Must-Read Advice for Every Small Business That’s Hiring Freelancers

By Brian Quinn

As a small business owner, there are only so many things you can accomplish in a day. With limited time and resources, one of the best ways to accomplish more work is by outsourcing some tasks to freelancers. Platforms such as Upwork have made it easier and more convenient to hire freelancers. These platforms can connect you to many legitimate, talented freelancers who are capable of helping you accomplish your desired goals. However, you may also have to sift through many unqualified applicants, some of whom will produce poor quality work, or work that is plagiarized.

In this article, we’ll walk through a few guidelines that will help your small business save time when hiring freelancers and build successful working relationships with freelancers for many years to come.

Start by selecting freelancer-friendly tasks.

Not every task is suitable for freelancers. When selecting tasks to outsource, you’ll want to start with simple tasks, which will not only enable you to make the job accessible to more freelancers, but also will increase the chances of that your job will be completed successfully.

In contrast, when it comes to complex tasks that require significant subject matter expertise, you may be better off completing these tasks yourself or assigning them to full-time staff. It will likely be difficult to find freelancers who have the desired expertise, and those who do have the expertise will charge a premium. If the freelancer doesn’t already have the relevant background, they’ll have to do research to learn about the subject, which may not make the task worthwhile for their time (and will therefore make it harder to hire for). It’s best to start off the working relationship with simple tasks, and then gradually introduce tasks that grow in complexity, once the freelancer demonstrates their ability to complete work that meets your standards.

For example, it is more suitable to ask freelancers to collect data from websites on an ad-hoc basis, than to ask freelancers to write an in-depth article about niche technology that requires technical knowledge. The in-depth article will be challenging to write, and it’s difficult to provide criteria that will make it clear to the freelancer when the job is done, since there are many subjective qualities to assessing such an article.

Clearly communicate the job requirements.

Once you’ve selected a suitable task to outsource, it’s important to spend time to write clear requirements about what you expect to be accomplished. Make sure that your requirements are crystal clear—if there is any confusion, and the freelancer does an adequate job, but doesn’t quite meet your requirements, you’ll likely need to engage in a lot of back and forth with the freelancer in order to receive a product that you’re happy with. These iterations can take up a lot of time, which defeats the purpose of outsourcing work in the first place. To avoid these time-consuming followups, it’s better to over-communicate your requirements, so that there’s no room for any misunderstanding.

Investing the time upfront to create a clear set of requirements will save both you and the freelancer time—and, in the event that you have to enter a dispute with the freelancer for incomplete work, these clearly stated requirements will make it easy for you to present your case and ask the platform to resolve the dispute.

Do your due diligence in hiring (at least initially).

When navigating platforms like Upwork, it’s important to do your due diligence in researching background information about the freelancers that you hire. All freelancers on Upwork are required to include their full name, as well as a profile picture. This makes it easy for you to do a quick search of the candidate’s web presence, to make sure that they are who they say they are, and that they’re qualified to complete the task. There are many fake profiles on Upwork, and you can largely filter out those who do not have any web presence. In addition, many profiles on Upwork include fake pictures, which you can identify by doing a reverse image search on Google.

Beyond doing a quick background check, you’ll also want to validate the quality of their work, at least during their first few assignments. Ideally, the work will require minimal edits (and if it does require any changes, you’ll want to make sure that the freelancer responds positively to your feedback, and incorporates the requested changes). It’s also important to make sure that their work isn’t plagiarized, which is a common issue. A quick search on Google should help you identify any work that is clearly plagiarized.

After you’ve worked with the freelancer on several tasks and you trust their work quality, then you can gradually spend less and less time evaluating their work, which will ultimately save you time.

Hire multiple freelancers, and establish long-term working relationships.

A good freelancer can be invaluable to your business. Therefore, it’s important to do whatever you can to find excellent freelancers, and establish a long-term working relationship with them. By hiring multiple freelancers simultaneously, you’ll inevitably come across some who don’t work out, but the goal is to identify just a few who can potentially complete quality work for many years to come. And, if you enjoy working with a specific freelancer, you may eventually want to consider hiring them as a full-time employee.

Ready, set, hire!

Hiring your first freelancer can seem intimidating at first, but these guidelines can help you streamline the process and choose freelancers who are likely to deliver quality work for many years to come. Ideally, you will eventually be able to establish long-term relationships with specific freelancers who can take on some work, thereby enabling you and your staff to focus on tasks that require more specialized knowledge.

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Brian Quinn

Brian Quinn is a co-founder of ValuePenguin Software, which provides in-depth product reviews and resources to help business owners make well-informed decisions. From highlighting industry-specific trends, to delivering extensive software guides, ValuePenguin Software helps small businesses select the best software for their needs, and increase their bottom line.


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