01
Product requirement sketch
- Who operates this daily? Who decides? Who gets blamed when it fails?
- What is the current workaround (spreadsheet, memory, inbox)?
- What does “done” look like on a Monday morning?
- Which errors are embarrassing vs career-threatening?
- Domain objects (e.g. company → file → matter) — not feature bullets.
- Out of scope for v1 — explicitly listed.
- Success signal you can observe in production (not vanity).
02
AI feature evaluation checklist
- Does this remove repeated work — or only impress in a demo?
- Where does the suggestion land? (Must be a review surface.)
- Can a wrong accept create silent liability?
- Is confidence visible beside every field/suggestion?
- What is the human override path?
- How will we measure usefulness after ship (time saved, rework, trust)?
- Is the model the product — or a stage in a workflow?
03
Product discovery checklist
- Watch one full real task end-to-end (not a interview summary).
- List every tool touched (drive, mail, sheet, WhatsApp, paper).
- Capture the moment trust breaks (wrong mark, missed deadline).
- Map who must confirm before the system of record updates.
- Note bilingual / messy input realities.
- Write the friction sentence in their words.
04
Engineering handoff template
- Purpose of this slice in one sentence.
- Domain objects touched; migrations required.
- API surface + auth assumptions.
- Failure modes and how they surface to the desk.
- How to deploy; how to roll back.
- What is intentionally unfinished.
- Link to decision / ADR if a tradeoff was locked.
05
Architecture review checklist
- Does the data model match how the desk already works?
- Where is tenant isolation enforced?
- What happens when OCR/AI is wrong?
- Can one person operate this stack?
- Expand-contract path for schema change?
- Observability: what do we log without PII?
- Diagram exists and is downloadable?
06
UX review checklist (non-technical operators)
- Can the task be completed without reading docs?
- Is the next action obvious after every save?
- Are dangerous actions reversible or confirmed?
- Does search return something trustworthy under time pressure?
- Are empty states honest (not marketing)?
- Mobile/desk: which device is primary for this role?
07
Release checklist
- Migrations applied (or expand step live).
- Feature flag / path for rollback named.
- Desk-critical path smoke-tested with real-shaped data.
- Changelog / journal note drafted (what + why).
- No silent AI write paths introduced.
- Status / product page updated if user-facing.
08
Deployment checklist (Cloudflare-first)
- wrangler / CI deploy of Worker + assets.
- D1 migrations version-checked.
- R2 / KV bindings present in prod.
- Secrets not in client bundles.
- Smoke: health, auth, one write, one search.
- Confirm previous version ID known for rollback.
09
Technical decision record (ADR)
- Context — forces and constraints.
- Alternatives — at least two real options.
- Decision — what we chose.
- Trade-offs — what we give up.
- Outcome — what happened after ship.
- Same today? — revisit date or yes/no with reason.
10
Incident postmortem template
- Problem — what the desk experienced.
- What happened — timeline of facts.
- Why — contributing causes (not villains).
- What changed — code, process, monitoring.
- What we’d do differently — prevention.
- Customer/comms notes if external impact.