tomevault-io PMO Retrospective Skill
Systematic capture and application of lessons learned at portfolio level.
Purpose
This skill provides a framework for:
- Lessons learned capture
- Pattern identification
- Process improvement
- Organizational learning
- Knowledge transfer
Retrospective Types
Type 1: Project Closure Retrospective
Trigger: Project completion or termination Scope: Single project Participants: Project team, sponsor, key stakeholders
Type 2: Portfolio Period Review
Trigger: Quarterly or annual review Scope: All projects in period Participants: PMO, project managers, executives
Type 3: Thematic Retrospective
Trigger: Recurring pattern observed Scope: Projects sharing the pattern Participants: Affected project managers, PMO, subject matter experts
Retrospective Gates
Gate 1: Context Setting
Objective: Establish retrospective scope and participants
Actions:
- Define retrospective type and scope
- Identify participants
- Gather project data
- Schedule sessions
Context Template:
| Element | Value |
|---|---|
| Type | Project/Portfolio/Thematic |
| Scope | [Projects/Period] |
| Participants | [List] |
| Data Sources | [List] |
Output: docs/pmo/{date}/retro-context.md
Gate 2: Data Collection
Objective: Gather objective data about performance
Actions:
- Collect final project metrics
- Gather variance explanations
- Document scope changes
- Compile risk/issue history
Data Points:
| Category | Data |
|---|---|
| Schedule | Planned vs actual duration |
| Cost | Budget vs actual spend |
| Scope | Baseline vs final scope |
| Quality | Defects, rework |
| Risks | Risks that materialized |
| Changes | Number and impact |
Output: docs/pmo/{date}/retro-data.md
Gate 3: Reflection
Objective: Identify what worked, what didn't, and why
Actions:
- Conduct retrospective session
- Identify successes to repeat
- Identify failures to prevent
- Analyze root causes
Reflection Framework:
| Category | Question |
|---|---|
| What went well? | What should we keep doing? |
| What didn't go well? | What should we stop doing? |
| What was confusing? | What needs clarification? |
| What was missing? | What should we start doing? |
| What surprised us? | What assumptions were wrong? |
Output: docs/pmo/{date}/retro-reflection.md
Gate 4: Pattern Analysis
Objective: Identify patterns across projects/time
Actions:
- Compare with previous retrospectives
- Identify recurring themes
- Assess systemic vs isolated issues
- Prioritize improvement areas
Pattern Types:
| Type | Indicator | Action |
|---|---|---|
| Systemic | Same issue in 3+ projects | Process change required |
| Capability | Same team struggle repeating | Training/hiring needed |
| Tool | Tool-related friction | Tool improvement/replacement |
| Communication | Stakeholder issues recurring | Communication improvement |
| Estimation | Consistent over/under estimation | Estimation process improvement |
Output: docs/pmo/{date}/retro-patterns.md
Gate 5: Action Planning
Objective: Create actionable improvement plan
Actions:
- Define specific improvements
- Assign owners
- Set timelines
- Define success criteria
Action Template:
| Improvement | Owner | Timeline | Success Criteria | Status |
|---|---|---|---|---|
| [Improvement] | [Owner] | [Date] | [Criteria] | [Status] |
Priority Framework:
| Impact / Effort | Low Effort | High Effort |
|---|---|---|
| High Impact | Do First | Plan Carefully |
| Low Impact | Quick Wins | Don't Do |
Output: docs/pmo/{date}/retro-actions.md
Gate 6: Knowledge Sharing
Objective: Distribute lessons to organization
Actions:
- Document lessons learned
- Update PMO knowledge base
- Present to relevant teams
- Update templates/processes
Knowledge Sharing Channels:
| Channel | Audience | Content |
|---|---|---|
| PMO Wiki | All PMs | Full lessons |
| Newsletter | Organization | Summary |
| Training | New PMs | Incorporated |
| Templates | All projects | Updated |
| Playbooks | Specific scenarios | Detailed guidance |
Output: docs/pmo/{date}/lessons-learned.md
Anti-Rationalization Table
See shared-patterns/anti-rationalization.md for universal anti-rationalizations.
Retrospective-Specific Anti-Rationalizations
| Rationalization | Why It's WRONG | Required Action |
|---|---|---|
| "We're too busy for retrospectives" | Learning gaps cost more than retrospective time. | Schedule and conduct retrospective |
| "We know what went wrong" | Assumptions miss root causes. | Formal analysis required |
| "It was a unique situation" | Patterns hide in "unique" situations. | Document and compare |
| "People will be defensive" | Blame-free culture enables learning. | Focus on process, not people |
| "Lessons will be ignored anyway" | Track action completion to ensure learning. | Follow up on actions |
Pressure Resistance
See shared-patterns/pressure-resistance.md for universal pressure scenarios.
Retrospective-Specific Pressures
| Pressure Type | Request | Agent Response |
|---|---|---|
| "Skip retro, team already on next project" | "Learning before moving on prevents repeating mistakes. Conducting abbreviated retrospective." | |
| "Don't document that failure" | "Failures are learning opportunities. Documenting with constructive framing." | |
| "Just move on, it's in the past" | "Past informs future. Retrospective protects future projects." |
Blocker Criteria - STOP and Report
ALWAYS pause and report blocker for:
| Situation | Required Action |
|---|---|
| Key participants unavailable | STOP. Incomplete retrospective misses perspectives. Reschedule. |
| Data unavailable | STOP. Data-free retrospective is opinion session. Get data. |
| Blame culture emerging | STOP. Reset to blameless framework. Not about individuals. |
| No action ownership | STOP. Lessons without owners become forgotten. Assign owners. |
Cannot Be Overridden
The following requirements are NON-NEGOTIABLE:
| Requirement | Cannot Override Because |
|---|---|
| Blameless approach | Blame prevents learning. Fear prevents honesty. |
| Action owner assignment | Unowned actions are never completed. |
| Data-driven analysis | Opinions without data lead to wrong conclusions. |
| Participant inclusion | Missing perspectives create incomplete learning. |
| Follow-up tracking | Lessons without follow-up are forgotten. |
If user insists on violating these:
- Escalate to orchestrator
- Do NOT proceed with incomplete retrospective
- Document the request and your refusal
Severity Calibration
When assessing retrospective findings:
| Severity | Criteria | Examples |
|---|---|---|
| CRITICAL | Systemic issue affecting multiple projects | Process failure causing 3+ project delays, compliance violation pattern |
| HIGH | Significant recurring problem | Same estimation error in 2+ projects, repeated resource conflicts |
| MEDIUM | Notable improvement opportunity | Communication gaps, tool friction, documentation quality |
| LOW | Minor optimization | Template improvements, minor process tweaks |
Document ALL severities. Prioritize action on CRITICAL and HIGH.
Output Format
Lessons Learned Report
# Lessons Learned - [Project/Period] - [Date]
## Context
| Element | Value |
|---------|-------|
| Scope | [Project(s)/Period] |
| Participants | [List] |
| Facilitator | [Name] |
## Performance Summary
| Metric | Target | Actual | Variance |
|--------|--------|--------|----------|
| Duration | X months | X months | +/- X% |
| Budget | $X | $X | +/- X% |
| Scope | X features | X features | +/- X |
| Quality | X defects | X defects | +/- X |
## What Went Well
| Success | Why It Worked | How to Repeat |
|---------|---------------|---------------|
| [Success] | [Root cause] | [Action to sustain] |
## What Didn't Go Well
| Issue | Root Cause | How to Prevent |
|-------|------------|----------------|
| [Issue] | [Root cause] | [Action to prevent] |
## Patterns Identified
| Pattern | Frequency | Systemic? | Action |
|---------|-----------|-----------|--------|
| [Pattern] | X occurrences | Yes/No | [Action] |
## Improvement Actions
| # | Improvement | Owner | Due | Status |
|---|-------------|-------|-----|--------|
| 1 | [Improvement] | [Owner] | [Date] | [Status] |
## Key Lessons (Top 5)
1. **[Lesson Title]:** [Description and application guidance]
2. **[Lesson Title]:** [Description and application guidance]
3. **[Lesson Title]:** [Description and application guidance]
4. **[Lesson Title]:** [Description and application guidance]
5. **[Lesson Title]:** [Description and application guidance]
## Knowledge Sharing Plan
| Audience | Channel | Date | Owner |
|----------|---------|------|-------|
| [Audience] | [Channel] | [Date] | [Owner] |
Execution Report
Base metrics per shared-patterns/execution-report.md:
| Metric | Value |
|---|---|
| Analysis Date | YYYY-MM-DD |
| Scope | [Project(s)/Period] |
| Duration | Xh Ym |
| Result | COMPLETE/PARTIAL/BLOCKED |
Retrospective-Specific Details
| Metric | Value |
|---|---|
| period_covered | [Description] |
| projects_completed | N |
| lessons_captured | N |
| process_improvements | N |
When Retrospective Is Not Needed
| Condition | Verification |
|---|---|
| Project was trivial (<1 week, <3 people) | Verify scope and team size |
| No significant issues occurred | Confirm no deviations from plan |
| Team explicitly requested skip | Written confirmation required |
| Previous recent retrospective covers patterns | Reference recent retro that applies |
MUST: Full retrospective REQUIRED for the following conditions:
| Condition | Why Required |
|---|---|
| Any project completion | Learning opportunity, even for successful projects |
| Any project termination | Understanding failure prevents repetition |
| Significant budget/schedule variance | Root cause analysis prevents recurrence |
| Team or stakeholder conflicts | Relationship and process lessons critical |
| Process improvement identified | Must capture and act on improvement |
MUST: When in doubt, conduct the retrospective. Skipped retrospectives become repeated failures.
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