How To Hire On Upwork (Complete Step-By-Step Guide)

There’s a few tools I’ve used that if they didn’t exist at the time, I wouldn’t be where I am today.

Upwork is one of them, and probably the most important one.

If you’re not familiar with Upwork, it’s a website that connects you with freelancers from all over the world to work remotely on your online projects.


Over the past 3 years I’ve worked with over 30 different freelancers, spending more than $15,000 hiring through the platform. While doing so, I’ve developed a very efficient system on how to hire the best people without spending a lot of time in the process.

In most cases, it makes a lot more sense to hire someone than to learn a completely new skill, or for menial work that needs to be done on a day to day basis. Like we’ve talked about in the past, time is money.

The Best Way to Hire on Upwork

Back when I started using Upwork in 2014, the platform wasn’t as developed as it now and it also used to be called oDesk.

However, I still employ the same hiring strategy today as I did back then.

Below are the exact steps I take to hire on Upwork:


1. Create a Job Post

This is pretty standard, as you have to create a job post describing what type of freelancer you’re looking to hire and how much you’re willing to spend. After you publish the listing, about 20 minutes later you’ll get a bunch of applicants submit proposals to get the job.

What I do is mention in the job post that in order to be considered for the role, to message me their Skype username.

It’s much easier to keep contact through Skype, and this also acts as a screening tool to see if they are actually reading the job post.

PS: It would be better to just list your Skype username in the job post, but Upwork prohibits this and will delete your post if you do so.

2. Message them all on Skype

After the applicants message you with their Skype username, go and add all of them and say, “Hey this is _____ from Upwork.”

It’s important to note that I still haven’t looked at the applicant’s profiles, as I’m looking to see how fast they accept my contact request and can talk to me about the job.

The one’s who get on Skype right away to talk are the ones who make it past the next step, the ones who fail to do so, I delete.

3. Give them a Test

At this point you’ll probably have 5 or so applicants who have made it this far.

Now all you gotta do is talk to them and describe what you’re looking for.

Pay attention to the applicants who are putting in a lot of effort into the conversation and seem like they know what they’re talking about. You’ll usually find one or two that stands out.

Now say something like, “Okay I want to hire you, but first I need to see if you can do the job.”

PS: This is all done through Skype text – you never have to call them as there is literally no reason to.


You’re then going to download Teamviewer, which is a program that allows you to give control of your screen and mouse to the freelancer.

Don’t worry as you can control the mouse too, and you can end the session at anytime. The freelancer isn’t going to hack you I promise.

Now just tell them to do a short 5 minute task that relates to the job. They’ll likely be able to do it pretty easily, as this is more so to just teach them how you want them to do the job after you hire them.

After that you pretty much have your guy, and all you have to do is officially hire them on Upwork and they will start working.

4. Setting up the Contract

In terms of the contract, I always do a fixed contract, which means that you’re specifying exactly how much you’re going to pay them for the job. Never use an hourly contract.

And if it’s a long term project, I’ll add separate payment milestones and dates in which each task needs to be completed by.

Once you actually click the Hire button, the freelancer will have to accept the offer, and then your money will be held in escrow until the job is complete.

When the job is finished, you will release the funds and the freelancer will get paid.

5. Treat your Freelancers Well

After the contract ends, you will rate them based on how they did. As long as they weren’t terrible, give them 5 stars. If you were good to them, they’ll give you 5 stars in return.

As time goes on, your client rating will grow and more prominent freelancers will apply to your job posts because they see you are an easy client to work with.

Furthermore, I like to give the freelancer a bonus after they complete the job. If you’re just starting out and you don’t have a lot of extra money you don’t have to do this, but adding a bonus goes a long way and they will be very appreciative.

This will leave a good memory with the freelancer, and they will prioritize you and your work in the future if you ever want to work with them again. It’s also just a nice thing to do.

Final Thoughts

Well, there you have it.

I’m pretty sure that you don’t want to spend a lot of time sifting through applicants, and this strategy ensures that you can hire a good prospect within an hour of publishing your job post.

Like I mentioned previously, I’ve hired over 30 different freelancers using this method, and almost all of them have turned out perfectly.


Lastly, I want to point out that you really want to be looking for long-term relationships. If you want to have a huge leg up while running online businesses, it’s crucial to have both an expert full-stack web developer and graphics guy.

I can’t even explain how much value this will give you, but I’ve had 2 guys that I’ve been working with since the beginning who are the best in the business, (thanks Max and Ade!).

However, I can’t recommend Upwork for graphics, as I found Ade through 99Designs.


Alright guys, that’s it for tonight.

I hope you got a lot out of this Upwork Hiring Guide, and let me know if you have any questions or experiences in the comments section below!

Best – Brian.

By | 2017-07-23T05:05:14+00:00 June 13th, 2017|Business|2 Comments


  1. George June 13, 2017 at 8:44 PM - Reply

    Nice post. You said you have spent about $15,000 hiring people. How much profit did you make during that period?

    • Loser 2 Winner
      Loser 2 Winner June 14, 2017 at 2:45 AM - Reply

      thx george.

      for a long time i wasn’t making much at all as i was always reinvesting back into whatever i wanted to grow. these past 6 months is when i started to make a healthy profit

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