Editor’s note: After writing this article and prior to publication, oDesk and Elance have merged and rebranded to Upwork. While quotes will maintain the use of the name oDesk, we will refer to the site as Upwork. Never fear—they are still essentially the same site.

As I write this, I am currently sitting in my home office, overlooking my sleepy little neighborhood in Southeast Portland. I can hear the low hum of cars in the distance, and once 3pm hits I’ll hear the school bus pull up at the corner, to drop off a gaggle of elementary schoolers.

I’m home at 11am on a weekday because I work remotely; I am employed by Palo Alto Software, but as they are located in Eugene, Oregon, and I am currently living in Portland, I am rarely in the office.

This is hardly uncommon; remote employees, freelance workers, and unconventional office setups are becoming the norm. The way businesses hire employees to get work done is shifting—where once it was considered standard practice to have all work completed in-house, more and more companies are looking to freelance employees to complete projects for them.

Is freelancing a good choice for your business?

It’s for good reason that freelancing is so popular: hiring freelance workers offers a level of flexibility that you often can’t get with permanent staff. Perhaps you need a specific skillset for a one-time project. Would it be sensible to hire a permanent employee for a one-off assignment?

Or, as sometimes happens, your local talent pool may come up a little short, and freelancing offers an avenue for finding qualified, skilled workers outside your town or city.

So, freelancing is often a great solution. It’s flexible, often less expensive, and you’ll find a freelancer skilled in pretty much any area you can possibly imagine. Sites like Upwork are popular, both with remote employees and employers.

How do you find great freelancers? Here are 11 strategies:

With the popularity of freelancing comes an often overwhelming applicant pool. How do you determine who is qualified, competent, and can complete your project in a timely manner—and do so well?

I asked Ben Patterson, our Senior Web Developer here at Palo Alto Software, to share with me his process for choosing freelance workers for projects here at Palo Alto (yes—we use freelancers sometimes too!). In addition, I heard from several entrepreneurs in various fields who have worked with freelancers successfully, and asked them how they decide who to hire.

Here is what these entrepreneurs had to say.

1. To potentially weed out unqualified candidates, create a detailed, specific posting

When using sites like Upwork, it’s important to make your search as easy as possible from the start. You will likely be wading through tens if not hundreds of replies, so streamlining the process as much as possible will save you a lot of trouble.

To that end, in order to eliminate freelancers who may be unqualified—or just throwing something against the wall to see what sticks—make your posting as detailed as possible.

“It will take a lot longer to review candidates than write your project description, so take time writing it and be explicit with desired background, skills, language competency and portfolio submission requirements,” says Nigel Ravenhill, head of marketing for AdChemix, Inc. “You’ll help weed out the unqualified.”

A high level of specificity from the start will help ensure that you get applicants who can actually fulfill every detail of the project you need completed. “Don’t say ‘I need a website built,’” says Mike Scanlin, CEO of Born To Sell. “Instead, say ‘I want a three page brochure site. Responsive mobile-friendly design, with a double-opt-in MailChimp email signup form, coded in HTML/CSS/Jquery/php, passes all w3 validation checks,’ etc.”

Not only will a clear posting help you avoid applicants that are unqualified, but it allows you to clearly lay out what you are looking for from the start. “Be as precise as you can be,” says Mike. “State exactly what you want and what you expect in the job description. This will avoid many arguments and bid adjustments later.”

2. Include a “unique identifier” in your post


Requiring use of unique identifiers—like using the term “purple frog” in an email subject line—helps weed out bots and those freelancers who aren’t paying attention.

Inserting a recognizable phrase in your post—which interested freelancers must include in their application—was one of the most common suggestions I encountered. It was almost universally recommended!

This could be anything from a silly phrase included in the email subject line, to asking applicants to answer a specific question, such as their favorite color. It ensures that the applicant actually read your post thoroughly and can follow directions, making it easier to sift through your applicant pool.

“Definitely the most helpful tip I have used for oDesk is adding a unique identifier that all oDesk workers who are applying to the job must quote,” says Paul Manwaring of Internet Marketing Hustle. “To take this one step further, I’ll place it at the end of a random sentence in the project brief just to make it harder and weed out all the auto bidders.”

Cale Dansbee, president and principal security engineer for Topstone, agrees. “Place a magic word or phrase in your project description—for example, in the middle of your project description, state: ‘Interested freelancers must include the words purple frog in their response.’ This helps weed out the bots and auto-responders that will quickly overwhelm your inbox. Those who mention the purple frog are telling you they actually read your project description.”

And for applications that do not include your unique identifier? “Anyone who doesn’t quote the ID at the top of the bid gets removed immediately,” Paul says.

3. Don’t lowball your price—you might drive away good freelancers

It is tempting to price your project low; because really, who wants to pay more for a service than they have to? It’s understandable that you might be inclined to lowball your price range, but be careful; you may end up with less skilled and less qualified freelancers.

“One key thing to keep in mind is that low-balling the price range will drive away more experienced/qualified responders,” says Joseph Chiu of ToyBuilder Labs. “If you ask for a 40 hours job and offer a $500 fixed-price budget, you’ll offend and drive away most of the quality producers.”

So, what is the solution? “Pay a little more and get a lot more,” says Cale. “By using crowdsourcing, you are already saving 60% or more on the cost of getting the work done, so don’t skimp.”

And if you’re worried about getting enough freelancers to respond to your posting? Don’t be. You’ll likely find that highly-skilled, well-qualified freelancers will respond, and the only “talent” you’ll be scaring away are those less skilled and willing to work for cheap. “If you offer a slightly higher purse in exchange for the work, you will most often get a much bigger response,” says Cale. “[…] as a result, can be more selective in who you work with.”

4. Check ratings and hours worked to get a sense of a freelancer’s experience

Screen Shot 2015-05-15 at 12.17.28 PM

Freelancer Cynthia Paul’s profile on Upwork.

“Not all contractors are quality,” Matt Harper of WebDiner says. “We only hire people who have over 100 hours of past work logged and a star rating of four or higher.” Sites like Upwork give you plenty of info about freelancers before you choose to hire them, and it’s information you should pay attention to.

Click on a potential freelancer and you will see the number of hours they have worked, their star rating out of five, their hourly rate, and reviews. Use this info to your advantage when choosing a freelancer; you can filter your results to only include those with a certain star rating or number of freelance hours under their belt.

Nigel says, “Use the hourly, minimum average feedback rating, language proficiency selection boxes to limit the number of unqualified. It works like search filters in reverse so you don’t have to wade through too many profiles.”

All that being said, you shouldn’t necessarily avoid new freelancers who have fewer hours—they are often eager to make a name for themselves and will go above and beyond to create great work and ensure they receive a high rating and great reviews. “While a lot of people say that you should only hire people with a large amount of good reviews, we’ve actually had better success with newbies on the site, who want to do some high quality work, for their first review,” says Mark Aselstine from Uncorked Ventures.

5. Skip the resume—ask to see prior work

A resume is generally the best way to determine if a candidate is qualified for a job, but in the case of hiring freelancers, it may slow you down. Not only that, resumes may not adequately illustrate if a freelancer can fulfill the particular role you wish them to fill, and actually execute your vision.

“The number one piece of advice I tell people who are looking to hire freelancers on platforms such as eLance and oDesk is to skip the C.V.,” says Lanie Lamarre, who, incidentally, helps entrepreneurs get out from under their massive “solopreneur” workload by hiring freelance help, and has a great deal of experience finding qualified candidates. “You have better things to do with your time than stare at a conga line of resumes. Besides, they don’t even tell you what you really want to know—which is, ‘How does your experience apply to my needs?’”

What should you do instead? “Force candidates to validate themselves to you rather than copy-and-paste what they do for everyone else,” Lanie says. To do this, ask to see examples of their past work, or ask them to work on a small “test” project before you hire them for a larger assignment—we’ll cover this more in #7.

6. Chat on Skype before hiring your freelancer

Schedule a brief Skype chat before you

Schedule a brief Skype chat before you commit to hiring, to make sure you and your freelancer are on the same page.

While it may seem like a lot of work to communicate so much with someone you may ultimately decide not to hire, a quick five to ten minute conversation with a potential freelancer will help you get a sense of them that you won’t be able to get through email alone. “We always manage people through Skype and chat with them before hiring,” says Matt. “This allows me to make sure they are a good communicator and understand my project.”

Not only will it help you determine if a freelancer understands your project, it will make you feel more comfortable working with them, and ensure that you both are on the same page.

“The biggest tip I can give when hiring on oDesk or Elance is: a phone call, or short Skype session goes a long way,” says Cody McGraw, founder of SCOUT Military Discounts. “I’ve hired a few freelancers on oDesk and having a simple five minute conversation can ease a lot of worries, such as: Is this person a robot? Can this person understand exactly what I’m looking for? Do they sound passionate about what they do?”

Come up with a few quick talking points and give potential freelancers a call beforehand; it will allow you to know for sure that they are a real person who understands the scope of the assignment and can communicate effectively via multiple platforms.

7. Try your freelancer on a small project first

So, you’ve found a freelancer who is qualified, and you have confidence that they will do a great job with an important project. You spoke via Skype, and they seem passionate, put together, and definitely not a robot. Great, it’s time to hire them right away for your big important project, right?

Stop—not so fast. Try your freelancer out on a smaller assignment first, perhaps a chunk of the larger project you hope they will move on to. This gives you a chance to make sure you work well together, that they communicate effectively as they complete their task, and that the finished product is up to your standards. “If you don’t like an individual for $50 of work, you won’t like him/her on a $5,000 project,” says Josh Lindenmuth, CIO of Payce, Inc. “I would sometimes even invent small projects specifically to evaluate people.”

You can also integrate this “small project test” into your selection process: “Let’s say you need 100 images created for a project. Run a small project on crowdsourcing sites, asking freelancers to respond with one or two examples of what they would do for you. From there, you can select a freelancer more in line with your needs,” says Cale.

8. Create small projects with a defined scope

Once you have determined that you like your chosen freelancer’s work, it’s still best to keep your freelance projects clearly defined and small. Ben Patterson, our Senior Web Designer here at Palo Alto Software, suggests keeping freelance assignments specific and narrow in focus. “The freelancers on oDesk are best suited to small projects with a well defined scope,” he says. “I wouldn’t hire anyone to do an open-ended branding development project, but I might hire someone to design three versions of a single logo.”

Joseph adds: “Be very specific. […] The more specific you are in what you’re looking for […] you make it easier for them to tailor a response that meets what you want.”

9. Keep in close contact with your freelancer

Don’t just hire your freelancer, put them to work, and expect your next time of contact to be upon completion of the project. Make a point to touch base with them frequently, as it will keep you both in the loop on what stage the project is currently in, if any input is needed, and so on.

“Once you’ve hired someone, expect to keep in close contact with them,” says Ben. “I like to get an update at least once a day. Some freelancers may not be up for that, but if they aren’t I’d consider that a flaw on their end.”

Good freelancers should be willing to communicate with you to ensure that they are giving you updates; so, be wary of a freelancer who isn’t that great at keeping you in the loop, especially if you are working on a project where time is of the essence. “My work often involves a fast turnaround time,” says Brett Bastello, content marketing and link building Inseev Interactive, “so for me it is important that the freelancer is checking their email/messages several times a day and that they show dedication to the assignment and project; that they truly want the opportunity.”

If you’re working on a project with more flexibility, this may not be as crucial an issue, but in general, a freelancer who fails to give you updates and communicate with you is generally a sign that the freelancer lacks necessary professionalism and communication skills.

10. Set clear milestones with multiple steps


Break your project up so that freelancers can accomplish clear milestones.

As I discussed in #8, it’s important to make your project plan clearly defined, and preferably small in scope, in order to best utilize freelance platforms like Upwork. However, you might not always have the luxury of small, easily assigned projects.

What if you are working on a huge project, and want freelance help? “Setup clear milestones if your project is large and involves multiple steps,” says Paul. “This will ensure you and your freelancer know what needs to be completed in order to get paid.”

Mike goes further: “Never give a large job to anyone, even if they completed your small job well. Always use milestones and pay by the week,” he says. This is potentially an effective strategy; if your freelancer does an excellent job, they will ultimately have completed a larger assignment when all is said and done, but by assigning small sections at at time, you avoid committing to a temporary employee who you have considerably less control over than a permanent staff member.

By including milestones and breaking the project into smaller sections, you can ensure that you stay on target and that every step is completed satisfactorily. “I’ve had jobs take as long as six months but I always paid weekly with milestones so that no one got off track,” says Mike. “The worst thing you can do is sign up for a $10K project without milestones. Recipe for disaster.”

11. International freelancers—yay or nay?

Freelancing sites can be a bit of a hodgepodge—you’ll get a little of everything, from highly skilled workers to the laughably terrible, to bots, and everything in between. The large pool makes it a bit of a gamble, and with freelancers from all over the world, it’s important to establish if you are comfortable working with international freelancers. “ODesk has a lot of international workers, so sometimes you have to take into account language barriers or time differences,” says Ben.

Determining if you plan to hire an international freelancer will depend a lot on your particular project, the specifics of your place of work, and time constraints.

“I tried to hire only Americans due to legality issues when I have a project that requires a NDA contract,” says Daniel Alarcon, a content writer for CallTools. Daniel also adds that timezone issues make working with international freelancers a bit problematic. “It’s a nightmare when you work with freelancers who are on the other side of the world. You have to stay up late and instruct on whatever you want done. It gets very tiring when you have to be up every night and hope that the freelancer gets on Skype.”

In addition to the time difference, potential language barrier issues are an important consideration to keep in mind. Dan Adler, cofounder of WinkBeds, divides freelance jobs into two broad categories: those that involve a lot of language comprehension and “creative decision making,” and those that do not.

He recommends going with freelancers who are fluent in your native language (and preferably in your timezone) for more creative, flexible projects. “You are relying on this person to understand your vision and competitive angle and to build out your company’s assets. Don’t waste time with people who may not understand your language, your vision, or the quality of work you expect,” he says.

That being said, for projects that do not require this kind of freelance work? “If your assignment does not involve many creative decisions or does not require many judgement calls, its perfect for outsourcing abroad. There are many talented developers overseas who can get task oriented jobs done very well when given proper instructions.”

So, there you have it. While you may run into snags due to the unique nature of your project, if you are thorough in your hiring process, make sure to communicate with your freelancer, and use freelancing services for clearly defined, measurable projects, the likelihood of building a successful freelancer relationship is much higher.

You’re now prepared to go out and find the best freelance talent you can. Good luck, and happy searching!

Have you had good luck with the freelance employees you’ve worked with through Upwork? Any advice for fellow entrepreneurs?

AvatarBriana Morgaine

Briana is a content and digital marketing specialist, editor, and writer. She enjoys discussing business, marketing, and social media, and is a big fan of the Oxford comma. Bri is a resident of Portland, Oregon, and she can be found, infrequently, on Twitter.