Questions to Ask a Copywriter
Questions for hiring a freelance copywriter or an agency writer: how to read their samples, test their process, and settle revisions, rights, and pricing before anything is signed.
The questions
Open any question for the note
What kind of copy do you write most, and what do you turn down?
Why ask it
The refusal list is more informative than the specialty list. A writer who says they do everything from technical white papers to radio scripts is either unusually experienced or has not yet noticed what they are bad at.
Can you show me two pieces where the brief was close to mine?
Why ask it
Portfolios are highlight reels spread across many kinds of work. Asking for two near matches forces a narrow claim, and a writer with no near match will either say so plainly or send something loosely related, which tells you how they will handle your brief.
Which of your samples performed best, and how do you know?
Why ask it
Many freelancers never see the numbers because clients do not share them. An honest 'I never got the data' is more trustworthy than an unverifiable conversion figure, and mentions of open rates, test setup, or sample size show they were actually near the results.
What do you need from me before you can start writing?
Why ask it
The list they give, existing brand documents, customer interviews, access to sales calls, past campaign results, tells you how much of your own week the project will consume. A writer who needs nothing is planning to guess.
How do you learn a product you have never used?
Why ask it
Watch for whether they use the product, read support tickets, or talk to customers. Writers who only skim competitor sites produce copy that reads fluently and says nothing a buyer could act on.
We do not have a style guide. How would you get our voice right?
Why ask it
Without a guide, voice has to come from samples of your existing writing plus interviews with whoever sounds most like the company. If the answer is 'I will match your website', ask which pages, because most sites contain three different voices.
Walk me through your process from brief to first draft.
Why ask it
You want a sequence with checkpoints: brief, research, outline, draft. If the process is only 'send me the brief and I will send you copy', the first draft is where all the surprises arrive at once.
Do you work from an outline I approve first, or straight to a draft?
Why ask it
Approving an outline catches structural problems before they are dressed in finished sentences. Writers who resist it often compose while drafting, which makes every later change expensive.
How many rounds of revision are included, and what counts as a new project?
Why ask it
This is where freelance relationships break. Get the definition in writing, and ask specifically what happens when your team sends three rounds of contradictory notes in one afternoon.
How do you want feedback delivered?
Why ask it
Some writers want tracked changes, others want a call, because written feedback tends to arrive as rewritten sentences rather than as a problem statement. Agreeing this in the first week saves several bad rounds.
What do you do when a client's edits make the copy worse?
Why ask it
Every experienced writer has a version of this story. Listen for whether they push back with evidence, offer a compromise version, or simply comply, then decide which of those you actually want from someone you are paying.
How long does a page of sales copy take you, and what slows it down?
Why ask it
Speed claims are meaningless without the constraint. The useful half is what causes delay: waiting on interviews, legal review, or their other clients' deadlines.
Who will actually write this, you or someone else?
Why ask it
Some copywriters subcontract and some run a small studio. Neither is a problem if you know in advance, but you should establish whose writing you were looking at in the samples.
How do you handle SEO requirements without wrecking the sentences?
Why ask it
Ask what they do with a keyword phrase that reads badly in English. Useful answers involve headings, page structure, and what the searcher was trying to do; weak ones are about density and repetition counts.
Do headlines and subject lines come with the job, and how many options do I get?
Why ask it
Headlines take a disproportionate share of the writing time, so they are a common place for scope to shrink quietly. Establish whether you get a set of variants for testing or one line per piece.
Have you written for buyers like ours before?
Why ask it
Buyer experience travels better than industry experience. Someone who has written for procurement committees can move between sectors more easily than someone who has only sold impulse purchases to consumers.
How do you price: hourly, per project, or retainer, and what triggers extra cost?
Why ask it
Compare structures against your real scope rather than comparing rates. Ask what adds cost: extra pages, added rounds, rush timelines, strategy calls, or attending your internal meetings.
Who owns the copy, and will you use it in your portfolio?
Why ask it
Rights and portfolio use are simple to agree now and awkward to unpick later. If the work is confidential or under an agreement with your own client, say so before they publish a case study about it.
What has gone wrong on a project, and what did you change afterward?
Why ask it
A candid failure story is the strongest signal in the whole conversation. What matters is the process change that followed, not the apology, since a writer with no changed habits will repeat the failure on your project.
If this first project goes well, what would working together for a year look like?
Why ask it
This tests whether they think in campaigns or in single deliverables. Retainer-minded writers will start describing a content calendar and an ongoing review load you may not have budgeted time for.
Hiring a copywriter
Practical guidance for the conversation itself
Before the call
Write down the job, not the job title
One landing page, six emails, and a product page is a scope. 'We need better copy' is not, and it produces quotes you cannot compare with each other.
Decide who signs off
Most delays come from an unnamed final approver who appears at draft three. Settle that person before you brief anyone outside the company.
Gather what you already have
Past campaign results, customer support transcripts, sales call recordings, and a list of objections buyers raise. Writers who get this material produce better first drafts, and writers who ignore it have told you something.
Reading the samples properly
- Ask what the brief was for each piece. Strong copy against a bad brief looks like weak copy.
- Look for a specific claim about a specific buyer, then check whether anything in the piece supports it.
- Notice how they open. Most weak copy has one paragraph of throat-clearing before the actual point.
- Check whether the calls to action match the stage of the buyer they are aimed at.
- If every sample sounds identical, you are looking at their voice, not their range.
If you want a test piece
- 1Pay for it. Unpaid tests filter for writers who need the work rather than writers who are good.
- 2Give a real brief with real constraints, and give the same brief to everyone on the shortlist.
- 3Keep it small: one email or one page section, not a full site.
- 4Ask them to send the outline and their questions along with the draft, so you can see the thinking rather than just the prose.
- 5Judge it on whether it says something true and specific, not on whether it matches the phrasing you had in your head.
Settle these in writing
- Deliverables, word counts, and what a round of revision means.
- Payment schedule, deposit, and what happens if the project pauses on your side.
- Copyright assignment and portfolio permission.
- Confidentiality, especially if you are their client's client.
- Who has the final call on wording when you and the writer disagree.