Sailboat Retrospective
A visual retrospective technique using the metaphor of a sailboat at sea. The boat represents the team, wind represents what drives progress, anchors represent what slows the team down, rocks represent upcoming risks, and the island represents the goal. The metaphor makes abstract team dynamics concrete and engaging.
How to run it
- 1
Draw a sailboat on a large whiteboard or flip chart with: sails (what drives us forward), anchors (what holds us back), rocks/reef (risks ahead), and an island (our goal).
- 2
Give each participant sticky notes and ask them to silently write ideas for each element (2–3 minutes per element).
- 3
Participants place their notes on the relevant parts of the drawing.
- 4
Read out each note, cluster similar ideas together, and facilitate a brief discussion.
- 5
Dot-vote on the anchors and risks to identify the most important items to address.
- 6
Agree on 1–3 concrete action items to address the top anchors before the next retrospective.
Tips
Keep the metaphor light — don't over-explain it.
Let the visual do the work.
For remote teams, use a digital whiteboard with a pre-drawn template.
Variations
Swap the island for a port (closer destination) to focus on short-term goals. Add a 'sea monster' for things completely outside the team's control.
Where it fits
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