checkpoint

name: checkpoint description: Use when the user wants to save session progress, log decisions, or wrap up a work session — triggered by phrases like "checkpoint", "let's save this", "save progress", "wrap up", or "log what we decided". Also use when the user asks to record decisions, document what was resolved, or capture where things stand before ending a conversation. disable-model-invocation: true allowed-tools: Read, Write, Edit, Glob

Think carefully before summarising — this requires reading back through the full conversation. Only call something a decision if it was clearly committed to, not just discussed. Take your time.

What This Skill Does

Saves the current session into the right context files depending on which persona is active. Think of it as a videogame save point — everything that matters from this session gets written down so the next session starts with full context.

Step 1 — Identify the Active Persona

Read back through the conversation to determine which persona was active: Co-CEO, Head of Design, or CTO. Look for cues like how the session was opened ("I want to speak to the CTO"), the nature of topics discussed (technical implementation vs. strategy vs. design), or explicit persona references during the conversation. If no persona was activated, treat it as a Co-CEO session.

Co-CEO Sessions

Read first: context/decisions.md, context/open-questions.md

Identify:

• New decisions: Anything explicitly agreed on or called as final. Must be a clear commitment, not just something discussed.
• Resolved questions: Any open question from open-questions.md that now has an answer.
• New open questions: Anything that came up but wasn't resolved.
• Changed direction: Anything previously decided that was reversed or modified. Look for phrases like "actually, let's go with...", "scratch that", or explicit reversals of earlier choices.

Categorise each new decision:

• Product — what we're building, how it works, the framework, artifacts, UX decisions
• Business — who it's for, distribution, pricing, partnerships
• Identity — Founder's Compass's own PATH, principles, what we stand for, taglines

Present this summary before writing anything:

## Checkpoint Summary — Co-CEO

**New Decisions:**
Product:
- [decision]
Business:
- [decision]
Identity:
- [decision]
(Omit categories with no new decisions)

**Resolved Questions:**
- [question] → [resolution]

**New Open Questions:**
- [question]

**Changed Direction:**
- [what changed and why]

After confirmation, update:

• decisions.md — append under the correct category with [YYYY-MM-DD] prefix; one sentence per entry; never delete existing entries
• open-questions.md — rewrite: remove resolved questions, add new ones, renumber sequentially
• project.md — only if the core direction, positioning, or PATH framework fundamentally shifted; be conservative

Head of Design Sessions

Read first: context/decisions.md (Design section), context/open-questions.md

Identify:

• Settled design decisions: Anything called as final — colour values, type choices, layout rules, brand voice rules, component patterns
• Reversed or updated decisions: Anything that supersedes a previous design decision
• New open questions: Unresolved design choices

Present this summary before writing anything:

## Checkpoint Summary — Head of Design

**Settled Design Decisions:**
- [decision — be specific: hex values, font names, layout rules, not vague adjectives]

**Updated/Reversed:**
- [previous decision] → [new decision]

**New Open Questions:**
- [question]

After confirmation, update:

• decisions.md — append under the Design category with [YYYY-MM-DD] prefix; if a decision supersedes a previous one, mark the old entry as ~~strikethrough~~ — superseded: [new decision]
• open-questions.md — rewrite: remove resolved questions, add new ones, renumber

CTO Sessions

Read first: context/technical-learnings.md, context/open-questions.md

Identify:

• Architecture changes: Any meaningful change to how the app is structured, what files do, or how data flows
• New lessons learned: Bugs that took real investigation to solve — what failed, what worked, the root cause
• New anti-patterns: Things discovered to be wrong in this codebase specifically — rules for future sessions
• Technical open questions: Unresolved technical decisions or unknowns
• Product/business decisions (rare): If the CTO session surfaced a decision that affects product or business, flag it — it belongs in decisions.md, not here

Present this summary before writing anything:

## Checkpoint Summary — CTO

**Architecture Changes:**
- [what changed in the codebase structure or data flow]

**New Lessons Learned:**
- [bug/issue] — [what failed, what fixed it, root cause in one sentence]

**New Anti-Patterns:**
- [rule]: [why]

**Technical Open Questions:**
- [question]

(Only include the section below if product/business decisions actually came up)
**Product/Business Decisions to Log:**
- [decision] → goes to decisions.md under [category]

After confirmation, update:

• technical-learnings.md:
  • Architecture section: update if something structural changed
  • Anti-Patterns section: append new rules
  • Lessons Learned section: append a new entry with the date, full description of what broke and how it was fixed
• open-questions.md — rewrite: remove resolved questions, add new ones, renumber
• decisions.md — only if product/business decisions were surfaced; append under the correct category

After Files Are Written (all personas)

Once all file updates are confirmed and written, end the checkpoint with this message — no variations, no additions:

Checkpoint saved. Tell me to commit and push when you're ready to back this up to GitHub.

Guardrails (all personas)

• Never write to any file without confirmation first
• If a target file doesn't exist yet, create it with a minimal header before appending
• If the session had no clear decisions or new learnings, say so — don't fabricate entries
• If something is ambiguous (discussed but not committed), flag it as an open question, not a decision
• Keep all entries concise and scannable — the conversation history is the source of truth, not the log
• Never delete previous entries in decisions.md — only append or mark as superseded