How to Work with a Freelance Writer (Without Getting Overwhelmed)
If you’ve chosen a freelance writer for your content project, great! But if you’re feeling a little unsure about how it all works, you’re not alone.
Many marketers at small and midsize businesses know they need content to drive leads. But finding the right writer and setting up the project can feel like one more thing on an already full plate. If you’ve never worked with a freelancer before (or had a not-so-great experience) it’s normal to feel uncertain about what happens next.
On the plus side, a seasoned writer can take a lot of work off your plate if you’re prepared with a few key answers up front.
What to Know Before You Kick Off
Here are a few questions that might come up during the discovery call. The more background information you’re ready to share, the easier it will be to get great results.
Why this project, and why now? What problem are you trying to solve, or opportunity are you seizing?
What is this project worth to your business? For example, if the goal is to increase leads or sales, can you estimate how many leads or what average deal size and value might result from it?
Who’s the target audience? The more you can tell the writer about your audience’s pain points and goals, the better the writer can address them in their content.
What makes your solution different? This helps your content and your offering stand out.
How will you measure success? Traffic, engagement, leads, sales support?
Who are the stakeholders and reviewers? Clarifying this early keeps the process smooth and cost-effective. (Note: Adding reviewers late in the process usually delays timelines and increases your costs.)
Questions a Professional Writer Might Ask You
Discovery calls aren’t just about pricing. They’re about understanding fit, goals, and process. An experienced freelancer might ask:
Have you worked with freelancers before?
Why did you reach out to me specifically?
What’s your budget?
What’s the timeline, and what’s driving it?
What might make this project challenging?
Do you have a creative brief, personas, or product messaging I should see?
Will I interview your subject matter experts (SMEs)?
How do you want to communicate and share files?
What will onboarding look like (tools, platforms, or process)?
These questions show that the writer is invested in helping the project succeed.
Quick-Start Checklist
Feel like you need a reset button before you dive in? Here’s a fast way to prepare:
Identify 1–2 pieces of content you need.
Write down the business goal for each.
Jot a few bullet points about your audience.
Gather background materials or content examples.
Book a 20-minute discovery call with a writer.
That’s it. You don’t need a 12-slide strategy deck to get started; just a sense of what you need and why.
The Takeaway
Working with a freelance writer isn’t complicated when you’re prepared. A good writer will help guide the process, ask the right questions, and deliver content that supports your business goals. And once you’ve got a good one in your corner, future projects get even easier.
Need Help With a Content Project?
I write SEO-smart blog posts, customer stories, and case studies for growing tech companies and B2B agencies. If you want strategic content without the drama, let’s talk. Contact me or connect on LinkedIn.
