Common Pitfalls of Hiring Freelance Writers (And How to Avoid Them)

By: Robert Jellison — September 12, 2018

You’ve read all about why content marketing is important. You know it’s right for your business. After some thought about whether to hire an in-house writer or outsource, you’ve made your decision—you’re going to hire a freelancer.

Congratulations! That’s the right call. The benefits of outsourcing are huge.

But now you’re faced with another big decision. Which freelancer are you going to hire? There are thousands out there, and to hear them talk, each one would be a perfect fit for your business.

It helps to read up about how to hire great freelance writers before making your decision. You need to hire a writer who:

  • Has the right subject specialties. Is their focus on healthcare, marketing, sports, travel, or something else?
  • Does the kind of writing you need. Do they write essays, product descriptions, or blog posts, or something else?
  • Has any additional skillsets you require: SEO, email marketing, lead generation, transcription, etc.
  • Has a strong portfolio that you can review to make sure they’re good at what they do.

Those are the basics. But if you really want to rest secure in the knowledge that you’ve hired an amazing freelancer who is going to deliver exactly the content you need, you have to go beyond the basics.

Read on to learn about the common pitfalls you should watch out for when hiring a freelancer writer, and how to avoid them.

1. You Need to Make Sure Your Writer Can Match Your Company’s Style

When you hire a freelancer, of course you’re going to look at their qualifications. As mentioned, you want someone who’s an experienced writer, and also has enough knowledge of your industry that they’ll feel comfortable writing about it.

But it’s not just about your industry. You also need a writer who will be able to hit your desired brand voice

Branding is a crucial part of the relationship you have with your customers, and it’s also something that Google values very highly. Some marketing experts have even declared that branding is “the future of SEO.”

It’s important. But how can you be sure your freelancer’s writing will fit your brand?

Onboard Your Writers With a Brand Style Guide

If you want your writers to be able to nail your business’s style, you need to provide them with a clear set of guidelines—what’s also known as a brand style guide.

Many businesses prepare style guides that comprehensively describe their brands. Some spend enough time and attention on them that the guides are themselves strongly branded and make effective advertisements.

On the following page from its style guide, Alienware warns its writers to stay away from the word “play.” It also describe its company’s philosophy.

alienware style guide

Note that both the writing and aesthetics of this page—and the entire style guide—are bold and distinctive, providing its writers with valuable context that helps them match Alienware’s style in the future.

Urban Outfitters, on the other hand, uses its style guide to emphasize that they communicate with its customers on the same level, as a peer.

urban outfitters brand style guide

Your style guide doesn’t need to be flashy. The Editorial Guidelines section of Adobe’s style guide does not feature any pictures—just text. It delivers its instructions clearly and simply, with high information density.

A comprehensive style guide will include concrete answers to specific questions, including but not limited to:

  • Punctuation style (when to use single quotes versus double quotes, whether to use hyphens or dashes, etc.)
  • Grammatical choices (is it okay to start sentences with conjunctions like “and”?)
  • Formatting and capitalization (which words in headings should start with capital letters?)
  • Numbers (should your writers use numerals or spell them out?)

Beyond that, it should declare your business’s purpose and philosophy, and describe the tone you would like your writers to match using at least five adjectives. (In the example, Adobe includes more than eight, starting with honest, visionary, smart and caring.)

If it contains examples of what you’d like your content to sound like, that’s even better.

The more information you can provide to your writers, the more likely they’ll be able to match your business’s style.

Learn to Recognize Writers Who Can Match Your Voice

Unfortunately, even given a comprehensive guide, not every freelancer will be able to write in your desired voice.

Tone can be tricky. Some writers struggle to keep their writing conversational. Others find it hard to produce writing that is technical or academic.

You don’t want to develop a relationship with a writer, only to realize after commissioning half a dozen projects that they’re just not capable of delivering content in the tone that you need. That’s not a situation that anyone wants to be in—you, or the writer.

To avoid it, you have to learn a little bit about writing yourself. You need to be able to look at a writer’s samples and evaluate how they’ll do at writing in your company’s style.

You need to ask every writer you hire for samples, and look them over to determine whether they’ve either:

  • Written in your desired brand voice in the past, or
  • Demonstrated so much versatility that you’re confident they’ll be able to hit it regardless

Doing this turns one simple task—determining whether a writer is qualified—into a complex, multi-stage process.

  1. First, you have to review enough examples of brands with distinct voices that you can tell the difference between a writer hitting one, and a writer trying and failing.
  2. You have to ask your writer for extensive samples, preferably going beyond the basic portfolio that many writers who work on freelance sites provide.
  3. You have to review the writer’s samples.
  4. Last, you have to cross-reference them with ones from all the other writers you’re looking at.

If this sounds like a bit of a pain—well, it is. It’s important, necessary work, but it is work, and it takes time.

2. You Have to Hire a Writer You Know Can Communicate and Deal With Criticism

Let’s talk a little bit more about entry number 2 in the list above—asking for those samples.

It’s an unfortunate fact that creative types often have big egos. Most freelancers will not balk at being asked to provide writing samples beyond what they have listed in their portfolio, but some will.

If a writer you’re considering refuses to do that, it’s a good sign that you shouldn’t hire them. You want a writer who is accommodating and easy to work with, not one who will always push back.

You need to pay attention to things like this in the hiring process, because your freelancer’s ability to communicate and accept your feedback is just as important as their skill at writing. If you ignore red flags that pop up in the early stages, you’ll regret it later.

Handling Criticism

Dealing with critical feedback is part of a freelancer’s job.

A good writer will get it right most of the time, but nobody gets it right all of the time. Whoever you hire, now and then, you will have to give them feedback and ask them to change how they do things.

When you do, you need to know they’ll handle your feedback well.

Sometimes you’ll need to tell your freelancer to fix something even when they didn’t do anything “wrong.”

There will be times when your freelancer writes something that’s good, but nonetheless is not what you’re looking for—a genuinely hilarious line in a blog post that’s not supposed to be funny, for instance.

In cases like this, you don’t want to have to convince your freelancer to fix the issue. You want them to make the changes promptly, without it turning into a big deal. You also want them to learn from your feedback so they don’t do it again.


When you’re approaching a project deadline and you need something fixed ASAP, the absolute worst word to hear from your freelancer is “why?”

Staying in Communication

It’s just as bad when your writer drops off the face of the Earth in the middle of a project. And make no mistake, this happens.

When it does, there’s not much you can do. You can terminate your relationship with the freelancer, of course, but if they fail to deliver on a project that you need imminently, the damage may be done.

What can you do to prevent these scenarios?

Establish Clear Communication Rules

It helps to lay some simple ground rules for how you and your freelancer will communicate. Do this right from the start.

When you do, make sure to be explicit about the following:

  • The hours you expect each other to be available.
  • How long it’s acceptable to take when answering emails.
  • What kind of progress reports they should deliver, and how often.
  • How you intend to deliver feedback or request changes.

Vet Your Writers for Their Communication Skills

As before, the clearest set of guidelines in the world won’t help you much if you hire the wrong freelancer.

Unfortunately, it’s not always easy to tell the wrong ones from the right.

There are freelancers with poor communication skills who have high feedback ratings because they are skilled writers. If you hire someone like that, things will probably go swimmingly—at first. Until suddenly, they don’t.

It helps to review a list of red flags to watch out for. Ultimately, to avoid hiring somebody who will cause problems for you, you need to rely on your intuition a little bit, and get good at feeling out whether somebody will have a difficult personality before you hire them.

3. You Need to Be Familiar With Your Writer’s Speciality

As mentioned, when hiring a freelancer, you want somebody who knows enough about your industry to write about it.

But you also need to do a little homework too, and learn about your writer’s specialty. “Freelance writing” is an umbrella term. There are a lot of niches within it. They all have their quirks, and you need to know about them if you want to avoid misunderstandings with your writers.

What Are Your Writer’s Expectations?

For instance, not every writer you talk to will have the same expectations when it comes to who their work will be attributed to. Ghostwriters are a good example of this.

Ghostwriters are not publicly credited for their work; that’s how ghostwriting differs from copywriting. It’s entirely reasonable—and very common—to ask ghostwriters to sign non-disclosure agreements when hiring them, stipulating that they not tell anyone about the job. The same request might be taken very badly by a more typical copywriter. After all, many copywriters are explicitly looking to build up portfolios that they can show to clients in the future.

ghostwriting confidentiality agreement

NDAs like this are commonplace for ghostwriters, but may seem wildly inappropriate to other freelancers.

This means that when you commission a project, you need to decide whether you want a copywriter or a ghostwriter, and make sure you’re approaching somebody in the right niche.

Industry-Specific Jargon

For another example, take transcription.

Some freelance writers also offer transcription services. You can hire them to take audio or video files—like interviews—and type them up in written form for publication in your magazine or on your website.

Most freelancers offer three types of transcript:

  • Verbatim transcripts are documents that exactly match the audio files. Every sentence is unchanged, with all the “ums” and “uhs” left in.
  • Edited or “clean” verbatim transcripts have filler words and false starts removed, and minor grammatical errors corrected.
  • Intelligent transcripts are substantially altered. Entire sentences may be removed or rephrased. Intelligent transcripts are ready for publication.

Before scrolling down, quickly answer this question in your head. Which kind of transcription would you guess is the most difficult to produce?

types of transcript

There’s a good chance you guessed intelligent transcription.

It makes sense. It’s the farthest version from the original. Editing an interview sounds like a lot of work. It sounds like it would take time. And it does—but not as much time as producing a verbatim transcript.

That’s right. The option that sounds the simplest is the most difficult.

It turns out that cleaning up an interview isn’t that challenging. It’s second nature for many writers. On the other hand, capturing all those “ums” is hard. Verbatim transcripts can take several hours longer to produce.

For this reason, verbatim transcriptions are usually the most expensive. This leads many clients to request them, assuming that they’re receiving a superior product. The opposite is true—verbatim transcripts are usually pretty hard to read.

When you and your freelancer don’t completely understand each other, it’s very possible to end up paying more and waiting longer for a worse product.

Almost every freelance niche comes with similar pitfalls.

A good freelancer will be more than happy to explain any jargon they use or assumptions they make, if their client asks. But you can’t assume they’ll always take the initiative in doing so.

This means that when you make the decision to outsource, you still need to do some research. Find popular, authoritative websites for whatever specialization you’re interested in, and read up until you feel you can commission a project, secure in the knowledge that you and your freelancer are on the same page.

Is There An Alternative?

To recap, when you hire a freelance writer, you need to:

  • Ensure that they’re a competent writer and that they can match your brand voice.
  • Provide them with a comprehensive style guide.
  • Vet them for their responsiveness to criticism and communication abilities.
  • Learn enough about their freelance niche that there won’t be any misunderstandings.

There’s a chance that after reading all that, you feel like giving up on the whole “outsourcing” idea.

After all, it sounds like a lot of work.

But before you give up, take a minute to remember the advantages it offers over handling your content creation in-house.

Outsourcing is much cheaper (potentially by tens of thousands of dollars annually) than paying for an in-house writer, and grants you access to a more diverse pool of specialty writers than it’s practical to keep in-house.

But you’d be forgiven for wondering if there’s any way to make the whole thing into less of a headache.

There is. You can sign up to a platform that takes the lengthy and stressful process described above and handles it all for you.

The Perfect Amount of Control

One question clients often ask us at is, “Can I choose my own writer?”

Our response is, “We arrange things so you don’t have to.

Picking your own writer seems appealing, from a distance. But the control it offers is offset by the amount of work it takes. To do it right, you have to learn a whole new skillset. That takes time—time that you could spend running your business.

With, you don’t have to worry about hiring an incompetent writer, because we vet all of our writers rigorously. We accept fewer than 1% of the writers who apply to our platform. When you’re assigned a writer on, you know right off the bat that they’ll be in the 99th percentile.

We don’t stop there. We believe you shouldn’t have to worry about whether your writer can match your brand voice, or whether they’ll be a good communicator. You certainly shouldn’t have to worry about any industry-specific jargon they might use.

We know all of our writers. When you commission a project on, we pick a writer for you who we know will be able to meet your needs: somebody who knows your industry and matches your style. When you create a business profile on, we walk you through creating a style guide.

In addition to their competence at researching and writing, we also vet our writers for their communication skills. Our revision procedure standardizes the process of delivering feedback.

With our Professional plan, we assign you an account manager who will step in and facilitate communication between you and your writer, in the very unlikely event that there’s a disagreement. This rarely happens, but we believe it’s important to offer it as a backup option.

With, we don’t just want to provide great content. We also provide peace of mind.

Of course, if you work with a writer and it goes well, our system is designed to weight your feedback very heavily. If you want to work with them again, you will. 

Providing great content is what our writers do best. Matching you with your ideal writer is what we do best.

If you want the benefits of outsourcing your content creation without all the hassle that comes with it, contact us.

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