How I Hired a Freelancer on Upwork and Got Results (On a Budget)


You can hire someone to do pretty much any business task for you on Upwork. But will you get results?

Have you ever tried to delegate your work and have it blow up in your face? Or have you been terrified by the thought of spending time to teach someone else to do your job? What if they can’t get it done? What if I lose time and money training them? Maybe you’ve told yourself, “…it’s best if I just do it myself.”

In a sense, you’re right. You can get the job done. But what about all that other work that’s waiting for you in the meantime? Doesn’t it deserve to be addressed? Should you really be working on what you’re working on now, when someone else can do it? And they want to do it?

I’ve found that the truly successful people in business are the ones who know how to delegate. But if any of you have tried hiring someone in the past from an online freelancer service, you know that it can be a mixed bag. There can be communication problems, time zone problems, and trust problems. I know there have been for me.

Bad hiring experiences in years past have kept me from hiring freelancers. On the other hand, I know I need to do this in order to develop and grow my freelance agency. So I decided not to give up. I know that it would be irresponsible for me not to seize the opportunity to get more work done using awesome freelancers from around the globe.

In this post I’m going to focus on one freelance service in particular: Upwork. Recently I hired someone on Upwork for the first time. And it was a success. But let’s define success for a moment. By success, I mean:

  • The project got done on time.
  • The project got done within the budget I set for it.
  • The project got done according to my specifications.
  • Bonus points: the freelancer gave me a good client review.

Before you hire on Upwork

A big part of success lies in how you communicate the work that needs to be done. Here’s how I set up my job to get the best results:

1. Pick a job you know how to do.

I specifically found a job that I knew the inner workings of, and could delegate from start to finish. It was a job I could do, but I knew if I did, it would come at the expense of my other projects. It was a perfect job to delegate – recreate a website built on the Rainmaker Platform* in WordPress.

Since this project was ultimately for one of my clients, the first thing I did was provide my client a project quote with delegation in mind. This defined my budget for hiring on Upwork. When it came time to post the job on Upwork, I knew what budget to set for the project. I also knew two other key points:

  • I needed to hire a WordPress expert. This helps because it narrows the search down from “Web, Mobile, & Software Dev” to what I specifically needed. Upwork gives you the option to receive proposals only from freelancers who have passed the Upwork WordPress test.
  • This would be a one-time job. This may seem obvious, but I’ve seen many clients who post jobs on Upwork with the promise of ongoing work for the potential freelancer. Dangling a carrot in front of someone is not a great way to start a working relationship. Stick to the job at hand, if it gets done successfully, then talk about the next job.

2. Work with a person, not with an agency.

There’s a place for agencies. I’ve hired from agencies in the past. I’m sure there’s a good way to do it, but my experience was negative. Since I myself am set up like an agency, I only wanted to hire one person, and work with one person. I specifically structured this job knowing it wouldn’t take more than one person to get it done. So if it only needs one person, hiring an agency just risks complicating things. You can have delays and miscommunications, because more people are getting added to the mix.

3. Get as close to your time zone as possible.

Not everyone has the luxury of hiring from their time zone. I happen to live in a European time zone area. This makes it easy for me to hire from regions around me, like Eastern Europe. So once I clearly described the job I needed done, I began looking for WordPress experts who lived in or near my time zone.

After one day, my job posting had received around 30 proposals. My next task was to sift through all of these proposals.

First off, the most interesting one:

One freelancer contacted my direct email (not via Upwork) and sent me a link where he had already rebuilt the site I needed done. I thought about this for a while – I mean, the guy has already done the job, right? Of course I should hire him! But on second thought, I realized that the job wasn’t done according to my exact specifications. I needed the site to be built on a specific WordPress theme, and on a specific server.

I took a moment and looked at this freelancer’s profile, and I saw that he worked almost entirely with one client. And that it didn’t end well, according to the client reviews. I kindly declined his proposal.

Side note: for this job, I didn’t require freelancers to have a long job history on Upwork. I made it a point to include “Rising Talent” (new freelancers without work history or client reviews) in my job post. I did this because I’ve worked as a freelancer like this before, and I know what it’s like trying to get your first job.

The rest of the proposals were reviewed, and I quickly shortlisted the ones that were from or near my time zone. Because by this point, I needed to get the client’s site exported from the Rainmaker Platform within three hours. This became a time-sensitive job that hinged particularly on one thing – availability.

So I messaged the three freelancers that I was most interested in:

  • They were in or near my time zone.
  • They were WordPress experts.
  • They made their proposals according to my budget (well, one of them proposed $5 more than my budget, but I kinda liked her initiative in doing so).

Note that although job history and good client reviews were a help, I still got in touch with one freelancer who had no job history. He hadn’t even set up his Upwork portfolio, but I liked the fact that he used a professional profile picture – it made the difference.

So, out of the three freelancers I messaged, only one got back to me in time to get the project done – the guy with no job history. After an exchange of messages on UpWork, he confirmed his availability. I hired him for the job – but I took a risk in doing so. He was a new hire, and I wasn’t sure he could get the job done in time. So I gave myself an “emergency” window of time where I would complete the job – if he couldn’t – at the expense of my own time.

After you hire on Upwork

Now here’s what I did to get the best results from my hired freelancer:

1. Be available throughout the job.

This was a time-sensitive job. So throughout the three hours of his work, I remained available online for any questions from the freelancer. There were a few, but nothing too demanding – he showed competence and the ability to work independently. He ended up finishing the job with a few minutes to spare.

2. Reply to all potential candidates and thank them.

Later on, the other two freelancers I messaged got in touch. They realized they would not be able to meet my availability requirements, and that they wouldn’t be working on this job. Still, I made it a point to reply to them and thank them.

3. Make prompt payment.

After I completed the job with my freelancer, I promptly paid him. Upwork gives you the option to fund escrow – to pay Upwork for the project upon hiring, and then release payment when the work is delivered. This is a no-brainer – it gives the freelancer the security to know you have the money for the work.

Finally, I did one more thing, I sent my freelancer the following message:

Thanks ******, I just made payment.

Hope things go well for you on Upwork.

A few quick questions:

1. Would you be interested in doing another job like this for me in the future? (I don’t have one now, but it’s good to know.)

2. I work with design, development, and writing – which of these are you most interested in working in? Can you give me an example of a kind of project you’d like to do?

Have a great weekend,


I left the door open for future work together, without committing to anything. And I wanted to get a better idea of which job would fit him the best. I also intend to revisit the other two freelancers who responded to my messages. It’s good to have more than one person to hire, if you need one.

I’ll leave you with this – Lee Iacocca has a great lesson he attributes to his former colleague, Robert McNamara:

He taught me never to make a major decision without having a choice of at least vanilla or chocolate. And if more than a hundred million dollars were at stake, it was a good idea to have strawberry, too.

* Affiliate link.

You can download a printable pdf of my Upwork hiring guidelines here:

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