How to Work With Freelance Writers (and Get the Results You Want)

Corey Wainwright
Corey Wainwright



Freelance writers are a great way to feed your ever-hungry content machine. And if you're paying your freelancer writers well (that's good, you should), you need to ensure you're getting your money's worth from what they deliver.

One way you can screw that up is investing a ton of your time managing them, engaging in unproductive back-and-forth, and, ultimately, just redoing their work.

To help lower the overhead cost of outsourcing writing, you need to nail the process of communicating with and managing those freelance writers. And that process is a little different than what you'd use managing your own internal writers.

Free Download: How to Hire and Work with Freelancers

So, here's how I've effectively worked with freelance writers to establish long-term relationships that require low time investment and produce good results that get us our money's worth. (FWIW, I've also worked as a freelance writer myself. I appreciated this stuff when I was on the receiving end, too.)

(Any freelancers reading? Building a relationship is a two-way street. One of the best ways to kick off a partnership on the right foot is to set payment expectations upfront. Here's a free Invoice Template Generator to help you with that.)

1) Invest some time up-front.

Most productive freelancer writer engagements require up-front time investment -- but it's a good use of time. If you can get them up to speed on basics from the get-go, it's more likely you'll get what you're looking for earlier on, eliminate rounds of revisions, and decrease the back-and-forth that ends up delaying projects and burying you in email.

Taking this time to train and prepare your writer to produce content at the start of your relationship will make your life much easier as you engage the writer in future projects.

Here are the basics that you should share with them for their first project with you that'll set them up for success in future projects:


Who are the personas, and for whom are you writing this specific piece of content? Do you want it to be written so it can apply to all personas, if you have more than one? How would the writing change to accommodate different readers? Do the tone, word choice, length, and/or structure need to be altered accordingly?

You should answer all of these questions for your freelance writer before they begin their engagement.

Products, Services, and Company Background

Yes, a writer can go read your About Us and product pages (and they should), but taking a few minutes to explain who you are, what you do, what you sell, and the value proposition that backs it all up is invaluable.

For instance, we would tell our freelancer about inbound marketing, how we talk about it, what tactics we promote, how those tactics relate to the software we sell, and how our software helps enable marketers trying to implement those marketing tactics.

Remember, you get all this stuff because you live and breathe it every day. Your freelancer does not. And even if they work in your industry, every company has its own nuances. It's your job to fill them in.


Provide a few core resources they can pull from, and tell them where they can find more so they're enabled to do more research.

For example, if we were outsourcing an ebook about landing pages, we could send them 1) our State of Inbound Marketing so they can pull data about landing pages; 2) a former ebook we've written about landing pages that we consider high quality; and 3) a few blog posts that talk about landing page best practices. 

Links to Exemplary Content

Provide a benchmark of what "good" looks like so your writer's expectations are properly set from the get-go. Explain what exactly is good about the content sample you provide so they can replicate the positive aspects of that piece of content in their deliverable.

Sometimes, it helps to also provide an example of what "not good" looks like and explain the core differences between the good and the bad.

Editorial Criteria and Processes

All companies have their own editorial process. Explain how you work -- and ask how they typically work -- to establish a process that makes sense. This discussion should include:

  • Sending along your style guide (if you don't have one, here's one you can use and customize to your own business)
  • Establishing the length you'd like for the piece
  • Agreeing on revisions (should they expect to do one revision? Two? Three?)
  • Agreeing on expected turnaround time for each revision
  • Nailing down a due date for the final piece

2) Explain the purpose of the piece of content.

Context is important. If your writer knows what your goal is, how the content will be used, and why it's important, they're empowered to use their judgment to make good decisions -- which means they won't be emailing and calling you for every little thing.

3) Work off a detailed outline.

As you get to know a freelancer writer (and they get to know you), basic bullet points will do. When you're first starting out together, however, be extremely detailed about what you want. You may find it most efficient to write the outline yourself and send it to the writer.

For instance, if you're outsourcing the writing of an ebook about landing pages, this is what a good outline would look like:

Introduction: Short (about 200 words)

Chapter 1: The Anatomy of a Good Landing Page (roughly one paragraph on each bullet)

  • Image
  • Form Length 
  • Headers 
  • Navigation 
  • Copy 
  • Button Design & Copy 
  • Value Proposition 
  • Social Sharing 

Chapter 2: Nailing Landing Page Copy (roughly one paragraph on each bullet)

  • Action-oriented Language
  • Value-oriented Language 
  • Keywords 
  • Writing in the Second Person 
  • Brevity & Clarity of Language 
  • Proofreading 

Chapter 3: How to Optimize Landing Pages (roughly one paragraph on each bullet)

  • Page Titles
  • URL 
  • Header Tag 
  • Image 
  • Rich Snippets 
  • A/B Testing 

Conclusion: Short (about 200 words)

  • Reiterate that these are just the basics, and provide a few resources (links provided in email) for people to go to for more information.

Once you send your outline, tell them that you're available to answer any questions about any of the bullets in the outline. For instance, make sure they know how to talk about how to optimize page titles, URLs, etc. on landing pages. If they don't know, be willing to explain it, or send them a resource that explains it.

4) Give iterative feedback.

Unless your content asset is very brief (like a 600 word blog post, for instance), don't have your writer complete the entire piece immediately. Tell them to write one section and then check in.

If they've done a good job, tell them to keep going. If there's something that was misunderstood or miscommunicated, it doesn't mean they're a bad writer -- they're just still getting used to working with you, and what you wanted was perhaps not communicated as clearly and straightforward as it could've been.

Checking in early on their progress, and redirecting if needed, saves the writer a ton of time on revisions and you a lot of time on giving feedback for those revisions.

5) Be clear in your communications and document them for reference.

Every communication you have should be documented in writing and extremely clear. You may feel like you're micromanaging by being so specific -- I mean, who wants to be micromanaged?

Don't worry. You shouldn't be afraid of being detailed with what you want. Most freelancer writers will appreciate your level of specificity, because it actually lessens their overall workload -- if they can give you what you want from the onset, it's less revisions they have to go through, and they've probably scored repeat work with you.

Know what you want, communicate it clearly (this is hard, but clear communication is a good skill to acquire), and write it all down in a follow-up email so they (and you) can refer back to it later on.

The Takeaways

Assume nothing. We take for granted that we all know our company story, our products, our services, who our personas are, and how we position things. Freelance writers we work with don't work within your four walls every day, and they don't live and breathe your language and methods. Be specific, and take the time to explain things.

If after some up-front handholding they don't work out, then sure, cut them loose. But if after handholding they rock, loosen the reigns a bit, and after a few projects together, you'll have a go-to writer that can turn around excellent content quickly and with minimal oversight.

how to hire freelancers


Topics: Freelancing

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