Shape Up Pitch & Codebase Analysis Skill

Shape Up Pitch & Codebase Analysis

Analyze Shape Up pitches against actual codebase to produce comprehensive kickoff documents with risk assessment and confidence rating.

References

Load as needed for detailed guidance:

references/shape-up-methodology.md - Shape Up concepts, pitch anatomy, betting criteria
references/risk-assessment.md - Risk categorization, rabbit hole identification, confidence scoring
references/codebase-analysis.md - Systematic code review approach, health signals, impact mapping

Examples

See for expected quality:

examples/example-pitch.md - Well-formed Shape Up pitch
examples/example-output.md - Complete analysis output demonstrating format and depth

Required Inputs

Pitch document - Shape Up format (problem, appetite, solution, rabbit holes, no-gos)
Codebase access - Available in current repository

If pitch not provided, ask user before proceeding.

Dual Perspective Analysis

Analyze as both Senior PM and Senior Developer:

PM lens:

Is problem clearly defined or solution disguised as problem?
Who benefits and why now?
What does "good enough" look like?
What's measurable?

Dev lens:

What does affected code actually look like?
What complexity hides in "simple" requirements?
What technical debt will we encounter?
What's missing from pitch that code reveals?

Principles:

Clarity over optimism—don't sugarcoat
Time is limited—honor the appetite
Be constructive—risks need mitigations
Challenge assumptions—mark as ✅ Safe / ⚠️ Risky / ❓ Unknown

Process

Phase 1: Understand Pitch

Read pitch document carefully
Extract: problem, appetite, solution, rabbit holes, no-gos
Identify explicit scope boundaries
Note assumptions (stated and implied)
Flag missing elements

Phase 2: Codebase Exploration

Identify affected code areas using Glob/Grep
For each area:
- Read relevant files
- Assess health (tests, complexity, docs)
- Note dependencies and integrations
- Flag legacy or fragile code
Map pitch requirements to code paths
Find hidden complexity pitch doesn't mention

Phase 3: Risk Analysis

Cross-reference pitch assumptions with codebase reality
Categorize:
- Known risks: Identified problems with clear impact
- Rabbit holes: Could explode in scope
- Unknowns: Need spikes to assess
Rate each: likelihood (High/Med/Low) × impact (High/Med/Low)
Propose mitigations

Phase 4: Synthesis

Rate bet confidence (1-5 stars)
List blocking questions
Suggest spikes, experiments, decisions
Note accepted trade-offs

Output Format

Generate project-kickoff-analysis.md:

# Project Kickoff – Pitch & Codebase Analysis

## 1. Project Summary (TL;DR)
One paragraph: problem, why now, who benefits. No jargon.

---

## 2. Understanding the Problem (PM View)

### 2.1 Problem Statement
- Real user/business problem?
- Clearly defined or solution disguised as problem?

### 2.2 Why Now?
- What triggered this pitch?
- Cost of not doing this?

### 2.3 Success Criteria
- How we know it worked
- What's measurable
- What's "good enough"

---

## 3. Proposed Solution (Critical Review)

### 3.1 Solution Overview
- Proposed solution summary
- Explicitly in scope
- Explicitly out of scope

### 3.2 Assumptions
| Assumption | Type | Status |
|------------|------|--------|
| Description | Technical/Product/User | ✅/⚠️/❓ |

---

## 4. Risks & Rabbit Holes

### 4.1 Known Risks
| Risk | Likelihood | Impact | Mitigation |
|------|------------|--------|------------|
| Description | H/M/L | H/M/L | Strategy |

### 4.2 Potential Rabbit Holes
List with concrete examples:
- What looks simple but isn't
- What could explode in scope
- Hidden dependencies

---

## 5. Codebase Review (Dev View)

### 5.1 High-Level Architecture
Brief tech stack overview relevant to this pitch.

### 5.2 Relevant Areas
| Area | Why It Matters | Confidence |
|------|---------------|------------|
| `path/to/module` | Reason | 👍/😐/🚨 |

**Legend:** 👍 Well understood, 😐 Needs exploration, 🚨 High risk

### 5.3 Code Health Signals
- Test coverage by area
- Complexity hotspots
- Technical debt markers
- Documentation gaps

---

## 6. Constraints & Boundaries

### 6.1 Time Box
- Fixed appetite: X weeks
- Must fit vs. can drop

### 6.2 Technical Constraints
- Required/forbidden tech
- Performance/security limits

---

## 7. Open Questions

| Question | Type | Can Proceed? | Risk if Unanswered |
|----------|------|--------------|-------------------|
| Specific question | Product/Tech/Data | Yes/No | Low/Med/High |

---

## 8. Bet Confidence

**Overall: ⭐⭐⭐☆☆** (X/5)

**Positive factors:**
- List

**Negative factors:**
- List

**What would increase confidence:**
- List

**What would kill the bet:**
- List

---

## 9. Suggested Next Steps

### Spikes to Run
- [ ] Spike name (timebox): Specific question to answer

### Experiments to Validate
- [ ] Experiment: What to test

### Decisions Needed Before Building
- [ ] Decision: What needs resolving

---

## 10. Final Notes
- Uncomfortable truths
- Trade-offs we're accepting

Quality Checklist

Before finalizing output:

[ ] Every risk has mitigation strategy
[ ] Code areas have specific paths, not vague descriptions
[ ] Confidence ratings backed by evidence
[ ] Open questions prioritized by blocker status
[ ] Spikes are timeboxed with specific questions
[ ] No vague or open-ended next steps

Agent Skills: Shape Up Pitch & Codebase Analysis

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