The Sailboat Retrospective uses a visual metaphor to help teams reflect on their journey. This creative format represents team dynamics through the imagery of a sailboat, making it engaging and memorable while still capturing actionable insights.
This template is perfect for teams who want a more creative, visual approach to retrospectives. It's particularly effective for teams that might find traditional formats dry or repetitive. The metaphor helps teams think differently about their challenges and opportunities.
The Sailboat Metaphor
The format uses four key elements:
- Wind (What helped us): Forces propelling the team forward—support, resources, positive factors
- Anchors (What held us back): Obstacles, blockers, or factors slowing progress
- Rocks (Risks ahead): Potential dangers, challenges, or risks on the horizon
- Island (Goals): The destination—what the team is working toward
This metaphor helps teams visualize their situation and think about their journey holistically, not just in terms of problems and solutions.
How to facilitate
Facilitation Tips
- Start with the Island: Begin by clarifying goals and destination to set context
- Visualize the journey: Encourage teams to think about their "sailboat" as a whole system
- Balance elements: Ensure all four elements get attention—don't focus only on anchors
- Connect elements: Help team see how wind, anchors, and rocks relate to reaching the island
- Make it visual: Consider drawing the sailboat on a whiteboard or using visual aids
Engaging the Team
- Use the metaphor consistently throughout the retro
- Encourage creative thinking—what kind of "wind" helps most?
- Help team identify which "anchors" they can actually lift
- Prioritize "rocks" that pose the greatest risk to reaching the "island"
When to use this template
Perfect For
- Creative teams: Design, marketing, or content teams who appreciate visual formats
- Longer retrospectives: 60-90 minute sessions where you can explore the metaphor
- Project kickoffs: Setting goals (island) and identifying risks (rocks)
- Team building: When you want to make retrospectives more engaging
Example Insights
Teams often discover:
- Unexpected sources of "wind" (support) they didn't recognize
- "Anchors" that are actually within their control to address
- "Rocks" that require proactive planning
- Clarity on their "island" (goals) that wasn't explicit before
