6 Tips for Working With and Evaluating Freelance Workers

Unlike traditional employees, managers can’t control a freelancer’s schedule. Your freelancer should give you a general timeline for deliverables and adhere to that timeline.

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6 Tips for Working With and Evaluating Freelancers

Here's what you need to know about working with freelancers:

  • Freelancers are not the same as employees.
  • Freelancers are responsible for paying their own taxes and social security.
  • Freelancers are professionals and define their own hours.
  • You and your freelancers benefit from participating in team meetings and events.

With freelancers and independent contractors making up 36% of the workforce, it’s no surprise that more and more hiring managers are moving to onboard these short-term workers.

Once you’ve finally found your freelancer “perfect fit,” you may find that maintaining an independent contractor/freelancer relationship may seem confusing. After all, a freelancer isn’t an employee. As an independent worker, you shouldn’t be dictating their hours or asking them to abide by company policy—unless the contractor has agreed to specific terms in their contract.

So, what does onboarding and evaluating your independent contractor look like?

Here are our top tips for successfully managing your contractor.

6 tips for working with and evaluating your independent contractor relationship

While freelancers work for a company or organization, they aren’t regular employees. As a result, many managers and HR professionals aren’t entirely sure how to integrate these workers with the team—or if they should even try.

Evaluating an independent ‘contractor’s performance is fairly straightforward in terms of the direct deliverables. But there are other aspects to consider when reviewing relationships with freelancers.

1. Ask your freelancer what they need to get started

Perhaps the easiest thing to do to onboard a freelancer is simply to ask what they need to start work. Ideally, independent contractors should be able to complete work on their own schedule with minimal input and deliver by the deadline.

But they may require a bit of support.

For example, copywriters might want to interview key stakeholders or glean information from other departments. A developer might need to be set up in your task management software, or you may want to organize regular departmental meetings that include your new worker.

2. Get feedback regularly from your freelancers

One of the best ways to evaluate your new worker is to keep the feedback loop open. This can help ensure that any issues can be swiftly dealt with and the contractor can continue with their work.

3. Consider regular raises

If you know you’ll need a freelancer for a longer period, perhaps a year or two, you may want to be the one to offer regular raises. Since companies typically save on benefits, materials, and many other expenses through hiring an independent contractor, offering a raise is a great way to retain talent and foster a positive relationship.

4. Get to know your freelancers

While freelancers aren’t traditional employees, they are still part of the team. Consider inviting them to virtual hangouts within their regular department, or keep them in the loop through official Slack or chat channels. Not only can this help the contractor learn more about the company culture and provide a better service, but they can also strengthen their bond with the company.

5. Be flexible with and expect flexibility from freelancers

Unlike traditional employees, managers can’t control a freelancer’s schedule. Your freelancer should give you a general timeline for deliverables and adhere to that timeline. But they may choose to work however they wish to during the day. This means you can’t always expect them to answer emails or commit to rush-work immediately.

6. It’s more than performance

The most crucial aspect of working with freelancers is whether they can complete the job well on time and on budget. But there are other considerations, too. Some common questions to consider when evaluating your contractor are:

  • Are they easy to work with?
  • Do they communicate well with the team?
  • Did they communicate delays?
  • Did they invoice or complete paperwork on time?

Likewise, the freelancer in question may be trying to answer the same questions about your company.

These small factors can make a difference in maintaining the relationship on both sides. And these types of questions are perfect for feedback loops. They ensure that both the employer and the contractor are on the same page.

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Should your freelancer be an employee?

Although freelancers aren’t classified as employees, there may ultimately be a time when you need to evaluate the independent contractor status of a worker. With the exception of a broad phrase in the Fair Labor Standards Act (FLSA) stating that “the degree of permanency of the working relationship” is part of the test for determining contractor vs. employee status, there’s no law restricting the time period you can work with a contractor.

Therefore, you will want to review the working relationship between your company and those who are designated as independent contractors periodically. This ensures you aren’t accidentally classifying a worker as a contractor rather than an employee.

Each state has its own rules regarding independent contractor classification. However, many of those rules tend to be similar to the federal rule. Some of the most common signs of an independent worker classification are:

  • Not under the direct control of a single company
  • Have complete financial control
  • Pay their own state and federal employment taxes
  • Often workers under an independent contractor agreement or contract
  • Can set their own hours and schedule
  • Contractors do not partake in employee benefits, workers’ compensation, etc.
  • When compared to regular employees freelancers require minimal training
  • They pay into their own social security

Worker misclassification is a serious offense. For misclassifying workers, the IRS levies a penalty of a $50 fine, 1.5% of the employee’s wages, 50% of the employee’s withheld taxes, and 100% of the matching FICA taxes.

More on managing freelancers

Independent contractors aren’t employees. But like your full-time hires, they are working to grow your organization.

Putting tougher a brief onboarding packet, ensuring contractors are paid well and on time, and garnering regular feedback can all go a long way toward building long-term relationships.

To learn how you can craft a strong independent contractor agreement and streamline your onboarding, check out our guide for hiring managers and HR on hiring freelancers.


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