Sailboat retrospective template
A boat, its wind, its anchors, and the rocks ahead.
Also known as: Sailboat retrospective, Boat retrospective, Speedboat, Wind and anchors.
The Sailboat is a metaphor retrospective: the wind pushes the team forward, anchors hold it back, rocks are the risks ahead, and the island is the goal. The metaphor does real work — it gives a team language for risks that have not happened yet, which a plain "what went badly" column never prompts anyone to write down.
The columns, and what goes in each
- Wind
- What is pushing us forward — the help, habits, and tools that give us speed?
- Anchor
- What is holding us back and slowing the team down right now?
- Rocks
- What risks are ahead that could damage us if we do not steer around them?
- Island
- What are we actually sailing towards — the goal this work is in service of?
When to use the Sailboat retrospective
- Teams that have gone flat on the standard format and need the frame to feel different
- Planning-adjacent retrospectives where upcoming risk matters as much as past friction
- Groups that include non-engineers — the metaphor travels well outside a delivery team
How to run a Sailboat retrospective
- Draw or describe the picture first: island ahead, wind behind, anchors below, rocks in the water.
- Start with the Island so the team agrees what it is sailing towards before it critiques the journey.
- Write silently for seven minutes across Wind, Anchor, and Rocks.
- Vote on anchors to cut and rocks to steer around; each winning card becomes an action.
Run this retrospective in RetroCanvas
Sailboat is built in — pick it when you create a board, or set it to recur automatically every sprint. Free, with no credit card required.