Clear red dice showing four and five on black surface

You do your best, but hiring the right person for the job is still a crap shoot.

If you’ve hired anyone, then you know finding good talent is a crap shoot. And that can be especially true if you’re looking to hire a freelance copywriter.

Every coach, manager, talent acquisition specialist, recruiter, and consultant have their method for discerning who’s the ideal candidate. I had my method too, and with a few exceptions, the people I hired proved to be excellent associates.

But doesn’t that prove my point?

If hiring was anything but a crap shoot, there would be no exceptions.

How to hire an employee would be a science. There would be a repeatable process and predictable results.

If hiring was predictable, there’d be one sure-fire way to sort through the candidates and find the person with the most relevant experience and the best skills.

But that’s not how it works.

Let’s imagine you’ve found a freelance copywriter for a project you’re leading. You want the best writer your budget can accommodate (with writers you get what you pay for.)

But they all look reasonably good:

  • Their samples are engaging; show proper grammar, spelling, and structure; and have a consistent voice.
  • They all have at least some experience with your industry.
  • They’ve previously written the copy you need… direct mail, email, case studies, etc.
  • You believe you could work well with any of them.
  • All the recommendations are good, but you expected that. (Who’s going to give you a bad referral?)

How do you decide who gets the contract?

Asking the following questions of your freelance candidates can stack the odds in your favor of hiring not just a good copywriter but a great copywriter.

Why Do You Consider Yourself a Professional Copywriter?

This open-ended question is meant to weed out the wannabes. Because someone can use a keyboard doesn’t mean they can write like a professional copywriter. That would be like saying someone who knows how to boil water can cook like a chef.

If you understand that writing is a profession, then you’ll understand why you want a professional copywriter.

Torso of a woman in a suite with a business card, facing outward,  in her right hand

A great freelance copywriter will keep their skills sharp and know the trends influencing their niche.

Professionals are people who:

  • study the newest industry trends;
  • read respected sources for information;
  • continuously work to improve their skills;
  • likely belong to a professional association;
  • illustrate their expertise through their work;
  • have the education or training needed to perform the job.

A professional freelance copywriter should be able to give an answer that incorporates several of these qualifications.

If your candidate is a good writer but struggles with promoting herself (many copywriters are shy and introverted), prompt them by posing questions that specifically address these qualifications. You could ask, “What was the last action you took to improve your writing or learn a new skill?” Or, “Who are the A-list copywriters you admire?”

If your candidate can’t answer these questions to your satisfaction, then thank them for their time and move on.

What is Your Process When Writing for a Client?

Writing is a creative process, but it’s still a process. Copywriters with a process are like drivers with a state-of-the-art GPS. The destination is clear. They’ve mapped the route. And there may be sites along the way to add interest to the journey without rerouting the entire trip.

Writers without a process will wander. They’ll visit the roadside attractions, stop at every yard sale, detour to find ice cream, and forget where they’re headed—assuming they knew where they were going when they started.

Desert scene with a sign post and three signs reading lost, found, and searching

Great freelance copywriters keep projects on track with a well-defined process.

These writers won’t be able to produce consistently good writing, will waste valuable time, and will miss the mark… leaving you in the lurch.

A Great Freelance Copywriter Tells You What to Expect

Not every copywriter will have the same process, but it should follow these general lines:

  • Determine the project’s goal and audience.
  • Offer a proposal with all the critical pieces (scope, timing, deliverable, fees, etc.)
  • Provide at least one draft with an opportunity for the client to give feedback.
  • Include the conditions for delivery and payment.

A Great Freelance Copywriter Will Ask Questions

Imagine your task is to plan a company event. You’re told the CFO will attend, where the event will be, and the date and time… that’s it. Would you know what to do? (“Winging it” is not an option).

Without asking questions, you’d have no idea what to do. To provide what’s expected you’d need to know the occasion, type of event, how many will attend, the budget, and more.

Without the answers, you will fail. Guaranteed.

Great freelance copywriters will ask lots of questions. At a minimum, a copywriter will:

  • want to make sure there is a good fit between what the client needs, what they can deliver, and when.
  • ask questions to drill down to specific goals and desired outcomes.
  • request prior marketing materials, buyer profiles, and if possible, a sample of the product or an experience of your service.

Why would a copywriter want a sample or experience? A great copywriter will want to experience features and benefits first-hand. Trust me—it will make for stronger copy.

A Great Freelance Copywriter Will Want to Communicate

Another good sign of great freelance copywriters is their insistence on clear and frequent communication.

Torso of a man sitting in meeting gesturing with his hands.

Critical to the success of any writing project is clear and frequent communication.

Copywriters are at their best when they know what to expect. Shifts in strategy, taking a new direction, rethinking the audience… these will knock a copywriter off the track if you don’t communicate changes with enough time to adjust.

Likewise, freelance copywriters will want to keep their clients in the loop. Touching base regarding progress toward completion or obstacles met along the way helps to ensure everyone is on the same page and that there are no surprises.

How Do You Think You Can Help Us?

I believe this question is more incisive than its cousin, “Why do you want to work for us?” It’s too easy for someone to BS their way through that one. But responding to how you can help… that takes research and specific know-how.

Every job applicant should find out what they can about a potential employer—that’s a no brainer.

However, a freelance copywriter needs to know more than what an online company profile can provide. Great freelance copywriters, depending on their expertise, could respond to this question in one or more ways:

  • Provide a specific example of writing you’ve produced and suggest ways they can improve it.
  • Draw attention to something that is lacking in a piece of writing and how to remedy it.
  • Refer to a topic you’ve addressed and how they’d put a different spin on it.
  • Recall their experience using your website and recommend improvements.
  • Review the strengths of other analogous companies’ copy, suggesting you might consider something similar.
  • Commend what they’ve read or seen, explain why it’s good, and suggest they can bring you more of the same.

Regardless, great copywriters will discuss proven formulas and fundamental principles, express their understanding of how different formats have different strengths and drawbacks, and discuss how they can use their expertise to your benefit.

There are many good copywriters available for hire. But why settle for good when you can get great?

Ask these questions the next time you want to hire a freelance copywriter and I promise, not only will you get impressive copy, you’ll enjoy working with them too.


Did I miss something? What questions do you routinely ask your freelancers? Share them in a comment.