How to Hire a Freelancer on Upwork (Updated!)
If you're new to Upwork and want to hire a freelancer, you might be wondering how to hire someone.
How to Hire a Freelancer on Upwork: A Guide for Small Business Owners
As a small business owner, one question I hear often is, “How do I find reliable freelancers?” It’s a common concern, and for good reason. Your time is limited, and the quality of your freelancers can make or break a project. That’s why I’ve put together this guide specifically for hiring on Upwork, one of the largest freelancing platforms in the world.
I’ve been using Upwork since 2016—before that, I worked with its predecessors, Elance and oDesk (which merged and rebranded as Upwork in 2015). My experience hiring freelancers dates back to 2014, and I’ve learned a few things that can help make your hiring process smoother and more successful.
Why Choose Upwork?
Upwork offers a wide pool of talent, whether you're looking for designers, developers, writers, marketers, or virtual assistants. It’s flexible, secure, and easy to use—perfect for small businesses looking to scale or outsource key tasks.
Step-by-Step: Hiring on Upwork
1. Write a Detailed Job Post
Start with a clear, specific job description. Outline the project scope, deliverables, required skills, language preferences, and your deadline. The more detail you provide, the better chance you have of attracting the right freelancer.
2. Review Proposals Strategically
Once your job is live, you’ll start receiving proposals. Begin by reviewing the highest-rated applicants. Look at their Upwork job success scores, client reviews, portfolios, and relevant experience. If someone looks promising, message them to clarify expectations and confirm their availability.
3. Decide on Fixed Price vs. Hourly
Fixed-price contracts are best for clearly defined projects. You won’t get progress visibility through Upwork’s tracking tools, but these contracts can be faster to close and often appeal to freelancers who prefer upfront clarity.
Hourly contracts allow you to monitor the freelancer’s work through Upwork’s time-tracking software. This is ideal for ongoing or open-ended projects.
Tip: Freelancers are often more motivated to accept fixed-price offers since they get paid as soon as the project is approved. That can help you secure top talent faster.
4. Request an NDA (If Needed)
If your project involves sensitive or proprietary information, consider asking your freelancer to sign a Non-Disclosure Agreement. Most professionals are familiar with this and won’t hesitate, but be prepared to explain its relevance to your project.
5. Use Upwork Tools to Manage the Job
Once a freelancer is hired:
Use the Upwork messaging system to communicate.
Share files and updates securely through the platform.
Monitor work progress (for hourly jobs) using Upwork’s built-in tracking tools.
Escrow protects your payment until you approve the final work.
6. Dispute or End Contracts if Necessary
If you're not satisfied with the work, you can dispute logged hours or request a refund from escrow for fixed-price projects. Upwork’s dispute resolution tools are there to help both parties reach a fair conclusion.
Final Tips
Don’t rush the hiring process, especially for large or complex projects. Taking an extra day to vet candidates can save you weeks of frustration.
You can also search for freelancers directly using Upwork’s talent search feature if you prefer to handpick rather than post a public job.
Your clear communication and realistic expectations will set the tone for a successful partnership.
Have you hired freelancers on Upwork before?
Share your experience in the comments to help other small business owners make better hiring decisions. At FTB Digital, we believe in sharing what works—because we know firsthand how the right freelancer can make all the difference.
Once you've chosen your freelancer, browse their portfolios and read feedback from other clients. Moreover, you can use the Upwork job success rating to find the best freelancer. The success rating is determined by feedback scores. A high score indicates that the freelancer has a history of meeting clients' expectations. A caution on ratings, I also pay close attention to the actual written reviews by other clients. Upwork ratings can be inflated because clients don’t want to hurt a freelancer’s ability to get more work so they don’t always give low ratings when they might have not had the best experience. Written feedback will sometimes reflect a not-so-great experience even though they freelancers has a high overall rating.
It's important to note that Upwork's bidding system is open to anyone, even if they're not American. In fact, I will often hire a less experienced freelancer when I know exactly what I’m looking for. I have several freelancers where I was their first gig. I get great work at a more affordable price by taking a little more time during the selection process. And some of these have turned into long-term relationships that have lasted for years. The great thing is that these freelancers continue to give me the low rate they started with because I gave them their first opportunity on Upwork.
This means that the competition for a job can be intense, so you need to choose your freelancer wisely. Also, you have the option to hire an individual or hire an “Agency.” Be aware that if you hire an agency, you may not be working with the agency member you will be contacted by from your job posting. So, if you are thinking about hiring an agency, make sure you ask the “manager” to see the ratings of the actual freelancer who will be working on your project.
It is important to make sure to post your job requirements in a way that makes it clear what you need. Be sure to add inspirational content or design prototypes. The more you know about your project, the more work you'll get, and you'll have more satisfied clients. And remember that you can change payment terms on Upwork if you need to. If you're not sure, ask other clients about their experience with a particular freelancer. If they've used Upwork for their freelance work, then they were satisfied with the results.
One of the main benefits of using Upwork is its simplicity. If you're a small business, hiring freelancers from this site will be easy. The site features over 10 million freelancers, and employers can rate the profiles of freelancers to find the most suitable independent contractor. Unlike other sites, Upwork has a greater number of positive reviews online than many competitors. So, if you're looking for a great independent contractor, give Upwork a try.
Again,
tell us about your experience in the comments section below.
