This month’s issue includes signs to watch for when interviewing prospective freelancers and a helpful article on AI search optimization.

Red Flags to Watch for When Looking for a Freelance Writer

If you’re preparing to work with a freelancer, you likely are looking for someone to make your life easier. You’ve got too much work and not enough time to fit it in. A freelancer writer or editor should know their craft well and be able to learn your business quickly, so they can deliver what you need when you need it.

I’ve written previously about what to expect when working with a freelancer. Below I share what to watch for that could signal a poor client-freelancer match.

Poor organization. Freelancing requires a lot of organization. We have to stay on top of all aspects of projects, keep track of different clients, track time, send out invoices, be mindful of which client follows what style guide, and more. If you’re looking to work with a freelancer and they seem disorganized, dig deeper. Is it a one-off forgetful moment, or a trend that could spell trouble over the lifetime of your project?

Bottom line: Know what’s most critical to getting your work done and decide how important organization is to your project’s success.

Lots of questions over many messages rather than compiled together. Freelancers are here to ease your burdens. A conscientious freelancer will aim to gather several questions together and send them all at once, to eliminate the burden on you.

Bottom line: If you’re annoyed by all of the back and forth when you’re vetting a freelancer, be aware that it may not get much better once the project is underway.

Multiple typos in written messages. I think this should go without saying. However, mistakes happen so I don’t hold it against people when typos happen. Unless they happen over and over again. Freelance writers (and editors especially) are typically really careful about sending out messages that are super neat and tidy when it comes to the written word. After all, it’s our job. If you receive messages that contain several errors in grammar, spelling or mechanics, know that any assignment they turn in to you may look similar.

Bottom line: Decide how critical attention to detail is to you before getting too far into this relationship.

Hemming and hawing over pricing. Experienced freelancers have been working on estimates, quotes and budgeting for a long time. We have a pretty good idea up front about costs for certain types of projects, or we know what questions to ask in order to work up an estimate for you. (Note: Newer freelancers might need a bit more time to figure out costs and that’s OK. It takes time to build that skill.) Be ready to clearly define the scope of your project to allow the freelancer to establish an accurate estimate.

Bottom line: If a freelancer you’re meeting with is slow to talk budget, ask why and see if it’s an issue you can work through.

When it comes down to it, you know the skills you need most. Weigh what’s most important to you and have that top of mind when you start looking for a freelancer.

And if you need someone who has the opposite qualities of all those described above, I’m your gal.

Something You Might Not Know About Me... I love handwritten recipes. If I ask you for a recipe, there’s a good chance I may ask you to handwrite it out for me. So many of the recipes in my recipe book tell a story not only in the food, but also in the handwriting. This one is from my mom. ❤️

What’s up? I'd love to hear from you! Here are some things to consider sharing: Are there other red flags you’d add to my list? Are you currently writing anything where you need to optimize for AI? Do you keep handwritten recipes? Reply to this email or comment here. Thanks for reading! Kate Harold Writer | Editor | Proofreader Kate Harold Freelance Writing LLC June 24, 2026 | Issue 21

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