Sailboat Retrospective Template: Winds, Anchors, Rocks and Island

The sailboat retrospective pictures your team as a boat heading for an island. Winds push you forward, anchors hold you back, rocks are risks ahead, and the island is the goal. Adding a goal and future risks makes it a good fit for longer projects, releases, and teams tired of the same three columns.

The four columns

Anchors vs rocks is the distinction teams get wrong most often. An anchor is already slowing you down. A rock hasn't happened yet. "Code review is slow" is an anchor. "Two of our three reviewers are on leave in December" is a rock.

Where it comes from. The format is adapted from Speed Boat, one of Luke Hohmann's Innovation Games (from his 2007 book Innovation Games). In the original, customers draw anchors to show what slows a product down. Agile teams later added the wind, rocks and island; nobody is credited with that step.

When to use it (and when not to)

Use it when:

• the team has a clear goal: a release, a milestone, a sprint goal with teeth
• risks matter: dependencies on other teams, a deadline, people going on leave
• the team is tired of What Went Well and needs a new angle
• you're at the midpoint of a long project and want to check the course

Pick something else when:

• the team has no shared goal. If the island is blank, the retro drifts. Fix the goal first, in planning, not in the retro.
• the work was short or one-off, with no future to look at
• people need to vent. Rocks and anchors become a complaint list. Run Mad Sad Glad first.
• you've run it every sprint for a while. The metaphor wears thin fast; save it for every few sprints or for milestones.

How to run it live (45 minutes)

1. Start with the island. Write the goal in the island column before anything else. If people disagree about it, spend the first few minutes on that.
2. Check last retro's rocks. Open the Previous Retro tab in the Action Items panel. Did the risks you flagged hit? Did the mitigations work?
3. Write silently. Set the shared timer for 10 minutes. Use the All Topics menu to show one column at a time if the board gets crowded.
4. Group and vote. Drag related notes onto each other, then vote and sort by Most Votes.
5. Discuss anchors and rocks separately. Anchors need removing: what's the smallest change that cuts the drag? Rocks need a plan: avoid, reduce, or accept and watch. Give winds the last few minutes. They tell you what to protect.
6. Look at the island again. Given everything on the board, is the goal still realistic? Changing it is a valid outcome.

How to run it async over a sprint

Sailboat suits async well, because rocks show up in the middle of a sprint. The best time to note a risk is the day you spot it, not two weeks later when it may already have hit.

1. Day 1: after sprint planning, the facilitator writes the sprint goal as the first note in the island column. In Retro Rabbit, the new board is ready as soon as someone clicks Start New Retro after the last retro.
2. During the sprint: anyone who spots a risk adds a rock straight away. Slow builds, blocked tickets and waiting time are anchors. People add notes on the board, in Quick Notes on the Team Room page, or with /retro your note if the team uses Slack.
3. Mid-sprint: the facilitator reads the rocks. If one is urgent, raise it at standup. The retro is a backstop, not the only place for risk.
4. Two days before the end: everyone adds winds (people forget these), then votes.
5. The day before: the facilitator groups notes and reads the CarrotIQ Sprint Summary for each column.
6. Retro day: a 20-minute call focused on the top anchors and rocks, or a written round in which each owner proposes a mitigation and the team replies.

See how to run an async retrospective for the full playbook.

12 example prompts

Winds

1. What gave us momentum this sprint?
2. Who or what made your work easier?
3. Which decision are you glad we made?

Anchors 4. Where did work sit waiting? 5. What did you have to do twice? 6. Which process felt heavier than the work it protects?

Rocks 7. What could stop us reaching the island next sprint? 8. Which dependency are we hoping works out? 9. What would hurt most if a key person were away for a week?

Island 10. Is the goal still the right goal? 11. How will we know we've arrived? 12. Are we closer to the island than at the last retro, and how do we know?

For more, see 60 sprint retrospective questions.

Facilitator tip and a common pitfall

Tip: give rocks the same airtime as anchors. Anchors are vivid because people have just lived through them, so they eat the discussion. Rocks are quieter, and they're where next sprint's anchors come from. Timebox anchors to half the discussion and protect the other half for rocks.

Pitfall: a board full of anchors and no winds. Teams that only list what's wrong leave the retro feeling worse and learn nothing about what to protect. If the winds column is empty two days before the retro, ask everyone for one wind before they vote.

How AI helps with this format

On Pro AI (and during the free trial), CarrotIQ handles the admin around the board:

• Group names. Drag "PRs wait a day" onto "reviewers always busy" and CarrotIQ names the group, for example "Code Review Delays".
• Summaries. The Sprint Summary summarizes each column and the whole retro. The rocks summary is worth sharing with whoever plans the next sprint.
• Suggested action items. CarrotIQ Suggest drafts an action from the notes, weighting the most-voted ones. Use it as a starting point for a mitigation, then edit and assign it.

Example action items

Anchors become removal actions; rocks become mitigation actions with a check date.

Next retro, start with these. The Previous Retro tab shows them all, and Old / Unresolved Items shows anything older that's still open. More in retrospective action items that actually get done.

Use this template in Retro Rabbit

1. Start a 14-day free trial. No card is needed.
2. Name your team and choose Sailboat as your retro format.
3. Write your sprint goal as the first island note, and ask the team to add rocks as they spot them.

Want a sun column for good vibes? Add it as a fifth column in the Team Room settings. See pricing for plans.

Related formats

• Start Stop Continue: when you need quick behavior changes
• 4Ls: reflective, with a "Longed for" column for what you wish you had
• What Went Well: the default, four-question format
• The complete guide to sprint retrospectives
• All retrospective templates