The Internet is brimming with freelancers who can help you with writing, photography, design and more. The problem is that it can seem like everyone is playing by different rules. Let’s demystify some of the top questions business owners have about how to hire a freelancer.


What should I look for in a freelancer’s portfolio?

Experienced freelancers should have a portfolio with samples of their work. Here’s what to look for:

  1. Type
    A great logo and an awesome website require different skills. If the freelancer hasn’t worked on the type of project you need, ask how he or she would approach the work.
  2. Tone
    If you’re looking for a Web developer to create a site that feels friendly and laid-back, beware a portfolio full of corporate-looking, formal work. Ideally, you’ll see strong samples in a range of styles. This is a good sign that the freelancer is versatile and adaptable.
  3. Topic
    Are there examples of previous work in your industry? If you need a tech writer and the portfolio is mostly travel articles, the writer may not have the expertise you need. An inexperienced designer might go for cliches.

Lack of experience in any one of these isn’t a deal breaker, but a sign to ask more questions. You want to hear enthusiasm for your project and qualifications that might not be reflected in the portfolio.

How do I make sure the freelancer and I are on the same page?


The project will go much more smoothly if the freelancer understands what you want. The more clear information you can give about the assignment, the better. For a film project, that could mean length, style, soundtrack choices, and important points that the video should include.

At 99designs, you can connect directly with great designers for anything from a t-shirt design to a full brand identity package. Whatever your project is, expect the designer to have a lot of questions at the beginning about your business’ voice, your target audience, and even your favorite colors. All that info helps them create something you’ll love.

Communicate your expectations about the work process, too. Do you expect status updates? What’s the best way to reach you with follow-up questions? Be open to figuring out a system that works for both of you.

Note: Be careful about asking for onsite meetings or availability at specific hours. The more control you have over when and where the freelancer works, the more likely it is that the government will consider him or her an employee instead, which could leave you responsible for taxes and penalties.

Do I need a contract?

Yes! Working with a contract protects both you and the freelancer. If you found the freelancer through a major site, like 99designs, there’s often a contract agreement in place already—that convenience is part of what you pay for to use the site. If you’re working with an individual freelancer, you may need to draft one together. You don’t need to have a lawyer write it or set up anything fancy. You can find templates online. In a pinch, even an email chain can hold up legally. Include details about:

  • The piece’s timeline, including draft and revision deadlines
  • How many revisions are included
  • Price and payment structure
  • Project scope
  • Rights
  • Confidentiality agreements

What rights should I get to the work?

Many freelance projects for a corporate client are work-for-hire. In a few rare cases, if a freelancer thinks they may be able to use the work elsewhere, he or she might ask to keep reprint rights after a certain period of exclusivity. Generally, though, it’s common practice for business owners to own all of the rights to the project upon completion.

One right you might consider giving freelancers is letting them include the final project in their portfolio. Our designers appreciate it when clients give them permission to show off work they’re proud of.

What are my tax responsibilities when working with freelancers?

One nice thing about hiring independent contractors is that they are responsible for paying all taxes, including Social Security. When tax season rolls around, though, you still have some work to do for your freelancers. Here’s how to be ready:

  • When you hire a freelancer, have them fill out a W-9. If you’re working with an individual, this is also a good time to ask them for proof that they operate as their own business.
  • Whenever you receive an invoice, file a copy of it with the W-9.
  • At the end of the year, add up the invoices. If you paid $600 or more, you need to send the freelancer a 1099-MISC form by the following January 31.
  • Finally, for your business tax return, complete Form 1096, listing all the freelancers you paid $600 or more to, and combined total.

Again, major sites that connect businesses and freelancers may have a service in place to help you manage this aspect of hiring a freelancer.

How much should I pay a freelancer?


This is one of the toughest questions to handle when you are looking to hire a freelancer. With rates ranging from pennies to several dollars per word, it’s hard to know what’s fair.

Working with freelancers allows you to work in the global economy. You’re not necessarily bound to any particular minimum rate. That said, as with pretty much anything, you get what you pay for. Seeking out experienced, reliable workers is going to be better for your business than looking for bottom-of-the-barrel rates.

Freelancers charge either hourly or by project. Project rates are nice because they’re predictable. They don’t penalize the freelancer for working quickly, and don’t penalize a business owner if the freelancer has an off day and takes longer to get the job done. A benefit of hourly rates is it’s easier to discuss changes to the scope or number of revisions for a project, since you’ve already agreed on the rate of pay.

As for what that rate of pay is? It’s going to vary. The freelancer’s experience and expertise, project complexity and timetable, and the project’s ultimate value to you all affect price. For an example of how professional rates typically vary in the freelance writing industry, you can check out Writer’s Market‘s guide. The important thing is finding someone who understands what you need for your company.

Looking to hire a freelance designer? Discover the awesome work of 99designers and start your contest or project today!