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Managing Freelance Writers: How To Find, Train & Retain Top Talent

Freelance writers can greatly increase ROI, but you have your work cut out in managing them. Here's how to find and train them – and let them go, if needed.

For most, the benefits of using freelance writers for your digital marketing agency or business far outweigh the challenges.

One of the greatest pros is the higher ROI you may enjoy as a result of not having to hire a full-time writer in-house, especially when content volume doesn’t call for it.

However, you may experience challenges around timeliness and getting freelancers to follow your outlines and direction.

There are other challenges, such as training them for growth and retaining them for the long haul, too.

And then there’s the most challenging situation of all – ending the contract with a freelance writer who just isn’t working out.

Outsourcing content creation comes with risks, as bad hires can damage your company image by plagiarizing content or spreading harmful gossip.

In this article, you’ll find tips to help avoid these potential pitfalls and make the most of your freelance writer relationships by learning how to find, train, retain, and even let go of freelance writers in the best possible ways.

How To Find Online Writers

Successful agencies have clients across various niches and can’t expect one writer to be an expert at everything for each client.

In fact, I’ve met only a few writers who write proficiently for every client.

Those types are difficult to find, and if you do discover one of these “factotum” writers, it’s best to retain them.

These freelance writers have the endurance to consistently turn out quality work.

They possess the desire to learn, and the discipline to follow instructions on things like formatting, citations, style, etc. that improve your content quality.

But these factotum writers are tough to find.

Recently, a long-standing client in the aftermarket auto industry asked us to ramp up content output.

This client needs over a year’s worth of product descriptions – more than 20,000 SKUs among a few agencies.

The writing requires a deep knowledge of the world of aftermarket automobile accessories within a few different model types, from quarter-mile muscle cars to off-roading.

I had two auto experts on my freelance staff but needed a lot more.

I launched some LinkedIn ads that were very specific regarding the subject matter.

It was clear that if the freelance writers didn’t understand the niche, they shouldn’t apply.

That didn’t happen. Just 2 out of every 10 applicants had the skills and knowledge required.

With that being said, here are a few tips to help you find the right freelance writers for your project online.

For Targeted Niches, Seek Journalists First

LinkedIn has been my go-to for the past five years when searching for freelance writers or other employees.

The more targeted the niche, the more you’ll need to search for a subject matter expert who can actually write. This is where journalists are great targets.

I work with many journalists across various top-tier publications within their niches, from finance to motorcycles.

Full-time writers within smaller niches are typically hungry for money.

Read the top publications and reach out to the writers via email or social media.

Some may be under contract or don’t want their name published.

Simply sign an NDA with them (I have loads of these, especially for my freelance ghostwriters in granular niches).

Another wise place to check is HARO (Help A Reporter Out).

You can create listings there as a business or agency looking for a specific type of expert journalist.

Also, Search Where Your Target Subject Matter Experts Hang Out Online

Thousands of forums exist online. Find one that speaks to the subject you’re writing about, and simply ask if any freelance writers are there.

You may be surprised.

Be Super Specific In Ads

Don’t just say you’re looking for an automotive product description writer.

Say you’re looking for a product description writer for “interior, body panels, and engine parts for first-generation Ford Mustangs.”

Have fun with it, too. You could say something like, “If you don’t understand the difference between a 1966 and 1967 Mustang, continue your search.”

Ask For Samples, Not Resumes

I know writers with zero writing education who create better content than those with an MBA in Creative Writing. Schooling doesn’t tell the story. Samples do.

Don’t discuss pay within ads. But do discuss money within the first email thread. This will keep you and the applicant from wasting any time.

Do quick research before responding. A quick Google search of the applicant’s name and a look through their social media profiles can reveal much.

If you’re looking for a freelance motorcycle writer whose social media feeds don’t show one motorcycle, it may be wise to move on. But with that said, some of the best writers have no social media presence at all.

Create a template for responses. I create templates for every response to interested freelance writers.

I also personalize each message after a quick bit of research on them or how they personally respond to the outreach.

My ultimate goal is to find freelance writers who have intrinsic value now, plus the ability to grow and prove themselves within their work.

Here are five must-have qualities in freelance writers:

  • They’ll never plagiarize. Ever. You don’t want to see a whiff of “borrowing” the work of others in their samples.
  • They’re highly specific and accurate. No research, you’re out!
  • They respect deadlines. Three strikes and you’re out.
  • They pay attention to directions/outlines. All of my freelance writers are provided “SEO Content Templates” for each piece of content they write. These are basically outlined for both content creation and SEO. The steps are clear, typically orderly, and always include the exact subtopics to use. They must follow directions, and the simpler the output, the better.
  • They make only minimal grammar mistakes/typos. Writers make mistakes. That’s why I mention “minimal” here. And every business or agency should also have copyeditors on staff, even if it’s just another set of eyes from a non-writer in the company/agency.

Now it’s time to train them so they can grow and prove themselves constantly within their work.

How To Train Freelance Writers To Keep Them Growing

Agencies or business owners tend to either overthink this piece or disregard it entirely.

Training your freelance writers to keep them growing will not only benefit you but build a respect-based relationship that will also benefit the writers, as well.

And when your writers are satisfied in their work, feeling respected and fulfilled, they not only stick around but tend to put out their best work.

Here are two tactics that have worked for my business over the years.

Constant Education On Writing And Subject

A portion of my full-time employees’ weekly workflow is reading five hours weekly about their subject matter.

This is a tough ask for a freelance writer who is not obligated to do anything but the writing task. So the solution is to provide them with a consistent flow of education.

The simplest ways are sending books on writing and the subject matter they’re covering, paying not only for online seminars but also for their time to attend them, and sending them to conferences within their niche.

Challenge Writer Growth With Out-of-niche Content Creation

I was hungry when I began as a freelancer. The more work I got, the more money I made. I realized quickly how much faster I could learn by deeply researching a subject and then writing about it.

Writing is the ultimate learning tool, not only for the subject matter itself but the actual writing process.

When a freelance writer is comfortable writing content within their expertise, the challenges are minimal.

But challenge them with a topic out of their niche, and they’ll grow. Be wise here, though; only delegate the entry-level work to begin with.

Many writers who have done this for me are now writing for a few different subjects, and some grew passions for the respective subjects over time, becoming SMEs there, as well.

How To Retain Freelance Writers

First, remember that people have different creative peak times. For example, nearly all of my top freelance writers submit content to me after midnight.

This is common for creative types and is based on what professionals call chronotype.

As ABC News journalist Diane Macedo simply puts it in The Sleep Fix, chronotype is:

“What time your circadian rhythm hits its daily highs and lows and is what determines whether you’re naturally inclined to fall asleep or wake early or fall asleep and wake up late.”

Most of the writers I know are the proverbial night owls, and I don’t expect to hear from them in the morning hours.

Even if they prefer to work during the day, creativity requires focus and constant interruptions can hinder the writing process.

Give realistic deadlines and don’t micromanage. You’ll earn more respect, and the writers will certainly stick around longer.

The rest of the retainment process comes down to monetary and educational incentives.

If I have a top producer, I’ll add extra money to the invoice as a quick thank you/performance bonus when warranted.

Nothing crazy, but just enough every so often to let those writers know I respect their time and energy.

A good target is 10% of an invoice every few months.

Taking on a much bigger project requiring many writers instead of one, such as my auto product description above? Amplify the top producer’s unknown bonus to 20%.

It may cut into the profit margins slightly, but that slight decrease will increase overall revenue in the long term because those writers will be more incentivized to do more quality work.

Another incentive includes adding to their personal growth factors, such as sending them to conferences, online writing seminars, or the latest books on the subject.

I also know the personal interests of my freelance writers, so if I’m sending them a book on writing development, I’ll send a book on their favorite interests.

Also, and this is as big as the bonuses and education – never overwork quality freelancers or exert nonsense pressure about deadlines.

They’ll either drop you or provide horrible work that will cost you more to fix in the long run.

Pressure for deadlines is typically the project manager’s fault. You can’t load up a freelance writer with 12 hours’ worth of writing work and expect them to turn it around in a day.

Good writing requires time for writing and taking breaks in equal measure, the latter allowing a writer’s mind to refresh and edit with clearer thoughts.

I have a 10–15 day turnaround time for most of my writers for pieces.

I typically work a month ahead for campaign clients, and if a client asks for something that needs a quick turnaround, I reach out to the freelancers before responding.

A few other factors that will help you retain your freelance writers include:

  • Constant communication. Plan weekly or monthly meetings, even if only a 15-minute catchup call to discuss workflow. Also, email/text them at minimum weekly to ask if they’re struggling with anything or need a hand with work. I email each freelancer every Monday, asking them if they are on target for deadlines and need any help.
  • Pitch new content. This is why it’s wise to understand your writers’ personal interests (passions are even better!). If another client or product/service line arrives, pitch the content to the writers you have already trained. I also found a foodie through the auto description writer hunt, which added serious value to content creation for a new client. This saved me much energy and time finding and training a new writer.
  • If local, schedule a surprise lunch or dinner. I work with dozens of freelance writers, but a few are local. So sometimes I’ll just email them asking them to meet for lunch or dinner at one of their favorite places. Not local? Read on.
  • Send lunch or a food/beverage care package. For those freelance writers that are not local, surprise them every so often with a food or beverage. A quick note from experience: don’t send meat to a vegetarian (or booze to a recovering addict).

How To Let Go Of Writers

Unfortunately, not all writers will make the cut. Some may have freelanced for your business or agency for years but suddenly became tardy or their quality slips.

The sooner you recognize a problem freelance writer, the easier it is to let them go.

For newbie freelancers, I typically give the standard three strikes. This is after I worked with them and trained them to match the voice of the client or clear up any confusion.

Longer-term freelancers each present their own unique set of challenges.

Sometimes family or personal issues surface. I’ve learned to always have a backup writer in case of emergency.

However, the problem is that SMEs who can actually write are extremely difficult to find (remember the auto product description example above).

Here are two quick tips on letting go of a freelance writer regardless of the situation:

  • Pay what’s owed. Even if it’s $10, pay them for work they completed.
  • Explain why they’re being let go, in detail. A quick email with bullet points as to what went wrong will not only be beneficial to your sanity but also the writer’s ability to learn from their mistakes. That writer may turn things around and you may run into each other on a client account or even end up working together again. That email may have done more than you know.

Always try to keep the relationship in good standing.

Humans make mistakes, whether it be minor grammar issues or more serious ones like plagiarism.

The ultimate successful freelance writer for a company or agency will have two main qualities: subject matter expertise and writing skills.

When both are present, your business will flourish, and your profit margins will increase because you’re using freelance writers.

The first problem is finding successful types.

The second problem is training and retaining them.

The third, which hopefully you’ll never have to experience, is terminating their contracts.

These tips were designed to ease these issues and save you much time that could be better spent growing your business.

More resources:

Featured Image: Ariya J/Shutterstock

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VIP CONTRIBUTOR Ron Lieback Founder/CEO at ContentMender

Ron Lieback is the author of “365 to Vision: Modern Writer’s Guide (How to Produce More Quality Writing in Less ...

Managing Freelance Writers: How To Find, Train & Retain Top Talent

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