How to Manage a Large Freelance Pool

Freelance manager meets with contractors.

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For managers of large freelance teams, efficiency is important. However, managing several employees who work during their time to meet set deadlines can be overwhelming — especially as you balance the responsibility with other important business tasks. 

As a content publisher, using a freelance pool is a great way to create written content without hiring an internal team. However, you need to be sure to manage them efficiently in order to meet their needs and get high-quality content on your schedule. If you’re wondering how to manage a freelance pool or the best practices for freelancer management, discover our seven tips to manage a large freelancer pool.

What is freelancer management?

Freelance management involves overseeing a pool of freelancers who work on a contract basis. Common tasks include holding one-on-one check-in meetings, assigning projects based on expertise and availability, managing a budget, ensuring deadlines are met, and more. 

Although freelance management might seem challenging, it can be extremely rewarding once you understand how to manage content writers. For instance, being able to turn to writers who work on a retainer agreement can free up your own time so you can allocate it elsewhere while relying on talented and experienced freelancers to get the job done well for you. 

You may be wondering “How do you manage content writers?” from onboarding to assigning work. Below, you’ll find actionable tips to manage your freelance writers.

How to manage freelance writers

As all business owners know, content is king in today’s digital world. This is especially true for written content like blog posts on a company website. Freelance writers can make a great asset to any team, but overseeing multiple workers at once is no easy feat. Here’s how to manage freelance writers.

1. Establish a central communication system

Using a specific messaging system to chat, whether it’s email or a communication tool like Slack, can be extremely helpful when communicating with your freelance writers. Often, contract workers will have questions that might occur at random times throughout the day or week — especially since they don’t work the traditional nine-to-five. As a result, having a set place for them to ask questions or raise concerns ensures you don’t miss a message.

Many freelance managers make the mistake of using various platforms to communicate. Offering too many ways to be reached can create confusion and make it more likely to let a message go unnoticed among other timely notifications. State your preferred communication method to your team and give them alternative opinions, only if they cannot reach you.

2. Define a standard process

Each month, there should be a routine for you and your freelancers so everyone is on the same page and knows what to expect. For instance, be ready to delegate all your assignments the first week of the month, ensure all content is outlined properly with the correct resources, and plan regular check-ins at the same time.

Defining a standard process for your contract workers decreases misunderstandings and questions that may otherwise arise and helps you plan your own management tasks accordingly. Without a process, it might feel like you’re being pulled in a million different directions — a common yet avoidable issue for managers of all sorts.

When developing your freelance management process, be sure to speak with each freelancer to understand how they do their best work, their preferred communication channels and frequency, and other logistical considerations. 

3. Ensure open communication

Scheduling check-ins shouldn’t just be part of your freelance management process. When it comes time for your regular one-on-one meetings, dive deep into an open conversation about your working relationship with the writer, including feedback on their performance, and allow them to share their feedback, too. Having transparent dialogue will build trust and respect between you both, and freelancers will be able to air grievances before resentment or further issues build.

In addition to the regular check-ins, remind your freelancers they can also contact you throughout the day, week, or month if concerns or questions arise. When doing this, however, make sure you set the right boundaries so you’re not getting messages in the middle of the night or throughout the weekend during your off hours.

4. Set reasonable deadlines

Freelancers typically have other responsibilities, clients, or even full-time jobs in addition to working with your company. While it might seem like they have all the hours in the world to get your projects done, be considerate and aware of their time as you assign projects to them.

A great rule of thumb is to space out their assignments for the month so they have plenty of time to complete each. Additionally, check in with them to make sure they’re comfortable with the deadlines you’ve set, and make the necessary adjustments if requested (with respect to your workflow, of course). That way, no one is scrambling or stressed out over their workload at the last minute. 

5. Understand their strengths and limitations

Every freelancer, just like every regular employee, has their strengths and weaknesses. You’ll want to take note of where each individual flourishes, as well as where they might fall short, so you can assign content that best aligns with their talents and passions.

For instance, perhaps one of your employees has a knack for creative writing but lacks the ability to conduct thorough research for more informative, factual content. Rather than assigning them an intensive article for your legal client, you might instead give them more blog posts for a local bakery owner you work with.

Recognizing how you can play off your freelancers’ skills is essential to getting the most out of your working relationship with them. While, with a full-time employee, you might dedicate more time to addressing their limitations so they can grow with your company, with freelance writers, your job is not to coach them in their career, rather work with them as they are and provide feedback when necessary. 

6. Track time accurately

Since writing processes are unique to each individual, some writers might take more time than others when working on a project. Content writers tend to have different writing processes that suit them, and tracking their time spent on an assignment can be difficult.

However, there are tools freelancers can use to measure the time spent on a specific project. While you can decide on a blanket per-word or per-project rate, allowing your contract workers to track their efficiency might increase their productivity and give you a better understanding of whether your rates are fair — to them and your business. 

7. Give consistent, helpful, actionable feedback

As mentioned above, providing transparent feedback is essential to getting the best work from your freelancers. If you feel one of your contract workers has been slacking, don’t wait to see whether they improve. Instead, have a discussion about their slip in quality work and ask whether you can help them in any way. Offering support rather than scolding them shows that not only do you care; you’re also committed to holding them accountable. 

When providing feedback, make sure it is helpful and actionable. Instead of simply telling them their recent article was poorly written, give them specific details about how it could be improved. Additionally, don’t forget to thank and praise them for their continued hard work. Only voicing your concerns will leave your workers feeling unappreciated and could eventually lead to burnout.

Tips for managing freelancers

Now that you know the basic foundation for managing freelancers, here are a few tips for managing freelancers effectively.

Hire carefully

As you go through the hiring process, it’s crucial to be incredibly specific about what tasks you’d like a freelancer to take on and the skills they’ll bring to the role. Trust is key when hiring a freelancer who will be completing projects and developing content in the name of your brand. Ensure you and your team click well with them.

Set clear expectations

Before you begin a working relationship with your freelancers, ask yourself what expectations you have for them within their role. Do you have a specific deadline you’d like them to stick with? Are there preferences when it comes to completing tasks? Compile a comprehensive list of your expectations when the freelancer enters their new role and share it with them on their first day.

Check in regularly

Schedule weekly or biweekly meetings where your freelancers can speak freely about their work and you can relay any feedback you have for them. Along with this scheduled meeting, check in either through a messaging tool or email to see how they’re doing and encourage them to reach out if they have any questions. 

Invest in growing the relationship between freelancer and manager

Make sure you’re taking time to properly invest in the relationship you have with your freelancers. Even if you’re only working with a freelancer for a short amount of time, that person is still working with you to write content on behalf of your business. It’s important to nurture this relationship as you would any other vendor.

Make them part of the team

Freelancers are more likely to stay on with an employer they feel is inclusive and treats them as an important part of the team. You can do this by acknowledging your freelancers in the day-to-day processes, including them in team meetings, and providing certain perks. When it comes time to expand your team, you can look internally at your freelance pool first to see if there are any qualified candidates.

Give clear feedback

The best action you can take to further a freelancer’s development with your business is to provide clear, concise feedback. Let them know what you like about their work as well as what they can improve upon. Be sure you’re helping them create an action plan to refine any issues or obstacles.

Compensate competitively

Just because freelancers are contractors to your business doesn’t mean they don’t deserve fair compensation. Seek to pay your freelance team at the market rate or even more depending on the scope of their work.

Listen to their needs

Ensure you’re available when your freelancers want to relay to you what they require to succeed in their role. Maybe they need additional time on a tough assignment or need feedback from a project with murky goals. Set aside time to intently listen and consider their requests.

Offer access to help and resources

If your business has access to certain tools that will help your freelancers within their role, consider sharing that information or getting them access. Encourage your team members to find tools that may assist them in their work, like the AP Stylebook, and try to leverage those resources across your freelance team.

Explore project management tools

Project management tools are a great way to streamline communication efforts, compile content, and submit either to a client or produce on your business’s website. This makes it easier for you to organize your freelancer’s assignments and gives them a singular place where all their projects live. A few popular tools you can utilize with your team include Asana, Trello, and Monday. 

Make sure you’re organized

Having a large freelance pool means you’ll have to stay organized to manage your team properly. This means creating editorial calendars to keep track of assignments, scheduling meetings, and managing payroll. The more organized you are, the easier it is to manage your time and provide clear direction and timely feedback.

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