---
name: vendor-dd-questionnaire
description: Auto-fill an inbound security/compliance questionnaire (SIG, SIG-Lite, CAIQ, or a custom format) by mapping every question to the firm's pre-approved control library, citing the control ID and supporting evidence on each answer, and flagging novel or low-confidence questions for the security team. Use as a first-pass drafter before a security-team final review, never as the submission-of-record.
---
# Vendor DD questionnaire
## When to invoke
Invoke when a customer or prospect has sent an inbound vendor diligence questionnaire — SIG, SIG-Lite, CAIQ, CAIQ-Lite, HECVAT, VSAQ, or a custom spreadsheet-shaped questionnaire — and the GRC / security-program-manager team wants a first-pass draft grounded in the firm's existing control library before a security analyst reviews and signs off. Typical trigger: a `.xlsx` lands in the security inbox tied to a deal in [HubSpot](/en/tools/hubspot/) or [Salesforce](/en/tools/salesforce/), and the assigned analyst wants the mechanical 70-80% of answers pre-populated so they can spend their time on the questions that actually require judgment.
Do NOT invoke this skill for:
- **Final submission to the customer.** The skill drafts; a named security analyst reviews every answer and the deal owner signs off before the questionnaire goes back. Auto-fill plus auto-send is the failure mode this rule guards against.
- **Anything routed through a non-Tier-A AI vendor.** Questionnaire content often includes the customer's procurement metadata, internal control numbering, and (in custom formats) free-text that quotes the customer's own architecture. If the configured model is not on the firm's approved vendor list with a signed DPA covering security-program work, escalate to the security team instead of running.
- **Novel control frameworks the firm has not mapped.** If the questionnaire references a framework the control library does not cover (e.g. a sector-specific reg the firm has not yet been audited against — FedRAMP Moderate, IRAP, BSI C5), the skill will pattern-match incorrectly and produce confidently-wrong answers. Map the framework into the control library first, then run.
- **Questionnaires that are part of an active incident-response or audit finding.** Those go straight to the security team — they are not drafting exercises.
- **Anything where the customer has explicitly asked for human-written, non-AI-assisted responses.** Honor the request; don't run the skill.
## Inputs
- Required: `questionnaire` — path to the inbound `.xlsx` (most common), `.docx`, or pasted text. The skill preserves the original structure when the input is `.xlsx` so the customer receives the file in the format they sent.
- Required: `control_library` — path to the firm's mapped control library in `references/`. Defaults to `references/1-control-library-template.md`. Replace the template with the firm's actual mapped controls, indexed by framework (SOC 2 CC, ISO 27001 Annex A, NIST CSF, CIS, etc.) before first run.
- Required: `evidence_index` — path to the index of supporting evidence documents (SOC 2 report, ISO certificate, pen test summary, BCP, IR plan, privacy policy, sub-processor list). Each evidence document has an ID the control library cites; the skill emits the ID, never the file contents.
- Optional: `prior_responses` — directory of previously-completed questionnaires. The skill pattern-matches new questions against prior answers and reuses the answer when the question text and intent match (with attribution to the prior questionnaire ID, never silently).
- Optional: `customer_context` — free-text on the customer (industry, jurisdiction, deal stage). Used to bias toward more conservative answers when the customer is in a regulated industry or the deal is large.
## Reference files
Always read the following from `references/` before drafting. Without them, every answer is a generic AI-flavored response disconnected from the firm's actual control posture, and every flagged item lacks a clear escalation path.
- `references/1-control-library-template.md` — the firm's mapped control library. One entry per control, indexed by framework, with the canonical answer, the supporting evidence ID, and the date the control was last audited. Replace the template with the firm's actual controls before first use.
- `references/2-answer-format-reference.md` — the literal answer formats expected per question type (Yes/No, Yes/No with description, descriptive, document upload, certification reference, N/A with justification). The skill emits answers in the format the questionnaire expects, not the format the model defaults to.
- `references/3-novel-question-escalation.md` — the rules that decide when a question flips from "skill answers with a control citation" to "skill flags for security review." Examples: questions that introduce a control framework not in the library, questions whose answer would commit the firm to a future change (forward-looking representations), questions about specific incidents.
## Method
Run the four sub-tasks in order. Do not parallelize: classification feeds control matching, which feeds answer drafting, which feeds the review-flag decision.
### 1. Question classification
For each row in the questionnaire, identify:
- **Response type expected** — Yes/No, Yes/No-with-description, free-text descriptive, document-upload (the customer wants the actual evidence doc), certification-reference (cite a cert and attestation date), or N/A-with-justification.
- **Topic** — access control, encryption-at-rest, encryption-in-transit, key management, BCP/DR, IR, sub-processor management, change management, vulnerability management, secure SDLC, privacy/DSR, etc.
- **Framework hint** — if the question text or column header references a specific framework section (`CC6.1`, `A.9.4.2`, `CCM IAM-09`), capture it. Framework-aware matching is more reliable than topic-only matching.
Why classification first, not "answer everything in one pass": question type controls answer format, and topic + framework hint together drive the control-library lookup. Skipping classification and letting the model free-draft is the most common reason auto-fill produces inconsistent or miscategorized answers.
### 2. Control-library matching
For each classified question, look up the matching control in `references/1-control-library-template.md`. Match priority:
1. Exact framework section match (the question cites `CC6.1`, the library has an entry for `CC6.1`).
2. Topic + sub-topic match within the same framework.
3. Cross-framework topic match (e.g. SOC 2 CC6.1 maps to ISO 27001 A.9.4.2 maps to CCM IAM-09 — the library notes the equivalences).
4. No match → flag as novel-question for escalation. Do not improvise.
Why control-library-first instead of letting the model improvise an answer from documentation: the library entries have already been reviewed by security and legal. Improvised answers reintroduce that review burden on every run, defeat the time saving, and create contractual-representation risk because every questionnaire answer is a representation the firm makes to the customer.
### 3. Answer drafting with citations
For every matched question, emit the canonical answer from the library in the format the question expects (per `references/2-answer-format-reference.md`). Every answer carries:
- The control ID cited (e.g. `SOC2.CC6.1`).
- The supporting evidence ID (e.g. `EV-SOC2-2025`, `EV-PENTEST-2025-Q1`).
- The library entry's `last_reviewed` date.
- A confidence score: `high` (exact match, library entry under 90 days old), `medium` (cross-framework match or library entry 90-180 days old), `low` (cross-framework match plus library entry over 180 days old, or stale evidence).
Pattern-match against `prior_responses` only as a tie-breaker on borderline matches; never let a prior answer override the current control library. Prior answers from 18 months ago can be flatly wrong.
### 4. Review-flag decision
For every question meeting the rules in `references/3-novel-question-escalation.md`, replace the drafted answer with a "needs security review" block. The block contains: the question text, the candidate answer the skill considered (so the analyst has a starting point), the trigger that fired the escalation, and any candidate control IDs the matching pass surfaced.
Also flag for review: any answer with `low` confidence, any forward-looking commitment, any answer that touches a specific incident or audit finding, and any question whose answer differs from the prior response on a recent (under 90 days) questionnaire — the divergence itself is a signal the analyst should look at it.
## Output format
Write the original `.xlsx` back with the answer cells populated, plus a sibling markdown summary the analyst opens first. The summary's literal format:
```markdown
# Questionnaire draft — <Customer name>
Questionnaire type: <SIG | SIG-Lite | CAIQ | HECVAT | custom>
Control library version: <control library last_reviewed date>
Total questions: <N>
- Answered (high confidence): <count>
- Answered (medium confidence): <count>
- Answered (low confidence — review): <count>
- Flagged for security review: <count>
- Document-upload required: <count>
---
## Q4.2 — "Do you encrypt data at rest using AES-256 or stronger?"
**Response type:** Yes/No-with-description
**Topic:** encryption-at-rest
**Framework hint:** CCM EKM-03
**Drafted answer:**
> Yes. All customer data is encrypted at rest using AES-256-GCM via
> AWS KMS-managed keys. Key rotation is automatic on a 365-day cycle.
**Citation:** control SOC2.CC6.7 / ISO27001.A.10.1.1 / CCM EKM-03
**Evidence:** EV-SOC2-2025 §6.7, EV-KMS-CONFIG-2025-Q1
**Confidence:** high
**Library entry last reviewed:** 2026-02-14
---
## Q9.3 — "Describe your process for handling FedRAMP Moderate boundary changes."
**Flagged for security review**
- **Trigger:** Framework not in control library (FedRAMP Moderate not
yet mapped).
- **Candidate control:** none — closest is `SOC2.CC8.1` (change
management), but the framework-specific question requires a
framework-specific answer.
- **Action:** Security analyst to draft. Do not improvise.
---
```
The `.xlsx` carries the same answers in the customer's original cell layout, with a comment on each cell containing the control ID, evidence ID, and confidence so the analyst can audit without flipping back to the markdown summary.
## Watch-outs
- **Stale control library produces confidently-wrong answers.** A SOC 2 Type II report from 2024 cited as evidence in 2026 will be rejected by any sophisticated customer. Guard: every output's summary header writes the control library's `last_reviewed` date and every cited evidence document's effective date. The analyst rejects any draft where the library is older than 90 days or any cited evidence is past its attestation window, and refreshes the library before re-running.
- **Answer-improvisation when the library does not match.** A model under pressure to "fill the cell" will free-draft an answer that sounds plausible. Guard: the matching pass emits explicit `no match → flag` rather than degrading gracefully. The skill refuses to write a cell without a control ID; cells without a citation surface in the summary as flagged-for-review, never as drafted answers.
- **Certification expiration.** A SOC 2 cited as current may have expired between the last library refresh and today. Guard: the evidence index carries an `effective_through` date per evidence document. If today is past `effective_through`, the skill drops the evidence cite and downgrades the answer to `low` confidence with a note that the cert is in renewal. The analyst chases the renewed cert before the questionnaire goes back.
- **Forward-looking commitments treated as facts.** "Will you support customer-managed keys by Q4?" is a roadmap question, not a control question. Drafted as Yes/No, it becomes a contractual representation. Guard: `references/3-novel-question-escalation.md` lists the linguistic patterns ("will you", "do you plan to", "by what date") that force a flag-for-review regardless of confidence.
- **Pattern-match drift from prior responses.** Last year's response said "365-day key rotation"; this year's policy says 90 days. Reusing the prior answer creates a contractual misrepresentation. Guard: prior-response matching is a tie-breaker only, never an override. When a prior answer differs from the current library entry, the skill flags the divergence in the summary so the analyst can see it.
# Control library — TEMPLATE
> Replace this template's contents with the firm's actual mapped control
> library. The vendor-dd-questionnaire skill reads this file on every run;
> without the firm's real controls, every answer is a generic AI-flavored
> response disconnected from the firm's actual security posture.
## How this file is used
The skill matches every question in the inbound questionnaire to one entry below. Match priority is: exact framework section → topic + sub-topic within framework → cross-framework topic → no match (flag for escalation). The skill never improvises an answer when no entry matches.
Each entry is keyed by canonical control ID and lists the equivalences across the frameworks the firm has been audited against. Add new frameworks here, not in the skill body.
## Library metadata
- `library_version`: replace with the firm's library version tag.
- `last_reviewed`: YYYY-MM-DD — the skill prints this in the summary header, and the analyst rejects drafts where this is older than 90 days.
- `frameworks_covered`: e.g. `[SOC 2 Type II, ISO 27001:2022, NIST CSF, CCM v4]` — questionnaires citing frameworks not on this list are flagged for security-team mapping.
---
## Entry: access-control / least-privilege
- **Canonical ID:** `IAM.001`
- **Framework equivalences:**
- SOC 2: `CC6.1`, `CC6.2`, `CC6.3`
- ISO 27001:2022: `A.5.15`, `A.5.18`
- CCM v4: `IAM-08`, `IAM-09`
- NIST CSF: `PR.AC-1`, `PR.AC-4`
- **Canonical answer:** Replace with the firm's actual one- or two-sentence answer. Example shape: "Access is granted role-based via <IdP>; quarterly access reviews enforce least privilege; provisioning and de-provisioning are logged."
- **Supporting evidence:** `EV-SOC2-<year>` (§<section>), `EV-IDP-CONFIG-<year>`
- **Last audited:** YYYY-MM-DD
- **Notes for the analyst:** any caveats — e.g. "answer differs for production vs corporate access; if question scope is corporate-only, flag for human review."
---
## Entry: encryption-at-rest
- **Canonical ID:** `CRYPTO.001`
- **Framework equivalences:**
- SOC 2: `CC6.7`
- ISO 27001:2022: `A.8.24`
- CCM v4: `EKM-03`, `EKM-04`
- **Canonical answer:** Replace with the firm's actual answer. Example shape: "All customer data at rest encrypted with <algorithm>; customer-managed keys available on the <tier> plan; key rotation every <N> days via <KMS>."
- **Supporting evidence:** `EV-SOC2-<year>`, `EV-KMS-CONFIG-<year>-Q<n>`
- **Last audited:** YYYY-MM-DD
- **Notes for the analyst:** if the question asks specifically about customer-managed keys (CMK / BYOK) and the firm offers them only on a higher tier, the answer changes by deal — flag.
---
## Entry: encryption-in-transit
- **Canonical ID:** `CRYPTO.002`
- **Framework equivalences:**
- SOC 2: `CC6.7`
- ISO 27001:2022: `A.8.24`
- CCM v4: `EKM-03`
- **Canonical answer:** Replace with the firm's actual answer. Example shape: "TLS <min version> enforced on all external endpoints; HSTS enabled; cipher suite restricted to <list>."
- **Supporting evidence:** `EV-PENTEST-<year>-Q<n>`, `EV-SSLLABS-<year>-<month>`
- **Last audited:** YYYY-MM-DD
---
## Entry: incident response
- **Canonical ID:** `IR.001`
- **Framework equivalences:**
- SOC 2: `CC7.3`, `CC7.4`, `CC7.5`
- ISO 27001:2022: `A.5.24`, `A.5.25`, `A.5.26`
- CCM v4: `SEF-02`, `SEF-03`, `SEF-04`
- **Canonical answer:** Replace with the firm's actual answer. Example shape: "Documented IR plan reviewed annually; tabletop conducted every <N> months; security incidents reported to affected customers within <N> hours of confirmation."
- **Supporting evidence:** `EV-IR-PLAN-<year>`, `EV-TABLETOP-<year>-<month>`
- **Last audited:** YYYY-MM-DD
- **Notes for the analyst:** notification SLA varies by contract; default to the policy SLA but flag if the customer's MSA carries a shorter window.
---
## Entry: business continuity / disaster recovery
- **Canonical ID:** `BCP.001`
- **Framework equivalences:**
- SOC 2: `A1.2`, `A1.3`
- ISO 27001:2022: `A.5.29`, `A.5.30`
- CCM v4: `BCR-01`, `BCR-08`
- **Canonical answer:** Replace with the firm's actual answer. Example shape: "RTO <hours>, RPO <minutes>; DR plan tested <frequency>; multi-AZ deployment with cross-region failover for <component list>."
- **Supporting evidence:** `EV-BCP-<year>`, `EV-DR-TEST-<year>-<month>`
- **Last audited:** YYYY-MM-DD
---
## Entry: sub-processor management
- **Canonical ID:** `VEND.001`
- **Framework equivalences:**
- SOC 2: `CC9.2`
- ISO 27001:2022: `A.5.19`, `A.5.20`, `A.5.21`
- CCM v4: `STA-07`, `STA-09`
- **Canonical answer:** Replace with the firm's actual answer. Example shape: "Sub-processor list maintained at <URL>; customers notified <N> days before adding a new sub-processor; right-of-objection per DPA §<n>."
- **Supporting evidence:** `EV-SUBPROCESSORS-<year>-<month>`, `EV-DPA-TEMPLATE-<year>`
- **Last audited:** YYYY-MM-DD
---
## Entry template — copy this for new controls
- **Canonical ID:** `<DOMAIN>.<NUMBER>`
- **Framework equivalences:**
- SOC 2: `<section>`
- ISO 27001:2022: `<annex section>`
- CCM v4: `<control ID>`
- NIST CSF: `<function.category-N>`
- **Canonical answer:** the firm's reviewed answer, one to three sentences.
- **Supporting evidence:** `EV-<DOC>-<year>`
- **Last audited:** YYYY-MM-DD
- **Notes for the analyst:** caveats, scope notes, deal-specific variants the analyst needs to know about.
# Answer format reference — TEMPLATE
> The vendor-dd-questionnaire skill emits answers in the format the
> questionnaire expects, not the format the model defaults to. This file
> documents the canonical format per response type. Replace the example
> phrasings with the firm's house style and tone.
## Why this file exists
A SIG question and a CAIQ question on the same control expect different answer shapes. SIG-Lite expects single-cell `Yes/No`. Full SIG expects `Yes/No` plus a free-text justification in the adjacent column. CAIQ expects `Yes/No/NA` plus a CCM-aligned response. The skill picks the shape from this file based on the response-type classification done in Method step 1.
If a question's expected format does not match any of the patterns below, the skill flags it for the analyst rather than guessing the shape.
## Format: Yes/No (single cell)
- **When used:** SIG-Lite, simple binary checklists.
- **Allowed values:** `Yes`, `No`, `N/A`. No prose.
- **Skill behavior:** If the canonical answer in the control library is not a clean binary, the skill downgrades to `low` confidence and flags. Binary cells are the most-misread; never improvise.
## Format: Yes/No-with-description (two cells)
- **When used:** Full SIG, most CAIQ questions, custom questionnaires.
- **Allowed values:** Cell A: `Yes` / `No` / `N/A`. Cell B: free-text description, typically 1-3 sentences.
- **Description shape:** lead with the affirmative, name the control, cite the evidence section. Example skeleton:
> Yes. <One-sentence statement of what the firm does>. Documented in
> <evidence ID> §<section>.
- **N/A justification:** when answering N/A, the description must explain why N/A applies (scope, applicability, alternative control). Bare `N/A` triggers a re-flag from the analyst.
## Format: descriptive free-text
- **When used:** "Describe your process for…", "Explain how…", "What is your approach to…".
- **Length target:** 3-6 sentences. Longer answers signal the model is padding.
- **Shape:** state the policy → state the implementing control → state the cadence (testing, review, audit) → cite the evidence ID.
- **Skill behavior:** must cite the canonical answer's source control ID; must not improvise process steps that are not in the library entry. If the library entry is shorter than the answer the skill wants to write, the skill writes only what the library covers and flags for analyst expansion.
## Format: document-upload
- **When used:** "Please attach your <SOC 2 / ISO cert / pen test summary / DPA / sub-processor list>".
- **Skill behavior:** the skill never writes a cell value. Instead, the summary lists the document the customer is asking for and the matching evidence ID from the index. The analyst handles the upload through the firm's evidence-sharing channel (NDA-gated portal, trust center, etc.) — never by attaching docs to the questionnaire file itself.
## Format: certification-reference
- **When used:** "Are you SOC 2 Type II certified?", "Do you hold ISO 27001 certification?".
- **Allowed values:** Cell A: `Yes`. Cell B: certification name + attestation period + auditor name. Example skeleton:
> Yes. SOC 2 Type II covering <period start> through <period end>,
> issued by <auditor>. Report available under NDA via <trust center
> URL>.
- **Skill behavior:** pulls dates from the evidence index, not from the control library entry. If the cert is past `effective_through`, the skill answers "in renewal" and flags. Never claim a current cert when the evidence shows it has lapsed.
## Format: N/A with justification
- **When used:** Question targets a capability the firm does not offer (e.g. on-premises deployment for a SaaS-only firm) or a framework the firm is not subject to.
- **Shape:** `N/A` plus a one-sentence justification naming the reason (scope, applicability, alternative control).
- **Skill behavior:** flag for analyst review even when the library entry says N/A — N/A answers are most likely to draw a follow-up question from the customer's security team, and the analyst should see them before submission.
## Format: forward-looking / roadmap
- **When used:** "Will you support…", "When do you plan to…", "Is this on your roadmap…".
- **Skill behavior:** never answer. Always flag for review. Roadmap answers are contractual representations and require product + legal sign-off, not security alone.
## Format: incident or audit-finding-specific
- **When used:** "Have you had a breach in the last 12 months?", "Describe any open audit findings", "Have you been subject to a regulatory action?".
- **Skill behavior:** never answer. Always flag for review. These questions require the security and legal teams; the skill cannot represent the firm on them.
# Novel-question escalation criteria — TEMPLATE
> The vendor-dd-questionnaire skill consults this file at the end of
> every question's processing. Any question matching one or more rules
> below is replaced with a "needs security review" block instead of a
> drafted answer. Replace the example thresholds with the firm's actual
> policy.
## Why this file exists
Auto-fill is safe only on questions the firm has already answered (via the control library) for situations the firm has already encountered. Everything else — novel frameworks, forward-looking commitments, incident-specific questions, low-confidence matches — is where the skill produces confidently-wrong answers if allowed to proceed. This file is the explicit list of "do not improvise" triggers.
If you find yourself wishing the skill would just answer one of these anyway, the right move is to add the situation to the control library (so the answer is reviewed once, then reusable) — not to weaken these rules.
## Hard escalation triggers (always flag)
A question matching any one of these is flagged for security review. The skill emits the question text, the candidate answer it considered (if any), the trigger that fired, and any candidate control IDs the matching pass surfaced.
### 1. Framework not mapped in the control library
If the question references a framework section the library does not cover (e.g. `FedRAMP Moderate AC-2`, `IRAP §<n>`, `BSI C5 OPS-01`) and no cross-framework equivalent is recorded, flag. Do not pattern-match to a "close enough" framework section — the customer is reading the answer through the lens of the framework they cited.
### 2. Forward-looking commitment
Linguistic patterns that flag automatically:
- `will you support`
- `do you plan to`
- `is on your roadmap`
- `by what date`
- `when do you intend`
- `future support for`
Roadmap answers are contractual representations and require product + legal sign-off, not security alone. The skill never answers these.
### 3. Specific incident or audit finding
Linguistic patterns that flag automatically:
- `have you had a breach`
- `describe any open audit findings`
- `regulatory action`
- `data subject request`
- `enforcement action`
- `material weakness`
These require the security and legal teams; the skill cannot represent the firm on them.
### 4. Customer-specific architecture or contract clause
Questions that quote the customer's own architecture, MSA, or DPA back at the firm and ask the firm to confirm — for example "Confirm your deployment matches the architecture in Schedule 3" — require deal-team review. The skill does not have access to customer-specific schedules and cannot confirm.
### 5. Low-confidence match
Any answer the matching pass scored as `low` confidence (cross-framework match plus library entry over 180 days old, or stale evidence) flips to flag-for-review even though a candidate answer exists. The candidate is included in the flag block so the analyst has a starting point.
### 6. Divergence from a recent prior response
If `prior_responses` contains an answer to a substantially-similar question from the last 90 days, and that prior answer differs from the current control library entry, flag both — the divergence itself is the signal the analyst should investigate. (Did the policy change? Did the prior questionnaire have a wrong answer? The skill cannot decide.)
## Soft escalation triggers (flag if combined)
Two or more of these together flag for review; one alone is allowed through with a note in the analyst summary.
- Customer is in a regulated industry the firm has not served before (per `customer_context`).
- Customer's deal size is in the firm's top decile (per `customer_context`).
- Question is in a topic the firm has fewer than 3 prior-response examples for.
- Library entry's `last_reviewed` is between 90 and 180 days old.
The "combined" rule exists because individually these are weak signals, but together they correlate with the questionnaires that get the most follow-up scrutiny.
## Allowed-vendors precondition
The skill refuses to run unless the configured AI vendor is on the firm's approved list. Replace this list with the firm's actual approved vendors.
- `<vendor 1>` — approved for security-program work, DPA on file dated YYYY-MM-DD.
- `<vendor 2>` — approved for security-program work, DPA on file dated YYYY-MM-DD.
If the configured vendor is not on this list, the skill exits with an error message naming the missing vendor. Do not bypass with a CLI flag; the precondition exists because questionnaire content is firm-confidential and customer-confidential simultaneously.
## Escalation block format
When a question is flagged, the skill emits the following block instead of an answer:
```markdown
**Flagged for security review**
- **Question:** <verbatim question text>
- **Trigger:** <which rule above fired; if multiple, list them>
- **Candidate control:** <control ID if matching surfaced one, else "none">
- **Candidate answer the skill considered:** <text or "none">
- **Action:** Security analyst to draft. Do not improvise.
```
The analyst sees the block in the summary, can accept the candidate as a starting point or rewrite from scratch, and signs off on every flagged question before the questionnaire goes back.
