Level-Up Feature: Data Collection Verification

Level-Up Feature: Data Collection Verification

Purpose: Verify that usage tracking works correctly to power /dex-level-up recommendations.

Data Flow Architecture

User Action → Command Execution → Usage Log Update → /dex-level-up Analysis → Recommendations

Tracking Points

1. Core Workflow Commands (Explicit Tracking)

These commands have explicit tracking steps added:

Verification:

• Each command file has a "Track Usage (Silent)" step
• Updates System/usage_log.md after completion
• No announcement to user

2. System Behavior (CLAUDE.md Guidance)

CLAUDE.md (lines 173-186) instructs Dex to track usage automatically:

Usage Tracking (Silent) Track feature adoption in System/usage_log.md to power /dex-level-up recommendations:

When to update (automatically, no announcement):

• User runs a command → Check that command's box
• User creates person/project page → Check corresponding box
• Work MCP tools used → Check task management boxes
• Journaling prompts completed → Check journal boxes

Verification:

• Guidance exists in CLAUDE.md
• Applies to all commands, even those without explicit tracking steps
• Updates happen silently in background

3. Feature Detection (Implicit Tracking)

Some features are tracked by detecting their existence in the vault:

Verification:

• /dex-level-up can read file system to detect usage
• No explicit tracking needed for these features

Scenario Testing

Scenario 1: New User (Week 1)

Actions:

1. User completes onboarding → No boxes checked yet
2. Runs /daily-plan for 7 consecutive days
3. Creates 2 tasks via MCP
4. Runs /dex-level-up

Expected State in System/usage_log.md:

## Core Workflows
- [x] Daily planning (/daily-plan)  ← Checked after first run
- [ ] Daily review (/review)
- [ ] Weekly planning (/week-plan)
- [ ] Weekly review (/week-review)
...

## System Features
- [x] Task created (via MCP)  ← Detected from 03-Tasks/Tasks.md
- [ ] Task completed (via MCP)
...

## Tracking Metadata
- Last dex-level-up prompt: (not yet prompted)
- First daily plan: 2026-01-21
- Setup date: 2026-01-20

Expected /dex-level-up Output:

Recommendations:

1. Daily Review - Complete the planning loop
2. Person Pages - Track relationships
3. Meeting Processing - Extract value from meetings

Verification Steps:

1. Check usage_log.md has correct checked boxes
2. /dex-level-up correctly counts 2 of ~25 features used
3. Recommendations are relevant to daily planning habit
4. No mention of weekly/quarterly planning (too early)

Scenario 2: Intermediate User (Week 4)

Actions:

1. Daily plans: 28 consecutive days
2. Daily reviews: 28 consecutive days
3. Weekly planning: 4 weeks
4. Meeting processing: 3 times
5. Person pages: 5 created
6. Tasks: 23 created, 15 completed
7. Runs /dex-level-up

Expected State in System/usage_log.md:

## Core Workflows
- [x] Daily planning (/daily-plan)
- [x] Daily review (/review)
- [x] Weekly planning (/week-plan)
- [ ] Weekly review (/week-review)  ← Not used yet
- [ ] Quarterly planning (/quarter-plan)
- [ ] Quarterly review (/quarter-review)

## Meeting Workflows
- [ ] Meeting prep (/meeting-prep)
- [x] Meeting processing (/process-meetings)
- [x] Person page created  ← 5 created
- [x] Person page updated

## System Features
- [x] Task created (via MCP)
- [x] Task completed (via MCP)
- [ ] Project page created  ← Missing
...

Expected /dex-level-up Output:

Recommendations:

1. Weekly Review - Natural next step after weekly planning
2. Project Tracking - Organize 23 tasks into projects
3. Quarterly Planning - Think 3 months out

Verification Steps:

1. System detects 5 person pages exist (file count in People/)
2. Recognizes weekly planning without weekly review = gap
3. Suggests project tracking (has tasks but no projects)
4. Recommendations build on established habits

Scenario 3: Power User (Month 3)

Actions:

1. All daily/weekly/quarterly workflows used
2. 15 person pages maintained
3. 6 project pages tracked
4. 47 meetings processed
5. Journaling enabled (morning & evening)
6. 12 insights saved
7. 156 tasks created, 134 completed
8. Runs /dex-level-up

Expected State in System/usage_log.md:

## Core Workflows
- [x] Daily planning (/daily-plan)
- [x] Daily review (/review)
- [x] Weekly planning (/week-plan)
- [x] Weekly review (/week-review)
- [x] Quarterly planning (/quarter-plan)
- [x] Quarterly review (/quarter-review)

## Meeting Workflows
- [x] Meeting prep (/meeting-prep)
- [x] Meeting processing (/process-meetings)
- [x] Person page created
- [x] Person page updated

## Organization
- [x] Inbox triage (/triage)
- [x] Learning capture (/save-insight)
- [x] Project tracking (/project-health)
- [ ] Product brief (/product-brief)

## Journaling
- [x] Morning journal
- [x] Evening journal
- [ ] Weekly journal

## System Features
- [x] Task created (via MCP)
- [x] Task completed (via MCP)
- [x] Project page created
- [ ] Content tracking used
- [x] Relationship tracking used

## Advanced
- [ ] Custom MCP created (/create-mcp)  ← Only unchecked advanced feature
- [ ] System improvements (/dex-improve)
- [ ] Prompt improvement (/prompt-improver)
- [x] Demo mode (/dex-demo)

Expected /dex-level-up Output:

Recommendations:

1. Custom MCP Integration - Automate CRM sync
2. System Customization - Make Dex yours

Celebration message: "You're using Dex like a pro! 🎉"

Verification Steps:

1. System recognizes power user status (21+ features checked)
2. Suggests only advanced features (custom MCPs, system improvements)
3. Acknowledges mastery
4. Suggests sharing knowledge with others

Critical Verification Points

✅ 1. Usage Log Gets Updated

Test:

• Fresh install → usage_log.md has all boxes unchecked
• Run /daily-plan → Box gets checked
• Run again → Box stays checked (idempotent)

Files:

• System/usage_log.md (the data)
• .claude/commands/daily-plan.md Step 7 (the update logic)

✅ 2. /dex-level-up Can Read Usage Log

Test:

• /dex-level-up command reads System/usage_log.md
• Parses markdown checkboxes correctly
• Counts checked vs unchecked items

Files:

• .claude/skills/dex-level-up/SKILL.md Step 1 (read logic)

✅ 3. Recommendations Are Contextual

Test:

• New user with only daily planning → Suggests daily review (close the loop)
• User with daily + weekly planning → Suggests weekly review (natural next step)
• User with tasks but no projects → Suggests project tracking

Files:

• .claude/skills/dex-level-up/SKILL.md Step 2 (pattern analysis)
• .claude/skills/dex-level-up/SKILL.md Step 3 (recommendation generation)

✅ 4. Smart Triggers Work

Test:

• Day 1-6: No prompt in /daily-plan
• Day 8+: Prompt appears if 3+ features unused
• After prompt: last_dex_level_up_prompt date updated
• Next 7 days: No prompt (respects cooldown)

Files:

• .claude/skills/daily-plan/SKILL.md Step 3.5 (trigger logic)
• System/usage_log.md Tracking Metadata section

✅ 5. Tracking Is Silent

Test:

• User runs /daily-plan
• Gets daily plan output
• No mention of "Updated usage log" or tracking
• Check usage_log.md → Box is checked

Behavior:

• All tracking updates are silent
• No user-facing announcements
• Updates happen in background

Edge Cases

Empty Usage Log (First Time)

Expected:

• /dex-level-up shows: "Looks like you're just getting started!"
• Recommends 3 essentials: daily planning, task management, meeting capture

All Features Used

Expected:

• /dex-level-up shows celebration: "You're using every feature in Dex! 🎉"
• Suggests custom MCPs, system improvements, sharing knowledge

User Says "Show Me Everything"

Expected:

• /dex-level-up says: "I could, but that's overwhelming..."
• Points to CLAUDE.md, .claude/skills/, and System Guide

Implementation Checklist

• Created System/usage_log.md with all features listed
• Added explicit tracking to core commands (daily-plan, review, week-plan, week-review)
• Added CLAUDE.md guidance for system-wide tracking behavior
• Created /dex-level-up command with pattern analysis logic
• Added README section highlighting feature discovery
• Added onboarding mention of /dex-level-up
• Added smart trigger to /daily-plan (7-day cooldown)
• Tested scenario recommendations (examples in dex-level-up.md)

Maintenance Notes

To add a new trackable feature:

1. Add entry to System/usage_log.md in appropriate section
2. Update CLAUDE.md if it's a new pattern (optional)
3. Consider explicit tracking in command file if it's a core workflow
4. Update /dex-level-up command if new progression patterns emerge

No need to:

• Update every single command file manually
• Create complex tracking infrastructure
• Store detailed analytics (simple binary checkboxes work)

Success Criteria

✅ New users discover features they didn't know existed ✅ Intermediate users progress naturally through workflows ✅ Power users find advanced capabilities when ready ✅ No feature blindness — everyone gets to full value ✅ Never overwhelming — 2-3 suggestions at a time ✅ Tracking is silent — no interruption to user flow

Result: Users get to value faster, system delivers on its promise, no FOMO.