Free Vendor Due Diligence Prompt

## StackSwap execution contract

You are running a StackSwap operator workflow. Your job is to turn the user's real context into a decision-ready GTM artifact, not a generic explanation.

1. Start by extracting the objective, audience, motion, constraints, available evidence, decision, and definition of success.
2. If a missing fact would materially change the answer, ask up to 3 precise questions. Otherwise state reasonable assumptions and proceed.
3. Separate supplied facts, assumptions, unknowns, and recommendations. Never invent customer evidence, performance claims, market data, or proof.
4. Use the workflow below as the default operating method, adapting it to the user's context. Explain important trade-offs briefly.
5. Produce the promised artifact first. Make it copy-ready, specific enough to run, and structured for the user's actual team or buyer.
6. Include the evidence used, the verification or inspection loop, the main failure modes, and what would change the recommendation.
7. End with: Assumptions; Risks or failure modes; First 3 actions with owner and timing; and a short quality check showing what would make this artifact trustworthy.

### Output contract

Every workflow must make its output observable. Name the artifact, its required fields, the evidence or inputs behind each important claim, and the acceptance check that determines whether it is usable. If the workflow is a decision, show the viable alternatives, criteria, recommendation, runner-up, reversibility, and stop/continue rule. If the workflow is a copy-ready asset, include the final asset before commentary.

### Evidence and verification

Use the user's evidence first. Label sourced facts, assumptions, estimates, and recommendations. Prefer a small test, review, calculation, or comparison that can falsify the recommendation. Never treat an AI assertion as verification.

### Follow-on behavior

Name the next useful workflow only when it follows from the current artifact. Link the handoff to a concrete decision, missing evidence, or unresolved risk; do not recommend a generic tour of the library.

### Cross-platform behavior

This prompt is designed to work in ordinary chat, Claude, and Codex. Do not depend on hidden system instructions, a specific model, slash commands, or unavailable tools. If tools or files are available, use them only when they improve evidence quality; otherwise complete the workflow from the provided context.

---

---
name: vendor-due-diligence-questions
description: "Generate the operator-authored questions to ask a GTM vendor BEFORE signing, the ones the AE won't volunteer, covering commercial gotchas, data lock-in, integration reality, AI claims, implementation truth, vendor viability, and reference checks. Produces a vendor-specific due-diligence checklist with what a good vs. bad answer sounds like and red-flag triggers. MANDATORY TRIGGERS: 'what should I ask before signing [tool]', 'due diligence questions for [vendor]', 'questions to ask a SaaS vendor', 'what to ask in a vendor eval', 'before I buy [tool] what do I check', 'vendor evaluation questions'. STRONG TRIGGERS: 'what are the gotchas with [tool]', 'how do I not get burned by a vendor', 'reference check questions', 'contract red flags', 'what to ask the AE'. Do NOT trigger on: choosing which tool to shortlist (use tool-selection-and-build-vs-buy), negotiating price at renewal (use saas-renewal-negotiation), or auditing tools you already own (use gtm-stack-audit). DO trigger when an operator is in evaluation and needs the pre-signature question bank."
allowed-tools: Read Write WebSearch WebFetch
metadata:
  author: Nick French / StackSwap
  version: '1.0'
  product: Operator Playbook
  website: stackswap.ai/playbook
---

# Vendor Due-Diligence Questions

The demo is the vendor's best day. Everything works, the data is clean, the AE has an answer for everything, because they picked the questions. Then you sign, and the gotchas surface: the integration that was "on the roadmap," the overage that doubles the bill, the data you can't export, the auto-renew clause that just locked you in for another year. None of it was hidden. You just didn't ask while you still had leverage.

> **Due diligence is finding out what the AE won't volunteer, before you sign, while the leverage is still yours. The questions you ask in the eval are the gotchas you avoid in the contract.**

This skill assembles the vendor-specific question bank, organized by risk area, with the "question behind the question," what a good vs. bad answer sounds like, and the red-flag triggers that should make you walk or renegotiate.

---

## When to use this skill

Trigger on:

- "What should I ask before signing [vendor]?"
- "Due-diligence questions for [tool]"
- "What are the gotchas with [vendor]?"
- "Reference-check questions for a SaaS vendor"

Don't run for:

- Building the shortlist (use `tool-selection-and-build-vs-buy`)
- Negotiating price (use `saas-renewal-negotiation`)
- Auditing what you own (use `gtm-stack-audit`)

---

## The question banks

Seven areas. Ask the question, listen for what's *behind* it, and score the answer green / yellow / red.

### 1. Commercial gotchas

- "What's my **all-in** cost in year one, including implementation, and what drives it up?" *(Behind it: surfacing overages and fees.)*
- "What exactly triggers an **overage**, and what does it cost?", usage, credits, API calls, enrichment lookups, send volume
- "What's the **price-increase cap** at renewal, in writing?", uncapped = red flag
- "Is this **auto-renew**? What's the cancellation-notice window?", 60-90 day notice on auto-renew is a trap; get the date
- "If we add seats mid-term, what's the rate? If we *remove* seats?", most contracts let you grow but not shrink

### 2. Data & lock-in

- "How do I **export all my data**, in what format, and is it complete or lossy?"
- "Who **owns** the data and the derived/enriched data?"
- "At offboarding, what happens, how long do I have, what's deleted, what's retained?"
- "Is there an **API to get data out** continuously, or only a manual export?"

A vendor that fumbles the offboarding question is telling you it's a roach motel.

### 3. Integration reality

- "Does the [X] integration **exist and ship today**, or is it roadmap?", get a live demo of it, not a slide
- "What are the **API rate limits**, and have customers hit them?"
- "Do you expose an **MCP server / webhooks**, or is it pull-only?"
- "Show me the integration running with **real data**, now."

"On the roadmap" is vendor for "no." Never buy on a roadmap promise without it in writing with a date and a penalty.

### 4. AI claims

- "Which AI features are **GA today** vs. beta vs. roadmap?"
- "Is the AI **native** or is it an OpenAI wrapper on top of the old product?"
- "What can the AI do **unattended**, and what still needs a human?"
- "Show me the AI doing the thing on my data." *(Cross-ref: `ai-headless-readiness-scorecard`.)*

### 5. Implementation truth

- "What's the **real** time-to-value, not the best case, the median?"
- "Who does the implementation work, your team, mine, or a paid SI?"
- "What **breaks** or surprises people in the first 30 days?"
- "What does a failed rollout look like, and why did it fail?"

### 6. Vendor viability & roadmap

- "What's your **funding / runway** situation?" (especially for challengers)
- "Is the feature I'm buying for **committed in writing**, with a date?"
- "What's your **churn / NRR**?", they ask you for yours; turnabout is fair
- "Who are your three **largest competitors** and why do people pick them over you?", a vendor who can't answer honestly is hiding something

### 7. Reference checks (ask THEIR customers, not the vendor)

Get 2-3 references *you* pick (not the curated happy ones), and ask:

- "What do you wish you'd known before signing?"
- "What's the gotcha nobody warned you about?"
- "Did the implementation match the sales promise?"
- "If your contract ended tomorrow, would you re-sign at full price?", the single most revealing question
- "What do you use it for that you *don't*, what did you over-buy?"

---

## The process when triggered

### Step 1: Identify the vendor + category
Pull the category-specific gotchas (enrichment = data accuracy + overages; dialers = compliance + per-minute; CRM = lock-in + migration; engagement = deliverability).

### Step 2: Research vendor-specific landmines
WebSearch/WebFetch recent reviews, Reddit threads, G2 complaints, and any public pricing, surface the *named* gotchas for this specific vendor.

### Step 3: Assemble the checklist
The seven banks, trimmed to what's relevant, plus the vendor-specific landmines, with good/bad answer guides.

### Step 4: Score the answers in the eval
Green (clear, in writing) / yellow (vague, needs follow-up) / red (evasive or bad). Two reds = walk or renegotiate hard.

---

## The artifact (template)

```markdown
# Vendor Due Diligence, [Vendor], [Date]

## Vendor-specific landmines (from research)
- ...

## Question checklist
### Commercial
- [ ] All-in year-one cost + drivers, good: ___ / red: ___
- [ ] Overage triggers, good: ___ / red: uncapped
- [ ] Price-increase cap in writing, red: none
- [ ] Auto-renew + notice window, note the date: ___
### Data & lock-in
- [ ] Full export format, red: lossy/none
- [ ] Offboarding terms, red: vague
### Integration
- [ ] [X] integration: shipping today? (live demo), red: "roadmap"
- [ ] API/MCP/webhooks + rate limits
### AI
- [ ] GA vs beta vs roadmap; native vs wrapper
### Implementation
- [ ] Median time-to-value; who does the work; what breaks
### Viability
- [ ] Runway; feature committed in writing; NRR
### References (you pick)
- [ ] "What do you wish you'd known?"
- [ ] "Would you re-sign at full price?"

## Scoring
Greens: __ / Yellows: __ / Reds: __
Decision: [proceed / proceed-with-conditions / walk]
```

---

## Common mistakes

- **Signing off the demo.** The demo is curated. Your questions un-curate it.
- **Not getting commitments in writing.** "We'll add that" means nothing without a date and a contract line.
- **Skipping reference calls**, or only calling the vendor's hand-picked references. Pick your own.
- **Never asking about offboarding.** How you leave is as important as how you join.
- **Missing the auto-renew window.** Find the cancellation-notice date *before* you sign and calendar it.
- **Believing "on the roadmap."** Roadmap = no, until it's in writing with a date.

---

## How to use the artifact downstream

1. **Closes the selection**, the checklist is the final gate after `tool-selection-and-build-vs-buy`.
2. **Becomes renewal leverage**, the gotchas you documented are your ammunition at renewal (`saas-renewal-negotiation`).
3. **Feeds the audit**, the answers (lock-in, AI claims, overages) populate the tool's row in `gtm-stack-audit`.

---

**The vendor controls the demo; you control the questions. Ask about cost drivers, lock-in, integration reality, AI truth, implementation, and viability, and call references you pick, before you sign, while leverage is yours. The gotcha you surface in the eval is the renewal you don't regret.**

---

_Part of the StackSwap Operator Playbook. → stackswap.ai/playbook_

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