# Context Aware Questions

> Use when asked 'what am I missing?', reviewing an issue or draft before submission, or checking documentation completeness - detects requirement, spec, and doc gaps and generates prioritized actionable questions

- Skill: `britt/context-aware-questions` (Agent Skill)
- Install (CLI): `npx skillmds@latest add britt/context-aware-questions`
- Raw SKILL.md: https://api.skillmd.com/api/skills/britt/context-aware-questions/raw
- Safety review: pending
- Works with: Claude Code, Claude.ai, OpenAI Codex
- Category: Docs & Writing
- Author: britt (https://skillmd.com/u/britt)
- Updated: 2026-09-10
- Page: https://skillmd.com/skills/britt/context-aware-questions

---


# Context-Aware Question Generator Skill

Analyze project context to surface information gaps and generate prioritized, actionable questions.

## When to Use

Activate when:
- User asks "what am I missing?" or "what questions should I be asking?"
- Reviewing issues before starting work
- Analyzing documentation completeness
- Preparing a draft (issue, PR, document) for submission
- During project planning or kickoff

## Fetching Issues

Where issues are needed, fetch them with the `gh` CLI (must be installed and authenticated):

```bash
gh issue list --state open --json number,title,body,labels,assignees
gh issue view <n> --comments
```

## Analysis Modes

### 1. Project-Wide Review

When asked "what am I missing?" or "what questions should I be asking?":

1. Fetch all open issues (see Fetching Issues)
2. Analyze project structure
3. Check README and documentation
4. Analyze all gathered data for information gaps
5. Generate prioritized questions

### 2. Issue Review

When asked to review a specific issue:

1. Fetch the issue and all comments (see Fetching Issues)
2. Analyze for missing requirements, unclear specs, and gaps
3. Generate targeted questions for that issue

### 3. Draft Review

When reviewing a draft (issue, PR, note) before submission:

1. Analyze the provided text for completeness
2. Check against standard templates and best practices
3. Suggest specific improvements

### 4. Documentation Gap Analysis

When asked about documentation completeness:

1. Read README.md and files in docs/
2. Analyze what the project contains
3. Identify missing documentation by comparing project content to docs

## Gap Detection Heuristics

### Issue Analysis
- **Missing acceptance criteria**: No checkboxes, no "done when" statement
- **Vague descriptions**: Less than 100 characters, contains "unclear", "might", "maybe"
- **Missing labels or assignees**: Issue has no labels or no assignee
- **Stale issues**: Open more than 30 days with no activity
- **Bug reports without reproduction steps**: No "steps to reproduce" section

### Documentation Analysis
- **Missing README sections**: No install, usage, or examples sections
- **No dedicated docs/ directory**: For projects with more than 10 files
- **Short README**: Less than 500 characters
- **Missing license information**: No LICENSE file or license section
- **No inline documentation**: Missing JSDoc/docstrings in key files

### Project-Wide Analysis
- **Conflicting descriptions across issues, README, and docs**
- **Missing architecture documentation**: No system overview for complex projects
- **Undocumented key files**: Entry points without explaining comments
- **No project overview available**: Run the `project-analysis` skill first to map the project structure

## Output Structure

Questions are categorized and prioritized:

### Categories
- **requirements**: Missing acceptance criteria, unclear specs, vague descriptions
- **technical**: Implementation questions, architecture decisions
- **documentation**: Missing docs, unclear README sections
- **process**: Workflow gaps, missing labels/assignees
- **consistency**: Conflicting information across sources
- **architecture**: High-level design questions

### Priorities
- **high**: Blocking or critical gaps that need immediate attention
- **medium**: Important gaps that should be addressed soon
- **low**: Nice-to-have clarifications

## Example Output

```markdown
## Information Gaps Found

### High Priority (3)
1. [requirements] Issue #42 lacks acceptance criteria
   - Context: "Add login feature" has no definition of done
   - Suggested Action: Add checkboxes with acceptance criteria

2. [documentation] No API documentation found
   - Context: Project has 15 endpoints but no API reference
   - Suggested Action: Create docs/api.md with endpoint documentation

### Medium Priority (5)
...
```

## Best Practices

### When Generating Questions
1. Always prioritize by impact
2. Group related questions together
3. Provide actionable suggested actions
4. Link to specific sources (issue number, file path)

### When Reviewing Drafts
1. Be constructive, not critical
2. Suggest specific improvements with example text when helpful
3. Acknowledge what's already good

### When Analyzing Documentation
1. Check against industry standards
2. Consider the project type (CLI needs different docs than library)