How to Manage Freelancers

How to Manage Freelancers

Managing a team of freelancers presents some unique challenges. One of the biggest hurdles you will encounter is aligning everyone’s schedules, especially in different time zones. You must keep track of everyone’s progress, or your project might fall behind.

With these responsibilities, you’re constantly juggling availability and project deadlines. We understand—it’s a lot to manage and can be overwhelming to keep everything running smoothly.

But here’s some good news: you can quickly rev up your freelance engine with the right strategies and tools. 

This article explores proven strategies and project management tools to manage freelancers while maintaining control over your projects and maximizing productivity. 

By the time you’re finished reading, you’ll be a pro at setting clear expectations for your freelance workers, managing everyone’s time and workload, and giving feedback that helps.

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Managing Freelance Talent: Benefits and Challenges

Advantages of hiring freelancers

Hiring freelancers offers several distinct advantages over full-time employees, making it an attractive option for many businesses; these include:

  • Cost efficiency: Freelancers can be cost-effective if you only need a surge squad for a specific project or a short period. For example, for a marketing campaign, hiring a freelance video editor for a few weeks will be cheaper than keeping a full-time employee on payroll all year round
  • Access to specialized skills: If you feel that your current team of full-time employees lacks expertise in specific areas, hiring freelancers lets you tap into their expertise, ensuring high-quality outcomes for niche tasks
  • Flexibility: With a freelance workforce, you can scale up or down your team quickly, which is ideal for handling peak workloads to prevent employee overload and burnout 
  • Reduced overhead: Since freelancers work remotely and manage their tools and workspace, you do not need to invest in additional office space, equipment, and other resources

Managing freelancers vs. in-house employees

Managing freelancers is quite different from managing full-time employees. You hire a freelancer for a specific task or project, whereas full-time employees fulfill an ongoing, evolving role. 

You must know the difference between freelancers and full-time employees to build positive relationships. 

Differences between hiring freelancers vs. full-time employees
AspectFreelancersFull-time Employees
CostOften cheaper, no benefits or long-term commitmentsSalaries, benefits, taxes, and long-term commitments
FlexibilityHire freelancers as needed for specific projectsLimited flexibility, fixed work schedules
ExpertiseAccess to a wide range of specialized skillsExpertise limited to the skills of current staff
ScalabilityEasy to scale up or down quicklyScaling requires hiring/firing processes
OverheadNo need for additional office space or equipmentRequires office space, equipment, and other resources
CommitmentShort-term commitment, project-basedLong-term commitment, ongoing employment
ManagementLess direct control, self-managedDirect oversight, more control over work
AvailabilityMay have varying availability, multiple projectsDedicated to your company, consistent availability
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How to Manage Freelancers Effectively in 7 Steps 

1. Define project scope, expectations, and budget 

Before you assign tasks to freelancers, set clear project expectations to avoid problems down the road. To ensure clear communication and understanding, here’s how you can get them on the same page:

Add project requirements

Be specific about what you want your freelancer to do. Provide detailed instructions on expectations and how to complete the task, including any necessary steps, guidelines, or project requirements

Define project details well—the more information you can give, your freelancer will be better equipped to deliver the work you need.

Example: If you’re onboarding a freelance writer to create a whitepaper for your company, provide additional context on the target audience, word count, and tone. Also, include specific product details and case studies. 

Mention deliverables with deadlines

When you assign any task to a freelancer, include clear deliverables, milestones, and deadlines to complete the project,

Example: We want four 1000-word blog posts from you every month. Please deliver one post every week on Monday.

Discuss availability

Discuss early on if you need freelancers to be available for meetings or calls so they can plan their schedules accordingly. 

Example: Every Tuesday, between 12.45 and 1.30 pm, we have a weekly Zoom catchup call between the freelancers and the relevant teams. 

The team meeting aims to discuss the project objectives, the results achieved, feedback for anything particular, and share product updates. 

Discuss payment terms

Clarify payment terms, including how often you will pay freelancers and your payment platform.

Example: We have a NET + 30-day payment cycle for the freelance team. The payment method is PayPal, and it is for all the approved blog posts you’ve written. 

The last thing you want to do is have these discussions after the freelancer working on your project raises the invoice. 

Use ClickUp’s Scope of Work Template to specify all the details in a centralized repository. This will save you time creating lengthy spreadsheets or emails to share this information. 

It provides an easy framework to outline the scope, objectives, and deliverables, along with sections for legal requirements, milestones, and project goals, which can be customized according to your needs.

Use ClickUp’s Scope of Work Template to define the critical details of the project at the very start

Pro tip💡: Use an AI-writing assistant, such as ClickUp Brain, to automate the creation of project descriptions and briefs. 

ClickUp Brain fetches necessary details from your project management tool and populates the scope, delivery dates, timelines, goals, and milestones within your Scope of Work and other SOP templates for freelancers that you use. 

Using ClickUp Brain to create a project description and outline for an e-book
Using ClickUp Brain to create a project description and outline for an ebook

2. Discuss communication and check-ins

Effective communication is key to managing any team, but it’s even more crucial when managing freelancers. You aren’t directly supervising their work; in most cases, they might be working remotely. 

And if you don’t communicate effectively, you’ll have to deal with:

  • Missed project deadlines
  • Misunderstandings
  • Scope creep 
  • Motivation issues 

To avoid these scenarios, make sure to discuss the following communication aspects with your freelancer:

Preferred communication mode 

Discuss with your freelancer the communication tool your company uses: Slack, Zoom, and any other online collaboration tools where they should be available to reply promptly. 

Meeting frequency

Agree on how often you’ll touch base. Do you want weekly check-ins or bi-weekly updates? 

Choose a frequency that keeps you aligned without overwhelming anyone’s schedule so you can tackle any issues before they escalate.

Handling changes

Discuss how you would discuss changes in their work. Whether through comments in a Google Doc or messages via a project collaboration tool, ensure a clear process.

Ideally, you want a single effective communication tool for team meetings, handling changes, and asynchronous communication, including direct messages.

That’s where ClickUp for freelancers serves as a project management tool with effective communication lines to centralize your schedule and communication with the many freelancers you work with.

ClickUp’s Chat View allows you to efficiently manage communications with your freelance talent so that nothing slips through the cracks. Send direct messages, assign tasks, share updates when you add or edit tasks, and share collaterals like links, attachments, and videos to support freelancers. 

ClickUp Chat View
Stay in touch with your team of freelance workers using ClickUp Chat View

For each assigned task on ClickUp, you can also add comments to mention updates or special notes. 

Pro tip💡: Within ClickUp, freelancers can highlight text to add a reply to specific parts of your comments using the ‘Quote’ option, reducing the risk of confusion even if you’ve added multiple points.

Quote option in comments in ClickUp
Using the Quote option in comments on ClickUp

But what if you need to give complex, detailed instructions?

Skip the text and use ClickUp Clips to create and share screen recordings, providing clear, visual guidance to prevent misunderstandings and ensure your freelancers understand each task. 

You can also embed these clips on any task or share a public link so freelancers can easily access them. 

ClickUp Clips
Use ClickUp Clips to share screen recordings in the chat window

3. Set up an effective onboarding system

What are the classic signs of a poor onboarding system? 

Your freelancers feel lost, not knowing what to do next. They have trouble figuring things out independently and repeatedly ask you the same questions. 

The worst, they’ll struggle to deliver quality work. 

This is not the best scenario when you hire the right freelancers as a long-term investment in your company’s success. 

Here is what you should include in your onboarding documents:

  • Company policies: Introduce your work and team culture and values, and include NDAs and agreements if needed
  • Training materials: Provide style guides, best practices, and industry-specific knowledge to ensure consistency and quality
  • Access to special tools: Equip freelancers with access to software or tools to specialized that they need for their job, such as graphic design software, project management tools, or communication platforms

To streamline the onboarding process, you can utilize ready-made frameworks. 

For instance, ClickUp’s New Hire Onboarding Template allows you to create detailed checklists, schedule training sessions with coworkers, assign due dates, and track project progress with custom statuses like To Do, In Progress, and Complete.

Add a detailed checklist within ClickUp’s New Hire Onboarding Template to ensure your freelancers are fully equipped with the essential details to kickstart the collaboration

Read more: Here are the top 10 tried and tested freelancing hacks to save time on soul-crushing admin work 

4. Use freelancer project management tools

Managing multiple freelancers across teams can make it difficult to keep up with various updates and deadlines, leading to confusion and disorganization. 

Project management software for freelancers can help you schedule tasks, track progress, view dependencies and bottlenecks, and ensure smooth operation. 

Here’s how ClickUp’s Project Management Software sets you up for success: 

Managing a to do list in ClickUp with Task Checklist
Create clear, multi-functional to-do lists to manage your ideas and work from anywhere so you never forget anything again
  • Whiteboards for brainstorming: ClickUp’s Whiteboards are your digital canvas, helping your regular employees collaborate and brainstorm with the freelance team and converting ideas into actionable tasks, even when everyone works remotely 
  • Docs for collaborative editing: ClickUp Docs is a single source of truth to list all project details—goals, guidelines, project proposals, milestones, etc. Collaborative editing allows multiple project team members to make changes, add comments, and assign tasks to these docs. You can also add role-based access as view-only docs 
collaborative live editing in ClickUp Docs
Create, edit, store, and share all company and project-related information with your freelancers using ClickUp Docs
  • Dashboards to track progress: As a project manager or team leader, ClickUp’s Dashboards allow you to add KPIs, track and visualize progress, and gain real-time visibility into opportunities and roadblocks 
  • Task organization: Use ClickUp Tasks to break down complex projects into smaller tasks, set deadlines, and help freelancers prioritize work effectively 
  • Get a birds-eye view of what the freelancer is working on: With ClickUp’s Kanban Board View, see at a glance what each freelancer is working on, what stage their tasks are in, and what still needs to be done
ClickUp’s Kanban Board View
Visualize multiple workflows with ClickUp’s Kanban Board View

If priorities change, you can move tasks through workflows using the drag-and-drop feature, allowing quick updates and reorganization.

Drag and drop any task into the next column to automatically update its status with ClickUp’s Kanban-like Board view
Drag and drop any task into the next column to automatically update its status with ClickUp’s Kanban-like Board view

Read more: 10 best contractor management software & tracking systems in 2024

5. Manage time effectively with trackers

Freelance time-tracking software allows you to manage billable hours and timesheets and track time in and out in a centralized location. 

ClickUp’s Project Time Tracking feature helps your freelancers track their hours. Use the built-in global time tracker to start and stop time from anywhere, add notes and labels to time entries, and get a roll-up of the total time they spent on your tasks.

ClickUp’s Time Tracking
Check estimated project time with ClickUp’s detailed time-tracking reports

Even if multiple freelancers, such as writers and editors, work on the same task, they can track their time individually. At the end, you can check individual time records and compare them to the time estimated at the beginning of the project. 

If there are any setbacks or delays, freelancers can update the due dates on the main task. All team members assigned to those tasks will automatically get a notification so they can adjust their schedules accordingly.

ClickUp’s detailed time-tracking reports ensure that all aspects of your project stay on track and that deadlines are met efficiently.

Read more: Top 9 people management software tools in 2024

6. Offer and get feedback regularly

No matter how talented your freelancers are, they need your guidance and feedback to meet your expectations. 

You must provide regular feedback to avoid endless revisions and frustration. Some best practices for sharing constructive feedback are: 

Be specific

Pinpoint what they did well or what needs improving.

Example: The section on the product’s features could use more detail. Can you expand on how each feature benefits the user?


Don’t wait until your freelancers have stopped working on the project to tell them what you think. Give them feedback early on so they can make changes quickly and easily.

Example: I just finished reviewing your article draft. Let’s hop on a quick call to discuss my feedback while it’s still fresh in my mind.


Suggest how they can improve or build upon their work.

Example: To improve readability, use shorter paragraphs. Use subheadings and bullet points to make your content easily scannable.


Appreciate them for what they did well, and point out areas where they can improve.

Example: Your research and data points were impressive and added credibility to your article. However, the conclusion fell a bit flat. It was a bit generic; we need to rewrite it so that it sums up the key takeaways of the post.

Provide your freelance team with constructive feedback, but remember to ask for their input regularly. 

Ask them about the issues they encounter while working. 

An easy way to gather insights from your freelancers is to use ClickUp’s Employee Feedback Template. This template allows you to collect detailed feedback on working with you, such as role clarity and development opportunities. 

This feedback loop can help you identify how to improve processes and better support your freelancers.

Get to know what your freelance workers think of your company culture, management, and work culture with ClickUp’s Employee Feedback Template

Pro Tip💡: Set up ClickUp Automations to automatically send feedback survey emails to your freelancers every quarter. 

You can use ClickUp’s Form View to collect feedback from your freelance team. This ensures consistent feedback collection and helps you identify and address issues promptly.

7. Invite freelancers to team-building activities

Although freelancers are an extension of your team, they will likely feel disconnected from its camaraderie because their interactions with it are limited. 

The result? 

It can impact their sense of belonging and motivation. Inviting them to team-building events helps them integrate and feel valued. 

For your employees, it reinforces that freelancers are essential teammates. When they participate together in team-building activities, they build rapport and strengthen their bond.

Here are examples of virtual team-building activities you can try:

Virtual escape rooms

For a virtual escape room activity, everyone joins the same online escape room game. They must communicate and collaborate to find clues and solve puzzles before time runs out to ‘escape.’ 

This fun game is great for remote teams with freelancers, as it encourages teamwork toward a shared goal.

Trivia night

Choose trivia questions about popular movies, TV shows, music, and other fun topics. Have a mix of freelancers and in-house members on each team.

Everyone can socialize in a relaxed, low-pressure setting since it’s just a casual, fun trivia game.

Plan such activities using ClickUp’s Team Docs Template. This customizable template lets you list icebreaker questions, set rules for various virtual activities, and organize all details in one space.

Use Team Docs Template in ClickUp to streamline core team documents and improve accessibility within projects

Keep the Team Docs Template in ClickUp handy during your virtual activities. It lets you see everyone’s job titles, experience, and contact information.  

Since it’s a collaborative doc, your entire team, including your freelancer workforce,  can contribute ideas and feedback.  This centralization fosters a more inclusive and organized planning process, ensuring everyone feels involved in the remote bonding experience.

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Use ClickUp to Power Your Freelance Team 

Remember that every successful freelancer wants to deliver quality work, and you are responsible for setting them up for success.

Start by clearly defining expectations and providing detailed directions. As the project progresses, provide regular feedback. Open communication will help them understand where they need to make changes.

ClickUp’s project management platform combines all the features you need to manage your freelance team members, including time tracking, team communication, and project management capabilities in one platform. 

Track work hours against the project budget, assign project tasks, set and track the project deadline, create AI-powered project descriptions, share critical files, and communicate within ClickUp’s project management tool. 

No more do you need to juggle multiple apps to manage your freelance team and independent workers. The answer to how to manage freelancers starts with signing up on ClickUp and taking its free features on a test drive.

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