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5 Lessons I Learned as a Content Manager Outsourcing Work to Other Freelance Writers That Can Help You

The following is a guest post by Laura Pennington.

Publisher Note: This article gives you an inside look at what content managers go through on a daily basis, which can help you as a freelance writer. How? By knowing what’s happening on the hiring end, you can avoid some of the faux pas that can get your queries, writing samples and responses to freelance writing job ads sent to the slush pile. Thanks to Laura for such a detailed post.

Managing Content for 400 Blogs Per Month — Oh Boy!

I own a freelance writing business. In 2015, I took on the role of content manager for two different companies. One required delivery of more than 400 blogs per month. It was not the first time I had hired or managed other writers, but it definitely was the highest volume project I had ever been a part of and it required me to strengthen up managerial skills quickly.

The other project required giving titles to, receiving, and editing the work of about 9 writers. I ended up resigning from both positions and for different reasons, but I learned some amazing lessons about hiring and managing other writers in the process. As it turns out, the second smaller project was actually MUCH more of a headache, and I’ll explain why below.

Project #1: Large volume of blogs.  I got to select writers, titles, delivery, and payment structure to writers.

Project #2: Volunteer writers completing an “internship.” Site owner selected titles and I had to coordinate the writers completing their work, at which point I would edit and publish it.

Mistakes to Avoid When Outsourcing to Other Freelance Writers

If your writing business is growing and you need help or if you are ever asked to step into a content manager role like this one, these tips should help you avoid some common mistakes that I learned the hard way.

How you hire and interact with writers can have a significant impact on whether or not you’re successful as a writing outsourcer or content manager.

Freelance Writer Outsource Challenges

Lesson #1: Work Samples Always, Always Matter

Project #1: Since I had to build up a pretty large team quite quickly, this is something I did right. If there were any errors in someone’s writing sample (even one comma) they were not hired.

I knew that with such a large volume I could not afford to keep up editing 400 blogs or having to manage an editor fixing that many mistakes. Our request for edits was so minor that I think we were asked to revise blogs less than 10 times total. My system of screening writers worked really well here.

Project #2: Writers here tended to be much younger and did not call themselves professional “writers”. Their work samples often indicated that lack of writing experience and this led to a lot of editing work overall.

Lesson learned: If someone cannot be bothered to send you good material as a sample, they are likely not that committed in terms of their on-the-project work either.

Lesson #2: About 1/8 of Writers Will Completely Flake on You

I’ve heard all kinds of metrics on this, but in my experience, one out of every six or eight writers you hire will disappear and never complete work. As in, this person literally never replies to you again or completes the first assignment.

Project #1: I always hired extra help knowing that some people would flake, and the invoice system I used required their work to be both submitted on time and approved in order to be paid.

Project #2: The drop-off rate looked different here, likely due to lack of writing experience. Every time we did a round of hiring, one or two girls would get “overwhelmed” after two or three weeks (and they were submitting one article per week.) Missing deadlines became a serious issue.

Lesson learned: Never pay someone until they’ve completed the work properly and hire extra freelancers to cover yourself. Use a test project to weed out who is likely to comply with your submission requirements.

Lesson #3: You Cannot Make Someone Care About Their Work

This gets back to writing samples, but it applies to submitted work, too. This actually wasn’t an issue with the first project because I screened the writers well, but I was not the one making all hiring decisions on Project #2, so this lesson is actually the reason I resigned from this position.

Project #2: Since the volunteer writers knew I was the editor and that I had writing experience, they turned in work with 20+ mistakes in it. When that’s one writer, it’s troubling, but it’s unbearable when it’s half the writing staff being that lazy. They just assumed I’d pick up the slack.

Aside from being disrespectful to me and the site owner, it also meant that I was on the hook to pick up mistakes lest I have my professional reputation associated with a site riddled with errors. Despite the lower volume, I found that after attempting numerous ways to encourage writers or explain common mistakes, the writers truly just were not as invested in their work.

Lesson learned: Only work with people who have a commitment to quality in their work.

Lesson #4: Have a Fair but Firm System In Place

From day one, any editor or content manager should have clear expectations. Otherwise you’ll end up spending all your time writing emails, correcting mistakes, and sighing from frustration.

Ground Rules That Should be in Place When Hiring Other Freelance Writers

Here are the basic ground rules you must lay when hiring other writers:

  • How will work be submitted?
  • What writing guidelines must all writers adhere to prior to submission?
  • If there’s a problem (not sure of the title’s meaning, personal emergency, etc.), who should be contacted and by what method?
  • What are the penalties for late work or work that does not meet quality standards?
  • What is the method by which revisions will be completed?
  • How will writers be paid, and when?

Project #1: Despite the high volume, I laid these rules down from the test project with the writing team. Every single person knew the drill.

We used Trello as it was a free and visual method to keep track of what was due when. My VA could also tell when someone was non-responsive so we could reassign quickly, and the public nature of work submission made people less likely to turn things in late (I hate to say it, but fear of public embarrassment is a thing and it works on big projects like this.)

The only issue we had was invoicing because despite crystal clear rules, people were constantly sending it in late, sending the wrong PayPal address, etc. I tightened up the rules that if your work or your invoice was late/problematic, you would not be paid until the next invoicing period. I stuck to those rules even when writers resisted.

Project #2: As I shared above, you cannot make people care about their work. I regularly raised my concerns about work quality to the site owner and we tried to engage the writers, but the submissions did not improve.

As a volunteer army, there were no real consequences to turning in bad work or turning it in late. I also got annoyed with the number of emails I had to sort through dealing with personal problems i.e. “Sorry my article is four days late. I’ve been really busy with college classes.”

I will also share that I worked on another content management project in 2015 in which we used a method of giving each piece submitted a score between 1-10. Anyone who had an average score that dipped below 7 was given a warning, then removed from the project. This worked well! A three-strikes rule can also work if you have the patience to let someone make mistakes three times.

With no consequences, the workload just continuously fell on me and it was time to cut ties.

Lesson learned: Lay rules from the outset. If you can’t and you’re stepping into the position, determine what positive and negative reinforcement you can use to make things happen.

If you’ve tried everything and there’s little to no improvement, consider leaving. As a freelancer, we get to choose who we work with and your time is not worth accidentally re-creating a j-o-b with lazy coworkers.

Lesson #5: Reward Your Most Reliable Writers

Project #1: I had a few writers who I knew would:

  • Always turn work in on time;
  • Always step in during an emergency, like another writer flaking and missing an important deadline; and
  • Always communicate professionally with me.

I worked hard to form a relationship with these writers and give them bonuses where I could. One of those working on this project was an absolute star and now works for me as a content manager. So always be cognizant of how amazing people can continue to work and grow with you!

Project #2: As this was a volunteer group, I simply shouted out the best writers in our group calls and chats and made efforts to thank them personally where possible. Although this helped keep them inspired, it did little to address the dead weight we were dragging with less-committed writers.

Lesson learned: Working with volunteer writers can be very hard. With any writing project, give kudos to your top performers.

Whether you’re hiring other writers for a specific client project or you’re too busy to handle all the writing work you have, make sure you follow these tips to have the best possible chance of success.

Managing other writers is hard sometimes, but it can also be a rewarding and educational experience.

Next Time … In my next post, I’ll be discussing ways to streamline and speed up your freelance writing process. Time is money, so I’ll be sharing my top ways to get organized and produce quality work to maximize your output!

Your Thoughts

Have you ever hired other freelance writers? What’s your experience been like? I look forward to reading your comments below.

About the Author: Laura Pennington is a former inner city teacher and corporate employee who fled the grind in 2012 to work at home. Since then, she’s focused on SEO content for law firms and insurance agencies, writing everything from ebooks to blogs to video scripts. She now blogs at www.sixfigurewritingsecrets.com.


P.S.: Learn how to take your freelance business to the next level by outsourcing.

It’s the number one way to grow your business to the point where you’re earning more, without working more.

P.P.S.: We’re always looking for great guest posts.

Inkwell Editorial is a highly ranked blog (PR4), so feel free to send in your guest post to get in front of thousands of freelance writers.

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