6 Questions to Consider When Hiring a Content Writer (+6 Experts on Hiring In-House)

13 minute read

Last fall, my wife and I bought a new house: a fixer-upper.

We had 30 days between our closing and our move-in date to gut and replace a kitchen, tear out and repair three walls, refinish and patch the entire main floor hardwoods, install a new electrical panel, replumb and rewire the whole house, and paint. Needless to say, it was a lot.

But, the trickiest part wasn’t managing the timeline or the budget, it was knowing who to hire. The problem isn’t finding someone to do the work, it’s finding someone we could trust. So many questions came up. Where do we start? How do we build trust quickly? What questions should we ask? Should we get references? Should we negotiate prices?

This is the same problem CMOs, heads of marketing, and marketing managers face all the time. They have projects to complete, tight timelines, and strict budgets. And many have absolutely no idea of where to find a good writer to help them.

As a guy who gets hired to write for a living, here’s what I think you need to know to find and hire high-quality copywriters and content writers.

Questions to Ask Your Writers

Adding a writer to your team can range from looking at full-time writers and strategists to contracted writers—with all the options, where do you start?

Use these questions to guide your search for freelance writers (and keep scrolling if you’re only interested in in-house writers):

1. Do You Need a Copywriter or a Content Writer?

I’m not trying to be coy here. You need to understand the difference. In my home renovations example, I didn’t want to hire a sewer company to handle my replumb. Yes, they’re similar, but they do very different things. Let’s lay it out:

  • Copywriter: writes persuasive copy that moves people to an action (called a conversion). It’s sales-focused and it’s fairly simple to evaluate results. Deliverables usually include sales pages, web copy, landing pages, emails.
  • Content writer: writes content that entertains, informs, or educates an audience in an effort to earn trust and credibility. Harder to measure results. Deliverables usually include ebooks, white papers, infographics, video scripts, etc.

Understanding the role of each will help you understand where to start your search. Some people do both. Some stay strictly in one lane. That doesn’t make one approach right or wrong as long as they can articulate the difference to you.

Tip: Be upfront about what you’re looking for. Ask them which camp they fall into—copywriter or content writer. If they don’t know, run away.

2. Define the Relationship: How Do You See the Writer Working with Your Existing Team?

Nothing derails a project faster than unclear roles. If you’re hiring a contract or freelance copywriter or content writer, treat them as a part of your team, even if they’re not full-time.

Decide ahead of time who the writer will answer to. How often would you like them to meet? How will they communicate? Who needs to be CC’d on emails or included on meetings?

Some of this will evolve as the relationship matures, but if you come in with zero sense of how the writer fits with the existing team, you’ll likely have communication breakdowns.

Tip: Introduce your writer to your designer, your head of marketing, and your developer. Invite them to all meetings that are relevant to their work (design and strategy, especially).

3. Should You Ask to See Samples or a Portfolio?

You should absolutely, 100% ask for writing samples. But with one caveat…They don’t have to be relevant to your business.

Instead of looking for an exact replica of what you’d publish, look for the following:

  • Can they organize ideas in a logical way?
  • Do they have a clear tone and style?
  • Do they understand their audience?
  • Is it easy to read?
  • Are sentences well-constructed?
  • Is the information clear and simply told?
  • Are all of these things consistent from the beginning to the end of a piece?
Tip: Try to get a general sense for whether the writer can think critically and execute an idea from start to finish. This trait will be more important than whether they know all the ins and outs of your industry.

4. Do You Need to Do a Test Project?

The answer to this should probably be “yes,” but the answer I’ll give you is, “it depends.”

It depends on why you’re asking for it in the first place.

More often than not, “test projects” tend to be a waste of time. They’re not connected to any larger strategy, they’re often made up for the sake of a test, and they don’t really showcase anything you can’t see from a well-constructed portfolio.

Most test projects, in my experience, are about trust. You don’t trust me yet, so you want to do something small together. If you can establish trust another way, don’t waste time on resources that lack a broader strategy.

Tip: Instead of a test project, step back to ask more questions. Request more samples. Ask the writer to explain their process in more detail. Ask for references if you have to. But don’t waste time and money doing something to test things out.

5. How Do They Charge?

This is an important question that every writer struggles with at some point or another. But the way they answer is critical for two reasons:

  1. It will demonstrate confidence in how they talk about it.
  2. They should have a clear reason for it.

The way a writer talks about their rates is really less important than the two reasons I laid out above. Everyone has their own style, preference, and business model. We all find ways to do what works best for us and what we’re trying to build.

I kept an hourly rate for the first year I was in business. I hated it. Now, I bill flat fees and I’m open and transparent about that with potential clients. I explain how flat rates help them stay on budget and helps all of us focus on the outcomes of the work.

My rates are not based on “market rates” or comparisons. They’re based on margins and running a successful business—as it should be. Too many people think freelance means “free.” Be prepared to compensate writers fairly based on the need they’re filling for you, not some arbitrary rates you saw on a website filled with writers from overseas.

And don’t shy away from retainers. Contractors love the stability of ongoing work and you’ll love having someone to work with consistently—assuming you have the volume to keep them busy, of course.

Tip: Don’t ask a freelance copywriter or content writer to negotiate their rates. It’s unfair and it puts them in an uncomfortable position (not to mention it creates unnecessary tension). If their rate is out of your budget, you can come up with more money, you can walk, or you can ask for less work.

6. How Comfortable Are You Working with This Person?

When I hired contractors to work on our house, I met every single one of them in person before I hired them. Most of them were great. A couple of them were full of crap.

The only way for me to find that out was to ask a lot of questions about how they work, what they like to work on, and how they’d approach my project.

You should do the same with the writers you’re interviewing. Spend 25-30 minutes on the phone just asking some general questions. Get a sense of whether they’re easy to talk to or not. Simply try to have a good rapport. Don’t get bogged down in project details yet. Just take some time to figure out their style, how easy they are to work with, and what their general demeanor is like.

Tip: Hiring a copywriter or content writer is about having someone on tap when you need them. Need them to stick around and help you grow.

Advice from Marketing Leaders on In-House Hiring

“But what about full-time, in-house writers, Chris?!”

I hear you. I’ve never worked as an in-house writer, so I turned to a few people who have some expertise in this area (actually, they’re some of the top marketers in the game). Here’s what they had to say about hiring full-time writers:

“Full-time writers must bring other skills to the table. They have to be a greater writer AND a great promoter, account manager, SEO, copywriter, or people manager. All full-time writers are asked to do things beyond writing and it’s important that companies screen for this during hiring.”

—Jimmy Daly, Content Marketing Director, Animalz

Jimmy’s advice might seem familiar to you if you’ve read this blog about why marketing writers need to do more than just write. Keep in mind that content teams are increasingly responsible for not just simple writing and editing but also the strategy and operations behind content.

They cite the following chart as support:

Jimmy and I—along with the marketing leaders who responded above—all agree that writers need to be multi-talented. But what about some of the squishier “soft skills” a writer should have? What’s something that’s harder to look for when interviewing potential in-house writers? Harendra Kapur, Head of Writing at Velocity Partners, has an idea.

“I think courage is super underrated. You want someone with the courage to break conventions and push you to a better story. Too often we think of copywriting as saying what someone else told us to say, only better. It’s incumbent on us to be an advocate for the reader. If we want to craft effective messages we have to be skeptical of the same things our prospects will be.”

We all know that hiring is more of a gut feeling than any rational decision, but how do we screen for some of these things? Hiring is imprecise, at best, but we can’t just go 100% on gut feeling. So, what should we ask these writers when they’re sitting in front of us to help determine if they’re up for the job?

Jay Acunzo, the Founder of Unthinkable Media and storyteller extraordinaire, offers this process:

“Here’s my all-time favorite question to ask during an interview: ‘If I could give you two years’ worth of money, but to get that money, you’d have to write a personal blog—it can be about anything you want, so long as it’s consistent—what do you write about and why?’ ”

“What I really want to test for with this question is two things:

“1. Do you have this intrinsic desire and motivation to WRITE?

“How I’d look for this: whether or not you lit up when I asked this question.

“2. Do you pursue personal passions come hell or high water on your own time?

“Side projects are like creative workouts. They’re invaluable. I want to see that you have a willingness to tinker, test, and take that drive to create and turn it into actual action.

“How I’d look for this: You have a topic or topics that immediately come to mind, and you might even point to an existing or past project you’d continue or revive.

“What I’m NOT looking for is pandering to the job. If I was hiring a writer for an in-house team for a company that sells marketing software, I don’t want to hear, “Well, I enjoy SEO and marketing technology, so I’d write about that.”

Final Thoughts on Hiring Writers

Let’s take stock for a minute…

So far, our experts have told us that in-house writers need to be:

  • Great, courageous writers who understand people and their motivations
  • Understand the technical side of content creation
  • Willing to call B.S. on clients who don’t keep prospects front and center

Oh, and although they know the technicalities of the job, they should also demonstrate a love of writing through passion projects. Easy, peasy. Anything else?

Well, sort of. Ann Handley, Head of Content at MarketingProfs and author of the WSJ bestseller, Everybody Writes, wants you to do your research too. She recommends probing for intent:

“By asking, ‘How did you prepare for the interview here today?’ you can tell how they’re thinking their skills can serve your brand. Did they subscribe to your company newsletter? Your competitor’s? Did they read your site FAQs? Social media? Exec. bios? Did they start to get a feel for your voice/point of view? Are they already thinking of how they could help & plug in?”

Lastly, entrepreneur, marketing consultant, and author, Ross Simmonds, wants a writer who knows how to stand on the shoulders of the copywriting giants who came before them.

“I like to see an interest in history. Whether it’s studying the history of an industry or old books on copywriting—folks with an appreciation for the past tend to use fundamentals (rather than trends) to create stories and messages that work.”

Let me wrap this up by saying that people love it when I talk about my background as a high school English teacher. They love that I have a poem I wrote in 5th grade on my website. They compliment me on my style and my humor. None of these things has anything to do with test projects or budgets, but they have earned me plenty of contracts. Taken whole—with the work demonstrated in my portfolio—these things show my love of writing, the kind of person I am, and my technical skills.

When I hired contractors to work on my house I wanted to know about their experiences, where they were from, how they got started, and what they enjoyed working on. I wanted to hear passion in their voices, even it was something I wasn’t passionate about myself. One electrician loved—loved!—installing new electrical panels. In fact, his entire website was just pictures of electrical panels he’d installed in our neighborhood. We needed a new panel, too, so guess who we hired? Not because he was the most technical or the cheapest. I barely asked about those things. I assumed the former and didn’t care too much about the latter.

Your instinct to grill writers about grammar or topic experience is way less important than you think. Instead, look for someone who is a clear thinker, a problem solver, is running a real business, and has a love for words. Best if they can speak articulately about all of those things as well.

Key Hiring Takeaway

Turns out, as I was finishing this post, John Bonini—Director of Marketing at Databox—was tweeting about this very topic:

John concludes his initial thought with a follow-up tweet:

“Want higher quality content? Hire writers that care about the craft, not the result. The latter will follow.”

I couldn’t agree more, John.


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