GSD: /gsd:discuss-milestone — batch gray-zone resolution before autonomous

Resolved 💬 2 comments Opened Mar 22, 2026 by DKistenev Closed Mar 22, 2026

Problem

Before running /gsd:autonomous on a multi-phase milestone, I want to resolve gray zones (ambiguous design/implementation decisions) across all phases at once — not one phase at a time.

Currently:

  • /gsd:discuss-phase N covers one phase
  • /gsd:autonomous runs discuss→plan→execute per phase sequentially
  • There's no way to front-load ALL gray zone decisions before starting autonomous work

This means autonomous mode either:

  1. Stops at each phase to ask questions (defeats the purpose), or
  2. Makes assumptions that may not match user intent

What I did manually (workaround)

After creating the v0.7 roadmap (4 phases, 34 requirements), I manually:

  1. Listed all gray zones across all phases (10 questions)
  2. Asked them one-by-one via AskUserQuestion with previews showing trade-offs
  3. Recorded all decisions in STATE.md under Accumulated Context > Decisions
  4. Then launched autonomous execution with full context

This took ~10 minutes but meant autonomous mode had zero ambiguity.

Proposed: /gsd:discuss-milestone

A new command that:

  1. Reads ROADMAP.md and all phase details
  2. Reads research (SUMMARY.md, FEATURES.md, etc.)
  3. Identifies gray zones across ALL phases — decisions where multiple valid approaches exist
  4. Presents them as a batch of AskUserQuestion calls (1 per question, with trade-off explanations)
  5. Records all decisions in STATE.md
  6. Outputs "milestone fully discussed, ready for /gsd:autonomous"

Gray zone detection heuristics

Questions worth asking typically fall into:

  • Visual/UX choices with multiple valid options (color, layout, flow)
  • Architecture trade-offs where research identified alternatives
  • Scope ambiguities in requirements (what exactly does "rich empty state" mean?)
  • Cross-phase consistency decisions (same pattern or different per surface?)
  • Priority/stretch marking (what gets cut first if phase slips?)

Integration with autonomous

/gsd:autonomous could check: "Has /gsd:discuss-milestone been run? If not, suggest running it first." This creates a clean workflow:

/gsd:new-milestone → /gsd:discuss-milestone → /gsd:autonomous

Context

Project: ЮрТэг (legal document management desktop app)
Milestone: v0.7 Визуальный продукт (4 phases, 34 requirements — full visual overhaul)
The manual gray-zone discussion resolved 10 decisions that would have otherwise blocked or derailed autonomous execution.

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