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Improve assumption handling: replace yield confirmations with comprehension iteration and judgement augmentation #50

@m2ux

Description

@m2ux

Problem Statement

Multiple stages of the work-package workflow collect assumptions and then present a yield checkpoint asking the user whether the assumptions are correct. This interaction pattern is not effective because users are asked to validate assumptions without sufficient context to make informed decisions — they must triage which assumptions are code-verifiable versus which genuinely require human judgement, a distinction the agent is better positioned to make automatically.

The reconcile-assumptions skill already exists and can autonomously resolve code-analyzable assumptions through iterative codebase analysis. However, not all assumption-generating activities use it, and the activities that do still present the remaining open assumptions as a flat confirmation prompt rather than structuring the interaction to assist the user in reasoning through the genuinely open questions.

Current state:

  • Activities 02 (design-philosophy), 03 (requirements-elicitation), 04 (research), 05 (implementation-analysis), 06 (plan-prepare), and 08 (implement) all collect assumptions and present assumptions-review yield checkpoints
  • Several activities list reconcile-assumptions as a supporting skill but not all do — activities 03, 04, and 05 lack it
  • The review-assumptions skill (skill 13) presents assumptions one at a time for binary confirm/correct responses, without trade-off context or structured guidance
  • Users are asked to confirm assumptions they may not have enough context to evaluate, leading to uninformed rubber-stamp confirmations

Desired state:

  • Every activity that generates assumptions uses the reconcile-assumptions comprehension iteration loop to autonomously resolve all code-analyzable assumptions before presenting anything to the user
  • Remaining non-code-resolvable assumptions are presented through a structured "judgement augmentation" process that highlights technical trade-offs and provides supporting context
  • The user interaction takes the form of an interview-style list of open questions, each with relevant context, alternatives, and trade-off analysis — enabling informed decisions rather than uninformed confirmations

Goal

Enable users to make well-informed decisions on genuinely open assumptions by automating resolution of code-verifiable assumptions and providing structured trade-off context for the remainder.

Scope

In Scope

  • Ensuring all assumption-generating activities (02, 03, 04, 05, 06, 08) include reconcile-assumptions as a supporting skill
  • Designing and implementing a "judgement augmentation" interaction pattern for the review-assumptions skill
  • Updating the assumptions-review checkpoints across affected activities to use the new pattern
  • Updating resource 13 (assumptions review guide) and resource 26 (assumption reconciliation) to document the new approach

Out of Scope

  • Changes to the reconcile-assumptions skill's convergence loop itself (it already works correctly)
  • Changes to activity 07 (assumptions-review) which posts to the issue tracker — this is a separate stakeholder-facing interaction
  • Changes to the workflow's transition logic or activity sequencing

User Stories

US-1: Automated assumption triage

As a workflow user, I want code-verifiable assumptions to be resolved automatically so that I am not asked to confirm things the agent can verify through codebase analysis.

Acceptance Criteria:

  • All assumption-generating activities include reconcile-assumptions as a supporting skill
  • The reconciliation loop runs before any user-facing assumption checkpoint
  • Only non-code-resolvable assumptions are presented to the user

US-2: Structured judgement support

As a workflow user, I want remaining open assumptions presented with technical trade-offs and supporting context so that I can make informed decisions rather than uninformed confirmations.

Acceptance Criteria:

  • Each open assumption is presented with: the question being asked, relevant technical context, identified alternatives, and trade-off analysis
  • The presentation follows an interview-style format (structured list of open questions, not one-at-a-time binary prompts)
  • The user can see why each assumption could not be resolved through code analysis

Success Metrics

Metric Target
Assumption-generating activities with reconcile-assumptions 100% (currently ~50%)
User-facing assumptions per activity Only non-code-resolvable (currently all)
Context provided per open assumption Trade-offs, alternatives, and rationale for each

References

  • review-assumptions skill: work-package/skills/13-review-assumptions.toon
  • reconcile-assumptions skill: work-package/skills/23-reconcile-assumptions.toon
  • Assumptions reconciliation resource: work-package/resources/26-assumption-reconciliation.md

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