Feature: Native auto-tracking of user asks during sessions #365

Product Gap: Squad Should Auto-Track User Asks During Sessions

Raised by: Dina Berry
Context: During long squad sessions (full-day work), there's no native way to see a structured list of what you've asked for. Users shouldn't have to remember to say "track this" — the product should handle it.

The Problem

Squad tracks what agents do but not what users ask. There's no structured "request registry" that extracts user asks as first-class objects and tracks their lifecycle.

What Squad tracks today:

What's missing:

• No automatic extraction of "user asks" from conversation
• No structured request registry that persists across context compactions
• No "show me my asks" command that works without prior setup
• No status tracking of asks (pending, in-progress, done, blocked)
• No end-of-session summary of what was asked vs. what was delivered

Proposed Phased Approach

Phase 1: Directive-Based Cataloging

Catalog common enhancements to Squad via directives. Treat auto-tracking as a directive pattern first — this validates the need and lets us iterate on what "tracking an ask" means in practice before building product features. Low cost, high learning.

Phase 2: CLI Switch (Opt-In)

Add a CLI flag to enable ask tracking per session:

squad --track-asks
squad session --tracking

• User-controlled, zero overhead when not wanted
• Tracking extracts asks from conversation turns into a structured format
• Natural language access: "What have I asked for?" / "What's still pending?"
• Storage: .squad/sessions/{id}/asks.json

Phase 3: Config File Option

Add a persistent config option in squad.config.ts:

export default defineSquad({
  session: {
    autoTrackAsks: true,
    askSummary: 'end-of-session', // or 'continuous'
  }
});

• Set once, forget — project-level setting
• Customizable: what to track, when to summarize, output format

Note: NOT turning this on by default. This should be opt-in at every phase.

Implementation Shape

1. Extraction — Coordinator classifies each user message:

• New ask (task, question, directive)
• Follow-up to existing ask
• Status check / meta-question

2. Storage — .squad/sessions/{id}/asks.json

[
  { "id": "ask-1", "text": "Set up Express server", "agent": "Dallas", "status": "done", "turn": 3 },
  { "id": "ask-2", "text": "Add search feature", "status": "in-progress", "turn": 7 },
  { "id": "ask-3", "text": "Always use Zod for validation", "type": "directive", "status": "captured", "turn": 12 }
]

3. Natural language access — no special commands needed:

• "What have I asked for today?" → structured list with status
• "What's still pending?" → filtered view
• "What did we accomplish?" → end-of-session summary with ask→outcome mapping

4. Survives compaction — because it's in a file, not just in-memory SQL

What This Unlocks

• Day-long sessions: Work all day and never lose track
• Handoff clarity: "Here's what the user asked, here's where we are"
• Session summaries: Automatic done / in-progress / not started report
• Cross-session continuity: Next session starts by reading yesterday's ask registry

Requesting opinions from @bradygaster and @tamirdresher on the phased approach and priority.