How To Effectively Manage a Team of Freelancers

How To Effectively Manage a Team of Freelancers
Geoffrey Whiting
March 25, 2021
11 Min Read

Whether you’re looking to augment your team, have a time-sensitive project, or need additional coverage, freelancers can bring the expertise you need to get the job done. Because they essentially run their own businesses, freelancers will interact with your team differently and have their own needs to get work done.

To help managers successfully manage freelance workers and remote teams, we’ve put together this guide. In it, we’ll look at:

Our perspective includes team managers as well as freelancers to try and help you create the right relationship. While hiring a freelancer is strictly a business decision, it’s important for you and the freelancer to remember that there’s a person on the other end of the equation.

Why you should work with freelancers

Freelancers offer teams a mix of project and business benefits that still help you get work done. If you’re unsure about engaging a freelancer, here are a few things that might make you lean more toward freelance talent:

  • Freelancers generally reduce payroll costs as you generally pay an hourly rate or their established fee, without the usual overhead costs of a full-time employee. 
  • Freelancers give you access to a specific skill or talent as you need it. If your company produces an ebook twice per year, working with a freelancer allows you to pay for an expert writer only when you need their skills.
  • In many cases, freelancers are remote. This gives you access to talent outside of your local region so you can access more skills and so you can save on things like office space, Internet costs, and more.
  • They offer greater flexibility by not needing to work during your hours. Hiring a freelancer in a different time zone for social media management during your off hours can ensure your global community stays engaged.

You also get more time to find the right person. If you don’t know a skill, such as web development, it can be hard to hire someone for that role. Working with freelancers allows you to evaluate a person based on small projects until you find someone who fits based on skill and personality. It’s a smart way to experience multiple perspectives and find the right person for your organizational needs.

The difference between managing freelancers vs. in-house employees

From a team management perspective, the core difference between managing a freelancer and an full-time employee is that you rely on freelancers for a specific task within a project while employees have a long-term role in your company that may evolve over time. Employees handle more than just project tasks, such as sending emails or posting to your social media accounts. The contract you have with a freelancer limits the types of work they can do without renegotiating that contract.

When the work ends, your relationship with a freelancer ends as well unless you retain them for an additional project. For employees, you’ll prepare them for the next project because they are a consistent part of the team.

Full-time employees often need significant training and supervision. They’re a long-term investment, but that can provide benefits for getting a team how you like it. Freelancers should come into a project with the skills you need and their onboarding should be limited to learning your project or business’s specifics. Typically, this means your freelancers will be more independent and autonomous.

With freelancers, you also have different HR-related requirements. Their work is governed by project contracts and there are some limits on the control you have over how the work is done. State and federal laws place restrictions on what contractors can provide for a company, so it’s useful to have a professional review your contracts and project assignments.

9 tips to help manage your team of freelancers

1. Build relationships with your freelancers

A freelancer is a business partner. Even if it is just a one-person shop, their organization is agreeing to do work with yours. Cultivate these relationships just like you would with a vendor, supplier, or regular customer. The freelancer relationship will have more elements similar to how you treat a team member, so taking time to get to know the freelancer as a person will help you better integrate them into your workflow.

Find something you can share and work to build a positive connection. It can improve responsiveness and the quality of work freelancers provide.

2. Define project details

A freelancer doesn’t know your company’s inner workings or how you like to complete projects. You’ve got to clearly define all project details and requirements to ensure that the final result meets your expectations. Take the traditional project management approach and set requirements for each phase of your project.

Start with high-level requirements and then get into specifics, including:

  • Skills and knowledge
  • Tools and software
  • Availability
  • Task completion and delivery
  • Final approval

The best place to start is in your job description when you post a job. Here you can set technical requirements and skills and provide an outline of how you want the process to go. Define the deliverables and how you want them provided. Then, as you hire a freelancer and the project progresses, everyone has a document they can look at for reference.

3. Provide proper documentation

Many freelancers will need some documentation to ensure their work meets your standards. These documents not only set specific requirements, but they help freelancers ensure the project maintains your brand identity. For example, writers will need editorial guidelines that discuss grammar and the tone your company uses for its blogs or website.

For programmers, documentation can instruct them how to leave notes within their code or build certain elements so your development team can use, manage, and update that code easily in the future. Clear documentation minimizes confusion for freelancers and follow-up work for your team, increasing your project’s overall quality.

4. Set expectations and a budget

Your agreement with a freelancer should set clear project expectations and the budget for the work. Stick to it. Respect your freelancer enough to pay separately for any additional work and ask them to respect you enough to fulfill their end of the contract at the negotiated rate. Align your budget to the project details mentioned above to keep everyone in agreement on what’s covered.

If you’re paying a freelancer an hourly rate, create related work and budget expectations. Ask how much work they’ll be able to do within a project’s hourly allotment, and request that they proactively communicate any issues to meeting the work requirement.

5. Streamline communication  

Choose your preferred communication channel and help the freelancer reach you there. For example, if you like communicating via email, share your address and a first message before the project kicks off, so you can troubleshoot any potential deliverability issues at the start.

Your project management tools like Asana may have messaging built-in to allow you to easily add someone to a specific task and tag each other in comments for direct notification. Or, if someone is working on a variety of daily and hourly tasks, communicating via direct messages such as on Slack may be easiest for you both.

Try to communicate with all freelancers through the same channels to avoid missing notifications and minimize the places you need to check for messages. When it comes to managing freelancers, the tool is less important than your ability to communicate easily and regularly. It’s always a promising idea for managers to establish required communications—such as a weekly check-in—at the start of a project.

6. Consider time tracking

Time tracking is essential for hourly jobs or those where you need to bill specific time to individual projects or clients. Coaching your freelance team on ways to improve their time tracking is also an important part of managing freelancers. 

Here are some of the best tools you can use to track freelancer time include:

  • Toggl Track for free time tracking
  • Upwork Desktop App for hour validation and payment protection
  • Harvest for tracking teams across projects
  • Everhour for managing team availability and integrating with project management tools
  • Clockify for freelancers who want to track their time and share it with clients
  • Screenshot Monitor for tracking time and taking screenshots regularly

Now, there’s a big caveat for some of these services. Track freelancer time when it’s appropriate to the job and task. If you’re paying someone hourly to make sales calls and have a tool that creates call logs, asking for a screenshot tool may create an antagonistic relationship, because it demonstrates a lack of trust. However, screen capture is generally appropriate for hourly data entry tasks. If you hire an expert programmer or copywriter to complete a project, screen and time tracking may not be appropriate. 

Freelancers should be treated like the professionals that they are and should respect you and your company in return.

7. Use project management tools

Project management tools simplify communication from asking for updates to delivering content and finalizing phases. Some of the most popular project management tools that will help you manage freelancers include:

  • Asana for ease of use. This project management platform lets you organize projects and tasks in multiple visual styles and provides clear places to add project requirements such as due dates, project type, tags, and assignees.
  • Trello for project boards from Kanban to Scrum. Its mix of boards, cards, and color-coding make visualizing project management and tasks easy.
  • Instagantt for simple task management. This Gantt chart project planning tool is easy to learn and use, even when tracking multiple projects.
  • Basecamp for large teams and notification controls. You’ll organize projects into camps and have dedicated HQ and HR channels, with multiple ways to send messages or tag people, allowing you to quickly reach one person or a whole team.
  • Jira for software and product roadmaps. Jira’s tools are focused on companies creating new products or releasing updates, so you and freelancers can more easily perform related tasks such as tracking bugs.
  • Monday for power users. Monday is perhaps the most robust tool on this list and offers hundreds of project management systems, styles, and tool integrations. It’s fully customizable, but many project management best practices are built into its templates organized by department, objective, or project type.

We also have a larger list of all the remote team tools you need, many of which fit perfectly with freelance talent.

8. Include freelancers in team building activities

Freelance and in-house remote workers perform better when they feel like a part of your team or company. Include them in any activities that you use to build the team up and create camaraderie. This starts with having effective communication lines so that people can speak with each other and know how to get in touch with you to ask questions.

Extend communication outside of the project itself and invite freelancers to some meetings where you catch up with people. Ask about their day and their hobbies. Have them work with your team on team building exercises or create virtual celebrations that build trust. If you use a communication tool like Slack, invite freelancers to the “#random” channel so they can share pet photos, talk about WandaVision, or get cooking tips.

In short, work to make freelancers feel like they belong. Consider having them go through the cultural part of your company’s remote onboarding process to help them become part of a stronger team and establish long-term relationships so you can rely on them for the next project.

9. Provide feedback

The majority of freelancers want to do a job so good that you’ll become a regular client. They want you to enjoy working with them. Creating that relationship can help you get the best work out of a freelancer too, making it easy to retain them again.

One of your best tools to maintaining a positive relationship and ensuring quality is to provide regular feedback. State what isn’t correct and then help the freelancer fix it. This applies to small and large fixes. 

You may say something like, “I really liked your introduction. The following sections need to focus more on the issues our customers face, but I’m excited to see how you do that.”

If the relationship turns negative and you won’t work with the freelancer again, still provide feedback when the project completes. It’s an opportunity for you to ask what might have avoided the issue and help another professional improve the services they offer.

What’s next?

Now that you know the benefits of working with freelancers and how to manage freelancers, it’s time to hire a freelancer for your next project. Upwork makes it easy for you to find, evaluate, and hire freelancers from around the globe with the skills you need while also giving your business advanced protections and contract management. Your new team member is waiting.

Upwork is not affiliated with and does not sponsor or endorse any of the tools or services discussed in this section. These tools and services are provided only as potential options, and each reader and company should take the time needed to adequately analyze and determine the tools or services that would best fit their specific needs and situation.

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Geoffrey Whiting
Writer and Business Analyst

Geoffrey has worked as a writer and analyst for more than a decade, focusing on how businesses can improve talent, services, and operations. Thanks to platforms like Upwork, he's worked with some of the largest software, shipping, insurance, and internal audit firms in the world.

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