they are going to work to achieve their goals.

Secret #2: Set Clear Expectations

Remember that remote freelancers tend to work with many different clients throughout one calendar year. Because of the large variety of clients, there is no standard of what is expected of them when working with new clients.

Unfortunately, they cannot read your mind either.

The second secret to effectively managing remote freelancers is to set clear expectations from the very beginning. These expectations are for communication, emergency situations, schedule, working hours, and goal setting.


Tell the remote freelancer the hours that you are at the computer and the best way to reach you. Share times that they should not try to reach you as well.

Emergency Situations

It often happens that remote freelancers have issues with electricity or Internet because of natural occurrences. In these situations, communicate what you expect them to do.


Set a schedule with each remote freelancer that works for both of you. By clearly communicating expectations of schedule, you can always know when a freelancer is on performing their given task.

Working Hours

Give the remote freelancer clear guidelines on how many hours they should be working each day on your tasks. You don’t want to get into a situation where you are paying too much for freelancers. Create a budget and stick to it.

Goal Setting

Similar to in-house workers, remote freelancers thrive off goals. If you have a task that is repetitive such as fulfilling orders, give a remote freelancer a realistic number of orders to complete each hour. This is one way to hold remote freelancers accountable and motivate them.

Secret #3: Create Required Daily and Weekly Updates

In order to hold remote freelancers responsible for their work and to keep regular channels of communication, we recommend requiring daily and weekly reports.


As you begin working each day, please Skype me to say that you will be starting. When you are done, Skype me a breakdown of what you accomplished and where you struggled, if you did.

At the end of each week, please send me an email summarizing your work for the week. This email should highlight if you met your goal and what your plan is for the next week.

By setting up these daily check ins, you always know what the remote freelancer is doing and you can provide feedback where it is needed.

Secret #4: Hold Biweekly or Monthly Meetingsmanaging remote workers

As I said before, remote freelancers are motivated by being part of the whole. We recommend holding 1-2 meetings per month with all remote freelancers to provide company updates, highlight anyone’s exceptional work, and welcome any new remote freelancers into the fold.

Group meetings inspire remote freelancers to feel a part of something bigger than their set of tasks. As with any freelancer, that feeling of being a part of the group and contributing to the big picture motivates them to work harder and stay focused on their tasks.

Secret #5: Give Remote Freelancers the Opportunity to Grow

Find ways to motivate remote freelancers by showing them how they can take on new responsibilities and improve their roles for the greater good. This can be as simple as monthly evaluations, goals that must be reached for promotions, and communication of opportunities to take on additional tasks.

Remote freelancers are highly skilled at their given expertise, but most also yearn to learn and contribute in other ways. If you can place remote freelancers in a position where they can grow, it will only benefit your company and raise the bar for remote freelancers that you hire in the future.

The Art of Managing Remote Freelancers

Be present and maintain structure. 

If you follow these 5 techniques and uphold them with remote freelancers, you are going to find success in having remote freelancers a part of your growing company.

Let us know if you need help with any of your remote management strategies…we’re always more than happy to help. Simply leave a comment. We respond to all comments within a timely manner with helpful responses and advice.


FreeeUp CMO Connor Gillivan, serial eCommerce entrepreneur and expert in online hiring, eCommerce, and bootstrapping businesses.Connor Gillivan is a serial eCommerce entrepreneur and an expert in online hiring, eCommerce, and bootstrapping businesses. With his first eCommerce business, he sold over $20 million worth of product and built a team of over 60 freelancers. He is now the co-founder Chief Marketing Officer of FreeeUp, the hands-on hiring marketplace connecting hundreds of online business owners with reliable, pre-vetted remote freelancers. He is an avid writer on his own site,, and his business advice can be found in top publications such as He currently lives in Orlando, Florida. 


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10 thoughts on “5 Secrets to Effectively Managing Remote Freelancers

  1. Hi Connor,

    Smart tips! Telling workers about you gives you a bonding/connecting point. So folks can get to know you, like you and trust you. Once you have the trust thing down, you are golden. Things flow so smoothly when both parties genuinely like each other. Thanks for sharing!


  2. Spot on!

    Thanks for this – I learned a lot.

    As a freelancer marketer, I’ve worked for clients who adopted most of the tips here, and needless to say, we had a smooth relationship.

    A key to success is being able and willing to effectively manage people. Remote workers want to see their employers as humans and not some buttoned-up order factory. So, this piece resonates with me.

    I’m glad I found it out!

  3. I really appreciate this post. I’ve been looking everywhere for this! Thank goodness I found it on Bing. You have made my day! Thanks again!

  4. I have to admit that I was skeptical at first, but I tried the relationship angle and it has greatly improved our mutual respect and communication, and then also our output. Game changer for me!

  5. For me, opportunity to grow has been the real game changer. Thanks for the other tips as well, will def be testing them out!

  6. Communication with remote hires and setting schedules are two of the most effective ways to get things done. Helpful tips, thanks!

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