Iterate Retrospective
Scannednpx machina-cli add skill product-on-purpose/pm-skills/iterate-retrospective --openclawname: iterate-retrospective description: Facilitates and documents a team retrospective capturing what went well, what to improve, and action items. Use at the end of sprints, projects, or milestones to reflect and improve team practices. 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
Retrospective
A retrospective is a structured reflection that helps teams learn from their experiences and continuously improve. By regularly examining what went well, what didn't, and what to change, teams build a culture of learning and adaptation. The value isn't just in the discussion—it's in the documented actions and follow-through.
When to Use
- At the end of every sprint (for agile teams)
- After completing a significant project or milestone
- Following a major incident or outage
- When team dynamics feel off and need addressing
- At regular intervals (monthly, quarterly) even without specific triggers
- When onboarding new team members to establish improvement culture
Instructions
When asked to facilitate or document a retrospective, follow these steps:
-
Set the Context Define what period or project this retrospective covers, who attended, and any significant events that occurred. This frames the discussion and helps future readers understand the context.
-
Choose a Format Select a retrospective format that fits the team's needs. Common options include:
- Start/Stop/Continue: Simple and direct
- 4Ls: Liked, Learned, Lacked, Longed for
- Mad/Sad/Glad: Emotion-focused
- Sailboat: Visual metaphor (wind=helps, anchor=holds back)
-
Gather Input Collect observations from all team members. Ensure everyone contributes—quiet voices often have important insights. Group similar items to identify themes.
-
Discuss and Prioritize Don't try to address everything. Focus the discussion on the most impactful items. Vote or discuss to identify the top 2-3 issues to address.
-
Define Action Items Convert insights into specific, assignable actions. Every action needs an owner and a due date. Avoid vague improvements like "communicate better."
-
Review Previous Actions Check the status of action items from the last retrospective. Celebrate completions and discuss blockers for incomplete items. This builds accountability.
-
Document for Future Reference Capture the key points so they're available for future team members and for tracking patterns over time.
Output Format
Use the template in references/TEMPLATE.md to structure the output.
Quality Checklist
Before finalizing, verify:
- All attendees had opportunity to contribute
- Both positives and improvements are captured
- Action items have owners and due dates
- Previous retrospective actions are reviewed
- Document is useful to someone who wasn't in the room
Examples
See references/EXAMPLE.md for a completed example.
Source
git clone https://github.com/product-on-purpose/pm-skills/blob/main/skills/iterate-retrospective/SKILL.mdView on GitHub Overview
Iterate Retrospective helps teams reflect at sprint ends, milestones, or incidents to celebrate wins, surface improvements, and define concrete actions. It emphasizes documenting actions and follow-through to close the loop.
How This Skill Works
A facilitator guides the session through context, format choice, input gathering, prioritization, and action item creation. The skill supports common formats such as Start Stop Continue, 4Ls, Mad Sad Glad, or Sailboat to structure discussion and ensure clear owners and due dates.
When to Use It
- End of sprint for agile teams
- After completing a significant project or milestone
- Following a major incident or outage
- When team dynamics feel off and need addressing
- At regular intervals monthly or quarterly for continuous improvement
Quick Start
- Step 1: Set the context including period and attendees
- Step 2: Choose a retrospective format and gather input from all team members
- Step 3: Define concrete action items with owners and due dates and document the results
Best Practices
- Ensure all attendees can contribute and be heard
- Capture both positives and improvements
- Create specific actions with owners and due dates
- Review previous actions and blockers
- Document the outcome for future reference and onboarding
Example Use Cases
- Sprint end retro for a mobile app team to surface UX issues and prioritize fixes
- Post incident retro after a production outage to address root causes and update monitors
- Quarterly retro to improve triage and on call playbooks
- Onboarding retro for new engineers to codify learning and culture
- Milestone retro to reassess scope and timelines for the next phase