First, what does it answer from?
This is the question that separates the tools. A general assistant answers from its training and from whatever you paste into the chat. A tool built for questionnaires answers from a knowledge base you control: your policies, your documents, the answers you approved before. The first produces fluent text about security in general. The second produces your answers.
Ask to see the knowledge base. Ask what happens when a question is not covered by it: does the tool say so, or does it fill the gap with something plausible? A plausible invented answer about your backup procedure is the single most dangerous output a questionnaire tool can produce, because it reads exactly like a true one.
Does it show its sources on every answer?
An answer without a source is an opinion. You should be able to open any drafted answer and see which policy, which document, which earlier answer it was built from, and read the passage. This is what makes the review fast: you check the source, not the sentence. It is also what makes the answer defensible a year later.
How does it handle uncertainty?
Every questionnaire has questions the knowledge base half covers. The tool should tell you which drafts it is sure about and which it is not, and why: the sources answer the question squarely, or only touch it; they are recent, or old. A confidence signal with reasons lets your team spend its hour on the twenty weak answers instead of re-reading all two hundred.
Where does your data go?
Your policies are sensitive by definition. Ask, and expect written answers: which region processes the data, whether the vendor trains models on it, which AI providers sit underneath and whether you can choose one or bring your own key, and who the sub-processors are. Then compare the answers with the vendor's own security page. A questionnaire vendor that cannot answer a security questionnaire about itself has told you something.
Does it keep the customer's file?
Customers send spreadsheets and Word documents in their own layouts, and they want them back in that layout. Check that the tool reads the file it was given, keeps every sheet and column, and exports the same file with the answer column filled. A tool that flattens everything into its own format creates a copying job on the customer's side.
Can your team work in it together?
A questionnaire is answered by several people. Look for assignment (this question is Maria's), review states (drafted, approved), a record of who changed what, and a way to leave the questionnaire open for a week without losing anything. If the "team" feature is one shared account, it is not a team feature.
What happens to the answers afterwards?
The value of a questionnaire tool compounds only if this quarter's approved answers become next quarter's starting point. Check that approved answers flow back into the knowledge base, that they carry a date, and that something reminds you when they age. Otherwise you have bought a faster way to do the same work from scratch each time.
A short scorecard
Take your last finished questionnaire to the demo. For each tool, note: the share of drafts you would have sent unchanged, the share it flagged as unsure and was right to flag, the share it got confidently wrong, and how many minutes the review took. The confidently wrong number is the one that matters. Here is how Responsemate answers those seven questions, and how it handles your data.
Questions people ask
Can an AI answer a security questionnaire on its own?
It can draft one. It should not send one. A security questionnaire is a set of claims your company is making to a customer, and someone accountable has to read and approve each claim. The right tool makes that review fast and well-informed; it does not remove it.
Is it safe to put our policies into an AI tool?
Only if you know where they go. Ask whether the provider trains on your data, which region the data is processed in, whether you can bring your own model key, and what the sub-processors are. If the vendor cannot answer those four questions plainly, the answer is no.
How do we test an AI questionnaire tool before buying?
Bring one of your own questionnaires, one you have already answered by hand, and compare. Look at the drafts it got wrong, not the ones it got right, and check whether it told you it was unsure about them.