# Pskoett Measuring AI Proficiency Plan Interview

> Plan Interview Skill

- Skill: `tomevault-io/pskoett-measuring-ai-proficiency-plan-interview` (Agent Skill, multi-file: 2 files)
- Install (CLI): `npx skillmds@latest add tomevault-io/pskoett-measuring-ai-proficiency-plan-interview`
- Raw SKILL.md: https://api.skillmd.com/api/skills/tomevault-io/pskoett-measuring-ai-proficiency-plan-interview/raw
- Safety review: pending (external: skill-scanner PASS, skillspector PASS)
- Works with: Claude Code, Claude.ai, OpenAI Codex
- Category: Coding & Dev Tools
- Author: tomevault-io (https://skillmd.com/u/tomevault-io)
- Updated: 2026-09-17
- Page: https://skillmd.com/skills/tomevault-io/pskoett-measuring-ai-proficiency-plan-interview

---


# Plan Interview Skill

## Purpose

Run a structured requirements interview before planning implementation. This ensures alignment between you and the user by gathering explicit requirements rather than making assumptions.

## When Invoked

User calls `/plan-interview <task description>`.

**Skip this skill** if the task is purely research/exploration (not implementation).

## Interview Process

### Phase 1: Upfront Interview (Before Exploration)

Interview the user using `AskUserQuestion` in **thematic batches of 2-3 questions**.

#### Required Question Domains

Cover ALL four domains before proceeding:

1. **Technical Constraints**
   - Performance requirements
   - Compatibility needs
   - Existing patterns to follow
   - Architecture understanding (if codebase is unfamiliar)

2. **Scope Boundaries**
   - What's explicitly OUT of scope
   - MVP vs full vision
   - Dependencies on other work

3. **Risk Tolerance**
   - Acceptable tradeoffs (speed vs quality)
   - Tech debt tolerance
   - Breaking change acceptance

4. **Success Criteria**
   - How will we know it's done?
   - What defines "working correctly"?
   - Testing/validation requirements

#### Question Generation

- Generate questions **dynamically** based on the task - no fixed template
- Group related questions into thematic batches
- **2-3 questions per batch** (do not exceed)
- Continue until you have **actionable specificity** (can describe concrete implementation steps)

#### Handling Edge Cases

| Scenario | Action |
|----------|--------|
| Contradictory requirements | Make a recommendation with rationale, ask for confirmation |
| User pivots requirements | Restart interview fresh with new direction |
| Interrupted session | Ask user: continue where we left off or restart? |

#### Anti-Patterns to Avoid

- Do NOT ask variations of the same question
- Do NOT make major assumptions without asking
- Do NOT over-engineer plans for simple tasks

### Phase 2: Codebase Exploration

After interview completes, explore the codebase to understand:
- Existing patterns relevant to the task
- Files that will be affected
- Integration points
- Potential risks

### Phase 3: Plan Generation

Write plan to `docs/plans/plan-NNN-<slug>.md` where NNN is sequential.

#### Required Elements

Every plan MUST include:

```markdown
## Success Criteria
[Clear definition of done from interview]

## Risk Assessment
[What could go wrong + mitigations]

## Affected Files/Areas
[Which parts of codebase will be touched]

## Open Questions
[Uncertainties to resolve during implementation]
- [ ] Question 1 - [Blocks implementation / Can proceed]
- [ ] Question 2 - [Blocks implementation / Can proceed]

## Implementation Checklist
- [ ] Step 1
- [ ] Step 2
...
```

#### Optional Elements

Include when relevant:

- **Rejected Alternatives**: Only for major architectural decisions
- **Decision Tree**: Only when multiple valid approaches exist
- **Visual Diagrams**: ASCII or Mermaid when helpful for understanding

#### Constraints

- **No time estimates** - describe what needs doing, not how long
- **No length limits** - plan should match task complexity
- Freeform structure beyond required elements

### Phase 4: Post-Approval

When user approves the plan:

1. **Auto-start implementation** immediately (no "proceed" confirmation needed)
2. Populate `TodoWrite` with checklist items
3. At **natural breakpoints** (significant decisions), compare progress to plan

## Fast Mode

If user wants quick planning, use **draft + refine**:

1. Perform task-focused codebase search
2. Generate draft plan
3. Run abbreviated interview to refine

## Resume Support

If a partial plan exists in `docs/plans/`:

```
AskUserQuestion: "I found an existing partial plan. Would you like to:"
- "Continue from where we left off"
- "Start fresh with a new plan"
```

## Example

```
User: /plan-interview Add OAuth authentication to the API

Claude: I'll help you plan the OAuth authentication feature. Let me gather
        requirements first.

[AskUserQuestion - Scope batch]
1. Which OAuth providers need to be supported (Google, GitHub, etc.)?
2. Is this replacing existing auth or adding alongside it?

User: Google and GitHub. Adding alongside existing JWT auth.

[AskUserQuestion - Technical batch]
1. Should OAuth tokens be stored in the existing session table or separately?
2. Any specific callback URL constraints from your hosting setup?

User: Separate table. We're on Vercel so callback URLs need to be configured per environment.

[AskUserQuestion - Risk/Success batch]
1. What's the acceptable degradation if an OAuth provider is down?
2. How should we handle users who already exist with the same email?

User: Fall back to standard login. Link accounts by email if user confirms.

Claude: [Explores codebase for auth patterns, session handling, database schema]

Claude: [Writes docs/plans/plan-003-oauth-authentication.md]

        Plan created. The main decision point is whether to use Passport.js
        or implement OAuth flows directly - I've documented both approaches
        with tradeoffs. Ready to review?

User: Looks good, go with Passport.js

Claude: [Auto-starts implementation with TodoWrite tracking]
```

---
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<!-- tomevault:4.0:skill_md:2026-04-13 -->

