By the time you are comparing copywriters, every option in front of you looks competent. The portfolios are polished, the testimonials are warm, and everyone’s rate card can be argued for. Portfolios are meant to look good; that is what they are for. The differences that will actually decide your project show up somewhere else: in the answers to a handful of questions most buyers never think to ask.

I have sat on both sides of this conversation for 28 years, as the writer being briefed and as the person helping brands buy writing. These are the questions I would ask.

What Will They Ask You?

The most revealing part of a first conversation is not what the copywriter says about themselves. It is what they ask about you. Who is this for? What does the reader believe before they arrive? What are you selling against? What has been tried, and what died?

A writer who starts writing without interrogating the business is decorating, not persuading. If the first meeting produces no uncomfortable questions, the copy will produce no uncomfortable claims, and copy that risks nothing usually says nothing.

Who Actually Writes?

Ask it plainly: who will write my copy? In larger shops the senior writer wins the account and a junior inherits the work, which is a fine model as long as you knew you were buying it. If the answer involves a team, ask who holds the pen and who reviews it. You are hiring judgement, and judgement is not transferable by CC.

Have They Handled Your Situation, Not Just Your Industry?

Category experience is comforting but overrated; a good writer learns a category in a week. What cannot be learned in a week is situational experience. Launching something nobody has heard of, repositioning against a bigger competitor, making a technical product make sense to a lay buyer, writing for a brand that is changing its mind about itself: these are the shapes that repeat across industries. Ask what they have written for situations like yours, and listen for the thinking, not the logos.

What Happens When You Disagree?

You will disagree; plan for it. The answer you want is neither “the client is always right” nor “trust the process”. You want a writer who defends a line with a reason, tells you plainly when a requested change will cost the copy its force, and then lets you decide with clear eyes. A writer who folds instantly is expensive dictation: you will get your own first thoughts back, retyped.

What Are You Paying For?

Be wary of anyone happy to quote per word. It prices the typing and gives away the thinking, and the thinking is the product. A fair quote prices the problem: what has to be understood, how many routes have to be explored and discarded, how many rounds of refinement the piece deserves. Ask what the fee includes, and ask what happens at revision three, before you are at revision three.

The Brief Decides the Other Half

Choosing well is half the outcome. The brief is the other half, and it is yours. A strong writer with a vague brief will still produce something weaker than a decent writer with a sharp one. I have written a separate piece on how to brief a copywriter; read it before the kickoff call, not after the first draft disappoints.

Ask these questions and the field narrows fast. Most of the polish washes out, and what is left is the thing you were actually shopping for: a senior copywriter for your brand who asks hard questions, defends the work, and prices the thinking rather than the word count.