Managing Remote Freelancers

Juan SalasJuan Salas

Juan Salas

As convenient as they make chatting with someone on the other side of the world, platforms can’t solve every problem. You will still need to encourage friendly, transparent communication across teams to ensure that you get the most out of your remote freelance teams.

Managing a group of freelancers is a challenge as well as managing a regular work group, you just have to know which approach to take.

By now, we all know that remote work is growing in popularity. In 2017, a Gallup survey showed that 43% of Americans worked remotely at least some for their job. And this trend isn’t just for full-time employees — as freelance continues to grow in popularity, talented workers now come from all over the world, working side-by-side with full-time employees as part of the blended workforce. These new trends are showing up across all different fields, from software development to marketing and will continue to expand to new industries in the age of the talent economy.

With this in mind, it’s important for leaders to take steps to learn to manage not just full-time remote employees, but also teams of remote freelancers. There’s a number of reasons for an organization to utilize freelance talent and embrace a blended workforce. Companies now have access to on-demand talent that can fill in gaps in skill present in their current teams, as well as take on projects that current full-time employees may not have the time or expertise to complete. Hiring freelance talent is also associated with lower costs and overhead than hiring new teams of full-time employees, meaning projects can be more cost-effective and get off the ground more quickly.

There might be an adjustment period when starting to work more with contingent talent. While it isn’t a huge departure from managing a full-time team, there are some things to keep in mind when building teams of remote freelancers.

Set Expectations

Just like regular new-hires, freelancers joining your organization will need to be brought up to speed with the company’s values and mission and will need to review any documentation or style guides necessary for them to start working within the company. Having a digital onboarding plan will help them get up and running more quickly and teach them how your organization runs and works together. Of course, a 10-hour-a-week freelancer may not need the same amount of onboarding as a 40-hour-a-week employee, so be sure to scale onboarding procedures as necessary to maximize efficiency.

Additionally, you’ll need to figure out how to measure progress and communicate expectations and project timelines. That’s why Celerative has dashboards that give data-driven insights into projects and progress on milestones. Utilizing data and metrics can help everyone get on the same page with project expectations and can help freelancers figure out how to manage the work within that time framework.

You may also have to set your own expectations for working with freelancers. While it’s not that different from working with full-time employees, it’s important to remember that professionals are able to thrive as freelancers primarily due to their expertise and experience in a field. Sometimes people hold the misconception that freelancers are a source of cheap, unskilled labor, but in reality, they’re able to make it on their own because they’re experts that are able to work independently and efficiently. So don’t be afraid to take their ideas and recommendations into account for a project. Since Celerative ensures you have access to the top talent, you can feel confident that the people working on your project have the right skills and in-depth knowledge necessary for the job.

Learn Effective Communication

Thanks to advances in tech, staying connected with remote workers is easier than ever. Tools like Slack, Skype, and shareable calendars like Google Calendar make it easy to stay connected with remote teams. But as convenient as they make chatting with someone on the other side of the world, these tools can’t solve every problem. You will still need to encourage friendly, transparent communication across teams to ensure that you get the most out of your remote freelance teams.

You want to make sure to build long-lasting relationships with freelancers. Being able to rely on them across multiple projects will become invaluable over time, as you’ll have quality talent with minimized hiring costs and overhead. Like any good full-time employee, you want them to stick around and feel like a welcome part of the team. How you communicate with them will become key to this.

One way to make freelancers feel more comfortable within the organization is to create open channels for virtual communication — for example, set a precedent of casual, friendly conversation in Slack by asking about the team’s weekend plans, families, etc. Studies have shown that informal communication and friendly relationships in the workplace can make workers more productive, so it’s important to help cultivate friendships, even online. Friendly chit-chat can also help other freelancers get to know each other better and empower them to work more closely as a team instead of a loosely-assembled group of individuals. Encouraging open communication also gives freelancers a chance to share their knowledge and expertise with the team. This can be invaluable if you are using a team of full-time employees and freelancers, as freelancers can help guide more junior employees.

Be sure to also set up a way to communicate feedback to teams and individuals. Like anyone else, freelancers want feedback and praise on for their hard work. Be sure to have a system of giving any remote worker feedback, even if it’s as simple as a shout-out in Slack or a short video meeting where the team discusses their achievements that week. This is, of course, also important for you as you guide the team toward the goals of the organization. Valuable feedback can help freelancers adjust quickly if changes need to be made to how they approach a project or task. Be specific and concrete in your feedback and highlight where they’ve done well and where they could improve.

Remember Why They Freelance

Possibly the biggest change for managers will be learning to work with talent that embraces flexibility and autonomy. Freelancers may not work regular hours or be in the same timezone as you. They’re also self-employed and are used to managing their own time and work. None of this means they can’t produce quality work or will be unavailable when you need them — it means they achieve these things in different ways. They also are not the only ones who can benefit from this flexibility. A developer in a different timezone can fix site-breaking bugs before your office even opens and is aware there is a problem. It also means you can work together to find what payment structures work best for you both. You may be able to work out a system that works better for you than standard hourly pay, such as paying per project or when milestones are reached. Just remember that remote workers can be extremely productive and effective, and learning to work with and manage them effectively can have a huge positive impact on your organization.


The ability to manage teams of remote freelancers will become more important over time, but it’s not that different from managing a regular team. The primary differences are in how you communicate and how freelancers generally work on a day-to-day basis. But as with any other worker, it’s important to set up methods of measuring progress, giving feedback, while creating a friendly and collaborative culture. Just making minor adjustments in tools, expectations, and mindset can ensure you’re successful in utilizing teams of freelance talent.