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ring:pmo-retrospective

Portfolio retrospective skill for capturing lessons learned, process improvements, and organizational learning across completed projects.

personAuthor: jakexiaohubgithub
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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:

  1. Define retrospective type and scope
  2. Identify participants
  3. Gather project data
  4. 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:

  1. Collect final project metrics
  2. Gather variance explanations
  3. Document scope changes
  4. 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:

  1. Conduct retrospective session
  2. Identify successes to repeat
  3. Identify failures to prevent
  4. 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:

  1. Compare with previous retrospectives
  2. Identify recurring themes
  3. Assess systemic vs isolated issues
  4. 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:

  1. Define specific improvements
  2. Assign owners
  3. Set timelines
  4. 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:

  1. Document lessons learned
  2. Update PMO knowledge base
  3. Present to relevant teams
  4. 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:

  1. Escalate to orchestrator
  2. Do NOT proceed with incomplete retrospective
  3. 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

<MANDATORY> MUST: Retrospective is minimal only when ALL conditions are met: </MANDATORY>

| 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.