--- skill: 'program-planning' version: '2.0.0' updated: '2025-12-31' category: 'organizational' complexity: 'advanced' prerequisite_skills: [] composable_with: - 'milestone-tracking' - 'stakeholder-management' - 'risk-assessment' - 'change-management' --- # Program Planning Skill ## Overview Expertise in creating and executing vendor replacement programs using the proven 30-60-90 day framework, including milestone planning, resource allocation, dependency management, and phase gate governance. ## Core Framework: 30-60-90 Day Planning ### Phase Structure **Phase 1: Planning & Preparation (Days 1-30)** - **Focus:** Build foundation, make decisions, prepare for action - **Key Activities:** Business case, tool selection, team prep, risk assessment - **Deliverables:** Approved plan, selected tools, trained pilot team, baseline metrics - **Success Criteria:** Executive approval, budget allocated, team ready **Phase 2: Pilot & Validation (Days 31-60)** - **Focus:** Prove the approach works with real projects - **Key Activities:** Pilot execution, metrics tracking, vendor comparison, validation - **Deliverables:** Quality data, cost validation, Go/No-Go decision - **Success Criteria:** Quality ≥90% vendor, cost validated, team satisfied **Phase 3: Transition & Scale (Days 61-90)** - **Focus:** Full rollout and vendor cutover - **Key Activities:** Team training, vendor wind-down, cutover, optimization - **Deliverables:** Full deployment, vendor exit, success validation - **Success Criteria:** Production live, vendor exited, ROI achieved ### Planning Principles 1. **Start with the End:** Define success criteria before planning 2. **Phase Gates:** Clear go/no-go decisions between phases 3. **Risk-Based:** Identify and mitigate risks proactively 4. **Iterative:** Adjust plan based on learnings 5. **Stakeholder-Driven:** Align with stakeholder needs and constraints 6. **Measurable:** Track progress with objective metrics 7. **Realistic:** Buffer for unknowns and learning curves 8. **Documented:** Write everything down, share widely ## Program Planning Process ### Step 1: Program Charter Development **Program Charter Template:** ```markdown # Vendor Replacement Program Charter ## Program Overview **Name:** [Program Name] **Sponsor:** [Executive Sponsor Name, Title] **Manager:** [Program Manager Name] **Duration:** [Start Date] - [End Date] (90 days) **Budget:** $[Amount] ## Business Case **Problem:** [Vendor pain points and costs] **Solution:** [AI-augmented team approach] **Expected Benefits:** - Cost reduction: [X]% ($[Y]/year) - Productivity gain: [X]x multiplier - Quality improvement: [Metrics] - Strategic value: [IP retention, flexibility, etc.] ## Scope **In Scope:** - [Function 1 - e.g., backend development] - [Function 2 - e.g., API development] - [Team size - e.g., 5 FTEs] **Out of Scope:** - [Function 3 - e.g., frontend development - future phase] - [Constraint 1 - e.g., production support (vendor retained)] **Success Criteria:** - Phase 1: Executive approval, tools selected, team ready - Phase 2: Pilot quality ≥90% vendor, cost validated - Phase 3: Production live, vendor exited, 60% cost reduction ## Stakeholders **Executive Sponsor:** [Name] - Budget approval, strategic decisions **R&D Leadership:** [Name] - Team allocation, technical decisions **Finance:** [Name] - Budget tracking, ROI validation **Security/Compliance:** [Name] - Risk assessment, approval **Vendor Account Manager:** [Name] - Transition coordination ## Assumptions 1. Executive budget approved by [date] 2. Pilot team available full-time for weeks 5-8 3. Vendor will cooperate with 90-day notice 4. No major production incidents during cutover 5. AI tools perform as demonstrated in POCs ## Constraints 1. Budget: $[X] maximum 2. Timeline: Must complete by [date] (fiscal year end) 3. Resources: 5 FTEs available, no new hires 4. Vendor contract: 90-day notice required 5. Risk tolerance: No production downtime acceptable ## Governance - **Steering Committee:** [Members] - Monthly reviews - **Program Team:** [Core members] - Weekly meetings - **Phase Gates:** Day 30, Day 60, Day 90 - **Status Reporting:** Weekly to sponsor, monthly to executives ``` ### Step 2: Milestone Planning **Milestone Planning Framework:** ```markdown ## Program Milestones ### Phase 1 Milestones (Days 1-30) **M1.1: Program Kickoff (Day 1)** - Executive sponsor approval - Program team assembled - Communication plan launched **M1.2: Business Case Complete (Day 7)** - Executive presentation delivered - Financial model finalized - Board approval (if required) **M1.3: Tool Selection (Day 14)** - Evaluation completed - Security cleared - Procurement initiated **M1.4: Pilot Team Ready (Day 21)** - Team identified and committed - Training curriculum complete - Baseline metrics established **M1.5: Phase Gate 1 (Day 30)** - All deliverables complete - Executive go-decision - Pilot launch authorized ### Phase 2 Milestones (Days 31-60) **M2.1: Pilot Launch (Day 31)** - Tools deployed - Team trained - First project started **M2.2: Parallel Run Start (Day 35)** - Vendor and AI outputs being compared - Metrics dashboard live - Daily tracking initiated **M2.3: Mid-Pilot Review (Day 45)** - Preliminary results analyzed - Issues addressed - Plan adjustments made **M2.4: Pilot Complete (Day 53)** - All pilot projects finished - Final metrics collected - Team feedback gathered **M2.5: Phase Gate 2 (Day 60)** - Go/No-Go decision - Full rollout approved - Vendor transition plan finalized ### Phase 3 Milestones (Days 61-90) **M3.1: Full Team Training (Day 65)** - All team members trained - Tools deployed organization-wide - Support structure in place **M3.2: Vendor Transition Start (Day 70)** - Contract wind-down initiated - Knowledge transfer executing - Parallel run continuing **M3.3: Cutover Ready (Day 80)** - Knowledge transfer complete - Quality parity achieved - Cutover approved **M3.4: Production Cutover (Day 85)** - Vendor contract concluded - Full internal operation - Monitoring intensive **M3.5: Phase Gate 3 / Program Close (Day 90)** - Success metrics validated - ROI achieved - Program closed ``` ### Step 3: Dependency Mapping **Dependency Types:** 1. **Finish-to-Start (FS):** Task B can't start until Task A finishes 2. **Start-to-Start (SS):** Task B can't start until Task A starts 3. **Finish-to-Finish (FF):** Task B can't finish until Task A finishes 4. **Start-to-Finish (SF):** Task B can't finish until Task A starts (rare) **Critical Path Analysis:** ```markdown ## Critical Path: Longest Dependent Chain Day 1-7: Business Case → Budget Approval [CRITICAL] ↓ Day 8-14: Tool Selection → Security Clearance [CRITICAL] ↓ Day 15-21: Procurement → Tool Deployment [CRITICAL] ↓ Day 22-30: Training → Pilot Launch [CRITICAL] ↓ Day 31-60: Pilot Execution → Validation [CRITICAL] ↓ Day 61-70: Full Training → Team Readiness [CRITICAL] ↓ Day 71-85: Vendor Transition → Cutover [CRITICAL] **Total Critical Path: 85 days** **Buffer: 5 days** Any delay on critical path delays entire program. Non-critical tasks (e.g., documentation, case study) have slack. ``` ### Step 4: Resource Allocation **Resource Planning Template:** ```markdown ## Resource Allocation Plan ### Core Program Team (Full-time) - **Program Manager:** 1 FTE × 90 days = 90 person-days - **Change Manager:** 0.5 FTE × 90 days = 45 person-days - **Technical Lead:** 0.5 FTE × 60 days = 30 person-days **Total Core:** 165 person-days ### Pilot Team (Phase 2: Days 31-60) - **Developers:** 5 FTE × 30 days = 150 person-days - **QA/Validation:** 2 FTE × 30 days = 60 person-days **Total Pilot:** 210 person-days ### Full Team (Phase 3: Days 61-90) - **All Team Members:** 20 FTE × 30 days = 600 person-days - **Training time (20%):** 120 person-days - **Productive time (80%):** 480 person-days ### Support Resources (Part-time) - **Executive Sponsor:** 2 hours/week × 12 weeks = 24 hours - **Security/Compliance:** 8 hours/month × 3 months = 24 hours - **Legal:** 16 hours (contract review) - **Finance:** 8 hours (ROI tracking) ### External Resources - **Vendor Transition:** Vendor team cooperation (no cost) - **Tool Vendor Support:** Included in licensing - **External Consultant (optional):** 40 hours @ $200/hr = $8,000 ``` ### Step 5: Budget Planning **Program Budget Template:** ```markdown ## Program Budget ### AI Tools & Technology - GitHub Copilot: 20 users × $39/mo × 3 mo = $2,340 - GPT-4 API: $500/month × 3 months = $1,500 - Infrastructure: $300/month × 3 months = $900 **Subtotal Technology:** $4,740 ### Training & Enablement - Training curriculum development: 80 hours @ $150/hr = $12,000 - Training delivery (workshops): $5,000 - Training materials and resources: $2,000 **Subtotal Training:** $19,000 ### Transition & Knowledge Transfer - Vendor knowledge transfer sessions: Included in contract - Documentation sprint: 40 hours @ $100/hr = $4,000 - Parallel run costs (overlapping): $10,000 **Subtotal Transition:** $14,000 ### Program Management - Program Manager: 90 days @ $1,000/day = $90,000 - Change Manager: 45 days @ $800/day = $36,000 - Technical Lead: 30 days @ $1,200/day = $36,000 **Subtotal Management:** $162,000 ### Contingency & Buffer - Risk buffer (10%): $19,974 - Scope change reserve: $10,000 **Subtotal Contingency:** $29,974 **TOTAL PROGRAM BUDGET: $229,714** ### Cost Avoidance (Savings) - Vendor costs avoided (3 months): $120,000 - **Net Cost Year 1:** $109,714 - **Savings Year 1 (months 4-12):** $360,000 - **Year 1 ROI:** 228% ``` ## Phase Gate Governance ### Phase Gate Purpose - **Ensure readiness** before proceeding to next phase - **Validate assumptions** and adjust plans - **Obtain approvals** for continued investment - **Identify and mitigate risks** early - **Prevent costly mistakes** from proceeding when not ready ### Phase Gate Process **1. Gate Preparation (1 week before)** - Program Manager compiles evidence - All deliverables finalized - Metrics and data validated - Stakeholder pre-briefings **2. Gate Assessment (Gate day)** - Criteria scorecard review - Evidence presentation - Stakeholder Q&A - Risk review - Decision discussion **3. Gate Decision** - **PASS:** Proceed to next phase as planned - **CONDITIONAL PASS:** Proceed with specific conditions to address - **DELAY:** Address critical gaps before proceeding - **CANCEL:** Abort program (rare, but possible) **4. Post-Gate Actions** - Document decision and rationale - Communicate to all stakeholders - Update plan based on conditions or delays - Kick off next phase ### Gate Criteria Examples **Phase Gate 1 Criteria:** ```markdown | Criterion | Weight | Target | Evidence Required | |-----------|--------|--------|-------------------| | Executive approval | 20% | Signed charter | Approval email/signature | | Budget allocated | 20% | $[X] committed | Finance confirmation | | Tools selected | 15% | 2+ options evaluated | Evaluation scorecard | | Security cleared | 15% | No red flags | Security signoff | | Team ready | 15% | 5 trained | Training completion % | | Baseline metrics | 10% | Defined and measured | Metrics dashboard | | Risk mitigation | 5% | Plans for top 5 risks | Risk register | **Pass Criteria:** ≥85% weighted score, no individual criterion <50% ``` ## Common Planning Pitfalls ### Pitfall 1: Unrealistic Timeline **Problem:** Trying to do 90-day program in 60 days **Why it fails:** Corners cut, quality suffers, team burns out **How to avoid:** Use proven 30-60-90 framework, buffer for unknowns ### Pitfall 2: Insufficient Planning Time **Problem:** Rushing into pilot without adequate preparation **Why it fails:** Missing foundation, poor tool selection, team unready **How to avoid:** Spend full 30 days on Phase 1, don't skip ### Pitfall 3: Vague Success Criteria **Problem:** "Improve productivity" without specific targets **Why it fails:** Can't measure success, stakeholders disagree on outcomes **How to avoid:** Quantify everything (≥90% quality, 60% cost reduction, etc.) ### Pitfall 4: Ignoring Change Management **Problem:** Treating as purely technical program **Why it fails:** Team resistance, adoption failure, quality issues **How to avoid:** Dedicate resources to training, communication, support ### Pitfall 5: No Risk Management **Problem:** Assuming everything will go as planned **Why it fails:** Surprises cause delays, cost overruns, failures **How to avoid:** Identify risks early, mitigate proactively, monitor continuously ### Pitfall 6: Poor Stakeholder Management **Problem:** Executives surprised by issues, Finance questions costs **Why it fails:** Loss of support, budget challenges, program cancellation **How to avoid:** Weekly reports, transparent communication, early escalation ### Pitfall 7: Inadequate Knowledge Transfer **Problem:** Rushing vendor exit to save money **Why it fails:** Critical knowledge lost, team struggles, quality drops **How to avoid:** Allocate 4-6 weeks for thorough knowledge transfer ### Pitfall 8: Skipping Parallel Run **Problem:** Cutting directly from vendor to AI **Why it fails:** No validation, quality unknown, high risk **How to avoid:** Minimum 3-4 week parallel run for comparison ## Program Planning Checklist ### Initial Planning - [ ] Program charter drafted and approved - [ ] Success criteria defined (quantified) - [ ] Stakeholders identified and mapped - [ ] Budget estimated and approved - [ ] Timeline baselined (30-60-90 days) - [ ] Risks identified (top 10) - [ ] Governance structure defined ### Detailed Planning - [ ] All milestones defined with dates - [ ] Dependencies mapped - [ ] Critical path identified - [ ] Resources allocated (names, not just roles) - [ ] Budget breakdown by category - [ ] Phase gate criteria defined - [ ] Communication plan complete ### Execution Preparation - [ ] Tracking tools set up (dashboards, reports) - [ ] Kickoff meeting scheduled - [ ] Team roles and responsibilities clear - [ ] Escalation paths defined - [ ] Change control process established - [ ] Quality standards documented - [ ] Lessons learned process defined ## Tools and Templates **Program Management Tools:** - **Gantt Chart:** Microsoft Project, Monday.com, Asana - **Kanban Board:** Jira, Trello, Linear - **Dashboards:** Tableau, Looker, Excel - **Communication:** Slack, Teams, Email - **Documentation:** Confluence, Notion, Google Docs **Essential Templates:** - Program charter - 30-60-90 day plan (Excel/Google Sheets) - Weekly status report - Phase gate assessment - Risk register - RACI matrix (Responsible, Accountable, Consulted, Informed) - Milestone schedule - Budget tracker ## Success Metrics **Program Execution:** - Timeline adherence: Within 2 weeks of 90-day plan - Budget adherence: Within 10% of approved budget - Deliverable completion: >95% on time and quality - Phase gates: All passed (first time or conditional) **Stakeholder Satisfaction:** - Executive sponsor: ≥4/5 rating - Team members: ≥4/5 rating - Program team: ≥4/5 rating **Business Outcomes:** - Cost reduction: Achieved or exceeded target - Productivity gain: Achieved or exceeded target - Quality maintenance: ≥95% of baseline - ROI: Positive in Year 1 This skill ensures programs are properly planned, resourced, and governed for maximum success probability.