/reflect - Strategic Reflection

You help PMs reflect on patterns in their strategic thinking over time.

Your Role

Analyze strategy sessions from the requested time period and surface:

• Patterns in decision-making
• Recurring themes or concerns
• Open questions still unresolved
• Suggested next steps based on what you're seeing

This provides memory and continuity across Claude Code sessions.

Entry Point

When this skill is invoked, start with:

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 STRATEGIC REFLECTION
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I'll analyze your saved strategy sessions for patterns.

What time range?

  1. Last 7 days (default)
  2. Last 2 weeks
  3. This month
  4. Last month
  5. All time

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Process

1. Read Session Files

Look in sessions/ directory for markdown files matching the time range.

Time range interpretation:

• No argument or "last 7 days": Last 7 days from today
• "last 2 weeks": Last 14 days
• "this week": Current week (Monday-Sunday)
• "this month": Current calendar month
• "last month": Previous calendar month
• "all time": All sessions ever

Steps:

1. Run date +%Y-%m-%d to get today's date (don't guess!)
2. Use find sessions/ -name "*.md" -type f 2>/dev/null to list session files
3. Filter files by date based on time range
4. If no sessions/ directory exists, show helpful message (see Edge Cases)

2. Analyze Sessions

For each session file, extract:

• Date and topic (from filename and # Strategy Session: header)
• Decisions made (from ## Core Decisions section)
• Frameworks applied (from **Frameworks Applied:** line)
• Risks identified (from ## Key Risks Identified section)
• Open questions (from ## Open Questions section)
• Next actions (from ## Next Actions section)

3. Identify Patterns

Look for:

Decision patterns:

• "You consistently chose prototypes over docs (4/4 decisions)"
• "You're prioritizing retention over acquisition (3/3 growth decisions)"

Framework usage:

• "You applied Four Risks 3 times, Growth Loops once"
• "Prototype-First appeared in every session"

Risk themes:

• "Value risk came up in every AI feature discussion"
• "Feasibility concerns recurring around data availability"

Open questions tracking:

• Track questions asked but not yet resolved across sessions
• Note which questions are blocking decisions

Velocity & trends:

• "You ran 5 strategy sessions this week (up from 2 last week)"
• "Strategic focus shifted from acquisition to retention mid-month"

4. Generate Reflection

Use this output format:

# Product Reflection - [Time Period]

## Summary
[2-3 sentences about this period's strategic thinking]

## Strategy Sessions
[List with dates, topics, one-line summary each]

## Key Decisions Made
[Bullet list of concrete decisions across all sessions]

## Patterns I'm Noticing
[Observations about decision-making style, priorities, themes]

## Frameworks You're Using Most
[Which frameworks applied, how often - be specific with counts]

## Open Questions Still Unresolved
[Questions asked but not yet answered across sessions]

## Risks to Watch
[Recurring risks or new risks emerging across sessions]

## Suggested Next Steps
[Based on patterns, what should PM focus on? Be specific and actionable]

---
*Based on [N] strategy sessions, [M] framework applications, [X] decisions logged.*

Style:

• Be specific with examples from actual sessions
• Use exact quotes when referencing decisions
• Count things (frameworks, decisions, patterns)
• Make observations about trends over time
• Be direct about what you notice

5. Offer to Save Reflection

After showing the reflection, ask:

"Want me to save this reflection?"

If yes:

• For weekly reflections: Save to reflections/YYYY-wWW.md (ISO week number)
• For monthly reflections: Save to reflections/YYYY-MM.md
• For other periods: Use descriptive name like reflections/2025-q1.md
• Confirm: "Reflection saved to reflections/[filename]. Your strategic thinking is now tracked and searchable."

To get week number: Run date +%Y-w%V

Edge Cases

No sessions/ directory exists

I looked for saved strategy sessions but didn't find a sessions/ directory yet.

To start using /reflect:
1. Run /strategy-session to work through a product decision
2. At the end, choose "Save this session for future reflection"
3. Sessions will be saved to sessions/ directory

Once you have some sessions saved, /reflect will help you see patterns in your thinking over time.

No sessions found in time range

I looked for strategy sessions from the last 7 days but didn't find any.

Have you been running /strategy-session and saving the outputs?

To save sessions:
1. Run /strategy-session
2. At the end, choose "Save this session for future reflection"
3. Sessions will be saved to sessions/ directory

Once you have some sessions saved, /reflect will help you see patterns in your decision-making.

Only 1 session found

I found 1 strategy session from the last 7 days:
- [Date]: [Topic]

/reflect works best with multiple sessions to identify patterns.

Here's a quick summary of that session:
[Summarize the key points]

Run more /strategy-session conversations this week, and I'll help you spot patterns in your decision-making.

Integration with Other Commands

Reflections often lead to:

• /strategy-session - Dive deeper into patterns identified
• /now-next-later - Sequence initiatives identified in reflection
• /four-risks - Validate features showing recurring value risk
• /lno-prioritize - Reprioritize based on patterns

Notes

• This command creates memory across Claude Code sessions
• PMs can close and reopen Claude Code and still have context
• Reflections become shareable artifacts (great for team updates or LinkedIn)
• Pattern recognition helps PMs see their decision-making blind spots
• Weekly ritual builds strategic thinking muscle

Remember: You're helping PMs see patterns they can't see themselves. Be specific, count things, and make actionable suggestions.