What is the Sailboat retrospective?

The Sailboat is one of our favourite retrospective formats. Imagine you’re on a boat, the wind whistling through your hair, heading to a distant island…

The Sailboat retro asks the team to pretend they are on a boat travelling through the sea. It combines backward and forward-looking elements that ask a team to assess what is holding them back and pushing them forward towards their goal. The wind, rocks and anchor are metaphors for things that help or hinder the team, while the island represents the goal.

You can also run this session at the beginning of a project to help a team define their goals.

How to run the sailboat retrospective?

Time needed: 60-75 minutes

1. Introduce and explain the template to the team.
2. Start with asking the team to write what they think the overall team goal is, and place their sticky notes on the island. Group similar sticky notes and discuss (10 mins)
3. Ask the team to start thinking about the current sprint. What was an ‘anchor’ holding the team back, and what was ‘wind’ pushing the team forward?
4. Ask the team members to write their ideas and place them in the anchor or wind sections (10 minutes)
5. Group the items as a team and discuss them (10 minutes)
6. Move on to the final section: what hidden rocks are coming up, and could ground the ship? (10 minutes).
7. Group these items again and discuss (10 minutes).
8. Now look at the combined past and future groups and see if there are any further common groups you can make. (5 minutes).
9. Hold a voting session to uncover the three most important themes (5 minutes).
10. Brainstorm and discuss solutions and actions for the top themes (10 minutes).
11. Group the solutions and hold a voting round (5 minutes).
12. Decide an owner for each of the top three actions.
13. Finish the retro or hold a closing activity.

Bonus questions to ask the team during the sailboat retrospective

• Have the actions they’ve taken got them closer or further from the island?
• Are the team relying too much on the wind (external factors)?
• How much is the anchor trailing behind, can we do something to pull it in quickly?
• Do the team really know where all the rocks are? Should they scout ahead again?