Documents/planning/Planning & Timeline

Planning & Timeline

Project Planning — Man-Month Breakdown & Team Assignment

Detailed workload allocation by man-month, specific dev assignments
Timeline: 9 months (6 cycles × 6 weeks) | Team: 5 engineers | AI 2x multiplier


1. Team Roster

ID Role Seniority Primary Domain Secondary Domain
D1 Tech Lead / Fullstack Senior (8y+) Architecture, Gateway, ACL Travel Booking
D2 Backend Engineer Senior (5y+) Travel Booking Event Management
D3 Backend Engineer Mid (3y+) Event Management Communications
D4 Fullstack Engineer Mid (3y+) Workforce, Comms Frontend (React)
D5 Frontend / DevOps Mid (3y+) React Frontend, CI/CD Reporting

Actual capacity:

  • Raw: 5 engineers × 9 months = 45 man-months
  • Minus overhead (meetings, review, learning): ~60% productive → 27 productive man-months
  • AI 2x multiplier → 44 effective man-months (≈ output of 10 engineers)

2. Phase Overview

Month:      1        2        3        4        5        6        7        8        9
          ├────────┼────────┼────────┼────────┼────────┼────────┼────────┼────────┼────────┤
Phase 0:  █████████                                                          AI Foundation
Phase 1:           ████████████████████                                      Core Services
Phase 2:                               ████████████████████                  Scale Out
Phase 3:                                                    ████████████████████ Optimize
          ├────────┼────────┼────────┼────────┼────────┼────────┼────────┼────────┼────────┤
Cycle:    |--C0---|---C1--|---C2--|---C3--|---C4--|---C5--|
Phase Duration Focus Output
Phase 0 Month 1 AI Foundation + Infra AI toolchain, CI/CD, scaffold, Docker, IaC
Phase 1 Month 2–4 Core Services Travel Booking + Event Management go-live
Phase 2 Month 5–7 Scale Out Workforce + Comms + Reporting go-live
Phase 3 Month 8–9 Hardening Performance, monitoring, docs, Payment ACL v2

3. Man-Month Breakdown (Detailed)

3.1 Summary Table

Work Package Man-Months (effective) Assigned Phase
AI Foundation & Tooling 3.0 D1, D5 0
Infrastructure / IaC / CI/CD 4.0 D5, D1 0–1
API Gateway (YARP) 2.0 D1 0–1
Shared Kernel & Contracts 1.5 D1 0
Travel Booking Service 6.0 D2, D1 1
Event Management Service 5.0 D3, D2 1–2
Workforce Service 4.0 D4 2
Communications Service 3.5 D4, D3 2
Reporting Service 3.5 D5, D3 2–3
Payment ACL 2.0 D1, D2 1
React Frontend 5.0 D5, D4 1–3
Testing & QA 2.5 All 1–3
Performance & Hardening 2.0 D1, D2 3
Documentation & Handoff 1.0 All 3
TOTAL 45.0 ≈ 44 effective

3.2 Breakdown by Service

Travel Booking Service — 6.0 man-months

Task Effort Owner Support
Legacy analysis (AI-assisted) 0.5 D2 D1
Domain modeling + DB schema 0.5 D2 D1
API implementation (CRUD + search) 1.5 D2
Business logic migration 1.5 D2 D1 review
Contract tests (Pact) 0.5 D2
Integration tests + E2E 0.5 D2 D5
CDC setup (legacy → new DB) 0.5 D1 D2
Strangler Fig cutover 0.5 D1 D2

Event Management Service — 5.0 man-months

Task Effort Owner Support
Legacy analysis (AI-assisted) 0.5 D3 D1
Domain modeling + DB schema 0.5 D3 D1
API implementation 1.0 D3
Business logic migration 1.0 D3 D2 review
Event workflows (create, cancel, modify) 0.5 D3
Contract tests + integration 0.5 D3
CDC setup + cutover 0.5 D1 D3
Calendar integration 0.5 D3 D4

Workforce Service — 4.0 man-months

Task Effort Owner Support
Legacy analysis 0.5 D4 D1
Domain modeling + schema 0.5 D4 D1
API implementation (schedules, leave, assignments) 1.0 D4
Business logic migration 1.0 D4 D1 review
Contract tests + integration 0.5 D4
CDC + cutover 0.5 D1 D4

Communications Service — 3.5 man-months

Task Effort Owner Support
Legacy analysis 0.3 D4 D3
Domain modeling 0.2 D4
Email / SMS / Push notification APIs 1.0 D4
Template engine migration 0.5 D4
Event-driven triggers (subscribe to other services) 0.5 D3 D4
Contract tests + integration 0.5 D4
CDC + cutover 0.5 D1 D4

Reporting Service — 3.5 man-months

Task Effort Owner Support
Legacy analysis 0.3 D5 D1
Domain modeling (CQRS read models) 0.5 D5 D1
Report APIs + query optimization 1.0 D5 D3
Dashboard data aggregation 0.5 D5
Scheduled report generation 0.5 D3 D5
Contract tests + integration 0.5 D5
Cutover 0.2 D1 D5

Payment ACL — 2.0 man-months

Task Effort Owner Support
Legacy Payment API analysis 0.3 D1 D2
ACL interface design 0.2 D1
ACL implementation (adapter pattern) 0.5 D1 D2
Error handling + retry + idempotency 0.5 D2 D1
Contract tests (new service ↔ legacy) 0.3 D2
Circuit breaker + monitoring 0.2 D1

4. Timeline — Dev Assignment theo Month

Month 1 — Phase 0: AI Foundation

Dev Week 1–2 Week 3–4 Output
D1 AI toolchain setup (Cursor, Claude Code, prompts) Shared Kernel, API Gateway scaffold AI ready, Gateway MVP
D2 AI tool training, legacy Travel analysis Travel domain modeling Travel spec ready
D3 AI tool training, legacy Event analysis Event domain modeling Event spec ready
D4 AI tool training, legacy Workforce analysis React design system POC Design system base
D5 CI/CD pipelines (GitHub Actions) Docker Compose, IaC (Bicep), ACR setup Infra ready

Week 4 — AI Pipeline Validation: D3 + D4 pilot-migrate Communications module using agentic AI.
Output: Comms service deployed to staging. Validates AI migration pipeline before applying to Travel.
(Comms production go-live will be in Phase 2 — this is only a pilot validation.)

Month 1 man-months: 5.0 raw → 2.0 effective (heavy learning overhead, AI setup investment)

Month 2 — Phase 1: Travel Booking Sprint 1

Dev Week 1–2 Week 3–4 Output
D1 YARP Gateway routing, ACL scaffold Payment ACL implementation Gateway + ACL MVP
D2 Travel API (CRUD endpoints) Travel business logic migration Travel service 60%
D3 Event API scaffold Event CRUD implementation Event service 30%
D4 Workforce domain modeling React: Travel module UI Frontend Travel 40%
D5 IaC environments (Dev, Staging) Travel CDC setup Dev/Staging live

Month 2 man-months: 5.0 raw → 5.0 effective (AI kicking in)

Month 3 — Phase 1: Travel Go-Live + Event Sprint

Dev Week 1–2 Week 3–4 Output
D1 Travel cutover (Strangler Fig, 5% → 100%) Code review + architecture guidance ✅ Travel LIVE
D2 Travel contract tests, bug fixes Event business logic support (D3) Travel stable
D3 Event business logic migration Event workflows (create/cancel/modify) Event service 70%
D4 React: Travel UI polish React: Event module UI Frontend Event 40%
D5 Travel monitoring dashboard Event CDC setup Monitoring live

Month 3 man-months: 5.0 raw → 5.5 effective (AI mastery improving)

Month 4 — Phase 1→2: Event Go-Live + Workforce Start

Dev Week 1–2 Week 3–4 Output
D1 Event cutover (5% → 100%) Workforce architecture review ✅ Event LIVE
D2 Event contract tests, stabilize Payment ACL hardening ACL production-ready
D3 Event integration tests Comms service scaffold + analysis Event stable
D4 Workforce API implementation Workforce business logic Workforce 40%
D5 React: Event UI polish React: Workforce module start Frontend Workforce 20%

Month 4 man-months: 5.0 raw → 5.5 effective

Month 5 — Phase 2: Workforce + Comms Sprint

Dev Week 1–2 Week 3–4 Output
D1 Architecture review, tech debt cleanup Comms architecture, ACL improvements Tech debt resolved
D2 Workforce business logic review Comms event triggers implementation Comms 30%
D3 Comms API (email/SMS/push) Comms template engine migration Comms 60%
D4 Workforce business logic + tests Workforce CDC + cutover prep Workforce 80%
D5 React: Workforce UI Reporting service analysis + scaffold Frontend Workforce done

Month 5 man-months: 5.0 raw → 5.5 effective

Month 6 — Phase 2: Workforce Go-Live + Comms + Reporting

Dev Week 1–2 Week 3–4 Output
D1 Workforce cutover (5% → 100%) Reporting CQRS architecture design ✅ Workforce LIVE
D2 Comms event-driven triggers Reporting query APIs Reporting 30%
D3 Comms integration tests Comms CDC + cutover prep Comms 90%
D4 React: Comms UI React: Reporting dashboards start Frontend Comms done
D5 Reporting data aggregation Reporting scheduled jobs Reporting 50%

Month 6 man-months: 5.0 raw → 5.5 effective

Month 7 — Phase 2→3: Comms + Reporting Go-Live

Dev Week 1–2 Week 3–4 Output
D1 Comms cutover (5% → 100%) Reporting cutover (5% → 100%) ✅ Comms LIVE, ✅ Reporting LIVE
D2 Cross-service integration tests Performance baseline measurement All services connected
D3 Reporting scheduled reports Bug fixes across services Reporting stable
D4 React: Reporting dashboards React: cross-module integration Frontend 90%
D5 Production monitoring setup Load testing preparation Monitoring complete

Month 7 man-months: 5.0 raw → 5.0 effective

Month 8 — Phase 3: Hardening

Dev Week 1–2 Week 3–4 Output
D1 Performance optimization (hotspots) Security audit + pen test fixes Production-grade
D2 Load testing (40K users simulation) Performance fixes from load test Benchmarks met
D3 Bug fixes, edge cases Operational runbooks Stable services
D4 React: performance optimization React: accessibility (a11y) Frontend polished
D5 Alerting rules tuning Disaster recovery testing DR validated

Month 8 man-months: 5.0 raw → 4.5 effective (perf work = less AI leverage)

Month 9 — Phase 3: Polish + Handoff

Dev Week 1–2 Week 3–4 Output
D1 Architecture documentation Knowledge transfer, ADR finalization Docs complete
D2 API documentation (OpenAPI) Legacy decommission plan (Phase 2 roadmap) API docs live
D3 Runbooks, incident playbooks End-to-end regression suite Ops ready
D4 React: design system documentation User training materials Training done
D5 CI/CD optimization, monitoring docs Capacity planning for next phase DevOps mature

Month 9 man-months: 5.0 raw → 4.0 effective (docs = less AI leverage)


5. Capacity Summary

5.1 Man-Months by Dev

Dev M1 M2 M3 M4 M5 M6 M7 M8 M9 Total Raw Role Load
D1 AI + GW GW + ACL Cutover Cutover Review Cutover Cutover Perf Docs 9.0 60% arch, 40% code
D2 Analysis Travel Travel ACL Comms Report Test Load test Docs 9.0 80% code, 20% review
D3 Analysis Event Event Event Comms Comms Report Bugfix Runbook 9.0 85% code, 15% review
D4 Analysis React React Workforce Workforce React React React Docs 9.0 50% backend, 50% FE
D5 Infra IaC Monitor React React+Report Report Monitor DR DevOps 9.0 40% infra, 30% FE, 30% BE

5.2 Effective Output (with AI 2x)

Baseline (Analysis v2 — conservative, phase-by-phase):

Gross capacity:         45 man-months (5 eng × 9 months)
Overhead (40%):        -18 man-months (meetings, review, learning)

Phase-by-phase (variable AI multiplier):
  P0 (M1):    5.0 raw - 3.0 overhead = 2.0 net × 1.0 =  2.0
  P1 (M2-4): 15.0 raw - 6.0 overhead = 9.0 net × 2.0 = 18.0
  P2 (M5-7): 15.0 raw - 5.5 overhead = 9.5 net × 2.0 = 19.0
  P3 (M8-9): 10.0 raw - 3.5 overhead = 6.5 net × 1.0 =  6.5
────────────────────────────────────────────────────────────────
Effective capacity:    45.5 ≈ ~44 man-months (conservative)

Per-phase breakdown (variable multiplier):

                          Raw    Overhead   Net    Multiplier  Effective
                          ────   ────────   ───    ──────────  ─────────
Phase 0 (Month 1):        5.0    -3.0       2.0    ×1.0*        2.0
Phase 1 (Month 2–4):     15.0    -6.0       9.0    ×2.0        18.0
Phase 2 (Month 5–7):     15.0    -5.5       9.5    ×2.0        19.0
Phase 3 (Month 8–9):     10.0    -3.5       6.5    ×1.0**       6.5
                          ────   ──────                        ─────
TOTAL:                    45.0   -18.0                          45.5

* Phase 0: AI not yet set up → multiplier = 1.0
** Phase 3: Performance/docs → low AI leverage → 1.0x

~44 effective man-months (conservative baseline from Analysis v2).
Per-phase calc yields ~45.5, confirming 44 is achievable and defensible.

5.3 Utilization Heatmap

Dev:    M1      M2      M3      M4      M5      M6      M7      M8      M9
D1:    ████    █████   █████   ████    ███     ████    █████   ████    ███
D2:    ██      █████   █████   █████   ████    ████    ████    █████   ███
D3:    ██      ████    █████   █████   █████   █████   ████    ███     ███
D4:    ███     ████    ████    █████   █████   ████    ████    ████    ███
D5:    █████   █████   ████    ████    ████    ████    ████    ████    ███

Legend: █ = ~20% utilization    █████ = 100%

6. Milestones & Go/No-Go Gates

Milestone Date (End of) Go/No-Go Criteria Decision Owner
M0: AI Foundation Ready Month 1 CI/CD green, Docker local works, AI tools deployed D1 (Tech Lead)
M1: Travel Booking Live Month 3 100% traffic via new service, error rate < 0.5%, latency < 200ms p95 D1 + Stakeholder
M2: Event Management Live Month 4 Same metrics + calendar integration working D1 + Stakeholder
M3: Workforce Live Month 6 Same metrics + schedule/leave APIs verified D1 + Stakeholder
M4: Comms + Reporting Live Month 7 All 5 services live, cross-service flows verified D1 + Stakeholder
M5: Production Hardened Month 9 Load test passed (40K users), DR tested, docs complete D1 + Management

Go/No-Go Checklist (per service cutover)

□ All contract tests passing (Pact verified)
□ Integration tests green
□ CDC data integrity verified (new DB vs legacy = match)
□ Error rate < 0.5% on canary (5% traffic, 48h soak)
□ Latency p95 < 200ms (or within 10% of legacy)
□ Rollback tested and documented
□ Monitoring + alerting configured
□ Stakeholder sign-off

7. Risk Buffer

Risk Impact Buffer Mitigation
Travel Booking more complex than expected M1 delay 2 weeks 2 weeks Phase 1 buffer D1 pair-programs with D2, deprioritize Event
AI tools don’t reach 2x Total capacity reduced 25% Reduce scope: defer Reporting Measure velocity monthly, adjust
Team member out for 1 month Lose 1 man-month Cross-training (secondary domain) D2↔D3 can swap, D4↔D5 swap frontend
Legacy codebase undocumented Analysis takes twice as long Phase 0 analysis + AI ingestion Gemini 2.5 Pro 1M context for legacy scan
Azure Service Bus learning curve Event-driven flows delayed 1 week buffer per phase POC in Phase 0, D1 mentors team

Scope Lever (if behind schedule)

Priority:    MUST HAVE              SHOULD HAVE           NICE TO HAVE
             ─────────              ───────────           ────────────
Services:    Travel + Event Mgmt    Workforce + Comms     Reporting (CQRS)
Frontend:    Travel + Event UI      Workforce UI          Dashboard (Reporting)
Infra:       CI/CD + Docker + ACR   Full IaC (Bicep)      DR automation
Quality:     Contract tests         Load testing          Security pen test
Docs:        ADRs + runbooks        Full API docs         Training materials

Lever rule: If by month 4 there are not 2 services live → reduce Phase 2 scope to 1 service (Workforce only), defer Comms + Reporting to next phase.


8. Weekly Cadence

Monday:      Sprint planning (30 min) — what each dev does this week
Tuesday-Thu: Heads-down development (async standups via Slack)  
Friday AM:   Code review session (60 min) — cross-service PRs
Friday PM:   Demo + retrospective (every 2 weeks)

Cycle (6-week):
  Week 1-4:  Build (heads down)
  Week 5:    Integration + testing
  Week 6:    Cutover / cooldown / tech debt