How to Get Started Hiring Freelancers for Your Small Business

Freelancers are perfect for one-off projects, business consulting, or when you need a job done and aren’t terribly particular about when or how it gets there.

However, for a business accustomed to working with W-2 employees, hiring your first freelancer can be an intimidating process.

What’s a fair price for a freelancer? How do you manage someone who doesn’t technically work for you? What about taxes? Before bringing your first freelancer onboard, read this guide to learn the basics of finding, hiring, and managing freelance workers.

Where to Look for Qualified Freelancers

If you head to traditional job boards to hire freelancers, don’t expect to get many bites. Freelancers tend to stick to freelance job boards. There are both general job boards, like Freelancer, as well as industry-specific freelance sites (e.g., for designers, developers, writers, etc.).

You might decide to hire freelancers as outsourced workers for tasks that you don’t have time to complete. In this case, those freelance job boards will come in handy. If, for example, you need information plugged into databases and spreadsheets, you can search for and hire a qualified data entry specialist. Ideally, you’ll want a well-organized and detail-oriented freelancer for the job to help your business grow and succeed.

A good job description helps you attract high-quality freelancers. A freelance job description should include a description of the project and the skills a successful freelance applicant will have. Include relevant deadlines and what level of time commitment you expect from a freelancer, as well as the pay rate for the project. Leaving out these important details could cause the most qualified candidates to overlook you.

Keep in mind that a competitive rate for a freelancer is higher than you’d pay for an employee with the same skills. You shouldn’t be scared away by high rates, however. Since you’re not paying employment taxes or providing benefits, hiring freelancers can be a good deal.

Tax Tips for Hiring Freelancers

Keeping taxes out of the equation is one of the biggest perks of hiring freelancers. Outside of having freelancers fill out Form W-9 and filing 1099-MISC forms annually, there’s not much that businesses have to worry about when it comes to freelance taxes.

Of course, a freelancer isn’t a freelancer just because they call themselves one. Rather, it’s how you treat a worker that determines if they’re classified as a W-2 employee or an independent contractor by the IRS. The more you control where, when, and how a worker does their job, the more likely they’re considered an employee and subject to all the same legal and tax requirements as your other staff. Misclassifying employees as independent contractors carries a heavy penalty, so it’s worth making sure you’re following all the rules.

How to Collaborate with Freelance Workers

While you can’t exert too much control over a freelancer’s work, you shouldn’t be totally hands-off either. It’s important to maintain communication between a business’s in-house team and its freelancers to ensure everyone is on the same page and deadlines are being met.

The first step to a good freelance relationship is making expectations clear. Define milestones and objectives for the work, determine a payment schedule, and pencil check-ins into your calendar. Laying these terms out clearly in a freelance contract keeps freelancers accountable without needless micromanagement.

Additionally, video conferencing software makes it possible to have face-to-face meetings even with a distributed team. However, complications arise when freelancers are working in different time zones. If coordinating meetings poses a challenge, use high-quality speech-to-text transcription service to automatically transcribe team meetings and calls and send the notes to your remote team to keep everyone in the loop. While it’s still important to talk now and then, this eliminates the need to coordinate every conversation.

Project management tools are another great way to keep everyone working together even when your team and the freelancers you work with are separated by time and space. With these tools, you can easily share files, track progress toward deadlines, and see who is working on what.

I recommend checking out project management tools like Asana or Trello. These are both great for helping create more efficient, effective collaboration and increasing your productivity working with freelancers.

Final thoughts

Adding freelancers to your team can be a big shift, and it may take a while to refine the way you communicate and collaborate with your freelance workers. However, once you get started with hiring freelancers, you’ll love the flexibility it adds to your business. Start small with one or two freelancers so you can work out the kinks, then discover all the ways that freelance labor can help grow your small business.

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Courtney Rosenfeld

2 thoughts on “How to Get Started Hiring Freelancers for Your Small Business”

  1. Nice breakdown Courtney. I never worked with freelancers but did freelance write for a few bloggers over the years. Paying a premium weeds out less skilled freelancers who work for a pittance due to skills and credibility issues. Finding good matches for your needs helps, too, as identifying someone who fits your requirements makes the process flow seamlessly.


    • Those are good points, Ryan. You do get what you pay for when it comes to freelancing. You can get 1000 words for $10, but you’ll end up spending a couple hours editing the content, so you may as well pay more or write it yourself. 🙂


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