How to Hire a Freelancer on Upwork

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Things to Do When Hiring a Freelancer on Upwork
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7 Tips for Hiring a Freelancer on Upwork

Design services
July 22, 2020
8 minutes


Upwork is probably the first place you’d turn to for finding the best talent for outsourcing. Although the platform has a thorough vetting process and great freelancers, there are tips that will help you with the selection and ease of hiring.

Upwork is one of the most popular freelance platforms to outsource talent. This status comes with both a blessing and a curse: the best of the best are there, but there’s also a lot of scams, false promises, and problems with the workflow.

In order to ease the process and help you learn how to hire a freelancer on Upwork, we compiled eight pieces of advice to help you make a good hiring decision.

1. Test their professional skills to spot the best talent

Try to find a way that will give you some proof about the proficiency and scope of their skillset. For example, if you’re hiring a programmer on the freelancing website, ask them for a link to their GitHub or StackOverflow profile. Or similarly, if you’re looking for a content writer, ask them for their blog, or articles written in previous jobs. Be understanding, because freelancers often ghostwrite as well.

You could also do a test task, but be fair and don’t use their work for your own needs if you don’t decide to hire them. Otherwise, you’d be exploiting them for free.

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2. Write a detailed description of the project or job

We are prone to find the blame in others, but sometimes the problem with not having success in outsourcing is not having a good job description. Make sure it’s crystal clear for the freelancer what kind of work you’ve got for them in the job posting, and focus on details like deadlines, formats, tools, language. Maybe the best person for the job won’t apply because they don’t have sufficient information about the gig.

One way to be 100 percent sure that the freelancer read your job description well, and didn’t just skim through and apply, is adding a code word. Just ask them to write the word in their application when they use one of their Connects. A simple method, but it will help you know who is really interested and focused on the details.

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3. Do a quick interview

Before you hire freelancers, you can ask for an interview on Upwork. Interviews should be done exclusively through Upwork and not other apps like Skype or Google Hangouts to keep track of the conversation and prevent disputes. This will help you with the hiring process because you can ask them whatever is crucial for you to make a decision and double-check the authenticity and accuracy of their CV and cover letter. If it’s a full-time job or a longer project the freelancer will be working on, you need to know who you are working with.

The interview doesn’t necessarily have to be long, but it’s a good place to discuss the project in detail. Here are some questions you should ask:

  • What timezone do you work in?
  • What hours are you available to work in?
  • How will the project be done and delivered?
  • Do you need any resources from me to be able to start work?, etc.

This is also a possibility for you to decide on deliverables, milestones and deadlines, as well as how you’ll review their work.

You can also see the response speed of the freelancer on their profile. The most successful freelancers, according to Upwork, know it’s best to accept or decline invitations as soon as possible.

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4. Read their cover letter thoroughly

The cover letter is another source of reliable information for the professionalism and motivation of the freelancer. Good freelancers know that there is no “one size fits all” approach when it comes to finding a job, so they’ll update and write a new cover letter accordingly if they are really fitting for your job offer. You can also match the cover letter to the CV to find any inconsistencies. If it all checks out, you’re good to move onto negotiation.

Something that can help you spot inconsistencies in a cover letter is too many generalizations, evidence that they’ve used the same cover letter for other jobs, they downloaded a template and didn’t customize it, etc.

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5. Spot great talent with the Job Success Score

When you look at a freelancer’s Job Sucess Score, you might think it’s just what their past employers said about them. But the JSS actually measures client satisfaction with the overall work history on the platform. The Upwork system takes snapshots of the 6-month, 12-month and 24-month job history and bases the JSS on those three timeframes.

Three factors are taken into account: client satisfaction shown by relationships, feedback, and job outcomes over time.

The freelancer’s JSS can change because of public or private feedback, more higher-value jobs that they have in their resume, jobs completed in the past are outside the timeframe, or they haven’t received payment or feedback for several months.

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6. Weed out those who apply to every job

Newbies need recommendations and good reviews. They also need experience in order to climb up the ladders, so they might apply to every possible job. Upwork limits Connects (credits a freelancer has to apply for a job themselves) for the freelancer, so they can’t possibly apply to everything without buying more. Connects cost $0.15 (USD) each and are sold in bundles of 10, 20, 40, 60, and 80. So, if a freelancer invests a lot to buy these credits, it seems fishy. Either they don’t have good past reviews, or try to rise up the ranks really quickly without actual experience. Or, they might be scammers.

Usually, the best of the best wait for employers to reach out first. But to get there, you’ll have to apply for many jobs first. So be wary, but also keep this in mind. Sometimes a newbie can have tons of experience, but they’re new on the platform.

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7. Look out for red flags

There are some obvious details in an Upwork profile that will ring the alarm, but sometimes even the best talent at a first glance can turn out to be something else.

Apart from the obvious risk of scams, there are legitimate freelancers that might disappoint. Here are some of the red flags to look out for:

The freelancer won’t return your messages for a long time

At first, communication is good and they seem to be a good match for your needs. Then, right before you decide to make a decision and hire them, they disappear and don’t reply to your questions for more than a day or two. This disappearing act should be taken seriously. If they can’t reply, they sure won’t deliver on time and stick to a schedule.

They don’t have proof of past experience and references

If a freelancer has references, a stellar resume and cover letter, ask them for proof of all the projects and job experience they applied in the bio. If they try to explain that it’s in a different language and you wouldn’t understand, it’s a group project, they don’t keep the files or links, etc, it might be suspicious. Of course, sometimes this might be true, but if there’s an unlikely explanation for every entry in their resume, take that as a bad sign.

Bad reviews from previous collaborations

Reviews from other people hiring remote workers on Upwork can be a great source to detect who’s good and who isn’t. Check out for what your peers say about a certain freelancer and if they get the work done well.

They try to bargain

Trying to change the price, adding extra fees for something that is clearly described as being part of the service, trying to get a full-time salary for a part-time project… Some freelancers will try to bargain, and that is not always acceptable or logical.

Frauds and scams

If the previous scenarios were just a red flag towards work ethics and transparency of the freelancer, this is an outright scam where you can get nothing done for a lot of money. Although Upwork’s customer support does a great job in helping people who hire get their money back and pinpoint illegal activity, you need to be wary. You can also check if the work is authentic by using plagiarism checkers.

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We hope some (or all) of these tips helped learn how to hire a freelancer on Upwork, elevate your productivity and help your business grow. Whether it’s learning how to steer away from unprofessional freelancers, making sure you have the best job description, or how to spot the best talent using the Job Success Score, make sure you keep this advice in mind when looking for someone to hire on Upwork.

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Stefanija Tenekedjieva

July 22, 2020

Journalist turned content writer. Based in North Macedonia, aiming to be a digital nomad. Always loved to write, and found my perfect job writing about graphic design, art and creativity. A self-proclaimed film connoisseur, cook and nerd in disguise.