Dec 14, 2022

Outsourcing your creative needs is a smart business decision. You can tap into specialized skills without breaking the bank. But working with external workers is definitely different from working with in-house employees, and it does take some time to feel comfortable with the process. 

With more than half the US workforce expected to be freelance by 2028, there’s no better time than the present to put procedures in place to successfully manage current or future freelance talent. 

Table of contents:

Onboarding Freelancers: A Step you Don’t Want to Skip

There’s no way around it: working with freelancers requires preparation and carefully considered processes. While most organizations understand the importance of onboarding new full-time employees, many companies skip over this step when bringing on a new freelancer. Why spend the time and resources on someone who will be working on a one-off project? Right? 


Bypassing the onboarding phase with freelancers sets everyone up for failure. Freelancers need background information, context, and access to assets in order to do the job they’ve been asked to do. Proper onboarding allows companies to maximize the value of collaborating with a freelancer, for a single project or beyond.

How to effectively onboard your freelancers 

To ensure a smooth integration, put together a freelancer onboarding process that mimics the onboarding process you use with your full-timers. The upfront effort will eliminate loss of time, miscommunication, and unclear expectations in the future. It will also allow your freelancers to embrace – and contribute to – the company culture. 

  • Collect paperwork and share vital information. You’ll need to collect signed contracts, NDAs, and tax documents. In return, share your organization’s mission and values, contact information for those involved in the project, and other necessary details of working with your team. Do all of this before your freelancer starts work. 
  • Grant access to required tools, resources, and systems. Provide login information, instructions for using your systems, and links to things like previous campaigns, high resolution logos and fonts, and brand guidelines. 
  • Give clear communication expectations. Be explicit about how people in your organization communicate with one another, especially in a digital workplace.
  • Host a kickoff meeting. “Bridge the gap” between your in-house employees and the freelancer with a Zoom or in-person meet and greet. Be transparent about why you’re outsourcing for this particular project or skillset, as well as the joint benefits of bringing them onboard.

Gain more in-depth insight into onboarding. 

Briefing your Freelance Team: The Key to a Killer Project 

A creative brief is basically the written strategy for your project that you’ll share with your freelancer and any other collaborators. It should clearly communicate critical information, like timeline and budget, and big picture things, like target audience and overall project goals. The brief serves as a guide so the freelancer can deliver a well-executed project that meets your goals and eliminates wasted energy, time, and cost.

The ROI is in the brief. Don’t skip it.

Similarly to onboarding, this is a step that many clients working with outsourced creatives simply skip, thinking it’s a waste of time and resources. But forgoing the brief is a big mistake. A creative brief will allow your freelancer to work more efficiently and save LOADS of time and money in the long run. The likelihood of the freelancer delivering what you want significantly increases when they have access to the necessary information.

While each one will be tailored to an individual project, here are the key components to a creative brief:

  • Project Overview: How would you explain this project over coffee?
  • Project Deliverables: What do you expect at the project completion?
  • Project Mandatories: What MUST be included (logo, bullets, treatments)?
  • Project Goal(s): What will success mean for this project?
  • Audience and Delivery: Who will be the audience for this deliverable and where will it live?
  • Timeline and Budget: What is the firm deadline and budget range? 
  • Links to resources and relative files: What do they NEED to know and what is GOOD to know? 

Learn more about the importance of the creative brief.

How to Give Helpful Feedback to Your Freelancer

Delivering feedback to your freelancer is a necessary part of the creative process, and there’s no denying there is a bit of an art to giving useful, constructive feedback. 

The foundation for helpful feedback truly begins with the onboarding process. Explicitly sharing expectations and communication processes puts you and the freelancer on the same page. Then, providing a creative brief familiarizes the freelancer with the project and its goals. These two steps are crucial for a successful collaboration because when it’s time to actually deliver the feedback, you will have established mutual respect and expectations. 

Delivering helpful feedback

While freelancers expect you to critique their work, but flippant, unhelpful feedback can lead to awkwardness and even tension. 

Be sure to focus your feedback on the work itself. Include your reasoning, referring back to that creative brief you worked so hard on, and offer potential solutions to problem areas. This way, you ensure your comments are helpful rather than hurtful.  

Not helpful: I don’t really like it. Did you read the brief?
Helpful: The way you interpreted the brand message in Option 2 is awesome. Can you elaborate on your approach here? 
Follow-up: I feel other approaches could be strengthened this way. 

Respectful collaboration builds strong working relationships, helps with future partnerships, and will lead to a successful project. Follow these steps to guide you through a helpful – and comfortable – feedback process: 

  • Leave plenty of time to gather feedback, especially if multiple people need to review the work. And if possible, spend a few minutes highlighting the things that work well. 
  • Set a time for delivering feedback. Being in the right mindset to hear and accept feedback is important.
  • Choose a single point of contact (POC) to deliver the feedback. It’s overwhelming to hear comments from multiple people, especially at once. Consolidate all the feedback and deliver it in one batch. 
  • Skip the compliment sandwich. You’re not fooling anyone. 
  • Be specific, clear, and concise. Vague, general comments don’t put anyone on track to implement useful changes.
  • Get curious. Ask questions – talking through decisions and thought processes opens the door for understanding and reflection, and sets the stage for collaboration. 
  • Offer suggested solutions. This doesn’t mean you should tell your freelancer exactly what to do, but providing some structure or at least outlining the next steps allows your freelancer to make the changes that will meet your goals. 

As much as possible, make feedback a conversation. All parties are interested in producing a successful project. 

Read more about the feedback process.

Download the Freelance Team Starter Toolkit 

If you’re new to working with freelancers, we want you to feel confident working together from day one. 

We’ve put together some helpful templates to set you and your external talent up for success. Download the Freelance Team Starter Toolkit to get access to our onboarding worksheet, creative brief template, and feedback checklist. 

Now go hire a freelancer – you’ve got no excuse! 


Do you receive The Inkling, our monthly newsletter offering tips and resources like this? Sign up here.

Subscribe to our monthly newsletterĀ The Inkling.