How to Interview a Copywriter (When You’re Not One)

The most useful thing in a copywriter interview usually isn’t an answer. It’s a question — one the writer asks you.

I’ve spent more than twenty years placing copywriters, and I get something most interviewers never do: the follow-up call. I hear, six weeks later, whether the hire worked. Multiply that by hundreds of placements and you start to see which interview moments actually predicted the outcome — and which ones just predicted a pleasant hour.

Most marketing directors interview copywriters the way they’d interview anyone: a list of sensible questions, a read on the chemistry, a decision. And most of the time, the sensible questions tell you almost nothing. Here’s what does.

The standard questions are a rehearsal, not a test

Look up “copywriter interview questions” and you’ll find the same list everywhere. How do you handle feedback? Describe your research process. Tell me about a project with measurable results.

Reasonable questions. Useless answers. Not because writers lie, but because writers are professionally good at answers. You are interviewing someone whose entire craft is saying the persuasive thing in the polished way. Every copywriter you meet has a story about taking feedback gracefully and a case study with a tidy number at the end. The interview selects for exactly the skill being demonstrated in the interview — fluency — and fluency on a sofa is not fluency on the page.

I’ve placed writers who interviewed like a wet Tuesday and delivered work that made clients giddy. I’ve also, early on, placed a couple of dazzling talkers whose first drafts read like the meeting had been the whole performance. The feedback calls taught me to stop scoring the show.

Count the questions coming back at you

The single most predictive thing I’ve noticed, across hundreds of those six-week calls, is embarrassingly simple: the writers who worked out were the ones who interrogated the problem in the room.

A strong copywriter can’t help it. Tell them you need a campaign for a product launch and watch what happens. The good ones start digging before you’ve finished the sentence. Who’s it for? What do those people believe right now? What’s the one thing you’d want them to do differently? Why hasn’t the current messaging done it?

That instinct — to get underneath the ask before touching the ask — is the actual job. Copy is the last step of thinking clearly about someone else’s problem. A writer who spends the interview presenting themselves instead of probing your brief is showing you, in real time, how they’ll treat the work.

So flip the frame. Bring a real problem to the interview — a genuine one, current, slightly messy — and put it on the table. Then say less. The candidate who fills the silence with questions is telling you more than any portfolio walkthrough ever will.

Make them narrate one decision

Portfolios show you outcomes. Interviews are your one chance to see the decisions — so ask for one.

Pick a single piece from their book and ask: what did you say no to here? What were the lines that didn’t make it? What did the client ask for that you pushed back on, and how did that go?

Great writers light up at this question, because great writing is mostly rejection — the eleven headlines killed so the twelfth could live. They can walk you through the discarded options and tell you why each one died. Weaker candidates describe the finished piece again, slightly slower, because they were never really inside the decisions. Perhaps they executed someone else’s idea competently — which is fine, but it’s not what you’re paying senior rates for.

One question, five minutes, and you’ve learned whether the thinking in the portfolio belongs to the person in front of you.

Ask about the piece that died

Then go one step darker: tell me about work you were proud of that failed. Not the humble-brag version. The campaign that flopped, the rebrand that got shelved, the client who never called back.

You’re listening for two things. First, honesty — a writer with fifteen years and no bodies buried is editing the story, and if they’ll edit that story they’ll edit the ones about your project too. Second, diagnosis. The best writers can tell you why it failed: wrong insight, wrong audience, brilliant line answering a question nobody asked. That post-mortem muscle is what separates someone who produces work from someone who understands it. You want the second one, because when round one lands flat — and sometimes it will — the second one knows what to change.

Don’t hire the conversation

A last warning from the follow-up calls: the most expensive mistake I see isn’t hiring a bad writer. It’s hiring the best conversationalist.

Chemistry matters — you’ll be working closely, and a writer who can’t listen to you can’t write for you. But some of the finest copywriters I represent are quiet in a first meeting. They’re watchers. They warm up through the work, not before it. If you weight the interview toward charm, you’ll systematically filter out a certain kind of brilliant introvert and fill your shortlist with people whose best medium is the meeting.

The fix is to let each element do its own job. The portfolio tells you whether they can write. The questions they ask tell you how they think. The decision stories tell you whether the book is really theirs. The failure story tells you whether they’ll be honest with you when it counts. Charm gets to be a tiebreaker — never the criterion.

Hire the one who asked the questions. Six weeks later, you’ll be glad you did.

Jack Stafford is the founder of Copywriter Collective, a premium creative talent agency based in Amsterdam.