The four parts
Wind: what pushes us forward?
What helped the team move faster or with more confidence.
Prompts: What gave us momentum? What should we lean on more?
Anchors: what holds us back?
Things slowing the team down: process, dependencies, technical debt, distractions.
Prompts: What made us slower than we should be? What do we keep dragging along?
Rocks: what risks lie ahead?
Problems that haven't happened yet but could. This is what makes Sailboat different.
Prompts: What could sink our next milestone? What are we worried about but not talking about?
Island: where are we going?
The goal: the sprint goal, a release, an outcome for users. Writing it down keeps the rest of the board focused.
Prompts: What does success look like for the next sprint or release? Do we agree on it?
Retrocycle's template adds an Action items column at the end, so the conversation ends with actions that have an owner.
When to use it
- Before a big release or milestone.
- When the team has lost sight of the goal.
- When you want to talk about risks, not just past problems.
- Teams that enjoy a visual metaphor.
When something else may work better: for a quick, routine retro, the metaphor can feel like overhead. Went well, Didn't go well is faster.
A 50-minute agenda
- 1
Agree on the island (5 min). Start by writing the goal together, so everyone is steering towards the same place.
- 2
Write cards silently (10 min). Everyone adds Wind, Anchors and Rocks cards.
- 3
Reveal and group (8 min). Group similar cards and read the Rocks out loud: risks are easy to skim past.
- 4
Vote (3 min). Vote on the Anchors and Rocks the team most wants to deal with.
- 5
Discuss (18 min). For each top Anchor, ask how to cut it loose. For each top Rock, ask how to steer around it.
- 6
Agree on action items (6 min). Two or three actions with owners, including at least one that reduces a risk.
Example cards
From a fictional team two sprints away from launching a new checkout:
| Wind | Anchors | Rocks | Island |
|---|---|---|---|
| Product and design sitting in on refinement | Manual regression testing before each release | The payment provider's sandbox is unreliable | Launch the new checkout to 10% of users by the end of next month |
| Feature flags for every change | Waiting on another team's API changes | Nobody has tested the flow on older Android phones |
And the actions that came out of it:
- Ask the payments team for a stable sandbox or a mock by next sprint (owner: tech lead).
- Add two older Android devices to the test plan (owner: QA engineer).
Tips for a better Sailboat
- Write the Island first. Every other card should relate to it.
- Don't skip Rocks: they're the reason to use this format.
- Some teams add the Sun (what keeps morale up). Add a column if it helps.
- Revisit last Sailboat's Rocks: did any of them hit?
Run it in Retrocycle
Pick the Sailboat template, share the link, and your team joins as guests with just a name: no accounts needed. Turn on blur so cards stay hidden while people write, let people post anonymously if they want, vote, and close the retro with action items that carry over to the next one. How action items work
FAQ
What's the difference between Sailboat and Speedboat?
They're the same idea. Speedboat often uses only engines and anchors; Sailboat adds rocks and the island, which bring in risks and the goal.
Do I need a drawing of a boat?
No. The four columns carry the idea. A picture is nice, not necessary.
How often should we use it?
Every few sprints, or before an important milestone. Used every sprint, the metaphor wears thin.
Can guests join without an account?
Yes. In Retrocycle, guests join with the link and a display name, once a team member lets them in.