Should You Onboard Contractors?

Mar 17, 2025 | Articles, Onboarding

Imagine it: you’re a freelancer. You’ve just landed a brand new client. You don’t know much about them or their product, but you’re looking forward to getting started on the project you were contracted for. You just need some information about them and their product and you can get to work.

Except… there’s no information. The client gets your W-9 and just expects you to get started. You’re not exactly sure what their expectations are, and the only thing you know about their product is what you can glean from their website. As a contractor, I can tell you that this happens sometimes, and it’s usually a sign that a project is off to a bumpy start for both me and for the client.

This is why I love it when clients have a clear and structured onboarding process for freelancers. It sets the tone for our relationship, and helps me to understand the organization I am working with and produce better work.

The importance of onboarding freelancers

Onboarding is an introduction. It’s a structured plan that welcomes someone into your organization, acquaints them with your culture, people, and processes. Onboarding sets goals and expectations for everyone involved, and provides learning that’s essential for a newcomer to be successful with your organization.

It makes sense that you’d onboard anyone who is new to your organization: employees, partners, and customers. Not every onboarding process is the same, however. What about your contractors?

Contractors are an essential part of your enterprise; they provide key services and are often valuable team members. However the laws governing contractors can make it difficult to provide the same onboarding experience you’d provide for a new full-time permanent employee.

How can your organization provide the right level of onboarding for your contractors while staying compliant with industry and regional regulations?

Key differences between contractors and employees

Your favorite freelancer may seem like just another team member, but legally, there are some pretty big differences between contractors and employees. Different countries have different laws, but the U.S. uses the Economic Reality Test to determine the difference between contractors and employees, which takes six factors into account:

  1. Opportunity for profit or loss depending on managerial skill: does the worker negotiate the terms of their own work?
  2. Investments by the worker and the employer: Who pays for the equipment and office space used by the worker?
  3. Permanence of the work relationship: How long-term is the relationship?
  4. Nature and degree of control: Can you tell the worker how to produce the work?
  5. Whether the work performed is integral to the employer’s business: Is the work central to your mission?
  6. Skill and initiative: Does the worker bring their own skills to the job or do they need training?

In other words:

  • Contractors sign a contract with a client, agreeing to provide a specific service or product at an agreed-upon rate. This may be short-term or long-term, and as long as they produce the work, the contract is fulfilled. The client cannot tell them how to do the job. For example, the client can’t require a contractor to work certain hours, or do the work in a certain way. The contractor usually pays for their own equipment and space, and they can’t expect benefits from the client.
  • Employees are hired indefinitely. They work set hours, you can tell them exactly how to do their job, and certain behaviors can be required (like attending training). Employees are provided with benefits, equipment and office space by their employers. They get a salary rather than submitting an invoice.

Onboarding: employees vs. contractors

What does employee onboarding look like?

Creating a structured onboarding program for new hires is critical. A strong onboarding program for new hires usually includes the following:

  • Compliance information and paperwork
  • An orientation
  • An introduction to equipment and tools
  • Integration with the team and company culture
  • Information so the new hire can do their job well
  • Consistent check-ins with the new hire over the first several months

Other best practices include setting goals for new hires and providing learning for them.

What works for employee onboarding probably won’t work for contractor onboarding.

What does contractor onboarding look like?

You can’t require a contractor to take training in the U.S. — it’s considered behavioral control, and the contractor is supposed to be bringing their own skills and knowledge to the job anyhow. They technically should not need training.

For this reason, contractor onboarding is usually kept to a minimum:

  • Paperwork, such as tax documents, contracts and NDAs
  • Provisioning, if the contractor needs access to any platforms used by a client
  • Compliance information if needed

In some cases it’s even more basic than that — just a signature on a tax form.

Should contractors be offered more onboarding?

Once you find the right contractor, you probably want them to jump right in and start your project.

However, as eager as you might be to onboard a contractor quickly and get to work, both you and your freelancers can benefit from a structured onboarding process that goes beyond documentation and paperwork. Onboarding is meant to set expectations for both you and the contractor, so even if you’re only bringing on a freelancer for a small project, it can be helpful to create a checklist for onboarding.

This may include:

  • Paperwork: tax documents, NDAs, contracts, payment details, and any other paperwork that needs to be completed
  • Expectations: What is the scope of your project? What are the responsibilities of the contractor? What about your responsibilities? How will you communicate, and when?
  • Introductions: Introduce the contractor to the team that they will be working with.
  • Resources: If there are any resources the contractor needs to do their job, they should have access to those items. This might include guides, demos, or courses that help the contractor understand your company or product.
  • Permissions: If a contractor needs access to any systems or platforms, your onboarding process should include this.

Why onboard contractors at all?

It’s important to remember that while you can’t require your contractors to attend meetings or look at resources, you can set them up for success by providing the opportunity to get better acquainted with your organization.

In fact, many contractors welcome onboarding. So many times, we’re thrown into projects with very little information about the organization as a whole. But when I can see how the work I am doing aligns with my client’s business goals, I can be more effective. When I have a strong understanding of my clients’ product, I can produce stronger projects.

At the end of the day, most contractors want to do the best job we possibly can; our portfolios are our livelihoods. The work we do for our clients now will help us land more clients in the future. When you provide us with an onboarding program, you’re giving us an opportunity to produce our best work for you, and for ourselves. It’s a win-win.

Ready to accelerate your onboarding strategy? Access customizable resources to help your organizations streamline continuous onboarding for employees, customers, partners, and others across the enterprise. Download your free Ultimate Toolkit for Continuous Onboarding today!