The Complete Guide: How to Work Successfully with Freelancers from Upwork and Elance

One of the most effective ways to scale your business, is to take on additional staff. Whether you are a freelancer who wants to outsource some of your recurring tasks, or a business owner who wants to expand, hiring a freelancer is a great way to grow your operation.

With online workplaces like Upwork (formerly Odesk) and Elance giving you access to thousands of workers, of all abilities, from all over the world, the process of hiring a freelancer for a small job or ongoing employment has never been easier.

However, hiring and working with freelancers from these online workplaces doesn’t always result in success. As the process of signing up, posting a job description, and hiring a worker for your project, can be completed in just a few hours, it’s very tempting to dive right in and get started.

However, as with hiring any worker, the more preparation you can put into the process beforehand, the more likely you are to have a positive experience and get the results you want.

In this article we will provide you with some actionable advice and tips you can use to ensure that you are able to successfully hire and work with a freelancer. This can then help you to grow your business or outsource some of the daily tasks that are getting in your way of doing what you do best.


What Do You Want the Freelancer To Do?

As the leading online workplaces have made the process of hiring a freelancer so straightforward, it’s tempting to just go for it and hire first, and then define exactly what they will do later.

However, one of the key factors in finding the right freelancer for your project is to be completely clear in advance, of the tasks they will be working on. This in addition to knowing what the skills they will need to complete those tasks.

Approaching the selection process with a vague idea about what duties the freelancer will be performing is likely to end in disappointment for both parties. While hiring additional team members and assistants is one of the key ways you can grow your business or turn your service provision into a scalable business, hiring for the sake of it is never a good idea.

Therefore it’s vital that you draw up a list of duties and requirements for the task you want to hire someone to perform. Think about what qualities you’d like in a freelancer who will be working on your business.

Writing the Job Description

Once you’ve detailed the components of the task you need help with, as well as established what skills are required to complete them, you will then have the information you need to write an effective job description to post on sites like Upwork and People Per Hour.

When creating the job description try to be as detailed as possible. This not only makes you look more professional, helping you to attract professional freelancers in return, but it can also help reduce the amount of unsuitable speculative applications you receive.

To help you sift through the applications, which we will cover in more detail next, include some questions in your job description. You can then assume that any applicants who haven’t answered these questions didn’t read the job description in full, and therefore probably aren’t be a good match for the role.


Reviewing the Applications

At the most popular online workplaces, freelancers looking for work, greatly outnumber the jobs up for grabs. This means that, depending on the nature of your listing, you are likely to be inundated with applications.

Unfortunately, as finding a job on these sites can be a numbers game, many of these applicants will just be firing off applications indiscriminately. This means there will be a lot of unsuitable candidates to filter out before you even get started on drawing up the shortlist.

A good approach to take when reviewing the applications, is to ensure that you reply to all applicants within the first 24 hours of posting the advert. If you leave it any longer than this, there is a high chance that the quality candidates will have moved on and found work with someone else.

Therefore when setting time aside to hire a new freelancer, be sure to schedule a window for responding to all the applicants within 24 hours of the listing going live. You will also find that the number of applications you receive begins to decline after this period anyway.

Should You Interview Shortlisted Candidates?

Once you’ve created a shortlist of candidates, based on their application, skills, portfolio, and feedback from previous contracts, it’s time to reach out to a few of them to further establish their suitability.

Some people like to conduct a Skype interview at this point. However, this isn’t entirely necessary. If the task you are hoping to hire a freelancer to work on doesn’t require good English language abilities, or the ability to Skype with clients, then it might be better to skip this step.

If you are hiring an admin assistant or graphic designer for instance, then email communication should suffice. This should also allow you to proceed more quickly, as opposed to trying to schedule a Skype interview over multiple time zones.

However, if good face to face communication skills are a requirement of your role, or the project is a complicated one, then a voice or face to face interview is recommended. In short, don’t waste time on an interview if it’s not necessary.


Start With a Paid Trial

Whether or not you hold a Skype interview with your potential freelancer, before you offer a contract to a shortlisted candidate, it’s highly recommended that you hire them for a small task first.

This tactic gives you a great opportunity to not only gauge the quality of their work, but also determine how available they are, how they respond to constructive criticism, and whether they can work to deadlines or not.

Whatever attributes you think are important for the role you are hiring for, ensure your mini-assignment includes tasks that will test for those qualities.

While it’s not unreasonable to offer this trial on an unpaid basis and include it as part of the selection process, paying the worker for their time has a number of benefits. One is that you avoid alienating those high calibre candidates who value their time enough to turn down unpaid trials. Two is that by paying for this task upfront, you can see how motivated a worker is once they already been paid for the work they are yet to complete.

If the freelancer completes the task to your satisfaction, then you are ready to hire them and start your working relationship.

How to Manage Your Freelancer for a Successful Working Relationship

Online workplaces like Upwork provide you with the tools to monitor whether your freelancer is actually working when they say they are, so you don’t have to worry about that if you are paying by the hour.

The most important thing to focus on, in order to ensure the working relationship is a success, is that your instructions are clear and the worker knows what they should be doing at all times.

The more detailed your instructions and requirements are, the more empowered your freelancers will be to complete the task. This also increases your chances of receiving work that meets your standards.

It’s a good idea to always ask if a freelancer has any questions when you are issuing instructions. It can also be beneficial to sign off each email with a request for them to reply to confirm they have understood the instructions and requirements of the task.

While email can be an effective communication tool, there are other services you can leverage to improve this workflow. This could include tools such as Slack or Glip, and file sharing services such as Dropbox or Google Drive. Just be sure to define a toolset during the hiring process.


With countless freelancers on hand, waiting and ready to work on any task, no matter what its size, using an online workspace is a great way to grow your business or outsource some of those daily tasks that are slowing you down.

The casual and flexible nature of the contracts and hiring process can make it easy to underestimate the task of finding a suitable match for your vacancy. However, by following the advice above, and specifying exactly what you want, and then taking the time to vet the applicants carefully, you should be able to hire and manage your freelancer with success.

What tasks do you want to outsource? What difference would a freelancer make to your business? What’s stopping you from hiring someone to work on your business right now? Share your thoughts in the comments below.

Joe Fylan

Joe Fylan

Joe has been using WordPress for many years and spends his time creating content for a wide range of websites and blogs. If you need compelling content for your blog, visit his freelance services portfolio now.

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