Purpose
Assess whether your team/organization is truly AI-shaped (redesigning how you work with AI) or merely AI-first (automating existing tasks). Evaluates five competencies and provides a maturity score with specific recommendations.
Key Concepts
AI-First vs. AI-Shaped
| AI-First (Task Automation) | AI-Shaped (Workflow Redesign) |
|---|---|
| "Use AI to write PRDs faster" | "Redesign the PRD process with AI as a collaborator" |
| Same workflow, faster | Different workflow, better outcomes |
| Efficiency gains | Capability gains |
| Easy to adopt | Requires organizational change |
| Low ceiling on impact | High ceiling on impact |
Five Competencies
- Context Engineering — How well do you structure information for AI?
- Prompt Craft — How well do you communicate with AI?
- Evaluation — How well do you assess AI output quality?
- Integration — How deeply is AI woven into workflows?
- Culture — Does your team embrace AI as a partner?
Application
Question 1: Current AI Usage
Agent asks: "How is your team currently using AI in product work?"
Options:
- Not at all — We haven't started
- Ad hoc — Individual team members use ChatGPT/Claude sometimes
- Standardized — We have defined AI tools and prompts for common tasks
- Integrated — AI is built into our product workflows
- Native — Our workflows were designed around AI capabilities from the start
Question 2: Context Engineering
Agent asks: "When you use AI, how do you provide context?"
Options:
- Copy-paste everything — Dump full documents into the prompt
- Selective sharing — Choose relevant sections but no structure
- Structured context — Use templates, personas, and constraints
- Memory architecture — Maintain persistent context across sessions
- Automated context pipelines — Systems that automatically prepare context
Question 3-5: [Similar adaptive questions for Evaluation, Integration, Culture]
Output: AI Readiness Assessment
# AI Readiness Assessment
## Overall Score: [X/25]
| Competency | Score (1-5) | Level | Key Gap |
|-----------|------------|-------|---------|
| Context Engineering | [#] | [Label] | [Gap] |
| Prompt Craft | [#] | [Label] | [Gap] |
| Evaluation | [#] | [Label] | [Gap] |
| Integration | [#] | [Label] | [Gap] |
| Culture | [#] | [Label] | [Gap] |
## Maturity Level: [AI-First / Transitioning / AI-Shaped]
## Priority Recommendations
1. **Start with:** [Lowest-scoring competency] — [Specific action]
2. **Then build:** [Next priority] — [Specific action]
3. **Long-term:** [Highest-ceiling opportunity] — [Specific action]
Quality Rubric
| Dimension | 0 | 1 | 2 |
|---|---|---|---|
| Honesty | Aspirational answers | Mostly honest | Evidence-based self-assessment |
| Specificity | "We use AI" | Named tools/workflows | Specific examples per competency |
| Actionability | Score only | Recommendations | Prioritized actions with timeline |
References
Related Skills
skills/communication/context-engineering-advisor/SKILL.md— Deep dive on context competencyskills/strategy/product-vision-statement/SKILL.md— AI-shaped vision integration
Skill type: Interactive Domain: Strategy & Vision