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

For most people, the advantages of hiring freelance writers for your digital marketing agency or business outweigh the disadvantages.

One of the most significant advantages is the higher ROI you may enjoy as a result of not having to hire a full-time writer in-house, especially when the content volume is low.

However, you may encounter difficulties with timeliness and getting freelancers to follow your outlines and direction.

Other challenges include training them for growth and retaining them for the long term.

Then there’s the most difficult situation of all: terminating a contract with a freelance writer who isn’t working out.

Outsourcing content creation carries risks, as bad hires can harm your company’s image by plagiarizing content or spreading damaging gossip.

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

Where Can I Find Online Writers?

Successful agencies have clients in a variety of niches and cannot expect a single writer to be an expert in all areas for each client.

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

Those types are hard to come by, and if you do find one of these “factotum” writers, it’s best to keep them.

These freelance writers have the stamina to consistently produce high-quality work.

They have the desire to learn as well as the discipline to follow instructions on things like formatting, citations, style, and so on that improve the quality of your content.

However, these factotum writers are hard to come by.

Recently, a long-standing client in the automotive aftermarket asked us to increase content output.

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

The writing requires a thorough understanding of the world of aftermarket automobile accessories in a variety of model types, ranging from quarter-mile muscle cars to off-roading.

I had two auto experts on my freelance team, but I needed much more.

I ran some LinkedIn ads that were very targeted to the subject matter.

It was obvious that freelance writers who did not understand the niche should not apply.

That did not occur. Only two out of every ten applicants possessed the necessary skills and knowledge.

Having said that, here are a few pointers to help you find the best freelance writers for your project online.

Seek Journalists First for Targeted Niches LinkedIn has been my go-to for the past five years when looking for freelance writers or other employees.

The more specific the niche, the more you’ll need to look for a subject matter expert who can write. Journalists make excellent targets in this situation.

I collaborate with many journalists from various top-tier publications in their respective niches, ranging from finance to motorcycles.

Full-time writers in smaller niches are usually desperate for cash.

Some may be under contract or do not want their name to be made public.

Simply sign a non-disclosure agreement (NDA) with them (I have loads of these, especially for my freelance ghostwriters in granular niches).

Another good place to look is HARO (Help A Reporter Out).

As a business or agency looking for a specific type of expert journalist, you can create listings there.

Also, look for places where your target subject matter experts congregate. Online
There are thousands of online forums. Find one that speaks to the topic you’re writing about and simply ask if there are any freelance writers present.

You could be surprised.

Ads should be extremely specific

Don’t just say you’re looking for someone to write automotive product descriptions.

Assume you’re looking for someone to write product descriptions for “interior, body panels, and engine parts for first-generation Ford Mustangs.”

Have fun with it as well. You could say something like, “If you don’t know the difference between a 1966 and 1967 Mustang, keep looking.”

Request Samples, not Resumes.

I’ve met writers with no writing experience who produce better content than those with an MBA in Creative Writing. Schooling alone does not tell the whole story. Samples work.

Don’t talk about money in ads. However, do not discuss money in the first email thread. This will prevent both you and the applicant from wasting time.

Before responding, conduct a quick search. A quick Google search of the applicant’s name and a glance at their social media profiles can reveal a lot.

If you’re looking for a freelance motorcycle writer whose social media feeds don’t feature a single motorcycle, you might want to look elsewhere. However, some of the best writers have no social media presence at all.

Create a response template. For each response to interested freelance writers, I create a template.

I also personalize each message after conducting some preliminary research on them or observing how they personally respond to the outreach.

My ultimate goal is to find freelance writers who have intrinsic value right now as well as the ability to grow and prove themselves through their work.

Here are five qualities that freelance writers must possess:

  • They will never, ever plagiarize. Ever. You don’t want to catch a whiff of “borrowing” someone else’s work in their samples.
  • They’re very specific and precise. You’re out if you don’t do any research!
  • They adhere to deadlines. You’re out after three strikes.
  • They pay close attention to instructions/outlines. For each piece of content they write, I provide “SEO Content Templates” to all of my freelance writers. These are essentially laid out for both content creation and SEO. The steps are always clear, usually orderly, and include the exact subtopics to use. They must follow instructions, and the less complicated the output, the better.
  • They make only a few grammatical errors/typos. Writers make errors. That is why I use the word “minimal” here. And every company or agency should have copyeditors on staff, even if it’s just another set of eyes from someone who isn’t a writer.

It is now time to train them so that they can constantly grow and prove themselves in their work.

How to Educate Freelance Writers in Order to Keep Them Growing

Agencies or business owners either overthink or completely disregard this piece.

Training your freelance writers to keep them growing will not only benefit you but will also build a mutually beneficial relationship with the writers.

And when your writers are happy with their jobs, feel respected and fulfilled, they not only stay but also produce their best work.

Here are two strategies that have proven to be effective for my company over the years.

Constant Education On Writing And Subject

Reading five hours per week about their subject matter is part of my full-time employees’ weekly workflow.

This is a difficult task for a freelance writer who is not required to do anything other than write. As a result, the solution is to provide them with a steady stream of education.

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 in their niche are the simplest ways.

Challenge Writer Growth With Out-of-niche Content Creation

When I first started working as a freelancer, I was starving. I made more money as my workload increased. I quickly realized how much faster I could learn by thoroughly researching a topic and then writing about it.

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

The challenges are minimal when a freelance writer is comfortable writing content within their area of expertise.

However, if you challenge them with a topic outside of their area of expertise, they will grow. But be cautious; only delegate entry-level work at first.

Many of the writers who have done this for me are now writing for a variety of subjects, and some have developed interests in those subjects over time, becoming SMEs in those fields as well.

How to Recruit and Retain Freelance Writers

To begin, keep in mind that everyone has different creative peak times. For example, almost all of my top freelance writers send me content after midnight.

This is typical of creative types and is based on what professionals refer to as chronotype.

Chronotype, as ABC News journalist Diane Macedo puts it succinctly in The Sleep Fix, 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.”

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

Even if they prefer to work during the day, creativity necessitates concentration, and frequent interruptions can stymie the writing process.

Set reasonable deadlines and avoid micromanaging. You’ll gain more respect, and the writers will undoubtedly stay longer.

The remainder of the retention process is based on monetary and educational incentives.

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

Nothing out of the ordinary, but just enough to show those writers that I value their time and effort.

Aiming for 10% of an invoice every few months is a good starting point.

Taking on a much larger project that will necessitate many writers rather than just one, such as my auto product description above? Increase the top producer’s unknown bonus to 20%.

It may reduce profit margins slightly, but that slight decrease will increase overall revenue in the long run because those writers will be incentivized to produce higher-quality work.

Another incentive is to increase their personal development factors, such as sending them to conferences, online writing seminars, or the latest books on the subject.

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

Also, and this is as important as the bonuses and education, never overwork quality freelancers or put unrealistic deadline pressure on them.

They’ll either abandon you or provide subpar work that will cost you more money to repair in the long run.

It is usually the project manager’s fault that there is so much pressure to meet deadlines. You can’t give a freelance writer 12 hours of writing work and expect them to finish it in a day.

Good writing necessitates both writing time and breaks, with the latter allowing a writer’s mind to refresh and edit with clearer thoughts.

Most of my writers have a turnaround time of 10–15 days for pieces.

For campaign clients, I typically work a month ahead, and if a client requests something that requires a quick turnaround, I reach out to freelancers before responding.

Other factors that will help you retain your freelance writers are as follows:

  • Constant interaction. Plan weekly or monthly meetings, even if it’s just a 15-minute catch-up call to go over workflow. Also, email/text them at least once a week to see if they’re having any problems or need help with their work. Every Monday, I send an email to each freelancer, asking if they are on track for their deadlines and if they require any assistance.
  • Propose new content. This is why it’s important to know your writers’ personal interests (passions are even better!). If a new client or product/service line comes along, pitch the content to the writers you’ve already trained. Through the auto description writer hunt, I also found a foodie, who added significant value to content creation for a new client. This saved me a lot of time and effort in finding and training a new writer.
  • If you live nearby, plan a surprise lunch or dinner. I work with dozens of freelance writers, but only a few are from my area. So I’ll sometimes just email them and ask if we can meet for lunch or dinner at one of their favorite restaurants. Not from the area? Continue reading.
  • Send a meal or a care package containing food and beverages. Surprise those freelance writers who are not local on a regular basis with a food or beverage. A word of caution from personal experience: do not send meat to a vegetarian (or booze to a recovering addict).

How to Say Goodbye to Writers

Unfortunately, not all writers will be selected. Some may have freelanced for your company or agency for years but have recently become tardy or sloppy in their work.

The sooner you identify a problematic freelance writer, the easier it will be to let them go.

I usually give the standard three strikes to inexperienced freelancers. This is after I worked with them and trained them to match the client’s voice or to clear up any confusion.

Longer-term freelancers bring their own set of challenges.

Family or personal issues may arise from time to time. In case of an emergency, I’ve learned to always have a backup writer on hand.

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

Here are two quick tips for firing a freelance writer, regardless of the circumstances:

  • Pay what you owe. Pay them for work done, even if it’s only $10.
  • Explain in detail why they are being let go. A quick email with bullet points outlining what went wrong will not only save your sanity, but will also allow the writer to learn from their mistakes. That writer could turn things around, and you could end up working together again on a client account. That email may have had a greater impact than you realize.
  • Always make an effort to keep the relationship in good standing.

Humans make mistakes, whether they are minor grammatical errors or more serious issues such as plagiarism.

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

When both are present, your business will thrive, and your profit margins will rise as a result of your use of freelance writers.

The first issue is identifying successful individuals.

The second issue is that they must be trained and retained.

The third option is to terminate their contracts, which hopefully you will never have to do.

These suggestions are intended to alleviate these issues and save you a significant amount of time that could be better spent growing your business.

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John Harper

#1 File Information bestselling author John Harper loves to dispel the myth that smart men & women don’t read (or write) romance, and if you watch reruns of the game show The Weakest Link you might just catch him winning the $77,000 jackpot. In 2021, Netflix will premiere Bridgerton, based on his popular series of novels about the Why Files.

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