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'.
Sailboat retro prompts
Every prompt in the Sailboat deck, grouped by column. Shuffle them in the builder above or use the full list here.
Wind
- What's pushing us forward right now?
- What's giving the team momentum?
- What support, resource, or relationship is wind in our sails?
- What's the tailwind we should keep chasing?
- Whose work is propelling the rest of the team?
- What habit or practice is paying off in compound interest?
- Where did we get an unexpected boost?
- What's a system or tool that's silently doing heavy lifting?
- What's the morale lift we shouldn't take for granted?
- What recent decision has aged well?
Anchors
- What's holding us back?
- What's the slowest, heaviest thing we're dragging behind us?
- Where are we stuck in old patterns?
- What process or commitment have we outgrown?
- Where is bureaucracy costing us speed?
- What technical or organisational debt is the biggest drag?
- What recurring meeting is no longer earning its place?
- What dependency is consistently slowing us?
- What do we keep saying yes to that we should say no to?
- What's the ritual that's become noise?
Rocks
- What risks are on the horizon?
- What are we not preparing for that could hit us?
- What's the worst-case scenario nobody's talking about?
- Where is the team operating without a backup plan?
- What dependency could break and we'd be stuck?
- What capability would be a single point of failure if someone left?
- What's a slow-moving problem that's about to become urgent?
- What policy, regulation, or external change could disrupt us?
- Where are we one mistake away from a serious incident?
- What's the rock we've been steering around but not addressing?
Island
- Where are we trying to go?
- What does success look like a quarter from now?
- What's the goal we should be steering towards but aren't?
- If we got everything right, what would the team look like in six months?
- What's the version of this team we want to become?
- What outcome would make all of this worth it?
- What's the destination we keep losing sight of?
- What's the team's true north right now?
- What would 'we made it' look like?
- What story do we want to tell at the end of the year?
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.