Every content agency you talk to will pass the questions you're planning to ask.
Do you have health tech experience? Yes. Can we see samples? Here's a folder. What's your turnaround? Two weeks per article, usually. Every agency in your inbox has rehearsed these answers, because every marketer before you asked the same ones.
Those questions test whether an agency is competent. They don't test whether it's the right fit for a buyer who researches vendors like a background check. You need questions that test for that specifically, because a generalist agency can produce a polished, on-brand, grammatically perfect article that a dental practice owner or a clinical director still won't trust.
Start with how they think about your buyer, not their portfolio
Ask this before anything else: "Walk me through how a practice owner actually evaluates a vendor like us."
Listen for whether the answer is about your buyer or about content mechanics. A weak answer talks about SEO, keyword volume, and content calendars. A strong answer talks about procurement caution, who else needs to sign off, what makes a clinical buyer suspicious of a pitch, and why a demo alone rarely closes a deal in this market.
If the person on the call can't describe your buyer's evaluation process without you prompting them, they're going to learn it on your dime, one edit at a time, for the first 3 months of the contract.
Ask what they need from you before they can write anything good
"What do you need from us to produce your best work?"
A weak answer is "just a brief and access to your team." That sounds efficient. It usually means they'll lean hard on generic industry research to fill the gaps, because nobody handed them your actual market knowledge.
A strong answer is specific: recorded sales or demo calls, objection-handling notes, a list of who reviews for clinical accuracy and their turnaround time, and 30 minutes with whoever talks to your buyers most. That's an agency that knows the good material lives in your team's heads, not in a competitor's blog post.
Ask how they handle a claim they can't verify
This is the question most marketing hires never think to ask, and it's the one that matters most in a regulated or clinical market.
"If a draft needs a statistic or a claim you can't verify, what happens?"
You want to hear that they flag it and leave a marked gap for you to fill, not that they find something close enough from a general search and drop it in. A generalist agency writing for consumer SaaS treats unverified stats as a minor risk. In health tech, an invented or unsourced clinical claim is the kind of thing that ends up in front of your legal counsel, or worse, in front of a clinician who fact-checks it in public.
PulseCopy's answer to this, for what it's worth: flag it and mark it as a placeholder rather than inventing a number. It's the baseline any agency working in this space should already have.
Ask to see something that didn't work
Every agency will show you their best 5 pieces. Ask for something different: "Show me a piece that didn't perform the way you expected, and tell me why."
You're not looking for a disaster story. You're checking whether they measure their own work honestly, and whether they can diagnose a miss without blaming the client, the algorithm, or bad luck. An agency that can say "we wrote for the wrong reader on that one, and here's what we changed" is one that will tell you the truth 6 months into your contract, when something isn't working and you need to know why.
Ask what happens when the first draft misses
Every agency misses sometimes. The ones who claim otherwise are either lying or haven't been doing this long enough to have missed yet.
"Walk me through your revision process when a draft comes back needing real changes, not just line edits."
Listen for a defined process: how many rounds are included, what counts as a structural revision versus a style note, and how fast a second draft turns around. Vague answers here ("we'll just work it out together") are a preview of every future review cycle turning into an unstructured back-and-forth that eats your week.
Ask who actually writes it
Agencies sell you the person on the sales call. That's not always the person who writes your content.
"Who's writing my articles, and will I ever talk to them directly?"
Some agencies run a strategist-plus-freelancer-pool model, where the person you vet isn't the person producing drafts. That can still work, but you should know it going in, and you should ask how consistency gets maintained across writers if your retainer scales past 4 pieces a month. A single point of contact who is also the writer tends to produce a more consistent voice, faster, because nothing gets lost in a handoff.
Ask if they write for your competitors
Health practice tech and digital health are narrow markets. A content agency that's been operating in this space for a few years has likely talked to more than one company selling a similar product.
Ask directly: "Do you currently write for anyone we'd consider a direct competitor?" Then ask what their policy is if a competitor approaches them after you sign. A serious agency will have an answer ready, usually some version of one client per category at a time. An agency that hasn't thought about this hasn't been in the space long enough to have run into it.
The market knowledge an agency builds on your account, the objections your prospects raise, the language your buyers use, is exactly the kind of insight that makes their next pitch to your competitor stronger. You want a partner who treats that as a conflict, not a shrug.
Ask how they'll prove it's working
You'll answer for this content to someone, whether that's a VP, a CEO, or a board slide. Ask the agency how they plan to make that easier for you.
"What will your monthly update actually contain, and what would tell either of us this isn't working?"
A weak answer is a traffic screenshot. Traffic is easy to report and rarely the number your leadership actually cares about. A strong answer connects published content to the funnel: which pieces influenced a demo request, which keywords are climbing toward positions that convert, and what a realistic timeline looks like before any of that shows up, because health tech content takes longer to rank than a generic SaaS category.
You also want an agency willing to say when something isn't working, before you have to ask. That's a harder thing to fake on a sales call than a case study.
Ask for a smaller commitment before the big one
Nobody has to sign a 12-month retainer on the strength of one call and a portfolio folder.
Ask if they'll do a single paid piece, or a one-month trial, before you commit to an ongoing engagement. A confident agency should welcome this. It gives you a real draft against a real brief, not a portfolio sample they've already polished a dozen times, and it gives you a much better read on the questions above than any answer they gave you on the call.
If an agency pushes back hard on a trial and insists on a long minimum commitment with nothing smaller available, ask why. Sometimes there's a good operational reason. Often it means they're not confident the work holds up without the sunk cost of a signed contract behind it.
Ask how they price, and why
Per-word pricing rewards length over judgment. It also tells you the agency is optimizing for output volume, not for whether the fourth paragraph earns its place.
Retainer or project pricing tied to a defined scope, strategy included, is a better signal for a content partner rather than a content vendor. Ask directly: "Why do you price this way, and what does it change about how you work?" A thoughtful answer connects pricing to incentives. A dodge just restates the number.
The one question that filters out the generalists fast
"What's the difference between writing for a clinician and writing for a patient, and how does that change your process?"
This is the question a generalist B2B agency almost always fumbles, because the honest answer requires having actually done it. A clinician reads for evidence, precision, and a named source they can check. A patient or a practice owner reads for trust signals and outcomes, in language that doesn't assume a medical vocabulary. Getting that distinction wrong is exactly why so many digital health companies end up with content that reads like a hospital pamphlet trying to sell software, or a SaaS landing page trying to sound clinical.
If the answer is a shrug, or a version of "we adjust the tone," keep looking. The evidentiary standard is the real lever here, not tone.
Score the answers, don't just collect them
Once you've run 2 or 3 agencies through these questions, you'll notice the gap is rarely about writing quality. Most agencies that make it to a call can write a clean sentence.
The gap is in how fast they can operate without your team translating the market for them every single week. That's the real cost most marketers underprice when they hire a generalist: not the invoice, but the hours their own team spends explaining what a clinical buyer is actually afraid of.
Score each agency on 2 things. First, how much of your buyer's psychology did they already understand before you explained it. Second, how specifically did they answer the claims question and the revision question, versus how much they talked in generalities. An agency that scores well on both is one you can hand a topic to and trust the first draft back.
What this saves you, beyond the obvious
A vendor that needs constant correction doesn't just cost you edit time. It costs you the thing your VP actually cares about: a consistent publishing rhythm that compounds into rankings and pipeline, instead of a stop-start cadence that never builds momentum.
The right questions won't guarantee a perfect hire. But they'll tell you, in one call, whether you're looking at a partner who already speaks your buyer's language, or one you'll spend the next 2 quarters teaching from scratch.