Questions to Ask Your Next Freelance Writer (Before Hiring Them)

Hiring a freelance writer isn’t like bringing on a new team member. Screening a new employee requires tedious calls to references, background checking, and maybe even several panel or stress interviews (you sadist, you!) before making it official, but picking up a freelancer can be as easy as grabbing a carryout pizza — especially with today’s methods for finding qualified freelancers almost instantaneously online.

Picking up a freelance writer can be as easy as grabbing a carryout pizza. Click To Tweet

But hold up, there, cowboy. Though I agree that an extensive interview process isn’t necessary when you’re hiring a contract professional, you can save yourself some serious time and money by asking prospective ‘lancers these five questions upfront.

1. Do you provide content strategy, or prefer to just write on assignment? This question can be tweaked depending on the nature of your assignment, but the point is this: some writers are really excellent wordsmiths but terrible strategists, while others are proficient at both. If you’re planning on doling out a detailed brief or outline, you probably only need someone who is a great writer to materialize your great idea. But if you’re developing an eLearning course, a whole new blog, or a web content marketing campaign, you’ll need someone who understands the bigger picture — and who isn’t afraid to dig deep to get the necessary source material.

2. Can you show me something similar you’ve done before? This one can be extremely helpful when you’re on a tight deadline or working with a very high-stakes project. For instance, if I’m in need of an article about horse breeding, it’ll be far less of a risk to try the writer who has a byline in Equine Magazine than the one who has never written about horses.

However, this one comes with a caveat: most professional freelance writers (note: professionals, not dabblers) are extremely eager to try new things and please new clients. If the majority of a writer’s work is great, even if it’s not the exact type of writing you’re looking for, consider taking a chance on them. Great writers are those who can understand and communicate difficult concepts in an engaging way. They are often not experts in a subject to begin with; they are merely great at research, communication, and editing.

3. Why might you be a good fit for this project? This open-ended question gives the freelancer a chance to make a case for their own passions and expertise. Maybe they’re new to freelancing, but they have ten years of experience in HR — a perfect background for the HR infographic you’re developing. Or maybe they live in the town you’re writing a travel roundup about.

4. What can I expect in terms of your availability? Some freelancers take on many projects at once, while others may work at a slower or more exclusive pace. I’ve heard of some copywriters charging an extra fee for clients to “lock down” their services exclusively for a period of time. Some may only work weekends, and may never be available for calls during regular business hours.

5. Can you provide a quote, and what this includes? If you’re not sure of the industry standard for a freelancer writer’s pay (or you’re not working within a specific budget), it doesn’t hurt to ask the writer for an estimate. This will also help prevent miscommunication about billable hours. For instance, I always include all research, the first draft, and a “reasonable number of rewrites” in my flat fee projects. I include this for a couple of reasons: first, I’ve never had to do more than one rewrite on an article, so this promise isn’t much of a risk for me. Second, this reassurance helps clients know they’re getting good value for their purchase and I won’t try to bill them extra for any rounds of rewriting.

There are plenty of other questions we could have added to this list, but here’s another important truth about the freelance writer’s daily work: every hour we’re spending on prospecting, interviewing, and answering clients’ questions is an hour we could be spending on billable work. We’re essentially sacrificing our free time here, so it’s best if you keep your questions succinct and limited.

Leave out questions about how many hours it will take to write something (it almost always varies), or traditional interview questions like where we went to college or what our last salaried job was. Never ask a writer to do a “test” assignment — this is why we have portfolios, so you can see what we’ve done before.

In my own experience as a freelancer who has also subcontracted with other writers, I’ve developed the best working relationships when everyone is open about expectations and uncertainties upfront. The best writers will ask their new clients questions, too, but a good working relationship is a two-way street.

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