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Hiring a Freelance Contractor: 7 Top Tips to Success

By Paul

More and more these days we’re hiring freelance contractors to conduct all manner of jobs for our businesses. From web design, to graphic design, copywriting, and just about any other task you can possibly think of, the online freelance skills market is broad-ranging and vibrant. However, no matter which skills set you’re looking to engage, there are still some hard and fast rules that you should live by when making your decision to hire. To help you get the best possible result when hiring your next freelance contractor, make you sure you keep in mind the following top tips.

1. Don’t simply hire the cheapest contractor

It can be so tempting in life to go for the cheapest option when making a purchase, but in the freelance skills market, this is usually ill-advised. Because you’re likely to see a great deal of competition tendering for your freelance job, it’s highly unlikely that the cheapest option will provide you with the best outcome. Make sure you take the time to review each applicant on his or her merit, and soon you’ll gauge what’s a fair price for the completion of your job, and who’s simply gaming the tendering process. Remember that because certain skills have a different local value to that of your country, you’re likely to get a great price on your job anyway. So ensure you choose the best freelancer you can afford for your job.

2. Never hire a worker without seeing a portfolio of relevant examples

If I said I was a surgeon, would you hire me without some form of proof I could do the job? Absolutely not! Treat the hiring of your freelance contractors in this way and you’ll be far better off. You should always narrow your selection of freelance contractors based on their ability to showcase their talents. Even if it’s not the exact skill you’re looking for, if you contact the freelancer and ask them about the other similar skills they have, you’ll generally be able to get a feel for their expertise. If they’re unwilling to engage with you when it comes to their portfolio or skills, see this as a red flag and move on. The best freelancers are the ones who provide similar or relevant examples of work you can peruse so you know what you’re likely to receive for your payment.

3. Always come to an agreement on project milestones and review dates before starting

Milestone payments and project review dates are a great way to protect both the employer and freelance contractor on a given job. Clearly define the conditions by which a project gets completed; both in time and through payment terms. This way you’ll keep your project on track. When hiring a freelance contractor, you need to be upfront about your terms of engagement. If you have a reasonable set of terms which include a few milestone payments and a regular project review schedule, there should be no reason anyone who intends on completing your project correctly wouldn’t go along with this. Keep in mind though – when negotiating your terms, that if your project is of reasonable length, always opt for milestone payments, and be wary of upfront payment requests. This can be a sign that you may not receive the level of work you were hoping for.

4. Don’t be afraid to conduct an interview to gauge personality traits

Because so much of the process when hiring a freelancer is done online, often the personal element to making a hire gets overlooked. Even though the freelancer is generally not sitting in your office, you’re still going to have to interact on a project quite regularly to reach an outcome. If you’re wary that you may encounter language barriers, or the freelancer may not be the type of personality you’re looking for, or you want to ideally develop a relationship with this freelancer over time to complete other jobs, then set up a Skype or telephone call to set your mind at ease. Again, this should be no issue for a freelancer who is keen to work on your job, so take the time and effort to setup a short interaction, as this can really save you a lot of time and money in the long run.

5. Contact previous clients for a referral

If you can see that a particular freelancer has worked for a certain client, and you’re thinking of making hiring them, don’t hesitate to drop a previous client a quick email to find out if the freelancer was easy to deal with. Often you’ll find out that the freelancer was fantastic to work with, and had a wide-ranging set of skills, but occasionally you might dig up something that you didn’t anticipate finding. If your project is a lengthy one, this strategy can be well worth the extra time, and can really set apart candidates. In a normal job interview process, you’d ask to talk to a referee. There’s no reason this can’t be part of hiring of a freelance contractor. 

6. Always check employer feedback across the community

Most freelance websites have some form of review system where employers can review their contractor based on their performance. Better freelance sites will also provide feedback on how the contractor performed as an employer, which is also interesting to weight up in your decision-making process. Make sure you read the comments, and don’t simply look at their overall rating, which is generally a five-star type system. Check the details of what the community is saying about the contractor, and even Google a contractor for further review of their services. This will certainly help you gauge a contractor’s true performance.

7. Be up-front about project timelines

There are many freelance contractors who will be able to complete your job, but often they’ll have a number of clients in the queue ahead of you who are expecting their work delivered by a certain date. If your job is time-dependent, and you simply can’t wait, make sure that this is non-negotiable if the contractor wants your work. Most services allow you to either detail this in your job description, or provide a delivery date of some kind, so be upfront about this and ensure you double-check with your freelancer that this is feasible before you select them to complete your job. Often, schedules can change quickly in a freelancer’s timeline, so always double check at the last minute before you move forward.

Paul Dunstone is the founder of Job Stock, a freelance jobs marketplace where you can secure freelance work across more than 250 job categories. Paul is also the editor of the Job Stock blog, which discusses issues relating to the freelance industry.

Category: freelance writing

5 Comments on "Hiring a Freelance Contractor: 7 Top Tips to Success"

  1. Claude says:

    Be upfront about timelines is a good tip, but dont forget to listen to your contractor. He often has a better idea about the work ahead than you. Try to look ahead rather than forcing him into something.

  2. Yassin Madwin says:

    Where to get good writers to write about health topics. its seems all freelancers offer gigs about blogging, SEO..

  3. Nancy Badillo says:

    Great list of ways to hire a freelance. Will be sharing the post!

  4. Medha BN says:

    Insightful post. Checking for the employer’s feedback across the web is a good tip but I am wondering if you want the employer to check the contractor’s feedback or the contractor to check employer’s feedback?

    I guess it is like checking ‘feedback on how the contractor performed as an employee’ as against ‘feedback on how the contractor performed as an employer’.

    I read that paragraph twice and I am still confused.

  5. Great article, Paul, this is a great list of information!


Welcome! I'm Bamidele Onibalusi, a young writer and blogger. I believe writers are unique and highly talented individuals that should be given the respect they deserve. This blog offers practical advice to help you become truly in charge of your writing career.

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