I Have Spent $30k+ Outsourcing Freelancers from Upwork — Here’s My Ultimate Hiring Checklist.

I Have Spent k+ Outsourcing Freelancers from Upwork — Here’s My Ultimate Hiring Checklist.
I Have Spent k+ Outsourcing Freelancers from Upwork — Here’s My Ultimate Hiring Checklist.
Image by storyset on Freepik

My mind: “What if I hire someone to help me finish work for a client? I am sure this freelancer won’t do it my way, but I will focus on that person being more of a supporter.”

*Hires Someone on Upwork*

Client: “I don’t like this work…”

My mind: “This whole hiring from Upwork was a terrible idea. Let’s just thank that freelancer, pay her, and end her contract with a perfect five-star review. I know what a review could do to a freelancer.”

*A few years later*

My mind: “How about I hire someone else, pay that person more, and give that person more responsibility this time?”

*Hires Someone on Upwork*

Client: “I don’t like this work…”

My mind: “I will stick with what I know as a solo freelancer and never hire again.”

*A few years later*

The same thing happened, but there wasn’t a negative review. On the contrary, there was quite a good review. The difference is that I learned from previous experiences that a freelancer needs guidance to create things my way.

Then my mind realized the potential behind this — If I can succeed in doing this, I can expand to serve hundreds of clients, and it happened…

*A year after that*

I was able to help over ten clients at the same time with the help of my team of trusted freelancers. They’ve evolved into team members I trust in creating a perfect product.

This was the moment I realized it — I am a solo freelancer, but there are many people out there with whom collaborating could result in greatness.

Ever since that moment, I have been hiring from Upwork and Fiverr freelancers whom I got to know and work with for years personally. I try to make a difference in their lives and experience the difference they make in mine.

I’ve recently looked at my statistics and noticed that I had spent over $30,000 on those team members.

Image from Author’s Upwork Account.

In addition, a team member recently told me I had affected his life by working with him for over three years and teaching him how to create stunning business documents from scratch. His statement made me realize that selecting a long-term freelancer to work with was one of my most rewarding decisions.

I also noticed that I’m rated a 4.93/5 as an employer, which makes me feel that it’s good for both ends.

I do nowadays, due to a disagreement that I had with Upwork. Both Upwork and Fiverr have an incredible pool of freelancers that could do fantastic work. I’ve hired from both and believe they both have the same roots in freelancing.

The only differences are in technicalities (mainly, the speed of payment and approval of milestones.)

However, you can read thousands of articles about how online freelancers are imperfect, and they could be very misleading. So let’s showcase a couple of projects.

I was recently in need of a video editor to help in editing my personal Youtube videos. The following video resulted from one of the videos with a budget of around $10, as per his request.

Video of Author’s Educational Footage

I loved the animations he’s done and the work which led me to ask him to create an animation video for my company. His budget for that was around $110.

Video of Author’s Marketplace Animation Video

Then another…

Video of Author’s Marketplace Animation Video

While it’s not a world-class video, the time and flexibility in designing the video made me reach a decision — he’s now my go-to video editor (you can find him under the username: sjvisual21 on Fiverr.)

I’ve worked with over 50 freelancers in different industries and functions during this journey. Of course, some disappointed me, which is normal. Yet, the majority end up becoming long-term work partners by one thing that I advise you to do — empower them.

Hence, I started realizing that for a freelancer to pass the test and become a successful integration in my work methodology, they have to pass through this checklist.

1. Earnings do not matter.

It does not matter whether they’ve earned thousands or didn’t. In most cases, I prefer hiring newbies new to freelancing platforms. Why? Mainly because they are willing to learn my methods. An experienced freelancer usually says, “That’s not how I do it with most clients.”

2. Let’s take this to a video chat.

I’ve hired a few times a couple of individuals who turned out to be totally different people after their work was submitted. If credibility is not established from stage zero, then it’s not a good seed for a future prosperous work relationship.

3. Location does not matter.

I’ve succeeded with freelancers from third-world nations and failed with ones from developed countries and vice versa. It’s really about the person.

4. If the freelancer asks questions.

Questions are my guarantee that this freelancer is actually trying to understand. While some arrogant ones would deem questions a sign of weakness when working with a client to sign a contract, people who question are the ones that end up at the finish line.

5. Previous work is an essential formality.

The truth is, many would have fake portfolio elements that are fantastic. However, if I work with someone to install a tech element on my website, it’s a flag when that person has no other website in their portfolio.

6. Absolute lack of personalized messages to your job post.

I usually post something like, “I need someone to help me integrate Facebook and google logins to my marketplace website — albusi.”

  • Most freelancers on Upwork would paste a tremendously huge message of how they are amazing.
  • A few would act sneaky by copying my line and repeating it — “I read carefully your job about integrating Facebook and google login to your marketplace website — albusi, and I can do this perfectly in a few hours!”
  • The rare ones who end up as my long-term hires have thought of my job post rather than considered it a sales challenge. For example, “Tell me more, why do you need Facebook login? have you installed your pixel? Do you already have a database?”

7. Expect the freelancer to make mistakes.

Client: “I am relying on you! I will give you your total freedom to operate.”

Freelancer: “Okay, I won’t disappoint!”

*After delivering*

Client: “This is absolutely not what I wanted. The work is very disappointing; I regret this.”

Freelancer: “…”

Of course, the client regrets this because giving a freelancer the absolute freedom to operate means that that freelancer works in their own bubble. Therefore, do not expect them to release an output that fits in your bubble.

Freelancers will make mistakes, and your job is to help them perfect the output with them.

8. Motivate and Empower

You have no idea what this other person is going through. You might be why that freelancer will freelance for years to come or will stop freelancing forever.

Teach that person how to go from zero to what you want. If it doesn’t work, end it in peace and with gratitude.

That’s what I did with my team members. They’ve been working with me for years, and I would trust them with any work I can do. Such trust developed over time with hundreds of mistakes from my end and theirs.

This is an enriching journey that I strongly advise you to go through.

I’m Al, a business consultant in Zurich, Switzerland. I believe in the power of delivering value to you, the reader. Follow me on various social media platforms if you’re interested in the value of my content.

Note: There are no promotional links in this article. I was not paid on behalf of a person or an organization, and I will never be when it comes to my Medium articles.

Go to Publisher:

Entrepreneur's Handbook – Medium

Author: Al Anany