With September on the horizon, vacations are coming to an end and a new wave of marketing initiatives may be about to begin. For many organizations, 'tis the season to shop for talent, especially copywriters.

It looks easy enough. Just scroll through Craigslist or tap your talent agency, and you'll attract loads of well-scrubbed writers carrying handsome leather portfolio cases packed with clever, catchy copy.

But it's awfully hard to look beyond the leather to identify the talent who will really work for you. Too often, the new writer "just doesn't get it," cannot cooperate with your other talent or otherwise simply fails to articulate messages that really resonate with your audience.

Given human foibles, there are no fool-proof formulas for finding winners. But you can take measures—right at the start of your relationship—that give you a much greater probability of success. Here are some things you should look for in a writer at your very first meeting:

1. Connects creative work to underlying objectives

Face it: All the samples the writer proudly slides across the table to you are going to look pretty good. After all, your would-be writers cherry-pick their best work. Unless they're truly incompetent (most professionals are not), everything you read is going to be clean, smooth and attractive.

Your job is to dig deeper, to uncover the "why" behind each creative decision evidenced before you. Why was one benefit highlighted over others? Why use a particular catchphrase? What was the reasoning behind the diction, tone, point of view of the piece?

Good writing is never arbitrary, and every writer worth her salt should be able to connect her creative decisions to the underlying objectives of the project or the overall strategy behind the marketing campaign. Consider this your opportunity to expose the writer's thinking.

2. Wears many masks

Writers are like actors—they must be prepared to assume the voices and mannerisms of people who may be completely unlike themselves. As you flip through the samples, look for variety. You should "hear" different voices—manifested through changes in tone, rhythm and vocabulary—appropriate for different audiences. You should be able to guess the target demographic from the copy voice alone. The annual report for investment bankers should sound completely different from the direct mail pitch to porcelain doll collectors.

That's why industry experience may not be a significant criterion for selecting a writer. If a writer has the chameleon-like ability to match his voice to your audience's, chances are he can write effectively for your market. If not, no amount of industry knowledge will compensate for the inability to connect.

3. Asks questions—lots of them

Good copy is built on a foundation of understanding: who your customers are; what your prospects value and fear; how they shop. Also, what your product or service is; what makes it different; what role it plays in the purchasers' lives. Without this underlying knowledge, the resulting copy may be clever, but it won't be effective.

The only way a writer can reach that level of understanding is to dig for it by asking questions. Beware the passive writer who nods at everything you say and assures you she has everything she needs to proceed. Instead, look for the writer who pursues your comments with questions, then follows your answers with further questions. You want a writer willing to do this kind of spade work before writing a single word.

4. Listens well

Your interview should not become a dog-and-pony show for the writer's talent, limited to star-spangled presentations of beautiful brochures and self-adoring revelations of awards won, honors claimed. Sure, writers should be prepared to talk about themselves and their services. But, more importantly, they should be actively listening to you, taking pains to uncover your needs.

Do they ask questions (see preceding point) that logically follow your comments? Do they show genuine interest in what you do and how you work? And when you're speaking, is their body language reassuring? Do you see the kind of eye contact and body postures that indicate attentive listening? If they're not really listening to you now, when they're seeking your business, they probably won't when they're executing it.

5. Plays well with others

Ask anyone if he's a "team player," and you'll get prompt reassurances of the affirmative. No one will admit to being an arrogant prima donna, so you'll have to use indirect methods to gauge the writer's ability to work cooperatively with your team of designers, strategists, product managers and other marketing staff.

Take it as a good sign when a writer, without prompting, shares credit for a given project with other people who participated. Or openly admits that the driving concept came from someone other than himself. Or describes a project as a cooperative venture and articulates the value of the myriad roles that accomplished it. Conversely, regard the self-serving writer, the one who consistently hoards all credit to himself, with suspicion. Chances are, he'll make you and everyone who works with him miserable.

6. Demonstrates self-respect

We all want a bargain, and no one can fault us for desiring more, for less. After all, everything's negotiable.

Be careful what you wish for, however. A good writer may be willing to cut you a discount, perhaps in exchange for a guaranteed volume of work, but only the bottom-feeders will bite on rock-bottom project fees. Good writers respect the value of their work and expect to be compensated accordingly. If you insist on making price the most important criterion for selecting a writer, you may end up with a lot of grief you didn't bargain for.

In sum, it's not enough to review the resume, client list, samples or portfolio. You need to mind your prospective writer's behavior in the course of your first encounter. When you see curiosity, respect, intelligence and a healthy ability to listen carefully to others, you'll find a writer who's likely to work productively with you.

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image of Jonathan Kranz

Jonathan Kranz is the author of Writing Copy for Dummies and a copywriting veteran now in his 21st year of independent practice. A popular and provocative speaker, Jonathan offers in-house marketing writing training sessions to help organizations create more content, more effectively.

LinkedIn: Jonathan Kranz

Twitter: @jonkranz