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  3. Security Questionnaire Drafter
Featured
intermediate
Claude or ChatGPT (verify current model choice)
v1.0.0

Security Questionnaire Drafter

Turn your security posture into vendor questionnaire answers. Feed in your controls inventory, get consistent RFP responses that don't leak risk or contradict each other.

Full prompt

You are a security questionnaire answering assistant for {{COMPANY_NAME}}.

Your job: Read the vendor's security questionnaire and {{COMPANY_SECURITY_POSTURE_FACT_PACK}}. For each question, generate an answer that:
1. Is truthful and defensible (no exaggeration)
2. References specific controls from the fact pack
3. Includes a confidence level: [Verified] (documented, tested), [Documented] (policy exists), [In Progress] (roadmap), [Not Applicable]
4. Flags any gaps where the fact pack doesn't cover the question

Format output as JSON:
{
  "questionnaire_name": "{{VENDOR_NAME}} Security Assessment",
  "completed_at": "ISO timestamp",
  "answers": [
    {
      "question_id": "Q1",
      "question_text": "...",
      "answer": "...",
      "confidence": "[Verified]",
      "fact_pack_reference": "Section X.Y",
      "gap_flag": null or "string"
    }
  ],
  "summary": {
    "total_questions": number,
    "verified_count": number,
    "documented_count": number,
    "in_progress_count": number,
    "not_applicable_count": number,
    "gaps_requiring_disclosure": ["gap1", "gap2"]
  }
}

Do not invent controls. If the fact pack is silent, say so.

How to use

1. Build your security fact pack: a 1–2 page inventory of your actual controls (MFA, encryption, access logs, incident response process, backup frequency, etc.). Be honest—gaps are better than fabrications. 2. Paste the vendor's questionnaire into the prompt. 3. Run the workflow. 4. Review the output: check confidence levels, verify references, and flag any answers you want to soften or strengthen. 5. Use the gap summary to decide what to disclose proactively ("We don't have X yet, but it's on the roadmap") vs. what to omit. 6. Export as PDF or email directly to the vendor.

Example input

{{COMPANY_SECURITY_POSTURE_FACT_PACK}}:
- MFA: Okta, enforced for all staff and admins
- Encryption: AES-256 at rest (AWS KMS), TLS 1.2+ in transit
- Access logs: CloudTrail + Datadog, 90-day retention
- Incident response: On-call rotation, runbook in Notion, no formal SLA
- Backups: Daily snapshots, tested quarterly
- Penetration testing: None conducted
- SOC 2: Not yet audited

Vendor questionnaire excerpt:
Q1: Do you enforce MFA for all users?
Q2: What encryption standard do you use for data at rest?
Q3: How long do you retain access logs?
Q4: Have you completed a SOC 2 Type II audit?
Q5: Do you conduct annual penetration testing?

Example output

{
  "questionnaire_name": "Acme Corp Security Assessment",
  "completed_at": "2025-01-15T10:30:00Z",
  "answers": [
    {
      "question_id": "Q1",
      "question_text": "Do you enforce MFA for all users?",
      "answer": "Yes. We enforce MFA via Okta for all staff and administrative accounts. MFA is a prerequisite for account provisioning.",
      "confidence": "[Verified]",
      "fact_pack_reference": "MFA section",
      "gap_flag": null
    },
    {
      "question_id": "Q2",
      "question_text": "What encryption standard do you use for data at rest?",
      "answer": "AES-256 encryption via AWS KMS for all data at rest. In transit, we enforce TLS 1.2 or higher.",
      "confidence": "[Verified]",
      "fact_pack_reference": "Encryption section",
      "gap_flag": null
    },
    {
      "question_id": "Q3",
      "question_text": "How long do you retain access logs?",
      "answer": "90 days. Logs are aggregated in CloudTrail and Datadog.",
      "confidence": "[Documented]",
      "fact_pack_reference": "Access logs section",
      "gap_flag": null
    },
    {
      "question_id": "Q4",
      "question_text": "Have you completed a SOC 2 Type II audit?",
      "answer": "Not yet. We are planning our first SOC 2 Type II audit for Q3 2025.",
      "confidence": "[In Progress]",
      "fact_pack_reference": "Compliance roadmap",
      "gap_flag": "Vendor may require SOC 2 for contract signature. Escalate early."
    },
    {
      "question_id": "Q5",
      "question_text": "Do you conduct annual penetration testing?",
      "answer": "Not currently. Penetration testing is on our 2025 roadmap.",
      "confidence": "[In Progress]",
      "fact_pack_reference": "Security roadmap",
      "gap_flag": "Consider offering a third-party pentest before deal close."
    }
  ],
  "summary": {
    "total_questions": 5,
    "verified_count": 2,
    "documented_count": 1,
    "in_progress_count": 2,
    "not_applicable_count": 0,
    "gaps_requiring_disclosure": ["SOC 2 Type II audit", "Annual penetration testing"]
  }
}

Customization tips

  • Update your fact pack quarterly. As you add controls (new SIEM, incident response SLA, backup testing), refresh the document so questionnaire answers stay current. Stale facts = inconsistent answers = deal friction.
  • Create a 'confidence calibration' guide for your team. Define what [Verified] means (e.g., 'tested in the last 30 days') vs. [Documented] (e.g., 'policy exists, not yet tested'). Consistency in confidence levels builds buyer trust.
  • Add a 'vendor risk tier' field to the output. Flag questions that are deal-blockers (SOC 2, encryption) vs. nice-to-haves (annual pentest). Prioritize gap closure by deal impact, not by question order.
  • Use the gap summary as a roadmap input. If three vendors ask about penetration testing, it moves up your security roadmap. Let buyer demand drive your control investment.
  • Automate the export. Pipe the JSON output to a template that generates a PDF or Word doc formatted for the vendor. One less manual step = faster turnaround = better close rate.