How to Hire a Freelancer on Upwork

Hiring contractors through freelancing websites is a contentious topic.

Some entrepreneurs say online resources like Upwork and Fiverr are priceless, and have allowed them to get amazing work done at rock-bottom prices.

Others have had terrible experiences with freelancers who produced crummy work, missed deadlines, or agreed to a project through the site then dropped off the face of the earth. In my opinion, it’s all about shopping smart and screening your prospects.

You need to know exactly how to hire a freelancer on Upwork in order to get the best possible outcome.

With that in mind, I’ve got 5 tips to share! If you want to avoid disappointment when hiring through Upwork, here are simple rules you should follow:

New here? I also have the following posts to help women entrepreneurs outsource their business tasks like a boss:

And of course, you should definitely take my free quiz to find out the #1 task that you need to outsource to not only free up your time – but to give you the space to focus on revenue-generating tasks in your business.

How to Hire a Freelancer on Upwork Tip #1: Create Clear Parameters

It’s a hard fact of entrepreneurial life that sub-par work can stem from two sources: Bad execution, or lousy direction.

If the contractor you’ve hired doesn’t have the right skills or isn’t focused, she may deliver awful work. But if you’ve given her unclear instructions or limited information, she can’t be blamed for churning out results that aren’t up to your expectations!

So when you’re thinking about how to hire a freelancer on Upwork, consider your role: Get super clear on your project, including milestones and deliverables, and make certain you can explain all steps in easily comprehensible ways.

When you post a project to Upwork, the description should be as well-defined and coherent as possible so all freelance applicants know exactly what’s expected.

How to Hire a Freelancer on Upwork Tip #2: Don’t Game the System

Say you’ve found the perfect contractor on Upwork, but her fee is a bit higher than you’d like. You might be tempted to contact her outside of the site and negotiate down.

RESIST that urge!

Upwork takes a cut of every project fee, so prices may seem slightly inflated … but that added fee provides you with payment protection on both hourly and fixed-fee projects in case your freelancer turns out to be a dud.

If you decide to hire a freelancer on Upwork be sure to take advantage of that built-in coverage, and don’t work outside the system in exchange for a lower rate.

How to Hire a Freelancer on Upwork Tip #3: Read the Feedback

Every contractor on Upwork creates a profile, which includes experience, work history, feedback from other clients, and references. All of this information is helpful, but pay special attention to client feedback.

It’s true that most clients won’t bother to post a review if someone is downright awful, but they will offer a testimonial if the experience was outstanding. That means profiles with multiple glowing reviews are likely to connect you with skilled, reliable workers.

Wanna hire a freelancer on Upwork? Look for one whose past clients adore her!

How to Hire a Freelancer on Upwork Tip #4: Be Willing to Pay for Good Work

Upwork is open to just about anyone who has the time to cook up a profile, so you’ll find freelancers who are just getting started alongside multi-decade vets.

Naturally newer, inexperienced workers will be cheaper, but don’t shop by cost alone. Just like hiring someone through a colleague’s referral, hiring a freelancer on Upwork means seeking someone who fits your needs AND budget.

Upwork can be a race to the bottom of the pricing scale, so don’t fall for the lure of cheap labor; be willing to shell out so you can hire the right person for the project.

How to Hire a Freelancer on Upwork Tip #5: Start With a Small Project

Don’t dive into a multi-phase project with a new hire, Upwork-sourced or no!

Start with something small and relatively fast so you can see how you work together. In fact, consider using a paid test or “audition” project to qualify applicants. This weeds out the non-serious freelancers, and gives you a glimpse into the capabilities of an applicant.

When you hire a freelancer on Upwork, you have the option to post projects of any size and with virtually any parameters. So test the waters with an easy, simple project first.

If you’ve been wondering how to hire a freelancer on Upwork, I hope my tips have been helpful!

There are risks and rewards to using this site, but if you shop smart, you’ll have a much easier time connecting with talented, skilled contractors.




  1. Pingback: 6 Lessons that Have Changed the Way I Hire

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I’m Melissa. I’m an entrepreneur, mom to two teens and a dog, and married to the love of my life.

I’m an outsourcing strategist for women entrepreneurs who are sick of struggling to get everything on their to-do list done while also growing their business and income. Hiring help will free up more of your time to focus on your big vision and the actual creation of your dream business. You’ll be able to earn more, reach more, and have the freedom you crave.

Obsessed with: adventure, camping, books, and essential oils.

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