Security Questionnaire Autofill

Security Questionnaire Autofill

A single enterprise deal can arrive with a 300-question security questionnaire, and answering it by hand is a week no one has. This drafts the answers from your actual security posture, keeps the wording consistent across questions, and — critically — refuses to invent a control you don't have. What it can't answer truthfully, it flags, so you close the real gap instead of papering over it.

Answers must reflect reality. A fabricated "yes" on a security questionnaire is a misrepresentation that can void a contract — this skill flags gaps, it does not invent controls.

What This Skill Produces

• Drafted answers — one per question, grounded in your stated controls, in consistent language
• The gap list — questions you can't currently answer "yes" to, with what closing them would take
• Reusable snippets — a growing answer library so the next questionnaire is faster
• Evidence pointers — which policy/doc backs each answer (so reviewers can verify)

Required Inputs

Ask for these if not provided:

• The questionnaire — the questions (SIG, CAIQ, or custom), pasted or attached
• Your controls — your security posture: policies, certifications (SOC 2, ISO 27001), encryption, access control, MFA, backups, incident process — whatever's real
• Your posture doc / prior answers — if you have a security whitepaper or past questionnaire, feed it for consistency
• Honesty stance — confirm: flag gaps rather than best-case them (default: yes)

Framework: Answer From Truth

1. Map question → control. Each question is answered from a real control or marked a gap. No control, no "yes."
2. Consistent voice. The same control answered the same way every time it's asked (questionnaires repeat).
3. Evidence-anchored. Every substantive answer names the policy/doc/cert that proves it.
4. Gaps are findings, not failures. A flagged gap is an action item; a fabricated answer is a liability.
5. Scope honestly. "Yes, for production; not yet for the sandbox" beats a misleading blanket yes.

Output Format

Security Questionnaire — [customer] · [framework]

Summary: [N answered · G gaps · C need a human decision]

Answers

Gaps to close (ranked)

• [control] — effort to close, and whether it blocks this deal

Snippets saved for reuse

• [control] → [reusable answer text]

Quality Checks

• Every "yes" traces to a real, named control — none inferred or invented
• Gaps are flagged explicitly, not softened into misleading answers
• Repeated questions get consistent answers
• Scope is honest where a control is partial
• Anything requiring a business/legal decision is escalated, not guessed

Anti-Patterns

• Fabricating a "yes" to speed the deal — the single thing this skill must never do.
• Inconsistent answers to the same control across the sheet — reviewers notice.
• Vague answers with no evidence — "we take security seriously" fails a review.
• Hiding a partial scope behind a blanket claim.

Example Trigger Phrases

• "Fill out this security questionnaire from our controls."
• "Answer this SIG/CAIQ for a customer security review."
• "Respond to the vendor risk assessment — flag anything we can't truthfully claim."
• "Draft answers to this security review and list our gaps."