5 Ways to Improve Your Contractor Onboarding Experience

August 2, 2022

As the Great Resignation continues, the U.S. workforce has seen an increase in skilled freelancing, and more freelancers viewing working independently as a permanent career choice.  

If your company is working with freelancers or independent contractors, don’t forget an important first step – onboarding. Many companies have a structured onboarding experience for new employees. But for those that also work with independent contractors, the onboarding process is oftentimes overlooked or deprioritized because they are viewed as more temporary roles.  

However, to ensure a successful and engaging contractor experience, it’s just as important to invest the time to integrate them into your systems, ways of working and organizational culture.  

At Brilliant Ink, we regularly work with a community of independent contractors. We have found that providing a comprehensive onboarding process creates a strong foundation that empowers them to hit the ground running and be effective members of our team.  

There are several benefits to investing in the contractor onboarding process, such as:

  • Sets clear expectations – Building on what you’ve outlined in your scope of work or contract agreement, the onboarding phase allows you to clearly define the contractor’s roles and responsibilities and set expectations about your workflow, quality standards and standard operating procedures (SOPs) from the very beginning.  
  • Bolsters engagement and retention – When contractors feel like they are part of a team and have a greater understanding of the company’s broader goals, values and ways of working, they are more likely to remain engaged and motivated to continue working with your business. As an extension of your team, contractors who feel included and infused in your workplace culture may also become ambassadors for your business and refer additional great talent to include in your pipeline.
  • Saves time and effort – Arming contractors with the appropriate access, tools and resources at the beginning of the relationship will help minimize foundational questions and allow for smoother workflow. Also, taking the time to document your processes allows for quicker training and scalability.  

So, what does effective contractor onboarding include? Below are five key items to consider.  

1. Set the tone with a welcome meeting

On their first day, host a welcome meeting or call and walk through the contractor’s onboarding schedule. Use this discussion to ensure they’re properly set up in your system and can access the necessary software and tools.  

This is also a good time to share an overview of key contacts within your company, a brief summary of relevant teams/departments and their roles, and to explain who to go to for what.  

2. Create a single source of truth

For ease and convenience, create a one-stop shop contractor resource guide. It should house or a link to key resources like ways of working, company goals, brand style and standards, SOPs, and how to’s or best practices for various tools and systems.  

This can be a simple PDF, in a tracker like Smartsheet or Trello, or a landing page within your intranet. As you consider the format for your guide, keep in mind that people digest information in different ways. Determine what makes sense as a text document and where there may be opportunities for screen-sharing tools like Loom for a more thorough how-to.

You may also pre-record a collection of roadshow videos that share an overview of your business structure, departments, and initiatives – this is a great way to introduce contractors to other members of your company that they may not work with on a regular basis.  

No matter what direction you decide to go, aim to create accessible materials.  

3. Schedule relevant live demos

Schedule a video call or an in-person working session to walk through complex systems or tools that would be better explained live. This allows you to provide better context about exceptions or how to address different scenarios.  

It would also be worthwhile having a live discussion about your brand style and standards to give the contractor a chance to ask questions. This is a good opportunity to pull in other members of your team to lead these discussions and help the contractor begin putting faces to names. And while you're at it, keep accessibility top of mind!

4. Keep onboarding short and sweet

The key to a successful onboarding experience is finding the right balance of sharing enough relevant information in an efficient amount of time. After all, contractors are usually brought in for temporary, short-term projects and they want to get to work as quickly as possible.  

Onboarding activities could take approximately two weeks, depending on the amount of information you have to share and prepare them with.

5. Capture feedback from contractors

It’s important to make time to check in with your contractor regularly after they get started, perhaps at the end of week one, and at the 30- and 60-day mark. Some questions could include:  

  • What part of the onboarding process has been the most effective or beneficial? What could be changed?  
  • Did the trainings prepare you with the right tools and knowledge to do your work?  
  • So far, is the job what you expected it to be?  

Consider any necessary adjustments to your onboarding process based on their responses.

During my check-ins, I noticed that new contractors had additional questions about our time-tracking tool after reading the how-to guide, so we updated our process to include a working session on the tool. This quick fix ensures they are submitting accurate information to our accounting team.


From setting the tone with a welcome call to creating a one-stop shop resource guide to capturing their feedback, there are steps you can take to create a structured onboarding experience. Preparing your contractor with the systems, tools and resources they need will help them jump in, make an impact and have a meaningful experience with your company.  

At Brilliant Ink, we prioritize contractor onboarding and continue to look for ways to enhance it. Check out what our contractors have shared about their experience:

  • Cary Debenham, Graphic Designer: “As a freelancer, I have never experienced an onboarding process as developed and thorough as Brilliant Ink's. Not only has it given me a clear understanding of processes, expectations, and company culture it also has made me feel like a valued part of the team from the get-go.”  
  • Sarah Dietz, Senior Strategist: “Even though we’re fully remote, the onboarding process has felt extremely human and given me an opportunity to better understand the culture and atmosphere of Brilliant Ink. The roadshow videos and the clear and consistent tone throughout all the onboarding materials has helped me not just feel more prepared to work here but has helped me feel good about the team too. Even as a contractor I feel a sense of belonging and support.”  

Do you have a great onboarding approach or need help reimagining the experience for your employees or contractors? Drop us a line!

For more bite-sized brilliance, be sure to subscribe to our monthly employee experience newsletter, the Inkwell. While you’re at it, follow us on LinkedIn, Twitter and Pinterest!

Rowena Diaz

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