Retrospective Facilitator
FlaggedStructures sprint and project retrospectives with multiple formats, analyzes team feedback, and generates prioritized action items with owners.
$ Copy the SKILL.md file to your project's .claude/skills/ directory About This Skill
Retrospective Facilitator takes the most common failure mode of retrospectives — generating a list of complaints with no follow-through — and solves it by structuring the discussion to produce concrete, owned action items.
Retrospective Formats
Classic Start/Stop/Continue The standard format with theme clustering to surface patterns: - Groups similar feedback items across the three categories - Identifies the top theme in each category by frequency - Flags contradictions (one person's "start" is another's "stop")
4Ls (Liked, Learned, Lacked, Longed For) Richer format for surfacing learning opportunities alongside operational feedback.
Sailboat / Speed Boat Metaphor-based: anchors (slowing us down), wind (accelerating us), rocks ahead (risks), islands (goals). Visual and accessible for teams uncomfortable with direct feedback.
DAKI (Drop, Add, Keep, Improve) Action-oriented framing that naturally produces the action item list.
5 Whys Integration For any identified problem, the facilitator can drill down with 5 Whys to find the root cause rather than treating symptoms.
Action Item Generation
From the discussion, produces a prioritized action item table: | Action | Owner | Due Date | Success Metric | Priority |
Filters out vague action items ("improve communication") and replaces them with specific, measurable ones ("Establish a #decisions Slack channel — all decisions posted within 24 hours").
Team Health Metrics
Optionally produces a team health score across dimensions: psychological safety, alignment, execution, and learning — benchmarked against a healthy Agile team baseline.
Use Cases
- Facilitating Agile sprint retrospectives for engineering teams
- Running post-project retrospectives after major releases or incidents
- Analyzing anonymous team feedback to surface systemic issues
- Generating action item lists with owners from retrospective discussions
Pros & Cons
Pros
- +Multiple retro formats for different team contexts and preferences
- +Converts vague feedback into specific, measurable action items
- +5 Whys integration for root cause analysis
- +Team health score benchmarked against Agile best practices
Cons
- -Cannot run an interactive real-time session — works on provided text notes from the discussion
- -Psychological safety requires human facilitation — the skill handles structure, not culture
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