In a Sailboat retrospective, the team is a boat. The wind is what pushes it forward, the anchors are what hold it back and the island is where it wants to go. The metaphor makes it easier to talk about problems without pointing fingers.
It is a good fit for the end of a longer cycle, like a quarter or a project, when it pays to look beyond the day-to-day.
When to use it
- Wrapping up a project, release or quarter.
- When the team has lost sight of the goal and needs to realign.
- To change up the format and bring new energy to your retros.
The columns and their questions
What pushed us forward and sped up our work?
What held us back, slowed us down or blocked us?
Where do we want to be by the end of the next cycle?
Step by step (60 minutes)
- Draw the island 5 min
Start with the destination: what was the goal for this cycle, and what is the next one?
- Silent writing 10 min
Everyone writes wind and anchor notes without seeing anyone else's.
- Group and vote 15 min
Cluster similar ideas and vote on the anchors that cost the team the most.
- Discuss 20 min
For each top-voted anchor, ask what would pull it up. For the wind, ask how to get more of it.
- Action items 10 min
Agree on actions to lift the biggest anchors, each with an owner and a due date.
Facilitation tips
- A common variation: add Rocks (risks ahead) and Sun (what makes the team happy).
- Keep the island visible throughout the discussion; it is your yardstick for prioritizing.
- Anchors outside the team's control become a clear request to whoever can remove them.
Frequently asked questions
What's the difference between a Sailboat and a Speedboat retrospective?
They are essentially the same technique. Speedboat, from Luke Hohmann's Innovation Games, focused on the anchors slowing the boat down; the Sailboat version adds wind for what pushes the team forward, and often rocks and sun.
Does it work for remote teams?
Yes. On an online board, each column becomes a part of the picture, and silent writing is even easier.