What is the Sailboat retrospective?
The Sailboat (sometimes called the Speedboat) is a retrospective built around a picture: the team is a boat, sailing toward an island. Everything the team says about its work fits into one of four parts of that picture. The metaphor sounds twee and works remarkably well, because it gives people a neutral vocabulary for risks and drag that they would otherwise struggle to raise.
Island
The goal. Where the team is trying to get to: the release, the milestone, the quarter's objective. Agree on it first; a surprising number of retros reveal the team was not sailing to the same island.
Wind
What pushes the boat forward. Practices, tools, people and conditions that are helping. The things to protect.
Anchors
What drags. Slow processes, technical debt, unclear ownership, meetings that eat the afternoon. The things to cut loose.
Rocks
Risks ahead that could sink the boat. Not problems you have; problems you might have. This is the column no other common format has.
How to run one (about 45 minutes)
- Name the island (5 min). Write the goal at the top of the board and check that everyone reads it the same way. If this takes longer than five minutes, you have found the first action item.
- Collect (10 min). Everyone adds notes to Wind, Anchors and Rocks silently. Ask specifically for rocks; people default to the past and forget to look ahead.
- Group (5 min). Cluster similar notes. Anchors tend to repeat sprint after sprint; that repetition is itself a signal.
- Vote (5 min). Votes decide which anchors to cut and which rocks to steer around first.
- Discuss and act (20 min). For each top anchor: what would it take to cut it, and who does that? For each top rock: who watches it, and what is the plan if it gets closer? Wind items need no action, only a sentence about keeping them.
Sailboat examples for software teams
Wind
- The new CI cache cut pipeline time from twenty minutes to six.
- The product owner sits in our channel and answers questions within the hour.
- Pairing on tricky changes has cut our review round-trips in half.
Anchors
- Every deploy needs a manual approval from one person who is often in meetings.
- The legacy reporting module has no tests, so every change to it takes twice as long.
- Three recurring meetings on Wednesday leave no room for deep work.
Rocks
- The launch date assumes the payments team delivers their API by the 20th and they have not confirmed.
- Only one person understands the search indexer and they are on leave in November.
- The framework version we are on loses security support next quarter.
Island
- Ship the self-serve onboarding flow to all customers by the end of the quarter, with support tickets about signup down by half.
Facilitation tips
- Do the island first, out loud. Disagreement about the destination explains a lot of anchors.
- Every rock leaves with an owner. A risk nobody is watching is not a plan; it is a note.
- Distinguish anchors from rocks. If it is already slowing you down, it is an anchor. If it has not happened yet, it is a rock. Mixing them makes both columns mushy.
- Reuse the board. Sailboat works well as a quarterly check-in: the same island, and you can see which anchors were cut and which rocks were avoided.
Questions teams ask
What is a Sailboat retrospective?
A retro built on a metaphor: the team is a boat sailing to an island. Wind pushes it forward, anchors drag, rocks are risks ahead. Notes go in those areas, the team votes, and the top items become actions.
How is it different from Start, Stop, Continue?
Sailboat looks ahead. Start, Stop, Continue reviews the sprint that happened; Sailboat also asks what could go wrong next and whether everyone agrees on the goal.
What goes in the rocks column?
Risks that have not happened yet: an unconfirmed dependency, a single point of knowledge, an expiring support window, a schedule that assumes nobody takes leave.
How long does it take?
About 45 minutes. Agreeing on the island and discussing the rocks are where the time goes, and both are worth it.
More retrospective formats
See all five templates with guidance on choosing between them: Sprint retrospective templates. Related formats: Start, Stop, Continue, 4Ls, Mad, Sad, Glad, Rose, Bud, Thorn.
Run a Sailboat retrospective now
Create a board with the four columns, share the link, collect anonymously, vote, and give every rock an owner. No account required for the team.
Start the retro