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:

# 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:

## 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:

## 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:

## 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:

## 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:

| 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.