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Iterate Lessons Log

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npx machina-cli add skill product-on-purpose/pm-skills/iterate-lessons-log --openclaw
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SKILL.md
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<!-- PM-Skills | https://github.com/product-on-purpose/pm-skills | Apache 2.0 -->

name: iterate-lessons-log description: Creates a structured lessons learned entry for organizational memory. Use after projects, incidents, or significant learnings to capture knowledge for future teams and initiatives. phase: iterate version: "2.0.0" updated: 2026-01-26 license: Apache-2.0 metadata: category: reflection frameworks: [triple-diamond, lean-startup, design-thinking] author: product-on-purpose

Lessons Log

A lessons log entry captures significant learning from projects, incidents, or experiences in a format that's useful to future teams who weren't there. Unlike retrospectives (which focus on team improvement), lessons logs focus on organizational knowledge that transcends individual teams—patterns, anti-patterns, and hard-won wisdom.

When to Use

  • After completing a significant project or initiative
  • Following a major incident, outage, or failure
  • When you realize something important that others should know
  • After discovering a pattern that keeps recurring
  • When experienced team members leave (capture their knowledge)
  • During post-mortems to preserve learnings

Instructions

When asked to create a lessons log entry, follow these steps:

  1. Choose a Descriptive Title Write a title that someone searching for this topic would find. Include keywords that describe the situation and the learning. Avoid generic titles like "Project X lessons."

  2. Provide Context Explain the situation fully enough that someone who wasn't there can understand it. Include the project, timeline, team, and any relevant constraints. Future readers need this context to assess applicability.

  3. Describe What Happened Write a factual account of what occurred. Be specific about actions taken, decisions made, and outcomes observed. Avoid blame—focus on events and systems.

  4. Extract the Lesson Articulate what you learned clearly. The lesson should be actionable—something others can apply. Distinguish between what you observed and your interpretation of why it matters.

  5. Formulate Recommendations Provide specific guidance for future teams facing similar situations. What should they do? What should they avoid? What questions should they ask?

  6. Define Applicability Help readers know when this lesson applies. What situations trigger relevance? What context makes it more or less applicable?

  7. Add Tags for Searchability Include keywords and categories that will help future searchers find this entry. Think about what someone would search for when facing a similar situation.

Output Format

Use the template in references/TEMPLATE.md to structure the output.

Quality Checklist

Before finalizing, verify:

  • Title is descriptive and searchable
  • Context is complete enough for someone who wasn't there
  • Lesson is clearly articulated and actionable
  • Recommendations are specific, not vague
  • Entry stands alone (doesn't require external context)
  • Tags enable future discovery

Examples

See references/EXAMPLE.md for a completed example.

Source

git clone https://github.com/product-on-purpose/pm-skills/blob/main/skills/iterate-lessons-log/SKILL.mdView on GitHub

Overview

A lessons log entry captures significant learning from projects, incidents, or experiences to inform future work. It shifts focus from individual retrospectives to organizational knowledge, highlighting patterns, anti-patterns, and hard won wisdom that can guide other teams.

How This Skill Works

Use a seven step format to create a self contained entry: descriptive title, context, what happened, the actionable lesson, recommended next steps, applicability, and tags. The resulting entry stands alone and is easily searchable for teams that were not part of the original event.

When to Use It

  • After completing a significant project or initiative
  • Following a major incident, outage, or failure
  • When you realize something important that others should know
  • After discovering a recurring pattern that affects outcomes
  • During post-mortems to preserve learnings

Quick Start

  1. Step 1: Select a descriptive title and identify the key context
  2. Step 2: Write what happened and extract the concrete lesson
  3. Step 3: Add recommendations, applicability, and tags

Best Practices

  • Write a descriptive, keyword rich title
  • Provide enough context for someone unfamiliar with the event
  • Describe what happened factually and avoid assigning blame
  • Articulate the actionable lesson and how to apply it
  • Define applicability and include clear, discoverable tags

Example Use Cases

  • Lessons from a data-sync outage: documented root cause, remediation steps, and updated incident playbooks
  • Post-mortem after a late-stage feature rollout with user-reported issues and mitigations
  • Recurring bottleneck in handoffs led to process changes and a clarified ownership map
  • Knowledge transfer after senior team member departure to preserve critical tribal knowledge
  • Security incident logged detection gaps, response steps, and improved alerting rules

Frequently Asked Questions

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