How to Onboard Freelancers and a Contingent Workforce 

Businesses have known for years that a good onboarding process is critical for retention, productivity, and company culture. However, with the emergence of the gig economy, executives are realizing how important it is to also have an onboarding process crafted specifically to onboard freelancers in addition to an onboarding process for employees.

Onboarding a contingent workforce can be a challenge for executives and managers charging into the Future of Work, but it is essential to ensure that these workers feel like they are a respected part of the team. In this article, we will discuss how to overcome these challenges and successfully onboard freelancers and other contingent workers. We will also provide tips for setting clear expectations and avoiding micromanagement. 

Why is it important to understand how to onboard freelancers? 

Onboarding is the process of integrating a new worker into the company. A good onboarding system is clarifying and sets people and projects up for success. It is important to have a good onboarding process for all employees, but in recent years we have seen that it is especially important when onboarding freelancers. This is because freelancers are often working remotely, which can make them feel isolated from the rest of the team. 

Additionally, they may be working in a different country with a different culture, which can make it difficult to understand their needs and expectations. Without a good onboarding process, it is easy for freelancers to feel like they are not respected or valued by the company. Poor onboarding can also lead to freelancers feeling uncertain about expectations.

On the plus side, a remote onboarding process can increase productivity and the overall success of the initiative. Studies show that “companies with a standard onboarding process experienced 54% greater new hire productivity, saw 50% greater new hire retention, and two-times the level of new hire engagement as compared to those that did not.”

The freelance economy is booming

One of the most important reasons for understanding how to onboard freelancers is competitive advantage. A recent Forbes article states, “By any measure, the U.S. freelance workforce continues to increase by leaps and bounds. There are no signs it will slow down anytime soon.” 

As the contingent workforce continues to grow, it is important for companies to understand how to onboard these workers successfully. Since the freelance economy isn’t slowing down, the sooner companies have a freelancer onboarding system in place, the better. 

Challenges of onboarding a contingent workforce 

There are several challenges that come with onboarding a freelancer or contingent workforce. However, before you can onboard freelancers, it’s important to have the right contract in place. Here are some tips on how to create an effective freelance contract.

When it’s time to onboard freelancers, there are a few key challenges that executives and managers must overcome:

• The workers may be located remotely, which can make it difficult to ensure that they are properly integrated into the company.

• The workers may have a different culture than your company, which can make it challenging to ensure that they are properly respected.

• The workers may be working in a different country with a different legal system, which can make it difficult to understand their legal rights and put you at risk for noncompliance.

• The workers may be working on a project-by-project basis, which can make it challenging to set clear expectations and have systems in place for communication.

When you onboard freelancers, it is important to keep these challenges in mind. By understanding the challenges, you can develop strategies to overcome them. 

How to overcome challenges when you onboard freelancers

Now that we’ve discussed some of the challenges of onboarding a contingent workforce and freelancers, let’s talk about how to overcome them. Utilizing technology, setting clear expectations, encouraging questions, and allowing flexibility are all ways of overcoming challenges when you onboard freelancers.

It is also important to make sure that they feel like they are a respected member of the team. In a Forbes article about handling the growing freelance workforce trends, one expert writes, “Make them feel part of the team as opposed to a vendor, which means you must have a healthy team culture in the first place.”

In addition to the tips below, you can find more information in our article, 5 Tips for Effectively Managing Freelancers Around the World.

Tips for setting clear expectations with your contingent workers

When you’re onboarding an employee, it’s important to set clear expectations from the beginning. You’ll want to make sure that the objectives of the project are clear from the start. This includes telling them what your company culture is like and what you expect from them in terms of communication. It also includes defining the scope of work, deadlines, and deliverables, if you haven’t already done so in the contract.

You can do everything in your power to be clear, but it’s natural for questions to still arise. That’s why it’s important to have systems in place for communication, so that you can answer any questions that come up and keep the project on track. Be available to answer questions and let them know the best ways to get a hold of you or their point of contact.

Tips for avoiding micromanagement when you hire freelancers

Micromanaging a freelancer isn’t just harmful to the project, it could also put you at legal risk for misclassification. One of the fundamental aspects of a worker who can be legally classified as an independent contractor or freelancer is that they get to work how and when they want to. Allowing them flexibility in how they complete the task gives them space to utilize their expertise and mitigates risk.

Trust that they will complete the task as agreed upon and if you’re not sure send them an email or message. Giving them feedback and encouraging them to ask questions helps you stay involved in the project to a healthy degree while allowing them the flexibility and autonomy they desire.

The Future of Work and the role of the contingent workforce

As the Future of Work gains momentum, the significance of the contingent workforce will only grow. In order to successfully navigate this new landscape, it is essential that executives and managers understand how to onboard freelancers and other contingent workers. By following the tips and advice outlined in this article, you can ensure that your contingent workforce is properly integrated into your company culture and mission. 

We recently received this message from a worker using the GreenLight platform: “You win the award for easiest, smoothest onboarding. Thank you. Much appreciated. Well done.”

If you want to learn more about how GreenLight can help you create a world-class onboarding process for your freelancers, click here to book a demo.

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Jason Posel

Jason Posel

Founder and CEO of, Jason Posel is a sought-after expert in issues related to technology innovation in contingent workforce management, the gig economy, and the Future of Work. London > Atlanta > Miami > Palo Alto > Miami

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