How to Hire a Freelance Writer: 10 Key Questions to Ask

Reading Time: 6 Minutes

Contributed by Carol Tice

Longtime freelance writer Carol Tice founded the 1,400-member Freelance Writers Den learning and support community. Companies are welcome to find writers with a FREE listing on the Den Job Board.

Carol lives in Seattle. Known for her playful and informative writing style, she has personally written for clients including Alaska Airlines, American Express, Dell, Delta, and SunTrust. She is the author of Small Business Owner’s Guide to Starting Your Business on a Shoestring and Small Blog, Big Income.

Carol Tice founded the 1,400-member Freelance Writers Den learning and support community.

Have you decided it’s time for your business to hire outside writing help? Good for you! Too many businesses struggle to grow due to a long list of marketing tasks left undone, when a freelance writer can help make that marketing happen sooner.

Often, marketing managers don’t hire writing help because they don’t know how to find a writer. Or they’ve turned to mass platforms such as Upwork or Fiverr in the past, had a bad experience, and now don’t know where to look.

The good news is, with the guide below, you should be able to cut out the middleman to easily find and hire a quality writer on your own.

Table of Contents

How to Find and Vet Freelance Writers

What to Do Before You Contact a Freelance Writer

  1. Define your project.
  2. Define your goal.
  3. Define your budget.
  4. Define your timeline.

10 Questions to Ask a Freelance Writer

  1. What is your availability?
  2. What do you know about my industry?
  3. What samples can you show me of the type of writing I need?
  4. Do you have testimonials or happy customers I could speak to?
  5. How would we work together?
  6. What else can you provide?
  7. Are you willing to do an initial small project (for pay)?
  8. What are your rates and payment terms?
  9. Do you offer a discount for retainer work?
  10. Who will provide the contract?

How to Find and Vet Freelance Writers

To find writer candidates, I’d recommend you do a search on LinkedIn. Many experienced freelancers are active on this social-media platform, and you should be able to quickly find many appropriate candidates.

If you want someone local, search on LinkedIn for “[your city] freelance writer,” or if industry knowledge is more important, “freelance [your industry] writer.” Or go for broke and combine those, as in: “Atlanta freelance healthcare writer.”

Once you turn up a few candidates, see if their contacts are visible in their header, title, or About section of their profile. If not, send connection invites that let them know you’re seeking a writer. See who bites.

Once you connect, view their contacts and see if they have a writer website. Many wannabe writers don’t have a site, so this serves as a screen to help you find more accomplished writers. When you see a writer has a website, check it out and read samples from their portfolio, to get a sense of their writing style and expertise level. Some writers may not have a site, but may have clips uploaded to their LinkedIn profile for you to read.

At this point, you should have narrowed it down to a few intriguing candidates. Before you reach out to set up interview times, make a few key decisions that will help these chats go smoothly.

What to Do Before You Contact a Freelance Writer

If you’d like to work with a professional writer, it helps to understand what questions the writer will have for you. That way, you can have your answers ready when you start contacting prospective writers.

Before you reach out to writers, try to define the following factors.

Define your project.

You may have a long wish list of what you might have a writer do, if you like their work. But what are you hiring the writer to do, initially? Is it weekly 750-word blog posts, a case study, annual report, newsletter, press release, app copy, a sales page, an email sequence? Decide the details, so you can tell the writer what’s up.

Define your goal.

What is the value of this project to your organization – what additional leads, traffic, authority, awareness, or sales are you hoping it might it create? Understanding value helps you decide if you’re looking for the cheapest competent writer you can get, or if you need the best, most experienced writer you can find.

Define your budget.

What can you pay for the content you want written? A small budget may limit how much experience you’ll get.

Define your timeline.

Is this a rush emergency, or can you be flexible? Better writers are often booked out, so it may be hard to get a top writer if you’ve got a crisis on your hands. In any case, know when your writing work needs to be completed, to keep your marketing on track.

Now that you know why you’re hiring a writer and what you want them to write for you when, you’re ready to reach out and set up a few meetings.

10 Questions to Ask a Freelance Writer

What should you ask to qualify the right writer? Here are my top 10 questions:

1. What is your availability?

Your deadline may be a decider in whether a writer can do your assignment, so ask that up front.

2. What do you know about my industry?

The easiest road for any business is to hire a writer who already knows their industry. The writer might have prior day-job experience, or have written for similar clients, but find out what they already know. It will be a huge timesaver if you don’t have to educate the writer on how things work in SaaS or medical devices or whatever it is your company does.

3. What samples can you show me of the type of writing I need?

Sure, you’ve browsed their site, but ask them to show you their most relevant stuff to the particular project on offer, to get the best idea of what they’d create for you.

4. Do you have testimonials or happy customers I could speak to?

Any serious freelance writer should have collected testimonials and be able to offer references. If they can’t, that’s a serious red flag.

5. How would we work together?

Many freelance relationships fall apart right here, because your working style is different from the contractor’s. If you want someone you can ding 24/7 on instant messaging and they want one monthly Skype meeting and a few check-in emails, that’s not gonna work. So find out now.

6. What else can you provide?

Writers are often asked for additional services that complement their writing – to source photos, do SEO research, post inside your WordPress dashboard, add links, and more. Are you hoping the writer will also deliver social posts, or help you with content strategy? If so, make sure all that’s clear.

7. Are you willing to do an initial small project (for pay)?

Defining an initial small assignment allows you and the writer to see if you like working together, without a big commitment. Understand that asking the writer to do a first project free or on spec is a red flag for writers, as that’s a practice used by many scammy companies that stiff writers.

8. What are your rates and payment terms?

While some writers may have a rate card with standard hourly rates they charge, many professional writers don’t work on an hourly basis (we’re not clerks!) and will quote you a project fee. The writer may ask you what your budget is for writing help, ask what you’ve paid writers in the past for similar projects, or may ballpark you a rough project quote to see if you’re anywhere near agreement on price. Expect some give-and-take in negotiating rates. Then, see when payment is required – often, for a new client, that will be 50% up-front and 50% on completion.

9. Do you offer a discount for retainer work?

You may get more writing for your money by committing to an ongoing contract that’s paid at the start of each month. You might get charged $300 for one 1,000-word blog post, for instance, but $250 per post if you commit to 4 posts a month for 6 months. If you have ongoing writing needs you want to outsource, a retainer guarantees the writer saves time for you each month, and can earn you a discount as well.

10. Who will provide the contract?

The writer will want to memorialize this relationship in writing, so everyone is clear on what’s expected. Contracts can be as simple as a quick email that defines assignment, word count, deadline, allowance for rewrites (many writers include two rounds in their price), payment, and terms – but expect to execute some sort of contract before the writer begins work.


As you can see, asking some basic clarifying questions will help you find and hire the best writer for your situation. Consider this list a starting point, and add any other specific questions you have to develop your freelance-writer interview sheet.

As you hire writers, you may eventually decide to hire an editor to manage the writing process, or you might decide to become a professional editor yourself.

Having a simple, question-driven process will help you quickly identify and hire the freelance writer you need to help achieve your sales and marketing goals. Here’s to happy and productive freelance relationships and finding the perfect writer for your job!

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