Recruiting Freelancers for the First Time? Here’s What To Do

By: Sierra Rogers on August 12, 2022

Let’s start with the numbers: 91% of today’s HR leaders are concerned about employee turnover in the immediate future. At the same time, nearly half of today’s job applicants are considering at least two job offers simultaneously.[1]

Knowing that employers are worried about maintaining headcount, and that they also face tight competition when it comes to filling roles, it’s no wonder that last year 83% of organizations said they expect to increase their use of contingent workers, such as contractors and freelancers.[2]

As an affordable alternative to full-time employees, freelancers can help businesses fill skills gaps in a pinch. If you’re a hiring manager or business owner who’s considering hiring freelancers for the first time as a means of getting the labor you need to support your organization, we’re here to help.

Ahead, we’ll break down how to hire a freelancer in five steps, from identifying the skills and experience level you need in a candidate, to correctly classifying your workers.

Step #1: Draft a job description

Before you begin recruiting freelancers in earnest, you need an understanding of the skills and experience your organization is currently lacking, as well as which needs a freelancer can realistically fill.

As you might have inferred, some industries and roles are better suited for freelance workers than others. For example, it’s common for businesses to hire freelance developers, programmers, designers, and writers, but the same can’t be said for roles that require extensive familiarity with the operations and people behind an organization—for instance, a team manager, department head, or project coordinator are all roles that are best handled by a full-time employee.

With that in mind, pinpoint which teams within your business could benefit from the help of freelance employees, and then start detailing the specific skill set the ideal candidate would have.

To do:

Draft up a job posting for the freelance worker(s) you’re hoping to hire. Include a list of the hard and soft skills you’re after in a candidate, and give an overview of the core day-to-day responsibilities of the position.

Use the questions below to help you create a concise and specific job description:

  • What deliverables would the freelancer be responsible for on a weekly and monthly basis?

  • Is there a specific project the new hire will be assisting with, or will they provide support to an entire department?

  • How much decision-making will this person be expected to do?

  • What is the target start date for this position?

  • Who will this worker report to?


A job posting on Indeed for a freelance graphic designer position[3]

Step #2: Determine how the freelancer will be paid and managed

Ahead of publishing your job posting, you’ll want to spend time defining the expectations your organization will have for the freelancer, as well as how they will be managed and compensated. Doing so will ensure that you’re prepared to answer any questions that come up during the interview phase, and it will also help things go smoothly once the worker is onboarded.

Stop: Do you need a freelance worker or a contractor?

This is an essential question to answer, and there are a few key indicators that can help direct you one way or the other.

If your organization needs someone who can work a full 40 hours a week, or if you’re hoping to get help on a project that’s expected to take several months to complete, a contract worker may be preferable to a freelancer. Another important consideration is whether or not you’ll expect the worker to operate in-office; if the answer is yes, you’re also probably looking for a contractor.

Freelance workers set their own hours, and they typically have more than one client at a time and work remotely, so they’re best utilized as part-time support on ongoing initiatives or shorter projects.

With the above in mind, if you’d like to continue with your plan to hire a freelancer, get together with the leader of the department they’ll be working with and run through the to-do list items below.

To do:

  • First, determine how the freelancer will be managed. Someone within your organization will need to be responsible for communicating with the freelancer on a regular basis. In addition to assigning work and disseminating important information related to the freelancer’s contributions, they’ll also act as a point of contact for any questions the worker has.

  • Next, discuss how they will be paid. Freelancers are able to set their own pay rate, and the most common compensation structures are hourly and project-based rates. But there are other structures too; for instance, a freelance writer may opt to charge a per word rate. That said, it’s a good idea to have a pay structure and wage range in mind before entering the interview and negotiation phase of the recruitment process. Some cursory research on sites such as Glassdoor, LinkedIn, and Indeed should reveal what a normal pay range and structure is for the kind of freelancer you are hoping to hire. We recommend using two to three sources to confirm that the range you landed on is accurate.

  • Lastly, think about the long-term plan for this role: Do you truly need temporary help, or is there a chance that you’ll offer a full-time position to this worker after a few months of freelancing? Having foresight into your organization’s future needs and being transparent about them with potential candidates will improve your chances of finding someone who is the right fit for what you’re looking for.

Step #3: Recruit and interview candidates

You’ve done all the prep work, now it’s time to kick off your search for qualified candidates. For the most part, recruiting freelancers is the same as recruiting any employee, but we’ll provide some tips that are specific to finding freelancers in this section.

Where to find freelancers

  • Employee referrals are perhaps the best place to start your search. Ask your employees in an email or public channel of your collaboration software if they know of anyone who’d be interested in picking up some freelance work.

  • Freelance platforms such as Upwork, Fiverr, and Guru are all great places to start your search. You can publish your job posting on these websites or browse candidates’ professional profiles and reach out to those who seem like a good fit.

  • Job sites such as Indeed, LinkedIn, and ZipRecruiter are also helpful when it comes to sourcing talent. Most of these sites allow you to post your openings free of charge, but you can also opt to create a job ad if you feel like you’d benefit from a little extra promotion.

  • Freelancer agencies and service providers are organizations that partner with other businesses to provide cost-effective, fast labor in the form of freelance and contingent workers. One major benefit of using a service provider is that you don’t have to find the freelancer yourself, because they have their own network of talent to deploy.

To do:

  • Publish your job posting. If your business’s website has a careers page, post your opening there first, then publish the listing on external sites (such as LinkedIn and Upwork).

Tool tip: Applicant tracking systems (ATS) are tools used by HR professionals to automate parts of the recruitment process, including pushing job postings live on multiple channels and screening resumes. You can use an ATS to recruit a freelance or full-time employee.

  • Determine who will be involved with the interview process. As applicants begin to roll in, you’ll need to start scheduling phone screens and interviews. Typically, a member of your HR team (such as a recruiter or hiring manager) will handle the phone screen, but the individual who will be managing the freelancer should be involved in the later stages of the interview process as well.

  • Optional: Create a trial assignment. It’s common practice for freelancers to complete a trial assignment or project before they’re offered the job. For instance, if you’re hiring a graphic designer, you might ask them to create a social media post or an asset for your company’s website in order to judge their design skills, as well as their understanding of your organization’s brand. If you opt to screen candidates this way, we recommend that each applicant complete the same assignment so that you can easily compare the results to one another. And on another note, if you plan to use the work that an applicant completes, it’s best to let them know upfront or pay them for their work before doing so.

Step #4: Prepare an onboarding process for freelancers

Once you’ve found a candidate who’s a good fit, it’s time to bring them onboard. Onboarding a freelancer shouldn’t be as involved a process as onboarding a full-time employee because they don’t need to sign a formal offer letter, and they shouldn’t need much training to jump in.

The main thing to focus on when it comes to onboarding a freelancer is ensuring they have all of the knowledge and tools they need to be successful in their work.

To do:

  • Create an employment contract. Unlike full-time hires, freelancers do not have to sign an offer letter to work for your organization. In fact, there is no standard formal contract that’s required for freelancers to work, which is why it’s important to draft up your own contract. In addition to everything you’d expect (such as the worker’s contact information, signature, and a non-disclosure agreement), we’ve included a checklist of five must-have clauses in your freelance employment contract below.


  • Decide which internal tools the freelancer needs access to. Your new hire will likely need access to your collaboration platform in order to stay up-to-date on projects and in communication with coworkers. But what other tools will they need to use in their course of work? Thinking through this question before they’re onboarded will make the process of setting up their permissions easier, and it will also lower the risk of a tool being misused or sensitive internal information being leaked.

Step #5: Classify your freelancers correctly

If this is your first time recruiting freelancers, it’s essential to make sure that your organization understands how to correctly classify them. Especially considering that up to 20% of businesses currently misclassify at least one contract employee.[2]

Misclassification occurs when an organization incorrectly categorizes employees as independent contractors or contingent workers, resulting in audits from the IRS, and in turn, lawsuits or heavy financial fines. And while misclassification is a bigger concern with contract workers than freelancers, you should still educate your HR team on the differences between full-time, contingent, and freelance workers.

Note: If you need more information on this topic, take a look at this information from the Internal Revenue Service that details what employers need to know when classifying workers as employees or independent contractors[4]

To do:

  • Get your forms in order. While it’s true that freelancers don’t need to sign any contracts to begin work, some documentation is required for tax purposes. For instance, you’ll likely need to file 1099 and 1096 forms to report how much you paid out to self-employed individuals over the year. Learn more about 1099 forms below.

  • Know the limitations of employing freelancers. In the eyes of the law, freelance workers have control over where, when, and how they work. And under the Fair Labor Standards Act[5], it must be demonstrated that the worker actually exercises such control on a regular basis. That means that even though the freelancer will be “managed” by someone within your organization, the purpose of that relationship will be to have someone to communicate with, but not to report to in the typical sense of the word.

Make recruiting freelancers easier in the future by creating your own network of candidates

Software Advice ran the New Hire Premium Survey[*] in July of 2022 and polled over 650 hiring managers. Of those respondents, the majority (76%) reported that they either already hire freelancers or are considering it, with nearly a third (30%) of hiring managers stating that they do so to affordably fill skill needs.

Considering we’re experiencing the tightest labor market in 50 years, hiring freelancers is a strategy that every business needs to be able to execute on. And with the majority of organizations already putting this strategy into place, it’s also essential in order to keep up with your competition.

If you already have an established recruitment process for filling full-time roles, you’ve probably picked up on the fact that recruiting freelancers isn’t all that different. In fact, you can modify your existing recruitment pipeline to fit the five steps of we’ve covered in this article:

If you have an applicant tracking system, it will be even easier to roll out this process, because you can automate steps such as posting to job sites, screening resumes, and scheduling interviews.

Lastly, if you foresee your organization continuing to make use of freelancers in the future, you should consider creating your own network of freelance talent. Doing this is as simple as setting up profiles for freelancers you’ve worked with (or even just interviewed) in your candidate database. That way, the next time you need to find a freelancer, your first step can be to search through your existing database of qualified candidates.

Survey Methodology

* Software Advice’s 2022 New Hire Premium Survey was conducted in July 2022 among 1,289 U.S. employees at companies with at least 6 employees: 654 hiring managers who had a role in hiring at least one direct report in the past 12 months and 635 staff-level workers. The goal of this survey was to learn how the new hire premium is affecting compensation satisfaction and employee retention.


  1. Gartner Survey Reveals 91% of HR Leaders Are Concerned About Employee Turnover in the Immediate Future, Gartner

  2. Avoiding Employee Misclassification in the Gig Economy, Gartner

  3. Indeed freelancer job description image source,

  4. What Employers Need To Know When Classifying Workers as Employees or Independent Contractors, Internal Revenue Service

  5. Wages and the Fair Labor Standards Act, U.S. Department of Labor