Free Tool Selection & Build-vs-Buy 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: tool-selection-and-build-vs-buy
description: "Choose the right GTM tool for YOUR motion, stage, and switching tolerance, or decide to build it, or buy nothing yet. Produces a job-defined shortlist scored against your must-haves, a build-vs-buy verdict, a decision matrix, and a pilot plan that actually decides. MANDATORY TRIGGERS: 'which tool should I buy', 'help me pick a [category] tool', 'should we build or buy', 'evaluate [tool] vs [tool]', 'choosing a [CRM/dialer/enrichment] tool', 'what [category] tool is best for us'. STRONG TRIGGERS: 'build vs buy', 'is [tool] worth it', 'do we need a tool for', 'shortlist [category] tools', 'how do I evaluate a vendor', 'should we build this in-house'. Do NOT trigger on: auditing an existing stack (use gtm-stack-audit), the pre-signature question list (use vendor-due-diligence-questions), or renewal of a tool you already own (use saas-renewal-negotiation). DO trigger when an operator is selecting a NEW tool or deciding whether to build vs. buy a GTM capability."
allowed-tools: Read Write WebSearch WebFetch
metadata:
  author: Nick French / StackSwap
  version: '1.0'
  product: Operator Playbook
  website: stackswap.ai/playbook
---

# Tool Selection & Build-vs-Buy

Most GTM tools get chosen off G2 star ratings, a slick demo, and a peer's LinkedIn post. Then the team is locked into the wrong tool for 18 months, paying for features nobody uses, while the job it was bought for is still half-done. And "build vs. buy" usually gets answered by an engineer's ego or a budget-holder's fear, never by the actual math.

> **The right tool isn't the best tool, it's the best tool for YOUR motion, stage, and switching tolerance. And surprisingly often the right answer is "buy nothing yet," because the job isn't validated enough to automate.**

This skill runs a real selection: define the job, kill feature-FOMO, score a shortlist against *your* must-haves, apply the build-vs-buy gate, and design a pilot that decides. Output is a decision doc you could defend to a CFO.

---

## When to use this skill

Trigger on:

- "Which [category] tool should we buy?"
- "Should we build this or buy it?"
- "Help me evaluate [tool] vs [tool]"
- "Do we even need a tool for this?"

Don't run for:

- Auditing tools you already own (use `gtm-stack-audit`)
- The pre-signature question list (use `vendor-due-diligence-questions`)
- Renewing a tool you have (use `saas-renewal-negotiation`)

---

## The framework

A real selection scores six things. The vendor's feature list is not one of them.

### 1. Define the job, then must-haves vs. nice-to-haves

Write the **job-to-be-done** in one sentence: "Reliably enrich inbound leads with firmographics before routing." Not "buy an enrichment platform." The job anchors everything.

Then split requirements ruthlessly:

- **Must-haves**, if it can't do this, it's disqualified. Keep this list to 3-5. Anything longer is feature-FOMO.
- **Nice-to-haves**, tiebreakers only. Never let a nice-to-have outvote a must-have.

The discipline of a 3-5 must-have list kills 80% of the spurious "but it also does X" noise that drives bad purchases.

### 2. The category landscape (leaders, runners-up, skip list)

Don't just buy the Magic Quadrant leader, they're often the most expensive and the most bloated. Map the landscape in three tiers:

- **Leaders**, the safe, expensive, full-featured incumbents. Buy when you need the ecosystem and can afford it.
- **Runners-up / challengers**, often AI-native, leaner, cheaper, hungrier. Frequently the right pick for a sub-enterprise motion.
- **Skip list**, tools that look fine but have a disqualifying flaw (data lock-in, dying vendor, AI-blind, notorious overages). Name them and why, so they don't resurface.

### 3. The build-vs-buy gate

Three outcomes, decided by gate, not gut:

- **BUY** when the job is a commodity (everyone needs it, it's not your differentiation) and a tool does it well. Most GTM jobs are buy.
- **BUILD** only when *all* of: the capability is core differentiation, you have engineering capacity to build *and maintain* it, and no tool fits without heavy compromise. Building means owning forever, the maintenance tax is the part people forget.
- **NEITHER (yet)** when the job isn't validated. Don't automate a motion you haven't proven manually. The cheapest tool is a spreadsheet and a human until the job earns automation.

Operator note: "we'll just build it" almost always under-prices maintenance, security, and the opportunity cost of eng time. Default to buy for commodity jobs; reserve build for the 1-2 things that are genuinely your edge.

### 4. The AI-native filter

Before you buy *anything*, run the shortlist through the AI-readiness lens (`ai-headless-readiness-scorecard`). Buying an AI-blind tool on a 2-3 year contract is buying a liability. A cheaper AI-native challenger that an agent can drive beats a pricey incumbent with a bolted-on "✨ AI" button. Score it before you sign.

### 5. Total cost of ownership (not the sticker)

The sticker price is the smallest number. TCO includes:

- Implementation + onboarding time (yours, not just theirs)
- Integration build + maintenance
- The ramp cost (team learning the tool)
- **The switching cost of leaving LATER**, every tool you buy is a future lock-in; weigh how hard it'll be to exit before you enter

A "cheaper" tool with a brutal migration and no API can cost more than a pricier one you can leave in a weekend.

### 6. The pilot that decides

Never buy on the demo. Design a 2-week pilot with a **pass/fail decision built in**:

- One real use case, real data, real users (not a sandbox tour)
- A written success criterion *before* the pilot ("routes 95% of inbound correctly within 5 min")
- A scorecard against your must-haves, filled by the people who'll use it daily
- A hard decision date, pilot ends, you decide, no indefinite "evaluation"

A pilot without a pre-written success criterion is just an extended demo. Define the bar first.

---

## The process when triggered

### Step 1: Extract the job + must-haves
Ask: what's the one-sentence job? What 3-5 things must it do? What stage/motion/team size? What's the budget reality? What do you already own that touches this job (overlap check)?

### Step 2: Build the landscape
Use WebSearch/WebFetch to map current leaders, runners-up, and skip-list for the category, with *today's* AI capabilities, not last year's reputation.

### Step 3: Apply the build-vs-buy gate
Decide BUY / BUILD / NEITHER before scoring tools. If NEITHER or BUILD, stop and document why, don't shortlist tools for a job that shouldn't be automated yet.

### Step 4: Score the shortlist
3-4 tools, scored against the must-haves (weighted) + AI-readiness + TCO. Drop anything that misses a must-have.

### Step 5: Design the pilot
Pre-written success criterion, real use case, decision date, scorecard.

### Step 6: Recommend
One recommendation + the runner-up + the explicit why, including the switching cost you're accepting.

---

## The artifact (template)

```markdown
# Tool Selection, [Job], [Date]

## The job
[One sentence]

## Requirements
**Must-haves (disqualifying):**
1. ...
**Nice-to-haves (tiebreakers):**
- ...

## Build-vs-buy verdict
[BUY / BUILD / NEITHER-YET], because [gate reasoning]

## Landscape
- Leaders: ...
- Runners-up: ...
- Skip list: ... (reason each)

## Shortlist scorecard
| Tool | Must-haves met | AI-readiness | TCO (yr) | Switching cost | Score |
| --- | --- | --- | --- | --- | --- |
| ... | x/5 | 0-100 | $... | low/med/high | ... |

## Pilot plan
- Use case: ...
- Success criterion (pre-written): ...
- Users / data: ...
- Decision date: ...

## Recommendation
[Tool], because [why]. Runner-up: [tool]. Switching cost accepted: [...].
```

---

## Common mistakes

- **Buying on G2 stars.** Star ratings reflect who left reviews, not fit for your motion.
- **Feature-FOMO.** "It also does X" is not a reason to buy. Score must-haves only.
- **Building commodity capabilities.** If it's not your differentiation, buying is cheaper than building + maintaining forever.
- **Ignoring the switching cost you're entering.** Every purchase is a future lock-in. Weigh the exit before the entrance.
- **Skipping the pilot / no success criterion.** A demo is the vendor's best day. Pilot on your data with a pre-written bar.
- **Buying AI-blind tools on long contracts.** Run the readiness scorecard first.
- **Letting the loudest stakeholder pick.** Weighted scoring against the job beats the HiPPO.

---

## How to use the artifact downstream

1. **Due diligence before signing**, run the winner through `vendor-due-diligence-questions` to surface the gotchas the AE won't volunteer.
2. **Check the overlap**, confirm the new tool doesn't duplicate something you own (`gtm-stack-audit`).
3. **Negotiate the contract**, a new-logo deal is your highest-leverage moment (`saas-renewal-negotiation` covers the negotiation mechanics).
4. **Score the AI-readiness**, `ai-headless-readiness-scorecard` for the deep grade on the finalist.

---

**Tool selection isn't about finding the best tool, it's about matching the right tool to your job, motion, and switching tolerance, and being willing to buy nothing when the job isn't ready. Define the job, gate build-vs-buy, score the must-haves, pilot to a pre-written bar. Buyers chase features. Operators buy the job done.**

---

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

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