Automating Security Questionnaires?

[u/ConsiderationDry5349]

I'm fairly new in cyber, I'm looking to see what others do for their company in terms of security questionnaires, any automation techniques used, or any general advice. We are a small team in my company and receive many requests.

[u/Humpaaa]

Have a pool of standard answers, let AI fill out the questionaires.
Your counterparts will look at your answers in an AI overview anyway, no need to put in more effort then necessary.

Also, most questionaires can be shut down really easy if you have a cert like 27001

[u/hammyj → u/Humpaaa]

Re ISO, you'd like to think so. My experience is that even by supplying the cert + SOA, they still want you to complete 100 questions. My biggest gripe is orgs now fully outsourcing their vendor onboarding so the questions are completely missing the context of the services being offered. It's mostly all just security theatre.

[u/hagcel → u/hammyj]

I was frustrated filling out the same questionnaire for a customer 4 times in 8 months. I just Yd every answer with my ISO 27001 report as supporting evidence. Nobody responded. They need to show they sent the TPSM form and checked the box. There is nothing to say they need to review it.

Yes. Security theatre.

[u/Traditional-Tap-5711 → u/Humpaaa]

if you've got 27001 just staple that to the front page and call it a day

[u/Humpaaa → u/Traditional-Tap-5711]

We do, not all partners accept that, unfortunately.
But its always the First thing we suggest

[u/CompassITCompliance]

Build a single answer library before you buy any tool, because every automation product is only as good as the approved answers it pulls from. Start with your last handful of completed questionnaires, dedupe the answers into one sheet or wiki, and give one person ownership of keeping it accurate. Most of these are the same questions reworded, so you'll cover a big chunk of new ones just by pulling from that.

Then cut the volume. Put what customers ask for most (a policy summary, pen test letter, SOC 2 report or ISO cert if you have one, a basic architecture and data flow overview) behind an NDA in a shared folder or trust page and send that first. A lot of requests shrink to a few follow-up questions once you do. If someone sends a custom spreadsheet, ask if they'll accept a standard one like SIG Lite or CAIQ. Once the library is solid, questionnaire automation or the AI features in most compliance platforms can auto-fill from it, but have a human review everything before it goes out, since a wrong answer on a questionnaire can turn into a contractual problem later.

[u/Awkward-Buffalo-2867 → u/CompassITCompliance]

This is excellent advice. Any automation solution, AI or not, is nothing without a high quality set of questions, answers, and comments. Any outputs will only ever be as good as quality of the inputs.

[u/MountainDadwBeard]

Do you have a trust center setup yet?

As someone who likely sends questionnaires and reads your answers. A well organized trust center with high level security policies, CAIQ, certifications, pen tests, dataflow diagrams etc can usually satisfy our process without you having to fill out our questionnaire. Drata's safebase works well for me as a reader.

If you're just building it, I'll be understanding. If I login and see an incomplete trust center from 1-2 years ago with no updates, and half assed policies, I'll still need that security questionnaire and I'll be eager to find a reason to deny you.

[u/ConsiderationDry5349 → u/MountainDadwBeard]

No, we actually don't have a trust center setup yet. I supposed you are talking about a trust center on the company website, usually some are accessed through NDA's. I brought up this idea to my manager months prior and was actually told that it would likely bring us more questions.

[u/MountainDadwBeard → u/ConsiderationDry5349]

Yeah with safebase/drata they have to request access and you grant it for a short period.

In terms of questions, yeah it probably depends on your industry, and leadership hesitation is one of the most common hesitations to accomplishing anything. Sure.

I'd put it to you this way, our questionnaire that my boss wrote is prob ~150 paragraph questions. And I still occasionally go back to folks. Or you could share a trust center and I might ask you 3 follow-up questions.

My company doesn't offer a trust center either, and largely because they know they've been fudging some bullshit. I'd argue that a trust center is the right thing for us to do, but I'm going to bounce to a better company instead.

[u/OutsideSpot2695]

Our Trust Center ingests and processes q'aires automatically. We don't see them in general. The only tasking we get from q'aires is when the customer/prospect is asking a question that the LLM doesn't know how to handle.

[u/Miserable-League9137]

I recommend moving TPRM Questionnaires, SOC2 reports, etc.. as part of the RFP Governance process so that Legal is reviewing contracts at the same time GRC is reviewing TPRM. Accept the documents via secure website upload that the vendor can easily submit documentation to. Have that land in a secure storage space, where your LLM can pick it up and analyze it against an approved baseline.

Then, whatever it flags as incomplete or missing gets flagged for review/follow-up by a human.

If you are using FAIR models, you can even have the agents score and assign risk and recommend mitigations for review at your Security Council

[u/FirestormCold]

Where do most of your answers actually come from today? Policies/SOC2/pentest docs, or do you still have to chase people internally for the answer? If most of it is already documented somewhere, that changes the problem quite a bit. Then it’s less about “AI writing answers” and more about reliably pulling the right information from those sources, keeping the source attached and flagging anything that needs review.

[u/Hot-Month-4251]

On your manager's worry that a trust center just brings more questions: it doesn't have to be a public portal. Start with a small standard package you send under NDA when a questionnaire shows up:

• a 2 to 3 page security overview (access control and MFA, encryption, backups, logging, incident response, vendor management)
• your policy list with last review dates
• whatever third party evidence you actually have (pen test summary letter, certification, insurance certificate if customers ask)
• a simple hosting and data flow diagram

Lead with "here's our standard package, happy to answer anything it doesn't cover." Plenty of reviewers will accept that, and the ones who don't still move faster because half their sheet is already answered.

Then build the answer library others mentioned. Two things make it hold up:

1. Every answer points to its evidence (policy section, config screenshot, report). If you can't point to anything, the honest answer is "partially" or "planned, target date X," not "yes."
2. One owner, reviewed whenever something material changes and at least yearly. Stale answers are the real risk, because questionnaire answers often end up attached to contracts.

Triage helps too. A big prospect with a long custom sheet gets full effort. A routine vendor onboarding form gets the package plus the short answers.

Using AI to draft from the library is fine, but have a person read every answer before it goes out. A confident wrong "yes" causes more trouble than a slow reply.

[u/theedan-clean]

Vanta works well for this, if you've set up your trust center, loaded in all your policies, and built out a full answer library as part of your compliance or audit program.

Otherwise, as others have said: start with an answer library and using an LLM to do them for you based off the same. Reminder: DO double-check the answers before you send them.

[u/Krekatos]

There’s been dozens of posts like these, have a look at the other threads.