Letter #34: The ONE mistake you’re making when working with freelancers
And how to avoid it.
Hello hello! 👋
In my 5+ years of writing professionally for clients — first from various industries and then with SaaS and ecomm folks, I’ve seen this a lot:
✨ The key to success when working with freelancers is TRUSTING THEM ✨
The moment you start micro-managing, the risk of things going off-track grows.
I admit: trust doesn’t come easy. Hiring the right freelancers can help though.
So, here’s how to build trust in two parts:
A. Hire well
Take your time in exploring the right freelancer to work with.
Just because someone's referred a freelancer to you doesn’t mean they’re the perfect fit for your content requirements — especially if you’re in another industry.
I recommend you:
Go through the freelance writers’ work
Read through their bylined pieces to learn not only how they write but also to get a sense of the subjects they write about.
The best freelancers will always share related examples of their work with you when you reach out. Or, they’d share an easy-to-browse portfolio that arranges content in broad topics.
Read their testimonials
Look for lengthy testimonials that share their clients’ experience working with them. These reviews alone can tell you a lot about their work process, expertise, and communication.
Inquire about their process before sharing yours
Either jump on a call or email to learn their work process — how they work on their drafts, their process for optimizing content, what’s included in the deliverables, and so on.
This will give you a good sense of how thorough a freelancer’s work is and whether it’ll suit your process, expected turnaround time, and other requirements.
B. Work well
Once you’ve hired your freelancer, trust them.
Two things to focus on here: providing sufficient context and keeping checks.
Have brainstorming discussions
This applies to working with freelance content strategists, writers who work on thought leadership posts, and those you accept pitch ideas from.
The goal? To understand the direction they’re taking and to provide necessary input.
Ask for and share context
You can minimize the context you share yourself by documenting.
For example, document your brand voice, brand values and principles, formatting style, and so on.
On the flip side, ask freelancers to share their ideas but with context so you know why they’re suggesting something and how likely it is to succeed.
Provide resources they'll need and connect them with experts
Either source insights from internal experts (think: product managers) in the brief that you share or connect both parties.
Don’t forget to ask them what other resources they need. And while you’re at it, be responsive — nothing derails freelancers’ schedules (yes, they have one!) like a resource coming in late.
Check in frequently (but without being nosey)
Instead of inquiring after progress (the best freelancers will update you anyway), check in to ask if you can help with anything. Reframing your question like this makes your work relationship pretty strong and non-micro-management-y 😂
That’s it from my side!
Here’s to more trust and better work relationships 🍺