Questions to ask a copywriter before commissioning site copy

A copywriter's answers during your first conversation will tell you whether they'll waste your money or multiply it.

Most people waste copywriter time by not asking anything. They hire on portfolio alone, hand over a brief, and hope. Better ones ask about price and turnaround. The sharpest ones come prepared with questions that expose whether the writer understands their business, has a genuine process, or is just going through motions.

Your job isn't to quiz them like a job interview. It's to listen hard to what they say *and how they say it*, because evasion, jargon, and vagueness are red flags dressed as confidence.

"What's your process before you write a single word?"

A copywriter worth hiring will describe some form of discovery. They might ask you questions first, want to interview your team, request customer interviews, or dive into your analytics. They'll name the phases: research, strategy, drafting, revision. They might spend days in your world before opening a blank page.

If they say "I just get on with it" or "I'll write something and we'll see how it goes," that's a copywriter treating your site like a first draft. You'll be rewriting it three times, and they'll blame you for unclear briefs.

A vague answer—"I'm very collaborative" or "I work closely with you"—isn't a process. It's a promise to figure it out as you go. Press them: *What's the first thing you do? Do you interview customers? Do you look at competitors? How long does this phase take?* You're listening for specificity and a genuine methodology, not borrowed buzzwords.

"How do you know what actually works on a website?"

This separates writers who understand conversion psychology from those who just write well.

A strong copywriter will reference experience: "I look at your analytics to see which pages bounce most and what words bring visitors back." They might mention reading customer feedback, studying heatmaps, or tracking what language resonates in your industry. Some will tell you they've tested different headlines or value propositions and measured the outcome.

If they talk only about making it "engaging" or "compelling" without connecting that to your business goals—whether that's sign-ups, calls, or sales—they're focused on prose quality, not results. You need both, but without the latter, you're paying for a nice-looking site that doesn't earn.

Don't accept "Trust me, I know what works." Ask for proof: *What's the last client result you saw from your copy?* If they have one, great. If they're cagey or insist every site is "totally different," they're guessing like you are.

"How will we know if this is working—and what happens if it isn't?"

This question reveals whether a copywriter sees themselves as accountable or as a vendor handing over a product.

A copywriter who takes the work seriously will suggest ways to measure success before they start: page analytics, form submissions, customer feedback, or sales. They might ask what "working" means to you specifically. They might even propose a revision window—say, two rounds of feedback after launch, or a check-in at 30 days to see if the copy needs tweaking based on real reader behaviour.

If they say "Once it's written, it's done" or "We'll know it's working because the site looks good," they're abdicting responsibility. Your site isn't a book; it's a tool. It'll need tune-ups as you learn what your audience responds to.

An honest copywriter will also tell you what they *can't* control. They can't fix a site with broken navigation, poor design, or no traffic. They can't make people want something they don't need. They can write the clearest, most persuasive pitch in the world, but if your offer is weak or your audience never sees it, the words won't matter. That honesty is a good sign—they know the difference between good copy and a good result.

Before you commission a copywriter, sit with these three questions. The answers you get will show you whether you're hiring a craftsperson or someone going through the motions. When you're ready to talk to a real writer who can walk you through their actual process, Strove's verified copywriters in your province can share their approach and examples.