Managing a Remote Writing Team of 8: Here’s What I Learned

I attributed my enthusiasm to everyone else, and it backfired heavily.

Not to make this sound as if I did the whole recruitment on my own…

I didn’t deal with hiring, payments processing, or any of this stuff. My perspective is editorial, but I did learn a thing or two that could turn the tide for you.

A little bit of context

I’m a writing graduate. Been in content and marketing a while, though never thought I’d end up here. Most of my experience is either freelance or startup/agency-related.

As of now, I’m a full-time content marketer at a fairly established AI company/startup. Well, you got me; startup culture is hectic. More fun for you!

We have freelance writers that contribute to the company blog and Upwork hires that submit articles for guest posting as part of our link-building strategy. The insights below derive from my experience with both groups (and perhaps beyond):

#1. Writing assessment results do not guarantee quality

Wildly unexpected. Throughout hiring, we proposed a writing assignment on top of reviewing written samples, and guess what?

Those who turned in an astounding piece in the screening process ended up delivering inconsistent quality when assigned a task. Some were so messy (in terms of grammar, structure, sentence flow, etc.) that we got to question if those were written by a human.

And as hyperbolic as this may sound, we later figured they were NOT. My inner writer passed out upon the idea that I was handed in a piece generated by AI.

Lesson learned: Have back-ups. Always. You don’t want to fall behind on your strategy because of 1or 2 unsuccessful submissions (I suppose you’d cut ties with the writer with the third trashy submission).

Plan at least 2 weeks ahead, and count in worst-case scenarios, say delayed drafts, writers bailing on you without notice, or computer-generated content.

#2. A content style guide goes a long way

Can’t emphasize this enough: It saved us so much time and resources having a clear-cut welcome kit (pretty much a style guide). It’s a one-time investment but serves you for good.

Bonus tip: I cover SEO basics too in it. So my idea of a writers’ welcome kit is an all-inclusive training material, supposedly shared with the team before they’d outline their first draft.

Here’s what it covers:

• Niche-specific terminology
• A useful resource pack to explore the industry (if applicable)
• SEO fundamentals
• Finding authentic voice and tone
• Statement of originality
• Structure
• Idioms and buzz words for inspiration
• Writing your first post

Though this does not guarantee a 100% match with your requirements, it ensures as much correspondence with your style as possible from the early stages of content production.

Feel free to throw in niche-specific sections here and there if you find them relevant.

Think this way: What is it you wish you knew/had right off as a newbie writer in your field? Add those to the style guide.

#3. There will be a learning curve

Everyone’s learning pace is different. They won’t or will rarely jump in and deliver an all-shiny 100/100 piece.

What you can do on your end here is provide proper instructions and communicate the directions for every task.

You may even want to have more control in the early stages. Invite them to discuss the outline together. Initiate calls and brainstorming sessions, and perform live editing. Give them time to sort things out.

#4. They won’t read your feedback [not always]

Now, I was obsessed with elaborate feedback in the beginning.

I was the hardcore word choice police, the annoying grandma who detects misplaced commas with a microscope. I thought I was helping them adapt our style and grow faster than I did.

But it came at a cost. Not everyone would read my comments. Neither would they skim through article briefs. I attributed my enthusiasm to everyone else, which backfired heavily.

I realized I needed to accept that not everyone shares the same drive, which… is okay… you know. Writing is like planting a seed. Watering it. Making sure the seeds get enough light. And doing it consistently so that they grow. It takes time.

So, what do I do?

I’d be lying if I said I wasn’t stunned or challenged. For me, it was as much of a learning cycle as it was for them.

So here’s what I did and what you can possibly do to save time, cut off the learning phase, and establish a better relationship with your writers.

• Make them feel appreciated and point out the sections they did well!
• If there are major comments you want them to address, send out an email, or schedule a quick call to highlight critical issues and propose solutions.
• Are they comfortable speaking up? Ask for feedback on your feedback style. Is there anything they wish they had to supplement the writing process? Turn this into a routine.
• Share your success and highlight everyone’s contribution to it.

Cause, after all,

​​“Words are our most inexhaustible source of magic.”

Albus Dumbledore, J.K. Rowling

Managing a Remote Writing Team of 8: Here’s What I Learned was originally published in The Writing Cooperative on Medium, where people are continuing the conversation by highlighting and responding to this story.