Do we need to draw an actual boat?

It helps more than you'd think. Even a rough Miro sketch with four labelled regions makes the format work better. The metaphor is doing real cognitive work, especially for visual thinkers. Discarding the boat discards most of what makes Sailboat different from a four-column grid. Yes, your boat will look bad. Draw it anyway.

What goes in Rocks if we don't have any obvious risks?

Push the team to imagine. 'What would derail this project if it happened in the next six weeks?' If the team is genuinely confident there are no risks, that's a risk by itself, and you can name it as: 'We aren't preparing for anything because we think nothing can go wrong.' Then sit with that for a minute.

Can we run Sailboat for a normal two-week sprint?

It tends to feel oversized. The format wants medium-to-long horizons. For a two-week sprint, run Start, Stop, Continue or 4Ls and save Sailboat for the quarterly. Using Sailboat for a small sprint is like ordering a yacht for a trip across the river.

How do we handle disagreement on the Island?

Disagreement on Island is the most useful disagreement a team can have, because it usually means the strategy itself is unclear. Treat it as a feature, not a problem. Spend an extra ten minutes there if the team isn't aligned, and consider whether the next leadership conversation needs to clarify the direction the team is being asked to row toward.

Better than Mad, Sad, Glad, worse than Start, Stop, Continue. The visual sketch is the bottleneck. If you're going async, use a shared Miro or FigJam board with the boat pre-drawn, and require people to place their cards in the regions rather than listing them in columns. The placement is half the value. Anchors near the back of the boat. Rocks ahead of the bow. The shape teaches the format.

The toolkit · Sailboat

Sailboat retrospective

Wind in the sails, anchors holding back, rocks ahead, the island we're sailing toward. The retro format that talks about momentum, drag, risk, and direction at once.

40 prompts · 4 columns · free

💨

Wind

What's pushing us forward right now?

10 prompts in this bucket

⚓

Anchors

What's holding us back?

10 prompts in this bucket

🪨

Rocks

What risks are on the horizon?

10 prompts in this bucket

🏝️

Island

Where are we trying to go?

10 prompts in this bucket

Try another framework

Frameworks that pair well with Sailboat.

Start, Stop, Continue

The classic. Three columns, fast to run, hard to argue with.

Rose, Bud, Thorn

What's blooming, what's growing, what's prickly. Garden metaphor, real insight.

KALM

Keep, Add, Less, More. Subtler than Start/Stop/Continue.

Or see all 10 retro frameworks.

About the Sailboat retrospective

The Sailboat retrospective replaces the four-column grid with a visual metaphor: a boat being pushed by wind, dragged by anchors, threatened by rocks ahead, sailing toward an island. Yes, it sounds corny. Yes, it works. Each element corresponds to a question. Wind: what's pushing us forward? Anchors: what's holding us back? Rocks: what's coming? Island: where are we even going? The format excels for quarterly retros, project mid-points, and any conversation where momentum, drag, risk, and direction all need to be on the table at once. The visual sticks too. People remember a Sailboat retro a month later in a way they don't remember a Start, Stop, Continue. Use it when the team is making decisions that span longer than a sprint, when a project is at a midway pivot point, or when you want a retro that produces a story rather than a list of complaints with owners.

How long does a Sailboat retro take?

Sixty minutes is the floor. Ninety minutes is the right call for a quarterly or project-midpoint Sailboat. The format has four quadrants instead of three and rewards depth over speed. If you only have thirty minutes, pick a different format. A Sailboat squeezed into half an hour is just a worse Start, Stop, Continue with nautical decoration.

When the Sailboat works

End-of-quarter retros. Mid-project pivots. Post-launch reviews. Strategy sessions where the question is 'are we still pointed at the right island?'. The Island quadrant is the secret weapon. Most retro formats assume the destination is fixed and only inspect the journey. The Sailboat puts the destination back on the table, which is usually where the actual disagreement lives, hiding under a pile of stop-energy that nobody wanted to put there.

Sailboat versus 4Ls for project retros

The 4Ls reflects on what just happened. The Sailboat looks both backward and forward. Use 4Ls for a sprint that's complete and won't repeat. Use Sailboat for a project that's still going and needs course correction. The Rocks quadrant in particular is forward-looking in a way no other classic format is, which is the polite way of saying it's the one that finally makes the team admit what they're afraid of.

Common mistakes with the Sailboat

Skipping the sketch. The visual is the whole point. Without it, the format collapses into a four-column grid that's harder to facilitate than 4Ls. Second mistake: starting with Wind. The team doesn't know what's helping until they know where they're going, so always start with Island. Third mistake: treating Rocks as anxieties instead of risks. A Rock is a concrete thing that could hit the project, like 'the only person who knows the auth system is going on parental leave in three weeks'. Not 'I worry the codebase is bad'.

Frequently asked

Do we need to draw an actual boat?: It helps more than you'd think. Even a rough Miro sketch with four labelled regions makes the format work better. The metaphor is doing real cognitive work, especially for visual thinkers. Discarding the boat discards most of what makes Sailboat different from a four-column grid. Yes, your boat will look bad. Draw it anyway.
What goes in Rocks if we don't have any obvious risks?: Push the team to imagine. 'What would derail this project if it happened in the next six weeks?' If the team is genuinely confident there are no risks, that's a risk by itself, and you can name it as: 'We aren't preparing for anything because we think nothing can go wrong.' Then sit with that for a minute.
Can we run Sailboat for a normal two-week sprint?: It tends to feel oversized. The format wants medium-to-long horizons. For a two-week sprint, run Start, Stop, Continue or 4Ls and save Sailboat for the quarterly. Using Sailboat for a small sprint is like ordering a yacht for a trip across the river.
How do we handle disagreement on the Island?: Disagreement on Island is the most useful disagreement a team can have, because it usually means the strategy itself is unclear. Treat it as a feature, not a problem. Spend an extra ten minutes there if the team isn't aligned, and consider whether the next leadership conversation needs to clarify the direction the team is being asked to row toward.
Async-friendly?: Better than Mad, Sad, Glad, worse than Start, Stop, Continue. The visual sketch is the bottleneck. If you're going async, use a shared Miro or FigJam board with the boat pre-drawn, and require people to place their cards in the regions rather than listing them in columns. The placement is half the value. Anchors near the back of the boat. Rocks ahead of the bow. The shape teaches the format.

When not to use it

Short sprints under a week, or pure execution check-ins. The Sailboat needs a horizon longer than the work right in front of you. For a one-week sprint, use Start, Stop, Continue and put the boat away.

How to run a Sailboat retro

1Block 60 minutes minimum. The Sailboat is built for breadth and it punishes time pressure.
2Sketch the boat on a whiteboard or Miro. The visual metaphor is doing real work, don't skip it.
3Start with Island. Five minutes of group discussion, not silent writing. The team needs to align on the destination before naming what's helping or hurting.
4Silent writing for the other three quadrants, six minutes per quadrant. Wind, Anchors, Rocks, in that order.
5Discuss Anchors first. The biggest energy is usually here. Twelve to fifteen minutes.
6Discuss Rocks next, then Wind. End on Wind to leave the team focused on what's working.
7Identify one Anchor to cut and one Rock to mitigate before the next milestone. Owners assigned. Send the boat sketch and the two commitments in Slack.