How to start working with a freelance writer

If you’ve selected a prospective freelance writer for your project, you have groundwork to do. Note that the questions you should know the answer to and the ones the freelancer might ask overlap. But you’ll already know the answers to many of these:

  • Why this project/deliverable? What problem are you trying to address?

  • Why now?

  • What is the project worth to us? If you’re looking to increase sales, calculate by how much and multiply that by the average sale amount.

  • Who is your intended audience? The more you can tell the writer about your audience’s pain points, the better they can engage your audience.

  • What makes your offering unique?

  • How will you measure success?

  • Who are the stakeholders and reviewers? Knowing this will streamline the creation process and keep costs in check. Experienced freelancers usually indicate how many rounds of review are included in their statement of work. Last-minute stakeholders could increase your costs and delay publication.

This isn’t a complete list, but it’s a great start. Check out PJ Srivastava’s What to Know Before You Start a Project for more context and questions.

You may have already filled out a project information form or exchanged emails with the writer. But a discovery call will give you a chance to see if you’re a fit to work together.

Questions like these show that the writer understands the value and impact of the work and how to help the project run smoothly:

  • Have you worked with freelancers before? This answer will give the writer context.

  • Why did you reach out to me in particular? What do you like about my experience/approach?

  • What is your budget for a freelancer? If you don’t know, the writer can create options for you. Keep in mind the project worth from the previous list.

  • What’s at stake with this project?

  • What is the project timeline and what is driving the deadline?

  • Are there any challenges I should know about?

  • Do you have a creative brief or a content strategist? Audience personas or product messaging?

  • What background materials should I use? If you’d like the writer to interview your subject matter experts, talk to them before the project starts.

  • How often do you want to communicate and via what channel(s)?

  • How will you onboard me? The writer might need access to your timesheet or invoicing systems, or your internal document repository. Or you could exchange documents via email, like templates, guidelines, and creative briefs.

Thanks to Ed Gandia of High-Income Business Writing for ideas on discovery call questions.

Knowing the answers to these questions will help you and the freelancer. Pay attention to their questions and answers to see what they bring to the table.

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How to work with a freelancer: pricing

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The Portfolio Papers: freelancer writing samples