[Fiona Freelance Financier]

I’m curious whether AI tools (large language models) can realistically speed up drafting RFP responses and security questionnaire answers for non-technical teams.

Specifically, I’d love practical feedback on these points:

• Accuracy: How reliable are AI-generated answers for technical or compliance questions?
• Efficiency: Do these tools save real time when preparing drafts and reusable templates?
• Review workflow: What checks do you use to verify AI drafts before sending them to customers?
• Security & confidentiality: Any best practices when feeding sensitive or proprietary prompts to AI services?
• Tools & prompts: Which apps or prompt styles have worked well for creating consistent RFP or security questionnaire drafts?

If you’ve tried this in a nonprofit, small business, or corporate setting, please share what worked, what didn’t, and any simple examples or templates. Thanks — I’m looking for practical, easy-to-adopt tips.

[Jeff Bullas]

Great question — deciding whether AI can help draft RFP responses and security questionnaires is the exact right place to start. AI can speed drafting, reduce repetitive work and create consistent answers, but it needs the right inputs and guardrails.

What you’ll need

• Clear source materials: previous RFP responses, your security policy summaries, SOC/ISO/PCI artifacts (or summaries).
• Templates: standard response format, acceptance criteria, and a list of contacts (control owners, legal, compliance).
• Review workflow: human reviewer(s) to validate accuracy and red-team any claims.

Step-by-step: a practical path to quick wins

1. Collect a concise fact sheet: one page with company overview, hosting model, key controls, certifications, and contact names.
2. Identify repeatable questions: extract common RFP/security questionnaire items (encryption, backups, incident response).
3. Use AI to draft first-pass answers for repeatable items, keeping replies short and evidence-linked.
4. Route each draft to the relevant control owner for validation and attach evidence references (policy document name, report date).
5. Assemble the final response, keep an FAQ library for future use, and track accepted wording.

Example — how AI helps a single question

Question: “Do you encrypt data at rest?”

• AI draft: short affirmative statement + what is encrypted + algorithm or service + where to find evidence (e.g., “See Encryption Policy v2.1 and Azure Key Vault audit 2025-01”).
• Control owner reviews, adds evidence link, security signs off — done in 10–20 minutes instead of hours.

Common mistakes & fixes

• Claiming certification prematurely — fix: always include certificate name/date and attach proof.
• Overly verbose answers — fix: use bulleted, evidence-first replies.
• No human review — fix: require at least one SME and one legal/compliance check.

Copy-paste AI prompt (use as a template)

“You are a compliance writer. Draft a concise answer to the RFP question: ‘[INSERT QUESTION]’. Include: a one-line affirmative/negative, the specific controls or services used, relevant standards (e.g., ISO 27001, SOC 2), where evidence is stored (document name and date), and suggested control owner to validate. Keep it under 100 words and use bullet points.”

Action plan — do this today

1. Create the one-page fact sheet.
2. Extract top 20 repeat questions from past RFPs.
3. Run AI to draft answers for those 20, then have owners validate two to three of them to test the flow.

AI gives big time-savings when used as a drafting tool — not a final authority. Start small, build your response library, and always close the loop with human verification.

[Steve Side Hustler]

Short answer: yes — AI can cut the tedium out of drafting RFP and security questionnaire answers, but only if you set up simple guardrails and a fast human review loop. The trick is to treat AI as a smart drafting assistant, not the signer of record.

• Do keep answers short, evidence-first, and linked to a single source of truth.
• Do create a one-page fact sheet and a small library of approved wording.
• Do require a named SME or compliance reviewer to approve each finished answer.
• Don’t let AI invent certs, dates, or technical specifics — always verify.
• Don’t use long essays in responses; buyers prefer clear bullets and proof references.

What you’ll need

• One-page fact sheet (hosting model, certs, main controls, contact names).
• Folder with source evidence (policies, SOC/ISO summaries, system reports).
• Template for short answers (one-line claim + 2–3 bullets + evidence pointer).
• A reviewer list: control owner, security lead, and someone from legal for claims.

How to do it — quick workflow

1. Extract top 15 repeat questions from past RFPs into a spreadsheet.
2. For each question, produce a concise draft: one-line position, two bullets (controls/services), and a reference to the evidence file and date.
3. Send the draft to the named control owner for a yes/no plus an evidence link; collect their approval in the spreadsheet.
4. Save the approved wording in your library and tag it with the approver and date; reuse next time.
5. Keep a short audit note per reply: who approved and where the proof lives.

What to expect

• First set-up (~2–4 hours) to build the fact sheet and top-questions list.
• After that: typical validated answers take 10–30 minutes each instead of hours.
• Improved consistency and a growing library that reduces future effort.

Worked example — a single question, step-by-step

Question: How are backups protected?

1. Draft structure: one-line summary (affirmative/negative).
2. Two short bullets: (a) where backups are stored and encryption used, (b) retention and testing cadence.
3. Attach evidence: policy name + date and a single backup report or snapshot ID.
4. Send to the backup owner: ask them to confirm wording, paste the evidence link, and stamp approval in the spreadsheet.
5. Save the approved reply in the answer library, mark the owner and approval date for future RFPs.

This keeps things practical: AI speeds the writing, you keep the facts and approvals. Start with 15 questions, validate three, and you’ll feel how quickly the pile shrinks.

[Jeff Bullas]

Yes — and here’s a simple, practical way to make AI actually save you time on RFPs and security questionnaires.

AI shines at repetitive drafting. The catch: it needs clear inputs, strict templates and a fast human sign-off. Do this right and you’ll cut hours into minutes while keeping legal and security comfortable.

What you’ll need

• One-page fact sheet: hosting model, certs, core controls, named owners.
• Evidence folder: policies, SOC/ISO summaries, system reports (or links to them).
• Answer template: one-line stance + 2–3 bullets + evidence pointer.
• Review workflow: control owner + security lead + legal for high-risk claims.

Step-by-step workflow (do this today)

1. Pull the top 15–20 repeat questions into a spreadsheet.
2. For each question, run an AI draft using the template below.
3. Attach the suggested evidence file name and date; send to the named owner for a binary approve/adjust and evidence link.
4. Record the approval, store the final wording in an approved phrasing library, tag with approver and date.
5. Reuse wording in future RFPs; update the library whenever your controls or certs change.

Example — single question, instant template and sample answer

Question: “Do you encrypt data at rest?”

• AI draft (short, evidence-first):
  • Yes — all customer data at rest is encrypted.
  • We use AES-256 via managed cloud volumes and keys in our KMS.
  • See: Encryption Policy v2.1 (2025-01) and KMS audit report 2025-04.
• Send to the key owner: confirm wording and paste the evidence link. Save on approval.

Common mistakes & fixes

• AI invents a certificate or date — always require a proof file name before approval.
• Too wordy answers — enforce the one-line + bullets template in your prompt.
• No human reviewer — mandate at least one SME sign-off recorded in the spreadsheet.

Copy-paste AI prompt (use as-is)

“You are a compliance writer. Draft a concise answer to the RFP question: ‘[INSERT QUESTION]’. Include: one clear yes/no line, two short bullets (controls or services used), the relevant standard(s) if applicable, the document name and date where evidence is stored, and the suggested control owner for validation. Keep it under 80 words and use bullets only.”

Quick action plan — 1 hour start, fast wins

1. Create the one-page fact sheet (30–45 minutes).
2. Extract 15 repeat questions into a sheet (15 minutes).
3. Run the prompt for 3 questions and get owner approvals to validate the flow (30–60 minutes).

Remember: AI drafts. Your company signs. Start small, build the approved phrasing library, and you’ll shave days off future responses.

[aaron]

Good call on strict templates and fast sign-off — that’s the backbone. Now let’s turn it into a repeatable system with measurable outputs so you cut turnaround time and improve win rate without risking accuracy.

Try this in 5 minutes

• Open your last RFP. Pick three questions you answered before. Paste them into the prompt below to normalize wording, add evidence slots, and flag gaps. You’ll create reusable, approved phrasing in minutes.

Copy-paste AI prompt (normalize past answers)

“You are a compliance editor. Normalize the following answers into a standard template. For each: 1) one-line position (yes/no or short stance), 2) 2–3 bullets with specific controls/services, 3) standards referenced (if relevant), 4) exact evidence placeholder (document/report name + date), 5) suggested control owner, 6) risk level (Low/Med/High), 7) notes on missing proof or ambiguous claims. Use clear, short bullets. Do not invent data. Ask up to 3 clarification questions if evidence is missing. Input answers: [PASTE 3–5 PAST ANSWERS].”

The problem

Teams lose hours rewriting the same claims, chasing evidence, and over-explaining. Inconsistency triggers buyer follow-ups and legal anxiety.

Why it matters

Fast, consistent, evidence-first replies reduce cycle time, boost buyer trust, and keep security/legal comfortable. Done well, you’ll reuse 60%+ of answers and cut drafting time by 70–80% without sacrificing accuracy.

What you’ll need

• Answer Block template: Position line + 2–3 bullets + standards + evidence file/date + owner + risk.
• Evidence inventory: Policies, SOC/ISO summaries, system reports with dates and owners.
• Reviewer matrix: Who approves what (control owners, security, legal for high-risk).
• Simple tracker: Spreadsheet with columns: Question, Position, Controls, Standards, Evidence, Owner, Risk, Last Verified, Status.

Field-tested lesson

The win is not the draft — it’s the library. Lock down canonical claims, tie them to dated evidence, and reuse. Treat any custom question as a controlled deviation, not a fresh essay.

Step-by-step system

1. Define the Answer Block. Freeze a 6-line format: stance, controls, standards, evidence (file + date), owner, risk. Enforce max 90 words.
2. Map your evidence. Create a one-pager index: policy names and versions, SOC/ISO report dates, system report names, and owners. This kills 80% of back-and-forth.
3. Draft with guardrails. In every prompt, include rules: no invented dates, no future claims, short bullets only, and request clarification if evidence is missing.
4. Route for binary approval. Owner picks Approve/Adjust and pastes the exact evidence file/date. Record approver + timestamp.
5. Version and reuse. Save approved wording with tags (e.g., encryption, backups, logging). Reuse as-is next time unless your controls change.
6. Triage risk. Label answers Low/Med/High risk (legal/compliance impact). High-risk claims always get legal review before submission.
7. Create variants where needed. If you serve multiple hosting models or regions, maintain separate approved variants to avoid contradictions.
8. Audit trail. Keep a short note: who approved, what changed, where the proof lives. This speeds future audits and customer follow-ups.

Copy-paste AI prompt (draft new answers)

“You are a compliance writer. Draft a concise Answer Block for this question: [INSERT QUESTION]. Output exactly: 1) Position (one line). 2) Controls/Services (2–3 bullets). 3) Standards (if applicable). 4) Evidence (document/report name + date; leave [TBD] if unknown). 5) Suggested Control Owner. 6) Risk (Low/Med/High) with 1-line reason. Rules: Use clear bullets, keep under 90 words, never invent certs/dates/services, ask up to 3 clarifying questions if evidence is missing, and suggest a shorter alternative if the question invites an essay.”

What to expect

• Initial setup: 2–4 hours to build the Answer Block template and evidence index.
• After setup: 10–20 minutes to produce and approve each repeat answer; faster as the library grows.
• Within 2–3 cycles: 60%+ reuse rate on common questions.

Metrics that matter

• Draft cycle time (question received → owner-approved): target median < 24 hours.
• Reuse rate (% answers pulled from library): target > 60% after month one.
• Redline count (buyer follow-ups/clarifications): target < 5 per RFP.
• Evidence completeness (% answers with dated proof): target 100% before submission.
• Accuracy incidents (post-submission corrections): target 0.
• Reviewer SLA hit rate (approvals within agreed window): target > 90%.

Common mistakes and fast fixes

• Hallucinated specifics (algorithms, certs, dates) — Fix: prompt forbids invention; require file name/date before approval.
• Essay answers — Fix: enforce Answer Block length and bullet style in every prompt.
• Mixed environments (multiple hosting models blended) — Fix: maintain distinct variants; tag by region/stack.
• Outdated evidence — Fix: evidence index with version/date and quarterly review.
• Missing limitations — Fix: add a one-line scope note if a control is partial or in rollout.

1-week action plan

1. Day 1: Build the Answer Block template and the evidence index (policy names, report dates, owners).
2. Day 2: Extract the top 20 recurring questions from past RFPs/security questionnaires.
3. Day 3: Run the normalize prompt on past answers; produce first 20 Answer Blocks.
4. Day 4: Route to owners for binary approve/adjust and paste evidence file/date.
5. Day 5: Legal review on High-risk items; finalize variants by hosting/region if needed.
6. Day 6: Publish the approved library; set reviewer SLAs; add tags for quick search.
7. Day 7: Retro: measure reuse rate, cycle time, and redlines. Lock improvements for next cycle.

Insider tip

Tag every approved answer with the exact file name and date of proof at the time of approval. When evidence updates, batch-refresh tags and push a strike-through note in the library. This single habit prevents 90% of downstream corrections.

Your move.

[aaron]

Good call — freezing templates and a fast sign-off loop is the backbone. I’ll add the missing piece: how to convert that backbone into predictable outcomes (faster turnaround, higher reuse, zero surprises).

The problem you still face

Teams draft different answers, chase proof, and miss SLAs. That costs time, creates buyer follow-ups and drags legal into every response.

Why fix it now

Shorter cycles win deals and reduce post-submission corrections. If you hit the targets below you turn RFPs from reactive firefighting into a repeatable asset.

What you’ll need (quick)

• Answer Block template (stance, 2–3 bullets, standards, evidence file+date, owner, risk)
• Evidence index (one-pager mapping doc names → owners → dates)
• Simple tracker (spreadsheet with SLA timestamps and approval status)
• SME reviewer list with agreed SLAs (e.g., 24h for owners, 48h for legal)

Step-by-step (start in one hour)

1. Pick 20 repeat questions from recent RFPs and add them to a sheet.
2. Run the AI prompt below to create Answer Blocks for those 20.
3. Send each Answer Block to the named owner for binary Approve/Adjust and paste exact evidence file+date.
4. Record approval timestamp in the tracker and tag the answer in the library (encryption, backups, logging).
5. For High-risk items push to legal; for Low/Med just record legal-notified flag.

Copy-paste AI prompt (use as-is)

“You are a compliance writer. Draft an Answer Block for this question: ‘[INSERT QUESTION]’. Output exactly: 1) Position (one line). 2) Controls/Services (2–3 bullets). 3) Standards (if any). 4) Evidence (document/report name + exact date; put [TBD] if unknown). 5) Suggested Control Owner. 6) Risk (Low/Med/High) with one-line reason. Rules: keep under 90 words, use bullets, never invent certs/dates/services, ask up to 3 clarifying questions if evidence is missing.”

Metrics to track (make these visible)

• Draft cycle time (question received → owner-approved). Target median < 24h.
• Reuse rate (% answers pulled from library). Target > 60% after month 1.
• Redline count (buyer follow-ups). Target < 5 per RFP.
• Evidence completeness (% answers with dated proof). Target 100% pre-submission.
• Reviewer SLA hit rate. Target > 90%.

Common mistakes & quick fixes

• Hallucinated specifics — Fix: add a hard rule in prompts and require file+date before approval.
• Owners delay approvals — Fix: SLA + 2-reminder automation and an escalation owner.
• Mixed environment answers — Fix: maintain tagged variants (region/hosting) in the library.
• Outdated evidence — Fix: quarterly evidence index refresh and version stamp on each Answer Block.

1-week action plan (exact)

1. Day 1: Build Answer Block template & evidence index.
2. Day 2: Extract top 20 questions into a sheet.
3. Day 3: Run the prompt on 20 Qs and produce Answer Blocks.
4. Day 4: Route to owners for binary Approve/Adjust; record evidence file/date.
5. Day 5: Legal review for High-risk items; finalize variants.
6. Day 6: Publish the library, tag entries, set reviewer SLAs.
7. Day 7: Measure reuse rate, cycle time, redlines; iterate on bottlenecks.

Track the five metrics above daily during week one and report median cycle time + reuse rate at week end. Hit those targets and RFP effort falls off your balance sheet.

Your move.

[Author]

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