12 Experts’ Advice on How to Onboard a Freelancer

Use Video Tutorials for Onboarding

As a freelancer myself, I rely on a team of other freelancers to help me scale my time. Whenever I bring on a new freelance writer, I create a personalized video to show them how I want things done.

My team and I work in Asana, where I send assignments and move projects through different stages. It’s a user-friendly tool, but I created a video tutorial to show newcomers exactly how to use it, step by step. I’ll also answer frequently asked questions in the video and use this as an opportunity to express my excitement about our new partnership.

Videos are a great way to set the tone for a remote relationship. The other person has the benefit of hearing your positivity, plus it creates a personalized touchpoint that helps you stand out.

Foster Social Integration

My best advice for onboarding a freelancer is to prioritize social aspects. Freelancers have little understanding of your company culture and are alienated from the rest of the team. Integration would help them collaborate with your existing employees as a team.

This can be achieved by personalizing the onboarding process, fostering open communication, and providing access to company resources. You can also organize a social event to share company culture in action.

By taking these steps, you can create a positive and inclusive environment for the freelancer, helping them integrate into the team and contribute to the company’s success.

Understand Their Motivations

When onboarding a freelancer, one of the best pieces of advice is to go beyond only discussing the job parameters and contract details. Ask them about what motivates them and gets them excited about their projects.

For instance, it can be an uncommon practice to provide helpful resources such as books or online courses, but when providing such extra benefits, it helps make the freelancer even more engaged with their projects from day one and will often foster loyalty and tenure with your organization.

This shows that you are committed to helping develop their skills further, which shows your trust in their abilities and gives recognition for any extra efforts they put into achieving success on the project.

Communicate Clear Expectations

When onboarding a freelancer, it’s crucial to establish clear expectations from the outset. This should include delivering a detailed brief on the project deliverables, timelines, and communication channels. Set up regular check-ins to clarify expectations, answer questions, and provide feedback to ensure they remain on track.

Make sure they have access to any relevant resources and tools needed to complete the project and make them aware of any non-negotiables, such as budget limitations or specific deadlines. By setting clear expectations at the outset, you can help ensure a smooth onboarding process and a successful project outcome.

Conduct an Initial Meeting

This sounds like an obvious step, but many companies end up hiring freelancers based on reviews alone and don’t provide enough initial input or guidance.

During this meeting, ask them questions about their goals and objectives on the project, as well as how they prefer to communicate throughout the duration of their engagement with you (via email or chat).

It’s also helpful to discuss their availability for everyone to agree on timelines and deadlines throughout the process.

Set Freelancers Up for Success

When onboarding a freelancer, setting them up for success from the start is important. Begin by clearly defining ‌the project and communicating your expectations. Share any relevant information, tools, or resources they may need to excel in their work.

Establish simple lines of communication and provide proper training and guidance to familiarize them with your organization’s processes and procedures.

Foster collaboration and open communication throughout the project, providing regular feedback and reviewing their work to ensure it aligns with your expectations.

Clearly define projects and milestones, including deadlines and compensation terms. Clarify ownership and usage rights of any work created by the freelancer and conduct a thorough evaluation at the end of the project, providing constructive feedback.

Implement a Structured Onboarding Approach

I prefer to onboard freelancers in very structured ways. Regardless of what kind of work they are doing, they will still need to produce their work in ways congruent with our company culture.

Asynchronous communication, showing is better than telling, and valuing deep work are three examples of our culture that will be true for freelancers and employees, regardless of the work they are doing. These are articulated in our freelancer handbook, short and sweet. The follow-on quiz ensures they read and understand the material, instead of just checking the box.

Showcase Successful Work

You should honestly do this even if you aren’t onboarding freelancers, but it is one of the most helpful things you can do to make their onboarding process simpler and more effective.

By putting in the time to feature your best articles, infographics, videos, etc., you ensure that your freelancers have the same image in their heads when they hear the word success—show them what worked, explain why it worked, what you’d like them to take away from it, and where you could use their expertise to add something, and you’re golden.

Share Information and Feedback

Share all the information that your freelancers will need, including company rules, the roles and responsibilities of each department, your expectations from them, a list of all the go-to experts whose guidance they will need regarding work, and the brand style muse that your organization follows.

Also, encourage them to ask questions and share regular feedback to help them learn and grow. This will make them feel valued while ensuring a smooth onboarding. Remember, laying a sound foundation for understanding the work goals helps in the initial days and lets your freelancers perform more efficiently.

Document the Onboarding Process

This is probably the biggest mistake I see people making when onboarding freelancers—they always treat it as a unique process. The odds are high that if you hired one freelancer; you are going to be hiring more soon.

You should document the onboarding process, tinkering with it, and formalizing it for the future rather than just trusting that the project lead that’s hiring the freelancer will do a good enough job to avoid wasting everyone’s time.

Provide a Style Guide

When onboarding a freelancer, it’s crucial to provide them with a set of guidelines or expectations upfront. A style guide will help ensure that their work meets your standards and aligns with your mission and values.

The style guide should include topics like company purpose, tone of voice, logos, branding elements, formatting rules for text and visuals, social media guidelines (if applicable), etc.

For example, freelance writers include key phrases they should use and those they should avoid, as well as the style of language that’s expected. This will help the freelancer understand the type of content you’re looking for and make their job easier.

Offer a Welcome Package

I know what you’re thinking, “A welcome package? For a freelancer?” But hear me out. This unique approach shows your appreciation and commitment to the freelancer’s success and sets the stage for a positive working environment.

The welcome package could include essential company info, an overview of the project, and any resources they’ll need. Remember to sprinkle in personal touches, like a note expressing your excitement at working together or even a small gift relevant to the project.

This thoughtful gesture will show the freelancer their value, setting the tone for a collaborative and fruitful partnership.