Interviewing a Freelance Copywriter? The 12 Winning Questions that Savvy Marketers Ask

Ever hired a freelance writer who, after sending in the first draft, made you get Hulk Smash while questioning your sanity when you were hiring them?

Or is it your first time hiring, and you've probably heard of the terrible stories about freelance writers who ball up everything, and you don't want to be the next victim?

You might think that landing the perfect copywriter is a product of luck.

Well, to some degree, it is. Say 5% luck because you found this blog.

And the other 95% is knowing how to hire a freelance writer and being equipped with the right questions to ask yourself and your writer before onboarding them to your team.

Ready to get the questions that separate the wheat from the chaff?

Let's get in.

Interviewing the Right Copywriter is a Lot Like a First Date

Deep love needs deep trust. So start strong.

Remember the last first date you went to?

Oh, the good days. You talked, you flirted, you saw the best in one another and decided to grow together and build each other.

Conclusion: They were the one for you.

Or the date went from bad to worse, and you were eagerly waiting for that final hurdle before the awkward goodbye.

Conclusion: They were not the one for you.

It's that simple even when hiring a freelance writer.

However, this time around, instead of looking at their online profile, you look at their portfolio and previous samples. Instead of meeting for dinner at a restaurant, you meet online via Skype or Zoom. Instead of asking personal questions, you ask these expert questions I'm about to show you.

And I'll divide them into two categories of questions:

The Basic Questions- These questions are general and open-ended in nature, and any freelance writer worth their salt will comfortably answer them. They are more like "What do you do for a living" in the dating scene.

The Deal Breakers- These questions will help you differentiate the exceptionally valuable freelancers who understand their trade in and out from the not-so-great freelancers. These would be more like "If you had a crystal ball that could either change your past or tell your future, which one would you choose and why?" during your first date.

Basic Questions to Ask Your Freelance Copywriter

You see, there's no substitute to asking the right questions if you want to get the right fit. And these here, my friend, are the seeds to hiring the best freelancer.

1. What Type of Content Do You Create?

In my previous company, I had a colleague who could write exceptional copies. She would write the words and sentences that persuaded people to take the action she wanted. Her copies made audiences feel, think, and nod in agreement- and ideally take a step closer to the buy button. Anything salesy, trust her to hands down vacuum those leads.

However, when it came to writing informative and educative content like long-form articles and whitepapers, she couldn't let go of the "Whoops, I accidentally bumped into my ex haircut" type of writing.

Often, you'll find writers who can write great copies but cannot write long-form copies. Or you'll find freelancers who can write exceptionally fantastic content but cannot craft a curiosity-based email.

Asking a freelance writer what they're comfortable writing will help you know whether their skills align with what you're looking for. On the same, it's also worth noting that most freelancers are good at writing more than one piece of content, but not all.

2. What Industries Do You Specialize In?

Due to the nature of freelance work, most freelancers can write well in more than one niche. However, if they claim they can produce excellent content in both Tech, law, and Medicine, be wary-- they're spreading themselves too thin.

They might be "okay" writing for an industry they've never blogged about, but making such bold claims that they're exceptional in any specific industry is wrong in itself.

However, don't cancel them yet if they don't have some high-level knowledge in your industry. Just like your partner, you might be two different people as people but share the same values.

You might also be in two different industries with your freelance copywriter, but the writer can share in your brand's vision and articulate it exceptionally well in their content. All you need to know is that they create the kind of content you want. And that's what matters in the long run, right?

3. Describe the Tone You're Comfortable With

Every writer has a voice that is unique to them.

Some will write in a light-hearted, witty, and funny tone. Others will write in an objective, rigid and convoluted tone.

For instance, a technical software writer might not be the best for your blog-- a journalistic writer might. But if you need some high-level content that targets engineers, then the technical software writer must be your guy.

It's also great to note that most writers can combine their unique writing styles to fit your brand guidelines. Just be sure to ask this to get to understand them better.

4. What's Your Price and What Does it Include?

You can take a walk from Florida to Alaska, go for a golf play and crack jokes with your freelancer, but trust me, you're far from being friends if you haven't agreed on the budget.

Some freelancers bill by the hour, some per project and others per word. So be sure to ask this and compare it with your budget to know whether they're an excellent fit for you.

Also, beware. Some copywriters might be cunning in their dealings. Initially, they charge extremely low prices to bait you and then include some hidden costs (like edits, revisions, and optimization) and only bring them up after you award them the project.

So flesh out all the details and lay everything bare before you engage them.

5. Who Owns the Work?

Does the writer request a byline in the work, or do you own the blog? Are they comfortable ghostwriting for you, or will they request accreditation?

Some copywriters accept ghostwriting but will charge more for it because they don't get credit for it to build their portfolio further. After knowing who'll own the copyright, it's best to put it into writing to formalize that.

The Deal Breakers

These are what really separates the Johnny-come-lately and the bonafide writers who understand their trade and know why they write.

I've been on the interviewee end, and if any marketer asks any of these questions, I understand they know what they want.

You see, there are times you'll have about three talented prospects who are almost equally skilled. At this point, you should not be looking just for the signs to rule somebody in but signs to rule them out.

Let's continue.

6. Why Did You Become a Writer?

Asking why seems easy. After all, it's a little word.

Most marketers don't ask this because it sounds a little confrontational and hints at accusations. However, the way and tone you ask this could open up a world of possibilities in knowing the person you're about to hire and whether they're enthusiastic about writing.

It's not that your ideal candidate should have decades of writing experience. What you're assessing when you ask this is whether the candidate has a love for words, is a great communicator, and whether they're in love with writing.

A passionate writer will gleam with enthusiasm upon asking these questions, but anyone else there for the money will hit you with answers like:

  • Uhmm… I'm not sure, to make money, I guess.

  • My recent job sucked, and I loved the idea of freedom.

  • I didn't get a job after college, so this is my side hustle.

7. Tell Me More About the Book You Read

"If you don't read, you don't have the tools to write."

Great writers are avid readers.

More often, knowledgeable people who read are interested in having greater and in-depth knowledge about a wide range of things. I always find that there's always a positive correlation between good writing skills and avid reading.

Your writer doesn't have to tell you a book that's purely related to marketing (but if they tell you Epic Content Marketing by Joe Pulizzi, hire them immediately.)

If they start by telling you things like these, run!

  • I don't have the time to read; I focus on producing content for my clients.

  • I'm not good with books, so I focus on blogs only.

8. How Would You Define the Difference Between Content and a Copy

There's a significant difference between content writing and copywriting.

Copywriting aims to persuade and sell your brand to your different personas, while content writing is subtly telling an audience about a brand while delivering great, informative content.

However, some freelance writers don't even know the difference between the two.

If they begin with uhmm, mhmm, and some other responses below… please move to the next and, of course, look back at your own risk.

  • Ah, a tricky question that on, they're one and the same.

  • Copy, it's just about copy-pasting, and you don't want that for your blog.

9. Your Research Methodology

I have written for Tech companies on software I didn't have prior knowledge about.

What I do is research and compile a fact bank first, send it to the technical team for review. After the team has reviewed and validated the information to be factually correct, I proceed to flesh out the content while adding the nitty-gritty of the content. That's my research methodology.

Each content writer should not follow my way of doing things, but they should articulate how they go about the whole process.

Some of the answers to be on the lookout include:

  • I expect my client to conduct research for me and give me everything.

  • I dive straight into the content with no time to waste.

10. How Do You Optimize Your Content

First, understand that you're looking for a freelance writer, not a digital marketing strategist. After this, you can subtly test their knowledge in SEO.

A great freelance copywriter should know a lot about where to put the correct keywords, fix them in strategic positions, structure them, and format them. However, keyword research should purely rest on you as a marketer, not a freelance writer.

11. What's Your Biggest Grammar Pet Peeve

You know those times you want just to kick back and scroll through Facebook and come across a post where your friend has written your and you feel like your head will explode?

Frustrating, isn't it?

Everyone has a grammar pet peeve that drives them mad… and your writer isn't an exception.

Personally, I often add ellipses almost everywhere, especially when I'm writing content for my blog. When writing for clients, I can't resist the urge to add another… and another… and another.

So ask your freelance copywriter what theirs is, and if they start showing you how perfect they are, know they're lying.

12. Oxford Comma or Not?

There are two types of people: those who like the oxford comma and pedants. Just have a look at the self-explanatory photo below.

Well, that's just my opinion. It's not like I'm asking you to add milk to your tea; all I'm asking is you use the oxford comma.

Everyone has and is entitled to their opinion on this. So asking whether your freelance writer uses it or not shouldn't be a reason to rule them out, but if they have no idea of what this is, then rule them out.

They can respond with answers like:

  • Ah, Oxford comma, it's just like any other comma.

  • Those guys at Oxford seem to invent anything nowadays.

The Upshot

You've seen those photographs where the background is blurred, where the only part in focus is the person who is pictured, and everything else is non-existent.

That's your freelancer on your first date. Every other detail of them is blurred, and every part of you should focus on every aspect of whether he's the right fit or not. Not the words they say, not the budget they propose, not anything—just you, them, and these interview questions to stand between hired or the next candidate.

If you need a freelance copywriter for hire, feel free to reach out to me and I'll be more than willing to assist!



Photo by Camylla Battani on Unsplash and Eric Edelman

Thanks Camylla and Eric!