Taking The Headache Out Of Hiring – A Step-By-Step Hiring Checklist For Choosing A Freelancer On UpWork

Taking The Headache Out Of Hiring – A Step-By-Step Hiring Checklist For Choosing A Freelancer On UpWork
Taking The Headache Out Of Hiring – A Step-By-Step Hiring Checklist For Choosing A Freelancer On UpWork

Chances are that you are reading this because you have posted an Ecommerce project on Upwork. Whether you are an UpWork veteran with years of experience or a first timer, the guide I have outlined for you will help you with your hiring decision.

You are reading this because you understand that hiring a freelancer to work with your project is an important decision and definitely one that is not to be dealt with lightly.

After all you are about to give someone keys to your business and entrust them with your baby, your own store. Would you trust your baby to a stranger? Of course not! You would instantly imagine all the things the stranger could do to screw things up.

You might think that the baby example is a bit extreme but in fact the situation is identical with Ecommerce websites, a work that is done badly can seriously cost you later on. In fact, it is possible that there will be loopholes in security or coding that will make any further updates impossible. It is possible for everything to look good on the outside while it is a complete mess on the inside.

Now, if you are not that experienced in all the different facets of Ecommerce, or simply don’t have the time to take care of things yourself, it makes sense to seek help for your troubles. After all we can’t all do everything and know everything when it comes to running a business. You have decided to take it to the next level and improve, that is always a wise decision, kudos for that.

So at this point you have decided to hire someone and head over to Upwork created a job posting, submitted it and now you are looking at this long list of applicants from all around the world. At this point your head is probably filled with questions such as:

  • Who do I pick?
  • How do I decide who to pick?
  • How do I know who is the right person for the job?

And having these questions and doubts can very well put you a bit outside of your comfort zone. It can make you feel lost and a bit confused. So, if you are anything like most people who hire on these platforms you will feel quite
overwhelmed by the sheer amount of applications that you have received. And the hiring decision is not made any easier by the fact that you are hiring people to do something that you are not be an expert in.

Now, your confusion is mounting because the world of coding, design and development seems like a distant universe and you aren’t sure of where to start. As a result, you are likely to follow your gut instinct and go for someone you either like or someone who offers you the best price.

Unfortunately, both of these are bad reasons to pick a contractor. You are likely to overlook things and rush through the process just to avoid all the confusion and the pain that comes with an unusual situation. And that is where this guide will help you.

The 10-step formula to successful projects

Having hired on Upwork myself, I created this guide for you to ease your pain. I wanted to make things really easy for you, so I created a list of the most important things that you should keep in mind when you are hiring a freelancer for your Ecommerce project. I sincerely hope that you benefit from these ten tips, whoever you decide to hire.

1. Know what kind of end result you are after.

Don’t waste your time on a project that is not planned out properly, if you need to just go ahead and hire someone to consult you and plan the project before you hire for the entire project. Remember: planning will always save you time in execution. So get really clear on what it is that you want before you hire anyone for the actual job.

2. Know what kind of person you are looking for.

In order to not be swayed from your original goal you should have a freelancer avatar in mind of what it is that you are looking for. Before all of this, you need to understand what kind of result you are after (Step 1) and then, based on that you can form an idea of the person you are looking for.

Doing things this way lets you instantly screen out applicants that are not to your standards, making the list of applicants a lot less intimidating.

3. Know how involved you want to be with the project.

If you don’t have much time to babysit you should be looking to hire an expert who can work independently and suggest solutions to your problems. If you are busy and don’t want to micromanage your freelancer, I recommend to avoid cultures that are very hierarchical because these cultures expect the boss to tell them everything that they need to get done.

Rather hire someone from your own culture that focuses more on solutions, delivering value and doesn’t require constant babysitting.


Learn how you can also increase your store's eCommerce conversion rate today

Learn how you can also increase your store's eCommerce conversion rate today

4. Don’t automatically pick the cheapest contractor.

It can be very tempting to save money and go with the lowest bidder, however most of the time the freelancers who bid low are desperate for work. It is possible that you might get lucky and end up finding a great deal.

However, it is more than likely that you will end up spending a lot of time correcting the things that the freelancer has done. So remember that you are often better off investing a bit more capital initially to get someone who knows what they are doing and does the job right on the first try.

5. Background check the applicants.

It is worth doing a bit of snooping around to ensure that the contractor actually possesses the background that he is presenting. A lot of people out there are using fake portfolio sites to woo clients in to believing in their abilities.

A well expecting client can easily be swayed by these people because they want to assume good things of people. Please note that I am not asking you to expect everybody to be liars, but you should be a little skeptical and ask couple of difficult questions. I promise that you will be happy that you did.

‍6. Get on a call with your new hire.

If you were to hire an employee, you would never do a hiring decision without speaking to the applicant first. And there is a good reason for that, how could you trust a stranger? Just think about it: trusting your store in the hands of someone that you have never even talked to would be stupid.

I understand that most people don’t like conducting interviews, but you can keep it short and to the point. The goal is to feel out a person and get a good sense of whether or not the relationship would work out.

7. Establish a timeline.

It is important that you both know what is delivered and when. Too often delivery times are overlooked in the spirit of mutual trust. This can lead to a situation where the client finds out that since there was no set timeline, freelancers can then take almost however long they want to, and your project will always be towards the bottom end of their work pile.

8. Agree on communication.

Another easy thing to overlook is the communication needs between you and the freelancer. You should both agree on the frequency and the medium of the communication. It is important to keep in mind that with clear and regular
communication you know what is going on and you can spot possible problems early.

Once you get the communication right, you will be the captain who is just gently guiding the ship to its final destination.

9. Use fixed price to set the incentives correctly.

We should never underestimate the power of incentives. If you reward your freelancer for working slowly and spend a lot of time with the project, then that is what you are most likely going to get.

On the other hand, if you pay by the results and have a well-defined project (See step 1) you will be rewarding quickness and effectiveness. People are naturally a bit selfish and the best way to get the most bang out of your buck is to form your payments in a way that actually rewards the freelancer for results, not time.

10. Test and review.

After the work is done, make sure to check it out thoroughly. There’s often one or two things not quite perfect with the work and you can still ask the freelancer to fix issues before you are done with the project. Don’t rush to the finish line.


All in all, hiring on freelance platforms requires perspective and patience. Understand your project before you act and make informed hiring decisions based on these pointers. Remember a great hire will be there for you through the thick and thin and will want to build a long-term working relationship with you as well.

If you spend time to find a great contractor the first time around it will save you from constantly being on UpWork and posting new jobs all the time.

It can be painful to invest the initial time but keep in mind that a great hire will be an asset to your business and helps you get to the next level. Some of my best hires have proven to be long-term strategic partners that ended up saving me a lot of time and sweat.

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