How to Hire the Right Freelance Writer for Your Project

How to Hire the Right Freelance Writer for Your Project

As a startup or small business, you’ve doubtless turned to freelancers to provide you with some service. It’s the easiest way to get talent without making a big commitment on hiring them permanently. Platforms like Upwork and Freelancer have also made this very easy. What’s not easy, however, if picking the right freelancer, especially when it comes to finding a competent freelance writer who will deliver. As a veteran 10-year freelance writer who has both been hired and hired other writers, I know the ins and outs when it comes to finding the best writers for your project. Here are several important things you should consider when recruiting.

Determine What You Need

Ask yourself, when the project is done, what do I want to have in hand? How does the content look? How many words/ pages will it be? What will it read like? Put yourself in your readers’ shoes and imagine reading the content, what does it sound like, what does it make you feel? How do the sentences read? Are they long or short? Write all that down. If you are also looking at keyword optimization, also write this down. This is a needs assessment and will guide you on developing requirements for the job you are about to post.

Your Job Description

Using the points you came up with above, write out a job description that’s as detailed as possible. The clearer the job description, the easier it will be to recruit the right writer. I’ve read dozens of job descriptions on Upwork where the client isn’t clear on what they need. In many cases the job description is just two or three sentences. Ironically, these short descriptions tend to attract a higher number of mostly low-quality writers while long and detailed descriptions attract a shorter roster of high-quality writers. While brevity is sometimes important, you don’t want to be brief when looking for a freelance writer. Be as detailed as possible in your job description and don’t worry about not getting “many” applicants. Getting 100+ applicants is tedious and a huge waste of time. A detailed job description will snag you fewer applicants with the added benefit of helping you determine who has read through it when you begin reading application letters. A good writer will always mirror your requirements in their cover letter, a sign they have read and internalized what you require.

Skill vs. Experience

I find this to be a major dilemma website owners face when it comes to hiring writers. Here’s the thing, while getting someone with experience is great, I suggest you go for a blend of experience PLUS skill. You see, someone may have been writing for years and years, but their skill isn’t top notch, while a newbie may have just started but they are a natural when it comes to writing. The best way to determine a writer’s skill is to look at their cover letter. How does it read? Is it well crafted? Does it sound like the kind of writing you would like for your project? Poorly written cover letters are usually a sign of things to come so don’t get carried away by someone’s extensive experience, vet their skills as well.


The interview, whether via phone call or chat, is the clincher. While interviewing, do more listening than talking. While you may be tempted to go on and on about your project, what you want is to get a feel of the writer’s thought processes. How well did they understand your job requirements? Do they understand what the content is about? Have they done any additional research on your business industry? What are their thoughts on how best to position the content? And so on. These leading questions will give you a clear understanding of the kind of writer you are dealing with. I always say how someone thinks is how they write because all writing begins as thoughts in the writer’s mind. So, if you can get a sneak peek into their thinking, you have a good idea of how they will write.


Feedback is crucial. I must repeat this: Feedback is crucial. Think of a soldier who goes to the battlefront and then all communication is cut off. How do they advance? Do they need reinforcements? Is the enemy retreating or advancing? It’s the same for a writer. Once the task begins, it helps to be available to provide feedback on a regular basis. There’s nothing that kills creativity like working while wondering whether you are on the right track. To remove this speculation, plan regular feedback briefings with the writer to keep them on track and the whole project on track. Be open, candid and most importantly, clear about what your feedback is about. Just saying it doesn’t sound right isn’t much of helpful feedback. Saying instead you would like it to sound friendlier/more serious/ less serious/ funnier/ etc. works better.

There’s nothing like a perfect writer out there but there are some great ones. If you find one of the great ones they can be a real asset for your business. When hiring, be sure to follow these steps to avoid finding yourself stuck with one of the bad apples.