Automatically detects when users are discussing project planning, strategy, or feature prioritization. Guides them toward structured planning artifacts when appropriate. Use when conversations touch on project vision, goals, priorities, or what to build next.
View on GitHubdrewdresser/ai-dev-settings
ai-dev
skills/strategic-planning/SKILL.md
January 22, 2026
Select agents to install to:
npx add-skill https://github.com/drewdresser/ai-dev-settings/blob/main/skills/strategic-planning/SKILL.md -a claude-code --skill strategic-planningInstallation paths:
.claude/skills/strategic-planning/# Strategic Planning Detection
You have expertise in strategic project planning. When you detect that a conversation involves planning, strategy, or prioritization, you should guide the user toward structured planning workflows.
## When to Activate
Detect these planning signals:
- Discussions about what to build or build order
- Questions about project scope or priorities
- Conversations about success metrics or goals
- Discussions involving multiple stakeholders with different priorities
- "What should we focus on?" type questions
- MVP or scope discussions
- Competitive analysis or positioning discussions
- User persona or target market discussions
## What to Do When Detected
1. **Acknowledge** the planning nature of the conversation
2. **Assess** what planning artifacts exist by checking `/strategy/`:
- `VISION.md`
- `STRATEGY.md`
- `METRICS.md`
- `OKRs.md`
- `EPICS.md`
- `USER-STORIES.md`
3. **Guide** based on what's missing:
- If no plans exist: Suggest `/ai-dev:kickoff` for the full workflow
- If partial plans: Suggest the next appropriate command
- If plans exist: Reference them in your responses
4. **Check GitHub state** (requires gh CLI):
- List milestones: `gh api repos/{owner}/{repo}/milestones`
- List user story issues: `gh issue list --label "user-story"`
- Connect discussions to existing GitHub issues
5. **Connect** current discussion to existing artifacts:
- "This new feature idea - how does it connect to your North Star of [X]?"
- "Based on your non-goals, this seems out of scope for now."
- "This would support OKR [X] - want to add it as an epic?"
## Guidance Approach
Be helpful but not pushy:
- Don't interrupt every conversation with planning suggestions
- Trigger on substantial planning discussions, not casual mentions
- Offer structure as a tool, not a requirement
Example interventions:
**When they're discussing features without context:**
"I notice you're discussing feature ideas. Do you