Letter #64: 4 mistakes you’re making when working with freelancers

Plus a fun video I’ve been meaning to share with you for a long time now.

Jan 31

Marhaba lovelies!

How’s the last day of January treating you? I’m moving my way to the next month with Omah Lay and Justin Beiber’s Attention playing in the background.

Which brings to mind: do your relationships with freelancers need some attention? Because a lot many of us simply throw our hands in the air and say ‘there are no good freelancers out there!’

I say this based on my chats with a ton of content strategists and managers working with freelancers — complaining things aren’t going so well.

The solution? These ideas, brought to you by my experience working with content teams for six years with some of them doing exceptionally well in the freelance-client relationships department.

So let’s dig into possible mistakes you’re making and how to correct/avoid them:

1. You aren’t proactive in your communication

See, I get it — you hired the freelancer so they could present a ready-to-publish draft while you dig your head into other responsibilities.

But here’s the thing: creating content is a super collaborative process. So you not only need to be open to suggestions and questions around context but also improve comms by:

Telling freelancers you’re there to help and happy to answer their questions.
Replying quickly — get back to their questions as fast as possible so they can deliver by the agreed deadline.
Guiding them in understanding product use cases so they can create better product-led content (creating short explainer videos is a recyclable way to do this).

2. You aren’t working with freelancers on a long-term basis

If you don’t have regular content requirements, feel free to skip to the next point.

But if you do, there’s a goldmine of benefits you’re missing by not retaining your freelance writers. The biggest of these benefits: better content quality and reduced workload on you.

Here’s how:

Regular freelance writers have a strong grip on your product and its use cases.
They develop a deep understanding of your targets and their struggles.
They know which pieces to internal link — after all, they help with creating them.
They know your style guide like the back of their hand = fewer edits on that note.

Ready to retain freelancers? Here’s how my clients retain me and you can retain your freelancers:

Send them referrals and company swag. One of my clients sends regular referrals and trust me — I always prioritize their work.
Treat them like your team. Example: send them a note of appreciation outside of them asking for reviews. Here’s what a client shared recently (video). I was in party mode all day after watching this 🥳
Offer them free access to your tool/product. This one pays off big time as they learn to use and even recommend your tool in their circle.

Another idea: Invest in their craft with this template.

3. Your creative briefs and other documentation are unnecessarily long

Not all writers will read the brief from cover to cover. And I’m not alone in my observations.

My content manager friends say they’ve a hard time getting freelancers to stick with the style guide. And some of my clients have a highlighted “please read this for sure” in their briefs.

But why aren’t freelancers reading and following through such important docs? Because the readability levels are making it difficult for them.

The solution:

Use bullet points where you can
Create 1-page docs and link them to the brief
Make them easy to follow with short checklists
Use short explainer videos and visuals where needed

Dig deeper: Don’t make these brief writing mistakes.

4. You aren’t telling them about your struggles and content strategy

Even if your creative briefs are detailed enough, freelancers can’t get a big picture overview of where you’re trying to head with your content if you don’t share your strategy with them.

You also need to loop them in with your:

Content struggles — planning to drive more clicks? Tell ‘em. You’d be pleasantly surprised by the suggestions they send your way.
Reader feedback and high-performing pieces. This will help them improve or mirror creating more audience-relevant content.
Changing buyer/reader persona. Whether you or your team talks to your target buyers quarterly or biannually, be sure to share the new insights with your writers.

I could honestly go in with more mistakes. But I need to pause here because I’ve promised to keep my emails short + I’ve a looming deadline.

So I gotta go now.

See you next week,

Masooma

Content Workshop