How to Hire a Great Freelance Writer: A Comprehensive Guide

You’ve built a great product, found product-market fit, and now need to activate the marketing levers that get your product noticed by the right audience. You’ve heard how an effective content strategy can connect with potential customers at different points in their customer journey, help lower your customer acquisition costs and help retain customers once you have them. You also know that half of all marketers say they outsource some content marketing–it’s a smart move that allows you to work with pros and focus on what you do best. So the question becomes: How do you hire a great freelance writer?   

Firstly, your faith in the power of content and content marketing is well-founded. 91% of marketing pros surveyed by Semrush achieved success leveraging content marketing.  According to the Content Marketing Institute, 73% of B2B marketers and 70% of B2C marketers use content marketing as part of their overall marketing strategy.

Content is a key pillar of effective marketing in 2024, and a solid writer can make a huge difference. Great freelance writers understand the brands they are writing for, the platforms their content will appear on and the audiences that their content will reach, and synthesize this into something that connects, resonates and drives business results.

Having been in the online content business for over 15 years, I’ve hired and worked with hundreds of writers. Finding a truly great freelance writer can be like finding a needle in a haystack, but over time, I’ve developed an understanding of what makes a great freelance writer and how best to work with freelancers to achieve the best results.

This guide will provide a comprehensive overview of how to find, evaluate and work with freelance writers and most importantly: how to ensure your business meets its objectives with content.

Before Looking for a Writer, Define Your Content Strategy and Make a Content Plan

Before starting your search for a freelance writer, you should make sure you have a defined content strategy. It simply isn’t enough to create content and hope for the best. Your success with content depends on how you think about content holistically, and any individual piece of content is just a piece of that puzzle.

A content strategy encompasses the overall thinking around how you will create a distribute content to meet your business goals. It is effectively the blueprint for how you will use content and without it, you are almost guaranteed to waste time and money creating content piecemeal with limited results. As the famous saying from Benjamin Franklin goes: a failure to plan is preparing to fail. A content strategy focuses on these key areas:

• Objectives & Goals: What is it you are trying to achieve with content? Reach? Lead generation? Sales? Authority? 
• Target Audience and Ideal Audience Profile (IAP): Who are the groups you are trying to reach
• Target Channels:  Where you want your content to appear (search, social, etc.)

A content plan is the practical translation of your content strategy into an action plan. It encompasses the specific details of the content you will create and includes the following:

• Working titles
• Target publish date
• Target persona/Customer Profile
• Focus Channels (search, social, etc)
• Content Formats (Blog posts, Pillar pages, white papers, email, etc.) 
• Target Keywords
• Topic Cluster (The cluster of existing content on the same broad topic to which the new content will belong)
• The target Customer Journey stage (Awareness, Consideration, Decision, Loyalty–is there a stage this content is specifically being written for)

You shouldn’t expect that a freelance writer will have the capacity to create a content strategy or content plan. Great freelance writers will be good at interpreting the needs of clients and translating these into content. Great content strategy taps into different skill sets, including overall business, marketing, SEO and social media expertise. It takes a holistic approach to content and a substantial understanding of the underlying business to be successful. A company like Bread and Circuses develops content strategy and plans and leverages a network of outstanding writers to deliver outsized business results, so it’s worth considering whether you need a single freelance writer or a company that develops content strategy and has a great stable of writers dedicated to your overall success with content. 

What to Look for in a Great Freelance Writer

You’ve developed a content strategy and a content plan, and now it’s time to find a great writer (or writers) who will bring it all to fruition. 

You may think it is as simple as finding someone who writes well, but there are many considerations beyond that. In my experience, how writers work is a huge differentiator in the overall experience with them, especially if you are looking to work with someone for the long term. Some of the key considerations include:

• Attention to detail: It goes without saying that you want the time spent editing content from a freelancer to be minimal. Grammar, punctuation, spelling, citations and hyperlinks within text should be next to flawless, particularly with software tools like Grammarly that are available to automatically flag issues in the text.  High attention to detail is a basic requirement for a freelance writer. 

• Organization: You should be able to trust that writers know due dates, organize the information you provide them and submit projects on time. You don’t want to spend unnecessary hours going back and forth with writers on information they already have.

• Professionalism: You want a writer who truly cares about their own reputation and is unwilling to submit subpar work. These kinds of writers don’t see your gig as merely a paycheck but instead, see it as another opportunity to advance their skills and build their reputation. 

• Research abilities: For many writing projects, your writer will need to also be a researcher. This means finding relevant sources and tidbits of data and information that strengthen the content being produced, or even conducting interviews themselves. It requires not only having a good sense of content structure, but also how to incorporate external data to support it with an eye for credible sources (and certainly–not citing competitors).

• High confidence, low ego: Some writers view themselves as rare artists whose work in its rawest form we should consider ourselves lucky to have because it flowed from the creative rivers of their unique artistic talent. Other writers are employed. 

Seriously speaking, you want talented writers with a specific perspective who have conviction, but who are willing to be flexible. They need to be able to take constructive criticism and adapt to your requirements in an easy-going, low-friction manner. Ideally, the writers you work with have a wealth of experience, knowledge and skill but have a beginner’s mindset, always looking to learn. They should be willing to adapt their approach, do rewrites and generally ensure the final product is aligned with your expectations.

• Curiosity: Speaking of a beginner’s mindset and learning, you want writers who are genuinely interested in knowing more about the world. I’ve found that writers who view the writing process as an opportunity to learn vs just a paid gig will spend more time learning more about your company and the subject they are writing about. If they are motivated by their own curiosity, the end result can’t help but be better.

• A great verbal communicator:  In certain contexts, you will need a freelance writer to conduct interviews with team members or customers in order to create content (e.g. for interview pieces or case studies). Ease of communication is paramount to a successful outcome, as sometimes coaxing the right information from an interviewee can be challenging.

• Technical acumen and adoption: We live in an ever-evolving world, with continuous advancements in technology that make it easier to collaborate and produce quality content. The writer you chose should be capable of using a variety of tools relevant to creation and collaboration, such as Google sheets, Slack or project management tools like Asana and Click-up.  AI in particular is a boon to content creation but is seen as an existential threat by content creators, some of whom refuse to experiment with it entirely. I’ve found that the best writers are actively trying to understand how to integrate AI tools like ChatGPT into their processes to improve the original content they create, instead of rejecting it entirely.

• A sense of humor: Life is short, surround yourself with people you can laugh and have fun with.

Where to Find Great Freelance Writers 

Finding writers is easy, finding great freelance writers? Not so much. 

That said, you need to find them before you vet them. There are a few different places to find great writers:

• Word of mouth: a great way to find writers who do quality work and are easy to work with is through colleagues and acquaintances you trust who have worked with freelancers before.
• Social Media (particularly Linkedin): Generally good for connecting with B2B, technical writers and l and ghostwriters.
• Job Boards (not really a favorite of mine)
• Freelance Platforms (like Upwork): Helpful because of the rating system in place, there is some proof that the writers have completed successful similar projects with others.
• Companies or publications you admire: often the best way to find great writers is to look to the companies that have content you like and find out who their writers are. If they use freelancers, it could be as simple as identifying those key freelancers and hiring them yourself.
• Content Strategy Agencies: Agencies (Like Bread and Circuses) have existing stables of proven content writers. They basically have done the work for you. 

It is generally much trickier to find good B2B and technical freelance writers than lifestyle writers, and it’s important to know the distinction. Freelance writers who have experience creating B2B content will have a better sense of the logical structure of content designed to appeal to prospects and customers in its various formats and at different stages in the customer journey whereas lifestyle writers might be stronger in their understanding of pop culture, virality and writing for general consumer audiences.

How to Decide on a Shortlist of Great Freelance Writers

When looking for freelance writers, you aren’t only looking for people with good writing skills, but experience writing the formats you need in the industries you need them for. For example, if you work for a B2B SaaS cloud computing company and need to create white papers, you ideally would find a writer who has experience writing white papers for a cloud computing company. It is a substantial leap for an amazing celebrity writer or lifestyle writer to move to white paper writing. It just isn’t the same thing. Certain industries and certain formats require more researched, structured and methodical writing, while others are more aspirational, creative and informal, so in your hunt for writers, you should look for the following:

• Format experience: have they written the content format you are looking to write? (marketing emails, blogs, white papers, case studies, etc.)
• Industry experience: Do they have experience writing for your industry or closely adjacent industries?
• Past work and client testimonials: Is there evidence that they have done good work that has satisfied customers?
• Portfolios and samples: Do they have a portfolio or at least samples available for review?
• Cost: Are their stated fees aligned with your budget? (more on costs and budgets later).

Vetting and Evaluating Freelance Writers

Once you’ve started to create a list of potential freelancers for your project, it’s time to start narrowing them down. Here are the steps to take when vetting freelance writers

Review the Writer’s Portfolio

 Take the time to thoroughly go through portfolios and identify whether the writer’s work is clear, concise and compelling. Look for samples in formats and on topics most similar to the ones you will need for your project.

Reach out to the Writer With a General Overview of the Project

Once you have established a set of writers who have shown they can create the type of content you are looking for at the quality level you expect, connect with them to provide an overview of the project. Instead of sharing your budget (which they will surely figure out how to spend!) ask for their per hour, per word or per piece cost. I like to understand cost per word as it can be applied to content at different lengths and is helpful when establishing or managing a content budget. Note that more technical or research-heavy writing is bound to be more expensive, and more general content should cost less. At Bread and Circuses, we have a view on what hundreds of freelancers are charging and it can vary greatly. We suggest connecting with several freelancers to get a sense of the range of rates before committing to one writer. Freelance writers will also generally provide a discount based off of the volume of content that you are assigning to them, so don’t be shy to negotiate rate reductions accordingly.

Have a Video Interview with the Freelance Writer

Once you think you have found the right writer at the right cost, meet or have a video call with them. The point of this call is to get a sense of the writer’s personality and interests and evaluate whether they will be reliable and easy to work with. The reason I suggest a video call is that the writer may be working with–and potentially interviewing–other members of your team. A video call, as limited as it is, gives a better sense of the writer’s personality and ease of working with others.

Interview Questions for Freelance Writers

These are some of the questions I like to ask during interviews with freelancers (note that the depth of the interview will vary based on the assignment–I wouldn’t conduct such an extensive interview to write a single blog post:

• What do you know about the project?: checks how much attention they paid to the initial outreach and extra research they have done on their own.
• What makes a good writer? It’s good to know that they have thought about what makes the work they do valuable, and to see if their understanding matches with yours.
• What are your strengths and weaknesses? A classic question that checks humility and self-awareness and also provides obvious valuable insights
• What are your 3 greatest accomplishments in the last year? Establishes the types of results they are motivated by, whether they are extrinsic or intrinsic, and if they are focused on moving the needle for clients.
• What is your media consumption diet? Gives a sense of their personality, subject-matter expertise and general thoughtfulness. 
• What are the last 3 books you’ve read and why you’ve read them? Similar to media consumption, but books are a greater time investment, so goes a level deeper.
• What would coworkers/other clients say about you? Provides further answers about strengths and self-awareness.
• If you were to get this role/gig, what would be your biggest challenge, and how would you approach it? Tests for humility and maturity. 
• What do you most want to learn? People are motivated by their own learning objectives, so ideally the subject

During the course of the interview, I would also review their resume, get an understanding of their availability and their policy around revisions. While unlimited revisions are likely a lot to ask, freelance writers should be willing to revise their drafts until you are satisfied. Sometimes, there can be initial misunderstandings around the content that needs to be created or the approach that the writer should take. While these misunderstandings can generally be avoided (see the next section) it happens. The writer needs the appropriate flexibility to make changes that deliver the desired end result.

How to Work with Freelance Writers and get the Most out of the Relationship

Like a lot of things, the inputs define the outputs or said less eloquently: if it’s garbage in, it’s garbage out.

If you don’t provide guidance to the freelance writer, be it background research, access to experts within your organization and /or detailed content briefs, you can expect that even the best freelance writer will miss the mark. 

Working with writers means setting the appropriate expectations and giving them the tools to do their job.

Set clear deadlines for when the draft versions and final versions need to be completed. Depending on the writer’s availability and the urgency of the project.

We’ve written before about content briefs–the more detailed, the better. Content briefs should include the following information: 

• Background on your company
• The content topic or working title
• The focus keyword (if applicable)
• Target secondary keywords (if applicable)
• The purpose of the article
• Background information on the topic
• Focus distribution (search, social media, etc)
• Examples of similar content and content that matches the desired tone.
• A content outline (if possible, including suggested sub-topics, H2’s, H3’s, FAQ sections, etc)
• Any formatting guidelines

A good content brief is the difference between money well spent and money wasted. Take the time to create a detailed brief and save yourself headaches later. 

Note that AI tools like ChatGPT and SurferSEO can help with brief creation, particularly with SEO friendly article structure. Leverage these tools to help with the content creation process, or at least spark your creativity. 

Conclusion: Why you should Follow all of this Advice (and a Way to Follow None of it)

When you find a great freelance writer–you’ll find benefits beyond “good writing”. Great freelancers evolve–they begin to anticipate needs and become partners not only in content creation but strategy and ideation. With time, they will start to recommend content topics and will often require less and less guidance as they build great content for your company. For this reason, It’s worthwhile to follow the steps I’ve outlined above to ensure the best result. Some leg work at the outset will pay off in the long term. 

But getting to this place requires substantial effort, and even with a great writer, you may have overlooked the most important part of the puzzle: how your inbound marketing is connected with content and your overall content strategy.  What should your great freelance writer be writing about that leads to the greatest results for your business?

This is where an agency like Bread and Circuses can help. We develop a content strategy and plan based on a deep understanding of the needs of your business content, SEO and inbound marketing and then leverage a deep pool of great writers and editors to follow the plan for you. We collaborate with executives and marketing teams to take on the thinking and execution around content–leaving them room to focus on other areas. If you are interested in results, saving precious time (and in the end–not following my advice), book a meeting with me to discuss further.