5 Questions To Ask Before You Hire a Freelance Writer

A freelance writer can help you produce great content—without adding to your head count. But working with the wrong writer can spell disaster. To make sure you get the right fit, ask potential writers these five questions.

Swamped with writing projects? Facing a hiring freeze? Working with a contract writer can be a good choice. A contract writer can help you push through busy periods, getting multiple jobs done under tight deadlines. They can provide expertise in niche subjects, helping you take on projects your full-time staff can’t handle. They can bring a fresh twist to your sales message. And they can help you control overhead, taking on projects when you need them and then fading into the background when you don’t.

But hiring a writer—just like hiring any contractor, whether it’s a plumber or handyman—can be risky. If you hire the right person, you get great results. But if you hire the wrong person? You’re in for frustration, delay, and wasted cash. To stop that from happening, ask potential writers these five questions before you hire them. It won’t guarantee you get a perfect fit. But it’ll sure improve your odds.

Question 1: Do they have industry expertise?

A writer doesn’t have to know your industry to be the right choice. In fact, a good writer should be able to apply research, interviewing skills, and brainpower to learn any topic quickly. But prior industry experience does help. An experienced writer will have a shorter ramp-up on new projects. They won’t have to pester you with as many questions. They’ll understand what “ecocharrette” means in the construction industry—or what “BYOD” means in the world of cybersecurity. They’ll likely bring to the table some understanding of your market environment. Often, this kind of experience brings with it an intangible benefit—an ability to set your staff at ease and quickly convince higher-ups that you’ve made a good choice.

Question 2: Have they written this type of piece before?

First thing to know: Just because someone writes features, doesn’t mean they can write white papers. Just because they write white papers, doesn’t mean they can write ads. Just because they write ads, doesn’t mean they can write blogs. And so on. Each of these formats has a unique structure. And each plays a unique role in the sales process. Some build awareness; some provide detailed information to facilitate a buying decision. Others are meant to prompt an immediate sale. If a writer doesn’t understand the intent of your piece—and doesn’t understand how to structure it accordingly—all the industry knowledge in the world won’t make the piece succeed. Of course, a talented writer can learn to write in new formats. Just make sure you know whether your writer will be getting up to speed on your project—or whether they’ll know what they’re doing from the get-go.

Question 3: What’s their availability?

The upside of working with a great writer? You’re working with a great writer. The downside? If they’re that great, they probably have lots of other clients. Before you invest time coaching a freelance writer on your brand identity, services, and communications process, grill them about availability. Make sure they have enough time and flexibility in their schedule to make the investment worthwhile. Of course, a freelance writer can’t guarantee that they’ll be there every time you need them. They are a freelancer, after all. If you decide that you do need a guaranteed level of availability—10 hours a week, for example—then explore a retainer agreement. A retainer can ensure availability without adding to your full-time burden.

Question 4: How much do they charge?

No two writing projects are exactly the same. But that doesn’t mean that getting an estimate should be like pulling teeth. If you share the basic details of your project, a writer should be able to give you an estimate promptly. These details might include:

  • Type of project
  • General versus technical nature of subject matter
  • Length of project (number of words or pages)
  • Time frame
  • Number of interviews
  • Amount of independent research required by the writer
  • Number of review cycles expected
  • Whether the writer is expected to personally be a subject matter expert

If you’ve negotiated an hourly rate with the writer, ask how many hours of work will be required. Or, simply ask them for an estimated flat project fee.

If an estimate comes in higher than expected? Only you can decide whether you can afford it—and if the estimate is truly reasonable. Maybe you’re being taken for a ride. Or maybe, if you’re hiring an experienced writer who can quickly produce what you need and who is easy to work with, the estimate might be a bargain in disguise.

If an estimate comes in low? You could be getting a great deal. If so, go for it! On the other hand, an exceptionally low estimate can be a signal that you’re working with an inexperienced writer. Or one who doesn’t truly understand the amount of work required to execute your project. Either way, bad feelings and poor quality can result.

Question 5: How professional are they?

This is the least tangible of all the questions. Yet it’s the one that can make the most difference in developing a successful, long-term relationship with a writer. The most talented writer in the world can be unbearable to work with. Perhaps they bristle at feedback from your full-time staff. Sigh heavily when interviews are rescheduled. Send panicked texts when deadlines loom. Charge extra fees every time the scope of work changes, even a little. Working with a “difficult” writer may still get you a great end product. But the process isn’t going to be pleasant. And you’ll risk alienating your full-time staff—and perhaps your clients—in the process.

How do you gauge a writer’s maturity and professionalism? Ask a lot of questions, solicit feedback from your colleagues, and trust your gut. If managing their behavior becomes stressful, after their project is done, drop them. That’s the advantage of working with a contract writer. You don’t have to go through HR to get rid of them.

In summary

An outside writer can be a huge asset for you and your full-time staff. They can help you effectively manage peaks and valleys in your workload. They can expand your capabilities by bringing expertise with special subjects and types of writing.

And, like any good contractor, they can relieve stress by taking onerous projects off your shoulders. Just remember—before you embrace an outside writer, ask these five questions. Listen carefully to the answers. Then make an informed decision. If you do this diligently, you’ll have a great chance of hiring the right writer for your firm.

Cheat Sheet: Interview Questions to Ask Your Writer

Industry Experience

  • Tell me about your experience writing in this industry.
  • What are some of the challenges you’ve experienced writing about this area? What do you enjoy?
  • Could you send me some samples of writing you’ve done in this industry?


  • Tell me about your experience writing case studies/ feature stories/capabilities brochures, etc.
  • What do you think is important about writing in this type of format? What’s your approach to tone and structure?
  • Could you send me some samples of this type of writing?


  • What’s your availability over the next week/month/ quarter? Could you give me a sense of your average availability?
  • How quickly could you normally complete XYZ type of project?
  • How quickly could you normally start on a project, once you receive a request?


  • How much would this type of piece normally cost?
  • What’s your estimating process?
  • What’s your approach when a project goes outside of scope?


  • Tell me about a writing project you’ve done that went really well. What contributed to the success?
  • Tell me about a writing project you’ve done that went south. What happened?
  • How do you handle tight deadlines?
  • How do you handle getting feedback from multiple reviewers?

Don’t want to deal with any of the vetting yourself? Work with Dragonfly instead. We’ve got writers on demand who are ready to dive into your projects.

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