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How to Hire the Best Freelance Writers: The Path to Success!

You’ve done it! You’ve started to see returns on your content marketing efforts. Not only has your site started to get organic traffic (i.e. from Google) and social media traffic, you’ve gotten some leads and a few sales from it! But it was a ton of work! You had to:

  • Write the blog posts and social media posts
  • Create your lead magnets
  • Set up the landing pages
  • And automate email campaigns

This post was updated on March 6, 2020.

As a small or mid-sized business owner, you understand the value of content marketing, but you know managing it all yourself just isn’t sustainable! Enter: your freelance content team!

You have a lot of work to do before you can actually hire anyone. All of this work is an investment though. Because once you hire quality content creators, marketers, and/or a manager, you won’t have to worry about your content creation anymore.

Decide on Your Content Goals


What do you want from your content professional(s)? Do you want someone to write blog posts? Social media? Emails? All three?

What about your lead magnets? Lead magnets can be ebooks, white papers, quizzes, fillable workbooks and templates, slide shows, and so much more. It takes more time to create lead magnets, which means they normally cost more. However, the shelf life of a lead magnet and ROI of the lead generation you get is well worth it. What is a lead magnet?

A lead magnet is a valuable piece of content you use for lead generation for your consulting firm or professional service agency. They come in many forms, and your audience will give their contact information in exchange for a lead magnet they feel is valuable.

Also, you need to decide on your budget. Everyone can write, but not everyone can write well. Don’t expect to find great writers on the cheap. Content marketing is worth the investment, but you have to actually be willing to invest.

Freelance Content Strategist or Marketer

So obviously there is a lot going on here. If you need help deciding what your content strategy and plan should be (they aren’t the same), then you’re likely looking for a content strategist or marketer. This is someone who can:

  • Research your industry and business
  • Create your buyer personas
  • Plan your strategy
  • Create your monthly/quarterly content plan

If you also like their writing style and they have management experience, then they may also be able to manage any content creators you hire. (Most content marketers and strategists can also create content, but there’s really only so much you can expect from one person. Hiring a strategist and/or marketer who can then manage a team of writers is the most cost-effective option)

Difference Between a Content Strategy and Content Plan

I see freelance content writers make this mistake as well, so if you thought they were the same, you’re not alone. But a content strategy and a content plan are two different things.

A content strategy comes first. It’s comprised of a lot of different pieces but is the map for your content. A content strategy lays competitive analysis, your buyer personas, the types of content you should use, your key performance indicators, and more.


Next Comes the Content Plan

After your strategy is clear, a specific content plan based on the overarching content strategy and each specific content channel can be created. Many people assume that this is the content strategy, but it’s not.

Your strategy is the guiding light of all of your marketing efforts. The content plan is just the execution of those goals. It’s much easier to make a content plan (although still a lot of work!) than it takes to develop a company’s content marketing strategy.

A B2B content plan will include specific blog posts topics and publish dates, social media posts, lead magnet plans, and email campaigns. Anything noted in your content marketing strategy that needs to be created, published, and distributed will likely appear in your content plan.

Freelance Content Writer

If you feel like you have your strategy and plan well in hand, then you’re likely looking for a content creator (or content writer). This will be someone who will actually create the content laid out in your plan. You may need more than one writer depending on how aggressively you want to grow your content footprint.

Another thing to consider here is what other peripheral tasks you want your creators to do.

  • Should they look for photos to go with the content?
  • Should they be able to draft into your Content Management System?
  • What about writing things like meta descriptions and alt text for your blog posts?

If your freelance writers can do these things, it will save you a lot of time. Or perhaps you hire a virtual assistant to take care of these things.

Keep in mind that you may not find that “unicorn” content professional. There aren’t a lot of people who can do EVERYTHING. So do you want one person who performs most tasks in a mediocre fashion? Or two-three people who perform well?

How Do I Find Great Freelance Writers?


There are a lot of different places you can search for your ideal freelance writers:

  • Networking events
  • Online job boards and sites
  • LinkedIn
  • Referrals from family and friends

You may also find content professionals you’re interested in while you’re researching content in your industry. Don’t be afraid to reach out and see if they’re taking on more clients.

Many businesses are making use of job platforms like Upwork, Freelancer, Fiverr (and the list goes on). One of the main things you can do to make your job search on any of these platforms easier is to create a great job ad.

Creating a Great Freelance Writing Job Ad

When you create a job ad that is unspecific or vague, the best writers are likely to pass that job by (I do). These job boards can have a bad reputation for low-quality work, but many clients on these platforms write poor job posts that only low-quality writers will respond to.

To entice the best writers to submit a cover letter and samples to you for consideration, you need to create a job ad that shows:

  • Your passion for your business
  • Your intent to invest in your content
  • Benefits of working with you and your company
  • The tools they should know how to use
  • Any required topic, niche, or industry experience
  • What you expect from your freelance writers

The more specific you are in your job post the more likely you are to weed out the unqualified writers from the beginning. As a content strategist and marketer, I have a list of things I look for that either qualifies or disqualifies any prospective job post or client I come across.

You may wish to specifically include:

  • Information about your company and your website
  • Your ideal customer or target audience
  • What you think you need in terms of content strategy, marketing, planning, creation, or distribution
  • Other requirements or desires that would further qualify anyone considering your job post.


“Sites like UpWork, Fiverr or Craigslist might be a good fit, depending on the type or quality of content you’re working with. You are unlikely to find excellent B2B writers with industry experience on these sites, but you may find writers for lightweight, consumer-oriented content.” via How to Hire Freelance Writers to Scale Your Content Marketing

You can find excellent freelance writers, content marketers, and strategists on these platforms. I personally know quite a few. YOUR job ad is going to determine whether or not they apply. Most successful content writers have a full plate, so if you want them to work with you, put some effort into your job post or they may never reach out.

I Have My Freelance Writer Shortlist. Now What?

Now you have to vet your shortlist. You’ll disqualify most to get down to the few you think maybe a good fit for your business. Some of the things you can do:

  • Check their work examples thoroughly. You’re looking for:
    • Great grammar
    • Tone and style that you like
  • Demonstrated ability with past clients
  • Experience in your industry (or the ability to learn your industry. You may find someone who has everything BUT experience in your industry. This shouldn’t disqualify them if you have time for them to learn)
  • Do you like their writing? Do you think it will resonate with your target audience?
  • Finally, consider the quality of their proposal. They should craft a tailored proposal for your review.
    • If you think you received a copy and paste proposal or cover letter, then they aren’t showing you they take your job post seriously.

What Should I Ask These Content Writers During the Interview?

Next, you’ll conduct your interviews. Don’t be surprised if the writer prompts you to go over your job post again. In fact, they should. This helps them determine if they can actually help you.


Prior to the interview, you want to identify any specific requirements that are particularly important to you. Don’t be surprised if the writer also asks you about your budget before a call. Before you think they “just care about money,” consider this fact. If your budget and their fees are lightyears apart, then you’ve both wasted time.

You should plan out your questions so you can get an equal measure of each writer your interviewing. You can ask them about their bandwidth, turn around time, revision policy, and the content types they can create.

Most writers don’t expect to know if they’ve gotten the job during this initial call. Be upfront that you’re interviewing other writers, and let them know when they can expect your final decision.

It’s tempting to just never talk to the writers you don’t select, but it’s not very professional. You never know if you’ll need to reach back out to them.

Now It’s Time for a Test Writing Piece

Now that you have selected 1-3 writers that you’re really interested in, it’s time for a test project. A test project helps you determine if you like working with a particular writer. If your personality types grate on each other, then you won’t enjoy interacting with this writer, and they’ll probably dread working with you.

Your test project should be PAID. It should also be small, which will keep your costs down. You could posit a blog post topic and then ask them to write 500 words for a particular section. If the test project goes well, they can write the full post. But you need to expect to pay.

Most experienced writers won’t do free test projects, and they shouldn’t.

Have your test projects due around the same time frame so you can determine who you would like to move forward with. Again be upfront and let your writers know that other candidates are submitting test projects, and when they can expect your final decision.

That’s It! No Big Deal Write? (Haha, get it?)

Delegating content creation, marketing, and strategy benefits you as a business owner. You’re a pro at what you do, and you shouldn’t have to be a pro at what I (and my freelance colleagues) do as well. Bringing on freelance content professionals can seem intimidating, but it will free you up to work on other aspects of your business.

If you find a writer, marketer, or strategist you enjoy working with and you need to expand your content team, ask them who they know! Great professionals network with one another! You’ll have a stellar team in no time! Reputation is everything in the freelance world, so I know I would only recommend the best!

Have you hired a writer to create your content before? How was that experience for you? Please let me know in the comments!