Sailboat retrospective

Your team is a boat heading for an island. Wind pushes it forward, anchors hold it back, and rocks wait under the surface. One picture, and the whole team can see where it is going and what stands in the way.

Island

Your goal, mission, metric... Anything you're aiming for

Underwater rocks

What might you encounter along the way?

Anchors

What is holding you back right now? What prevents you from starting?

Wind in the sails

What gives you confidence? What helps you?

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What a sailboat retrospective is

A sailboat retrospective asks the team to describe its work as a voyage. The island is the goal. The wind in the sails is whatever moves you towards it. Anchors are what slows you down right now, and underwater rocks are the risks you have not hit yet. Everyone writes cards for each part of the picture, the team groups and votes on them, and the discussion ends with a few concrete actions.

The format grew out of the Speed Boat exercise from Luke Hohmann's Innovation Games, where customers described the anchors slowing a product down. Agile teams adapted it for retrospectives by adding the wind, the island and the rocks, and it became one of the most widely used retrospective formats.

Why the metaphor works better than a plain "what went well / what didn't" list:

• It puts the goal on the board. Problems are judged by how much they keep you from the island, not by how annoying they felt last week.
• It separates today's drag from tomorrow's risk. Most formats mix "this hurts now" with "this might hurt later". The sailboat gives each its own place, and each needs a different kind of action.
• An anchor is a thing, not a person. "Releases wait for a manual sign-off" is easier to say out loud than "Mark is slow to approve". The picture nudges people towards describing systems.
• It needs no explanation. A new joiner or a visiting stakeholder understands the board at a glance.

When to use it, and when not to

The sailboat works best when the team shares a goal and wants to check its course:

• at the start of a quarter, a project or a release, as a forward-looking session (often called a futurespective);
• halfway to a milestone, when you want to know whether you will make it;
• when your usual retro has gone stale and people answer on autopilot;
• with a mixed group — developers, designers, product, support — because nobody needs to know retro jargon.

Pick something else when:

• The team has just been through an incident or a conflict. People need to talk about what happened, not about islands. A focused format such as Elephant in the Room or a dedicated incident review fits better.
• There is no shared goal. Ask for the island and you will get six different ones. That is a useful finding, but then spend the session agreeing on a goal rather than on the full board.
• You ran it last sprint. Any format gets predictable if it is used every time. Rotate with Start Stop Continue, 4Ls or Mad Sad Glad.

The four parts of the board

In ProstoRetro the template opens with four columns: Island, Underwater rocks, Anchors and Wind in the sails. Here is what belongs in each, from the goal to the risks, with cards a real software team might write.

Island: where you are heading

The goal, mission or metric the team is aiming for. It should be specific enough that you would know when you have landed. "Better quality" is fog; "fewer than five support tickets per release" is an island.

• Ship self-serve onboarding by the end of March
• Get the time from merge to production under one day
• Bring the app store rating back above 4.5
• Hand the reporting module over to the new team without a drop in quality

Wind in the sails: what pushes you forward

Practices, people, tools and circumstances that help. This column is easy to rush, but it tells you what to protect and what to do more of.

• Pairing on tricky tickets halved the back-and-forth in code review
• Design now joins sprint planning, so fewer surprises mid-sprint
• Staging has finally been stable for three weeks
• Support sends us the top five customer complaints every Friday

Anchors: what holds you back right now

Problems that are already slowing the team down. The test: if it disappeared tomorrow, would you move faster this week? Then it is an anchor.

• Flaky end-to-end tests: we rerun the pipeline three or four times a day
• Tuesday and Wednesday are wall-to-wall meetings, with no time for deep work
• Requirements arrive in chat threads and get lost
• Getting access to production logs takes two days

Underwater rocks: the risks ahead

Things that have not hurt you yet but could wreck the trip. An anchor is already in the water; a rock is something you can still steer around.

• The only person who knows the search service is on leave in May
• Marketing announced the launch date before we estimated the work
• The maps provider retires its old API version this summer
• Holiday traffic is coming, and the new checkout has never been load-tested

Use this template — it's free

A 60-minute sailboat retrospective agenda

This plan suits a team of five to nine people. For a larger group, add ten minutes to the discussion.

1. Warm-up, 5 minutes. One light question to get everyone talking — pick one from our list of icebreaker questions. In ProstoRetro the board can start with an icebreaker round that chooses the question and the person who answers it.
2. Set the island, 5 minutes. Read out the goal, or let everyone add an island card and agree on one. Write it down where everyone can see it.
3. Silent writing, 10 minutes. Everyone adds cards to the wind, anchors and rocks. One idea per card. Cards stay hidden from others until the writing ends, so nobody echoes the first card they read.
4. Grouping, 7 minutes. Read the cards together and merge duplicates. ProstoRetro can suggest the groups for you, and you keep or undo them.
5. Voting, 5 minutes. Everyone gets a handful of votes to put on the topics that matter most. Votes are anonymous, which keeps the most senior person in the room from steering the result.
6. Discussion, 20 minutes. Take the top three or four topics. Ask a different question for each part of the boat: for an anchor, "what would it take to cut the rope?"; for a rock, "how will we see it coming, and what is plan B?"; for the wind, "how do we get more of it?"
7. Action items, 5 minutes. Turn the best ideas into actions with one owner and a due date each. Two or three actions that happen beat ten that don't.
8. Close, 3 minutes. Read the actions back and ask for a one-word reaction to the session.

If you set a meeting length when you create the board, ProstoRetro splits it across the phases and the discussion topics and runs the timers for you, so the facilitator does not have to watch the clock.

Running it with a remote team

• Write in silence, talk out loud. The writing phase works fine without anyone speaking. Save the call for grouping and discussion.
• Let people stay anonymous. Some anchors are decisions made above the team. Anonymous cards bring them onto the board instead of into a private chat after the meeting.
• Make joining effortless. When a board is open to anyone with the link, participants join with just a name — handy for a stakeholder, a contractor or a colleague from another team.
• Time-box each topic. Remote discussions drift more than in-person ones. When the timer ends, decide: an action, five more minutes, or move on.
• Collect cards ahead of time across time zones. A permanent board — an infinite room in ProstoRetro — lets people add cards before the meeting. They stay hidden until the team meets.
• Close the loop. At the start of the next retro, look at the anchors you chose to cut. Did they go? ProstoRetro reminds the owners of action items by email and shows the open ones at the next retro.

Variations

Add the sun

The common five-part version adds a sun: what makes the voyage enjoyable — the people, wins and habits the team is glad about. It brings back the warmth of "what went well" without losing the goal. In ProstoRetro you can build this as a custom template: Island, Sun, Wind in the sails, Anchors and Underwater rocks, five columns with your own descriptions and colours.

Speedboat for product feedback

In the original exercise the cards came from customers: they wrote the anchors, the things about a product that held them back. Run it with customers or your support team, ask "what slows our product down for you?", and you get a ranked list of pain points to feed into planning.

The quarter-long island

Keep the same island for a whole quarter and run the sailboat at the start, middle and end. Comparing the anchors between sessions shows which ones you actually removed and which keep coming back.

Common mistakes

• Skipping the island. Without a goal, anchors and wind become a generic list of likes and dislikes, and the session turns into an ordinary retro with nautical names.
• Treating anchors as a blame list. "Reviews take too long" leads to a fix; a name on a card leads to silence. Rewrite personal cards as process cards before the discussion.
• Mixing anchors and rocks. Anchors need removing; rocks need watching, a mitigation or a plan B. If you treat them the same, the risks never get an owner.
• Discussing every card. Vote, take the top three or four topics, and let the rest go. If a topic matters, it will come back.
• Ending without owners. "We should fix the tests" is a wish. "Dana splits the flaky suite into quarantine by Friday" is an action.

FAQ

What are the parts of a sailboat retrospective?

The island (the goal), wind in the sails (what helps), anchors (what holds the team back now) and underwater rocks (risks ahead). Some teams add a sun for what makes the work enjoyable.

How long does a sailboat retrospective take?

About an hour for a team of five to nine people, as in the agenda above. A 30-minute version works if the island is agreed beforehand and you discuss only the top two topics.

What is the difference between anchors and rocks?

Timing. An anchor is slowing you down today; a rock is a risk that has not hit you yet. Anchors call for removal, rocks for prevention or a backup plan.

Does the sailboat work for remote teams?

Yes. The picture carries the meaning, so it reads the same on a shared screen as on a whiteboard. Silent writing, anonymous cards and a timer keep a remote session as focused as an in-person one.

Can I run a sailboat retrospective online for free?

Yes. The Sailboat is built into ProstoRetro, which costs nothing to use. Agree on the island before the meeting, share the room link, and the team draws the rest of the picture together in the browser. For a full walkthrough of the app, read how to run a great retro, or browse the other retrospective templates.