shape-up-analysis_skill

Overview

This skill analyzes a Shape Up pitch alongside the codebase to produce a concrete kickoff analysis with identified risks, rabbit holes, and a bet confidence rating. It delivers a practical, prioritized set of spikes, open questions, and mitigations to enable a focused cycle that fits the appetite.

How this skill works

I read the Shape Up pitch to extract problem, appetite, solution, and explicit no-gos, then map those items to the actual code paths that will be affected. I assess code health, surface hidden complexity, categorize risks (known risks, rabbit holes, unknowns), and synthesize a kickoff document with a numeric/star confidence rating and actionable next steps.

When to use it

• When starting a new Shape Up cycle and you need to validate scope against codebase reality
• When someone asks to "analyze this pitch" or "review Shape Up pitch"
• Before betting: to surface blockers, unknowns, and rabbit holes
• When you need a kickoff document with spikes, decisions, and confidence
• To translate product assumptions into concrete technical questions

Best practices

• Provide the full pitch document and grant read access to the code areas touched by the pitch
• Keep the appetite explicit so risks are evaluated against a fixed timebox
• Accept trade-offs up front and mark no-gos clearly to reduce scope creep
• Run short timeboxed spikes for high-likelihood/high-impact unknowns before committing
• Prioritize open questions by if they block progress (Can Proceed? flag)

Example use cases

• Evaluate a user-facing feature pitch that touches payments and auth to find hidden integration work
• Review an internal tooling pitch to discover legacy code hotspots that could explode scope
• Prepare a kickoff summary for leadership showing confidence, blockers, and required decisions
• Identify spikes required to estimate effort within a two-week appetite
• Assess whether a pitch meets betting criteria and what would raise/lower confidence