Hiring a creative copywriter is hard for many of the same reasons that hiring a world-class software developer is hard: Unless you’re one of them, you probably don’t know what to look for.

If you’re like me, and you can’t tell PHP from Wingdings, then the smart thing is hire an expensive CTO-type to help you put together your dev team. He or she can pop the hood on someone else’s project and evaluate the skills (most notably, foresight and problem-solving) of the person who designed and built the code engine.

But what if we turn the tables? Maybe you’re the technologist. You co-founded a startup. You don’t give two craps about dangling modifiers, but in this early stage you must wear a bunch of different hats. The job fell to you to review the intern’s latest blog post.

Grammatically, the post seemed sound. The intern sprinkled in a few jokes, and the one bit about her grandmother eating sticks of butter was pretty funny. But the post lacked something, some element of swagger.

The post ended more with a fart than a bang.

Software typically does a good job at telling us it is broken. The “good” in good writing can elude us. What was missing from the post? You’re not sure what to tell the intern. You don’t want to publish the post. Too many farts on the blog, and people will stop coming back.

Content marketing can be an effective way to build traction until it’s not.

Perhaps I can help. Two degrees in English Literature and twenty years of practice have given me some insights into what makes good writing good. Running several businesses has also taught me about hiring talent and effectively managing freelancers.

By degrees I’ve turned into weirdo with a hodgepodge of competencies. I’m a CEO-type, a Chief English Officer (which I hope wins the prize for Most Self-Important Title of All Time).

creative copywriter

My friend Fynn encouraged me to share my thoughts about hiring good writers and saving non-CEOs time, money, and frustration.

Here goes…

The Single Most Important Trait of a Creative Copywriter

So how does one avoid hiring the wordsmiths who care too much about flowery diction and too little about deadlines? Also, the hacks who care too much about getting the job done (and getting paid) and too little about inviting readers out of their own lives and into an adventure?

Look for caring. The most basic attribute of a good writer is caring.

I don’t just mean caring about craft. Imagine if one of my clients asked me to write copy for a print ad in a trade magazine, and I sent her ten lines from a lyric poem. She wouldn’t be impressed by allusions to T.S. Eliot. She’d be pissed that I wasted her time.

In business writing has a chief aim other than personal expression or storytelling. It can’t just be pretty; it’s got to get a job done. A Husky might win a ribbon at the Westminster Kennel Club Dog Show. But harness the same dog to your Iditarod sled and you may end up bloody.

Caring, in the business context, means balancing the creative with the strategic; the strengths of the medium with the needs of the business.

When caring about writing hits the prism of a specific business, it separates into a new spectrum of habits and tendencies.

The following list is by no means exhaustive. But who has time for exhaustive anyway?

1. Character

It doesn’t matter if a writer can flaunt words like “tintinnabulation” if he is a narcissist; if after being let go, he badmouths the company and conveniently forgets the part he played in his dismissal: three missed deadlines and lying to his editor’s face.

That your Columbia grad’s stories made readers weep will be of no comfort after you catch her with her hand in the plagiarism jar.

These four character traits can mean the difference between award-winning prose and public apologies: personal responsibility, work ethic, honesty, and concern for others.

Hire for character first. Character is the gold ring. Skills are the filigree.

2. Attention to Detail

The last 2% of a project makes it. A boring or overly descriptive title deflects readers. A killer title draws readers in.

Grammatical errors can kick people out of an otherwise well-executed essay. A clean draft enables them to lose themselves.

Web-friendly formatting — shorter paragraphs, meaningful fragments, sub-headers — accommodates attention-deficient readers. Big blocks of text look intimidating on a screen.

That being said, comprehensive knowledge of the Chicago Manual of Style is less valuable than a young writer with crazy punctuation habits and an intuitive grasp of writing as persuasion. I’d rather hire a writer who scores an A+ on substance and a C- on polish, and simply pay a freelancer on Upwork $9 an hour to proofread and mop up the draft.

3. Voice

It’s easy to confuse voice with style. Cormac McCarthy has distinctive style. So did Hemingway. You can read passages they have written, and know the author as clearly as if they had signed the page.

But voice is typically more appropriate for projects where you’re wanting the brand, not the writer, to come through.

Voice comes through in prose in the form of sense of humor, wordplay, metaphor, structure, and even restraint. For example, too much wordplay on a web page tries people’s patience. Readers are thinking, “Enough of the antics. Get to the point.”

A writer with a good grasp of voice, as opposed to style, gets to the point, and keeps the reader entertained in the process.

4. Style

Here’s where the things get dicey. You’ve got to pay attention to style. Your brand’s voice depends on it.

At the same time, you don’t want your web content to sound like two astrophysicists speaking Klingon. Industry jargon makes people feel stupid. And business-y buzzwords — synergy, value-add, bleeding-edge — are BOR-ing. Look for something in between.

Look for prose style that a high school junior could manage. Simple prose style gives people better access to the ideas carried by the words. Access is what enables people to understand — and to convince themselves.

Good style is like window cleaning: it enables you to see more clearly inside, into the writer’s ideas.

5. Word Choice & Figurative Language

Good writing shows rather than tells.

Action verbs typically make stronger sentences than linking and passive-voiced verbs. For example, “The hike gets really strenuous” doesn’t paint this picture: “The trail winds through cabin-sized boulders, so be prepared to scramble and climb and sweat.”

Would your mom rather hear about your latest hike to that gorgeous waterfall or see the photos of the brilliant rainbow arcing from the mist? In the absence of photos, a skilled writer drives home the point not with dry description but with simile, metaphor, allusion, anecdote.

Good writing produces play, a delicious sense of discovery. Ask a writer whether he sees writing as an exchange of information or as a short odyssey, and you’ll know whether or not you want him.

6. Professionalism

I’ll take a B+ writer who delivers on time, on budget, any day over an A+ writer who misses deadlines.

Most people don’t notice the difference in quality between the two writers — because they lack that expertise — but they do notice when you don’t keep your word. If a writer does need an extension, expect her to make that request twenty-four hours before the deadline, not two hours after it.

Good writing is as much about time management and responsiveness as it is about style and structure. Certain stylistic weaknesses are easier to fix than a gap in professionalism, which may have its root in a deeper character issue — for example, “For me to go hang with friends in Asheville for the weekend is more important than for me to meet the Monday morning deadline I gave my client.”

7. Optimism

I meet writers many writers who are jaded. It’s not difficult to figure out why: making a living as a writer is difficult.

Many writers can’t support themselves with their creative projects. They sometimes project their artistic frustrations onto people who simply want to pay a fair price for web content or ad copy. They’re overly protective. They struggle to achieve emotional distance from critiques of their client work. They begin to see their clients as the enemy.

Don’t hire grumps, no matter how talented. They’re toxic to culture.

Jaded writers are simply harder to work with, which is why I prefer working with optimists. They enjoy the special challenge of picking words for a client’s email newsletter or blog post, and they don’t believe they’re bastardizing their writing gift by getting paid to write for someone else.

8. Enthusiasm

Utilitarian writing may fill the page, but it won’t keep people coming back. It won’t stick in people’s minds.

Look for people who already enjoy the subject. You can usually tell whether or not people care about your core business by checking out their Instagram, Facebook, and Twitter accounts.

If yours is a particularly dry industry — I’m looking at you Concrete Polishing and Modular Offices — then your writer of choice should at the very least tighten up your stuff with action verbs, cut out the jargon, and liven things up with a bad pun or two.

Wisdom for the ages: care enough to pun.

9. Curiosity/Inquisitiveness

You want someone who asks lots of questions.

Chances are, she doesn’t fully understand the project’s goals, and unless she has already worked with your company and immersed herself in your brand, she hasn’t nailed the voice. That takes time.

Old hands know that many of the most pithy phrases and statements bubble up during casual conversation with the people who know the business best. The job of a creative copywriter is to capture them and put them to work for the client.

10. Resourcefulness

Have you heard of lmgtfy.com? It stands for “Let me Google that for you.” On days when I’m feeling particularly wolfish, I’ll send the link to the dweeb who asks me a question that he can easily answer for himself.

(For the record, I have also be on the receiving end of said email.)

Subtle? No. Effective? Yes.

Technology can encourage a stealthy form of laziness: firing off an email (and creating a task for someone else) rather than taking initiative and using one’s own time and one’s own brain to hunt down an answer.

I really appreciate writers who hunt. In their project notes, they say things like, “I’m not sure which contact number you wanted to include. I found the one included on the client’s website.”

Thank you. I’ve got a single crocodile tear on my cheek, and a little more hope for humanity in my heart.

Conclusion

You’ll end up paying more for a creative copywriter who really knows his or her stuff, but you’ll end up saving time, money, and frustration too.

Do you want to build a profitable business you love?

Duh. Pony up that email address, and you can learn from my failures. You can laugh at my mistakes. You can envy my success at croquet, slow running, and modest bank accounts. Let’s make good money and leave the world better than we found it.

No-nonsense business advice for content writers and freelancers. Served warm with a side of dad jokes.

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