In a previous post, we discussed how to become one of that coveted group of freelance writers in the world: tips, tricks, and opportunities. This freelance writing guide is only one half of the equation, however.

What about those who have hired freelance writers, or who have been a freelance writer for a long time? We asked ten experts in the field about their experiences with this endeavor: How was the experience? What was positive and/or negative, and what worked and didn’t work about it? Here is what these thought leaders said.

Value of Long-Term Client Relationships

As a freelance writer, I have learned the value of long-term client relationships. They might not agree with your price increases, but they will provide consistent work to handle your bills. You might see the need to hire writers to help if you want to grow into an agency and specialize in writing for a niche like health, technology, education, or engineering.

Samuel Karugu, Content Manager, The Avalon Writer

Outsourcing Requires Quality Control

I’ve been blogging and freelance writing for five years. For the last two years, I’ve outsourced and hired writers for my three travel websites – Caribbean Uncovered, Barcelona Uncovered, and Oahu Travel Secrets.

While outsourcing overall, in my opinion, is always a positive experience, I started outsourcing around the time AI was booming. Because of this, it took much longer to find the quality of writer I was looking for.

What I’ve learned? Always request a test article for yourself (not a portfolio, since portfolios are filled with their “best” and sometimes outdated writing). If a writer produces a low-quality test article (consider: AI, poor grammar, not the tone of voice I’m looking for), I thank them for their time and pass. If they’re unwilling to put their absolute best foot forward on article #1, their content will not be up to my standards. Out of approximately 15 test articles over the last two years, I’ve come out with four writers who have excelled and exceeded my expectations!

As a freelance writer, I’ve written for some incredible websites and people, but it’s not always consistent. I’ve lost clients because of seasonality, updates, or long-term vacations. Learning someone’s writing style and processes can be difficult, but it’s a great way to earn income if you can keep a consistent client base.

Rachel Grenis, Writer, Oahu Travel Secrets

Communication and Organization Are Key

I have been a regular freelance writer for 13 years, and the number one thing companies do wrong when working with freelancers is poor communication.

Often, companies will talk with a number of freelancers, but they’ll only tell the ones they’ve decided to work with. The ones the company doesn’t want to work with are generally left in the dark about the company’s decision. This is not how you deal with freelancers. Companies should have templates on hand for form messages when they’ve decided not to work with a freelancer so they can easily send out a message to let freelancers know if they can expect to be getting some work from the company or not. It’s so easy to send out a form template nowadays that companies really have no excuse for poor communication.

Something else companies need to do better with is knowing if a project is 100% going forward or not. I’ve had many companies tell me they’ll be ready to go on a certain date and lead me to believe something is going forward only to disappear when that date comes because they are not as prepared as they thought they were. If you engage with a freelancer, you should know with 100% certainty that your project is going forward and you will have the budget you need to complete it. If you are telling freelancers that you are ready to go only to have to cancel the project (or, in worst-case scenarios, ghost the freelancer and pretend you never had a conversation with them), then your company is poorly organized and you need to address that.

I’ve had many wonderful freelancing experiences with various companies, but when it goes sour, those are usually the two main culprits. Lack of communication and lack of organization is not acceptable if you are looking to hire freelancers. Get your proverbial ducks in a row first and have a minimum amount of integrity before you look to work with a freelancer.

Rob Swystun, Content Strategist, Rob Swystun Content Marketing & Ghostwriting Inc.

Clear Briefs Enhance Writer Performance

I have experienced both sides of the freelance writing spectrum: being a freelance writer hired by others and later becoming a solopreneur who hired freelance writers to assist my clients. One crucial aspect that greatly benefits freelance writers, regardless of their level of experience, is receiving a clear and concise brief.

By this, I don’t mean merely providing them with copy points and content format. It entails sharing the keywords, objectives, tone and manner, and other pertinent details about what you aim to achieve with the content.

I have found it particularly helpful to run through the content strategy of the client with the freelance writer. This gives them a deeper understanding of the brand and its messaging, enabling them to introduce creative ways to effectively present the copy points you have provided. By stepping into the client’s shoes, they can better align their writing with the client’s vision.

Joyce Tsang, Content Marketer and Founder, Joyce Tsang Content Marketing

Quality Challenges in Hiring Freelancers

I am in the academic and content writing field, but I must say, hiring freelance writers is tough. Some freelance writers don’t even understand what they do.

There was a time I needed a freelance academic writer urgently for some gigs. 99% of those who applied shared irrelevant samples (that were not related to academic work).

Also, some of them understand what they do, but their work is of low quality. As a content writer myself, I understand that it’s hard to find writers who truly understand what quality content means and are able to write it.

So what I do is add writers who are great to my list so that when next I need one, I will select one of them rather than looking for a new one.

If I don’t do this, I will talk to other writers to recommend freelancers they trust with their work. This really works for me.

Maryam Awodele, Content Writer, Steady writer

Expert Input Elevates Freelance Content

Yes, for B2B SaaS reviews, I’ve hired 10+ freelance writers. In general, my experience has been great. Only one ‘flaked out’ on the assignment (and they weren’t really a freelance writer, but a practitioner who said they would be up for a freelance writing assignment). The freelance writers I’ve worked with have been professional, speedy, and thoughtful.

In my experience, what worked best was finding freelance writers who were willing and able to source input from experts to include in the content. Infusing the content with the voice of experts and authorities on the topic adds a lot of credibility to the piece and differentiates it from AI and low-quality content. Also, writers who made original screenshot images with arrows and text to show the reader something specific added great value that AI can’t provide.

What didn’t work was the combination of my ignorance of freelance writer costs and my inability to know what would make for a strong “E-E-A-T” post. For example, early on in the development of content on, I worked with one freelance writer who turned out to be on the very high end of the cost-per-word spectrum—87 times what a SurferAI post would cost—and delivered a piece that was comparable in quality to what SurferAI would produce.

In general, you get what you pay for, but it certainly helps to know a rough cost range and what good looks like for content that could rank or do what you need it to do for your business.

Joe Kevens, Founder and Director of Demand Gen, B2B SaaS Reviews 

Consistency Through Clear Guidelines

I often hire copywriters on Fiverr or Upwork for my SEO clients. Today, after several years in the industry, I consistently work with the same individuals. I must say that, except in a few cases, the experiences have been very good.

For me, the key lies in one thing: providing clear and concise content guidelines. It’s challenging to expect someone unfamiliar with a topic to write about it effectively, so detailed guidelines—including the keywords to use, proposed article structure, and examples of similar articles—can greatly impact the final result.

Marco Genaro Palma, Freelance CMO and SEO Consultant,

Over-Communicating Aids Freelance Collaboration

I’m a freelance writer who has hired other freelance writers as part of my team. Until I made my first hire, I didn’t realize the complexities businesses face in choosing and working with freelancers. This gave me a unique perspective on my role as a writer and how I can give myself an advantage when approaching new clients.

In my experience in hiring freelance writers, I realized the value of over-communicating and the need for consistent processes. I had to be very specific about formatting needs, how to submit content, etc. And even with step-by-step instructional videos, some of my writers still didn’t “get it.”

I hired a great writer based on her writing samples. I made timely payments, gave positive feedback, and kept solid lines of communication. She seemed genuinely excited to work together. But within a few weeks, she completely ghosted me. A few days later, she posted on LinkedIn begging for freelance writing work. To this day, I’m still not sure what pushed her away with no explanation.

Overall, hiring freelance writers was a mostly positive experience. But it can be a very mixed bag. I don’t think writing samples alone are enough to make quality hires. I would suggest looking at the full package: who they’ve written for, their track record, portfolio, pay expectations, how they communicate, and references. Also, don’t underestimate the power of a paid trial. These can usually tell you everything you need to know and set the tone for what’s to come.

Alli Hill, Founder and Director, Fleurish Freelance

Freelancers Need Specificity and Timeliness

I am the author of nine published books and someone who has been contributing/freelancing in the writing arena for over 30 years. Magazines, newspapers, and online media are great to work with and understand the word “freelance.”

Companies, however, tend to treat you like an employee and expect you to attend meetings upon meetings when you are only paid to write. Freelancing is a service/contract work. Be specific with what you want and when. Then let them deliver! Freelancers—be sure to deliver high-quality content and ON TIME. It’s a great relationship when it is handled properly.

Lorraine Bossé-Smith, Chief Solutions Officer, Concept One LLC

Clear Briefs Mitigate Rushed Writing Errors

I’ve been using freelance writers for the last three years to write content for me. On the whole, the experience has been positive. The only problem I’ve encountered on a repeated basis is writing that is rushed, which ends up having spelling and grammar errors.

This is usually because the freelancer has taken on too much work and cannot easily meet their deadlines. Otherwise, as long as you create a clear and detailed brief, the writing typically meets my expectations.

Marc Bromhall, Founder, StorageBuddy

Freelance Writing Isn’t As Simple As It Seems

Hiring or becoming a freelance writer isn’t a simple one-click button. You need to prepare briefs, be specific, and work hard to make sure it all comes out right — but it’s better than simply using an ethically-compromised mindless AI to generate static, generic, and boring content for you.

Want to hire a professional agency for your copywriting and content marketing? Contact Mandel Marketing today.


→ Need to improve your writing? Check out An MFA For Your MBA, by Phillip Scott Mandel, out now!