Schedule Milestones

Assign start and end dates to milestones for the quarter, enabling Gantt chart visualization in ClickUp.

Arguments

$ARGUMENTS - Quarter identifier (e.g., "2025-Q1") or empty for current quarter

Instructions

Phase 1: Load Quarter Data

1. Determine quarter:

   • If $ARGUMENTS provided, use that quarter
   • If empty, determine from current date

2. Read quarter file from .roadmap/quarters/{quarter-id}.md

   • Get list of epics
   • Get sprint schedule (which weeks)

3. Read all epic files for the quarter

   • Extract milestones with their sprint assignments
   • Note which milestones already have dates

4. Calculate sprint date ranges:

   Sprint Schedule
   ===============
   2025-W01: Jan 6 - Jan 17
   2025-W03: Jan 20 - Jan 31
   2025-W05: Feb 3 - Feb 14
   ...
   

Phase 2: Show Current State

5. Display timeline overview:

   Q1 2025 Schedule
   ================
   
   Milestones by Sprint:
   
   2025-W01 (Jan 6-17):
   ┌──────────────┬─────────────────────┬────────┬───────────┬───────────┐
   │ Epic         │ Milestone           │ Points │ Start     │ End       │
   ├──────────────┼─────────────────────┼────────┼───────────┼───────────┤
   │ User Auth    │ M1: Auth foundation │ 8      │ -         │ -         │
   │ Dashboard    │ M1: Chart setup     │ 5      │ -         │ -         │
   └──────────────┴─────────────────────┴────────┴───────────┴───────────┘
   
   2025-W03 (Jan 20-31):
   ┌──────────────┬─────────────────────┬────────┬───────────┬───────────┐
   │ User Auth    │ M2: OAuth providers │ 13     │ -         │ -         │
   └──────────────┴─────────────────────┴────────┴───────────┴───────────┘
   
   Unscheduled (no sprint assigned):
   - Dashboard M2: Data integration (8 pts)
   

Phase 3: Auto-Calculate Dates

6. Offer auto-scheduling:

   Auto-schedule based on points? [Y/n]
   
   This will:
   - Sequence milestones within each sprint
   - Calculate duration: 1 point ≈ 0.5 days
   - Set start/end dates accordingly
   

7. If yes, calculate dates:

   For each sprint:

   • Sort milestones by epic priority, then by milestone ID
   • Calculate duration: points × 0.5 days
   • Assign sequential dates starting from sprint start
   • Allow overlap if total points > sprint capacity (parallel work)

   Auto-Scheduled Dates
   ====================
   
   2025-W01 (Jan 6-17):
   │ Epic         │ Milestone           │ Points │ Start  │ End    │
   │ User Auth    │ M1: Auth foundation │ 8      │ Jan 6  │ Jan 10 │
   │ Dashboard    │ M1: Chart setup     │ 5      │ Jan 6  │ Jan 8  │
   
   Note: Milestones may overlap (parallel work assumed)
   
   Accept these dates? [Y/n/adjust]
   

Phase 4: Manual Adjustments

8. If user wants to adjust:

   Adjust dates for which milestone?
   
   1. User Auth M1 (Jan 6 - Jan 10)
   2. Dashboard M1 (Jan 6 - Jan 8)
   3. User Auth M2 (Jan 20 - Jan 27)
   q. Done adjusting
   
   > 1
   
   User Auth M1: Auth foundation
   Current: Jan 6 - Jan 10
   
   New start date (YYYY-MM-DD or Enter to keep):
   > 2025-01-06
   
   New end date (YYYY-MM-DD or Enter to keep):
   > 2025-01-13
   
   Updated: Jan 6 - Jan 13
   

Phase 5: Save and Summarize

9. Update epic files:

   • Add/update Start and End columns in milestone tables
   • Preserve other milestone data

10. Show final schedule:

    Schedule Saved
    ==============
    
    Q1 2025 Timeline:
    
    Jan 6  |████ Auth M1 ████████|
    Jan 6  |██ Dash M1 ██|
    Jan 13                        |████ Auth M2 ████████████|
    Jan 20                                                   |██ API M1 ██████|
           ─────────────────────────────────────────────────────────────────────
           W01                    W03                        W05
    
    Total: 4 milestones scheduled
    
    Next:
    - /clickup-sync:push to sync dates to ClickUp
    

Date Calculation Formula

duration_days = points × 0.5
end_date = start_date + duration_days (excluding weekends)

Important: These are milestone-specific estimated dates, NOT sprint dates.

• Sprint dates = the 2-week window (e.g., Jan 6-17)
• Milestone dates = when that specific work is planned (e.g., Jan 6-10 for an 8-point milestone)

For overlapping milestones (parallel work):

• Different epics can run in parallel
• Same epic milestones are sequential

Notes

• Dates are stored in epic files (milestone table)
• ClickUp receives dates via push command
• Gantt chart available in ClickUp after sync