Updated: Nov 9, 2021
Before I started freelancing full time, I managed contractors in various roles for multiple companies. Developers. Designers. Writers.
Among them, writers were by far the hardest to nail down. This isn't to say that they weren't lovely people —most of them were. But I would consistently spend hours upon hours editing drafts and redoing 90% of the content.
Collectively, my contractors and I would spend 12+ hours on a 1,000-word blog. It was like being in college again, staying up all night just to submit an A-worthy paper.
To make matter worse, I always held on to contractors too long. I held up faith that we could make the relationship work until time (and money) finally got the best of me. I had to learn the hard way that managing a team of writers means finding people who can write well and meet other less-obvious criteria.
1. Experience in Your Niche
People who claim to be able to write about anything under the sun are lying to you. Those writers tend to lack a specialty and/or simply want to pump out content as fast as they can.
Quality is often an issue because writers lack the knowledge or motivation to write deeply enough your topic. They may misuse words or botch technical concepts. Or, they may rely on generic statements to fill up word count.
That said, writers with some familiarity in your space can always be trained. Just beware of those who overpromise. Freelancers should always be honest about their capabilities and be willing to put in the extra grunt work to familiarize themselves with new topics.
2. Ability to Adapt to Your Voice and Style
Every writer has a unique voice. However, professional content writers know that their work doesn't revolve around them. Their job is to represent your brand and your team's personality.
This, admittedly, is tough. I imagine it's kind of like when an actor needs to learn a new character or accent for a role. Getting good at it can take some time.
To help your writer out, provide them with your company's style guidelines. Allow them to get familiar with your team through calls, decks, or any other resources you can provide.
Your freelancer should proactively check out your blog, social profiles, and other accounts to get a sense of your brand's voice, but you shouldn't assume that they'll know your exact preferences right off the bat.
3. Courage to Ask Questions
When you're a contracted writer, you're left in the dark about a lot of important details: internal processes, product roadmap, ICP, overall marketing and sales strategy.
This is no one's fault. It's just the nature of the job/relationship. However, your freelancer should be in the habit of asking questions when they need to. They shouldn't jump to their own conclusions about your stance on a subject or write without a deeper understanding of your target audience.
Oftentimes freelancers will refrain from asking questions for fear of bothering you. While I can fully sympathize with this, it's not a valid excuse to let content quality slip.
Be ready to receive and answer questions, as well as help your writer fill in the blanks about your company.
4. Desire to Be a Team Player
One of the biggest disappointments I ever faced in terms of contracting a writer is when I realized that the writer was just not that into us.
He was an experienced journalist who had just sent over a great piece for our review. We requested a few revisions to the story angle, all of which would take ~30 minutes to complete. The writer took a few days to respond, only to reject our request for edits entirely.
Safe to say, we didn't hire him again. Despite his strong writing skills, we couldn't comfortably partner with him, lest he took the take-it-of-leave-it stance on every project we gave him.
Your contracted writer should be willing to work with you (within reason-this is my freelancer side speaking). They should be collaborative, communicative, and always kind.
5. Thick Skin
Writers tend to have big egos. (I feel like I can say that because I am one, right?) Chances are you've already ran into one who doesn't receive constructive criticism well…at all.
Some writers may grit their teeth and force a smile as you share your feedback. Others may flat-out contest what you have to say.
While writers should be confident and offer their expert advice, they shouldn't be opposed to receiving your comments on their work. Feedback is part of the job, and it's what makes them better writers.
If you feel like you're always at odds with your contractor, then consider going your separate ways before the relationship becomes toxic.
6. His/Her Own Opinions
This may sound like it contradicts #5, but don't worry, it doesn't.
The point here is that writers are experts at their craft. They should have their own methodology and hypothesis about what makes a good blog, webpage, ad copy, etc. - especially if it has to do with a more technical skill like SEO.
Note: your contractors may not always be right. Nevertheless, they should be striving to apply what they've learned from previous projects to your work together, always looking to test and improve upon successful strategies.
7. An Eye for Editing
Attention to detail. Consistency. Appropriate use of "I" and "me." These are all marks of a good editor.
Unfortunately, not every writer makes a good editor. I can't count the amount of times I've received drafts marred by grammar errors or inconsistent formatting (e.g., ecommerce vs. eCommerce vs. e-commerce).
In order to represent you brand in the best light, your writer must be able to back up good copy with careful editing. It's a bonus if s/he is well-versed in AP Style, MLA, or another grammar style.
8. Overall Compatibility
Last but not least, hire someone you actually enjoy talking to-or, as one of my former managers used to say, "Someone you could imagine being stuck in a room with."
Even though you may not chat with your writer day in and day out, you'll need to be able to build trust and a positive working relationship. Being able to connect with your writer at a human level simply makes everything easier.