hackathon-milestone-monitor

Goal

Evaluate current project progress against the planned milestone schedule, identify slippage or risk, and recommend concrete next actions to ensure the demo is ready before judging begins.

Trigger Conditions

Use this skill when:

• A milestone check-in is due (at 25%, 50%, 75%, or 90% of hackathon time)
• The team is uncertain whether they are on track
• A task has significantly overrun its time budget
• A scope change has occurred and the plan needs to be reassessed
• Invoked during Phase 5 (Build) at each milestone marker; re-invoke any time the critical path is threatened

Inputs

Outputs

Rules

1. Compute percent_complete as completed_tasks / total_tasks × 100.
2. Compute percent_time_used as elapsed_hours / hackathon_duration_hours × 100.
3. If percent_complete < percent_time_used - 15, flag status as behind.
4. If percent_complete > percent_time_used, flag status as ahead.
5. Otherwise flag status as on_track.
6. Any task on the critical path that is blocked must generate a critical recommended action.
7. If percent_time_used > 75 and the demo flow is not yet connected end-to-end, recommend scope cuts immediately.
8. scope_recommendations must only cut features that are not [FAKE-OK] impossible and not the wow-factor feature.

Output Format

progress_report:
  completed_tasks: <number>
  total_tasks: <number>
  percent_complete: <number>
  percent_time_used: <number>
  status: "<on_track|behind|ahead|critical>"
  summary: "<one-sentence assessment>"

current_phase: "<Phase name and number>"

milestone_status:
  - name: "<milestone name>"
    target_hour: <number>
    actual_hour: "<number or 'not yet reached'>"
    status: "<completed|on_track|at_risk|missed>"
    notes: "<context>"

critical_path_health:
  status: "<healthy|at_risk|broken>"
  bottleneck_task: "<T-XX or null>"
  description: "<what is slowing the critical path>"

recommended_actions:
  - priority: <number>
    urgency: "<immediate|this_hour|today>"
    action: "<what to do>"
    rationale: "<why this matters now>"

scope_recommendations:
  - feature: "<feature name>"
    recommendation: "<cut|defer|simplify>"
    time_saved_hours: <number>
    rationale: "<why this can be safely cut>"

recommended_skills:
  - "<skill-name>"

Example

Input:

project_title: "AnchorAI"
hackathon_duration_hours: 24
elapsed_hours: 14
milestones:
  - name: "Backend skeleton live"
    target_hour: 7
  - name: "Frontend connected"
    target_hour: 11
  - name: "Memory working"
    target_hour: 16
  - name: "Demo-ready"
    target_hour: 19
tasks:
  - id: "T-01"
    title: "Set up FastAPI and Supabase"
  - id: "T-02"
    title: "Implement OpenAI chat endpoint"
  - id: "T-03"
    title: "Implement session memory"
  - id: "T-04"
    title: "Build chat UI component"
  - id: "T-05"
    title: "Wire frontend to API"
  - id: "T-06"
    title: "Add crisis card (mocked)"
completed_tasks: ["T-01", "T-02", "T-04"]
blocked_tasks:
  - id: "T-03"
    reason: "Supabase cold-start issue unresolved; falling back to Redis"

Output:

progress_report:
  completed_tasks: 3
  total_tasks: 6
  percent_complete: 50
  percent_time_used: 58
  status: "behind"
  summary: "3 of 6 tasks done at 58% time used; session memory is blocked and the demo flow is not yet connected."

current_phase: "Phase 5 — Implementation"

milestone_status:
  - name: "Backend skeleton live"
    target_hour: 7
    actual_hour: 8
    status: "completed"
    notes: "Completed 1 hour late due to Supabase setup delay"
  - name: "Frontend connected"
    target_hour: 11
    actual_hour: "not yet reached"
    status: "at_risk"
    notes: "T-05 (wire frontend) is blocked on T-03 (session memory); UI is built but not connected"
  - name: "Memory working"
    target_hour: 16
    actual_hour: "not yet reached"
    status: "at_risk"
    notes: "T-03 is blocked; 2 hours remain before this milestone"
  - name: "Demo-ready"
    target_hour: 19
    actual_hour: "not yet reached"
    status: "at_risk"
    notes: "Only 5 hours to complete T-03, T-05, T-06 and run full demo flow"

critical_path_health:
  status: "at_risk"
  bottleneck_task: "T-03"
  description: "Session memory (T-03) is blocked; it gates T-05 (frontend wiring) which gates demo-readiness"

recommended_actions:
  - priority: 1
    urgency: "immediate"
    action: "Abandon Supabase for session memory; switch to Redis in-memory fallback — saves 1–2 hours"
    rationale: "T-03 has been blocked for >1 hour; Redis fallback was planned in risk analysis"
  - priority: 2
    urgency: "this_hour"
    action: "Start T-05 (frontend wiring) using a hardcoded stub memory response while T-03 is resolved"
    rationale: "Decouples frontend progress from memory implementation; demo flow can proceed in parallel"
  - priority: 3
    urgency: "today"
    action: "Run full demo flow end-to-end by H+16 even if memory is mocked — freeze demo path first"
    rationale: "Demo-readiness milestone at H+19 requires 3 clean end-to-end runs"

scope_recommendations:
  - feature: "Mood trend dashboard"
    recommendation: "cut"
    time_saved_hours: 3
    rationale: "Not in MVP demo flow; team is behind schedule; dashboard was already deferred"

recommended_skills:
  - "hackathon-code-implementer"
  - "hackathon-deployment-prep"

Context Files

Knowledge Base

• knowledge/hackathon-mvp-strategy.md
• knowledge/hackathon-common-failures.md
• knowledge/hackathon-winning-patterns.md

Playbooks

• playbooks/hackathon-workflow.md
• playbooks/24h-hackathon-playbook.md
• playbooks/36h-hackathon-playbook.md
• playbooks/48h-hackathon-playbook.md