Sailboat Retrospective

What is a Sailboat Retrospective?

A Sailboat Retrospective is a visual reflection activity that helps a team examine its progress toward a goal.

The team imagines itself as the crew of a sailboat. An island represents the destination. Wind helps the boat move. Anchors slow it down. Rocks represent dangers ahead.

These four parts turn a broad question such as "How did the sprint go?" into a more varied conversation:

The image gives people a small imaginative detour. Instead of listing positives and negatives directly, participants think about the work through movement, drag, danger, and destination. That change of frame can surface ideas a Stop / Keep / Start Retrospective would leave hidden.

Research on visual metaphors in graphic facilitation describes how metaphors help people view situations in a new light, make abstract subjects concrete, and build memorable shared reference points. That broader research supports metaphor as a facilitation frame, although it doesn't prove that Sailboat will produce better answers for every group.

Where the Sailboat Retrospective comes from

The modern Sailboat Retrospective grew from Luke Hohmann's Speed Boat Innovation Game. His original activity was designed for customer understanding: the boat represented a product or system, while anchors represented features, frustrations, or problems holding customers back. Participants wrote their anchors, explained what was causing pain, and could prioritize which anchors would have the greatest impact if removed.

I know Luke and have spoken with him many times, and in 2013 I attended his Certified Innovation Games for Customer Understanding training in London. One piece of his advice has stayed with me ever since: understand each concern before defending the product or rushing into solutions. You'll find that principle echoed throughout this guide, because it applies to the retrospective version just as much as to the original game.

Agile facilitators later expanded the image into the Sailboat Retrospective used today. Wind brought in the forces helping the team. Rocks introduced future risks. The Island made the destination visible. The Agile Retrospective Resource Wiki describes the idea as starting with Hohmann and then being modified by the community over time.

When to use it

Use a Sailboat Retrospective when a group needs to reflect on recent work while keeping a future goal in view.

It works well for:

• sprint and project retrospectives;
• milestones in a longer transformation;
• team health conversations;
• project kickoffs and pre-mortems;
• strategy workshops where progress and risks need to be discussed together;
• groups that have grown tired of direct retrospective questions.

The activity is especially useful when the team needs to separate current blockers from future risks. Anchors describe what is already creating drag. Rocks describe what may cause trouble next.

Choose another format when the metaphor doesn't fit the group or topic. A playful visual exercise can feel out of place during a serious conflict, a sensitive incident review, or a conversation where people first need stronger psychological safety.

Understand the Sailboat metaphor

The boat

The boat represents the team, project, or shared effort, and it gives the other elements a common context. Most templates treat it as scenery: the four questions cover Wind, Anchors, Rocks, and Island, and the boat simply sets the scene.

Nothing stops you from using the boat as a fifth question. Ask about the crew, the state of the vessel, or what is happening on board when the group would benefit from reflecting on itself.

The island

The island is the destination: a sprint goal, a project outcome, a team ambition, a customer result, or a better way of working.

Everything else in the exercise depends on it. Wind toward what? Drag on which journey? A vague destination weakens every other prompt, so clarify what journey the group is discussing before asking about wind, anchors, and rocks.

The wind

Wind stands for the forces pushing the group forward. Useful habits, supportive people, good decisions, effective tools, clear communication, favorable conditions.

Teams often treat this area as a quick round of celebration and move on. That wastes it. Ask what the team should protect, repeat, or strengthen, because wind that nobody tends to has a way of dying down.

The anchors

Anchors are the blockers and sources of friction already slowing progress. Dependencies, unclear ownership, recurring delays, difficult processes, missing skills, habits the team could change.

The test for a good anchor card: does it describe a current source of drag on this specific journey? A general complaint with no connection to the destination belongs somewhere else.

The rocks

Rocks are the risks and threats that may damage future progress. They push the team to look ahead instead of only reviewing what has already happened.

Keep rocks distinct from anchors. An unresolved dependency affecting the team today is an anchor. A supplier change that may affect the next release is a rock.

How to run a Sailboat Retrospective

A typical session takes 30 to 60 minutes. Adjust the depth to the size of the group and the importance of the journey.

How to debrief the Sailboat

A useful debrief moves through three levels.

Understand the picture

Ask:

• What pattern do you notice across the boat?
• Where do Wind and Anchors act on the same part of the work?
• Which Rocks are close enough to require action now?
• Does the Island still describe the destination we want?

Find the leverage points

Ask:

• Which anchor would release the most energy if we removed it?
• Which source of wind should we protect or strengthen?
• Which rock could cause the greatest damage?
• Are we addressing a cause or only a visible symptom?

Turn insight into action

Ask:

• What can the team change itself?
• What needs help from outside the team?
• What is the smallest useful experiment for the next cycle?
• Who will own it?
• When will we review whether it worked?

The completed picture is an intermediate artifact. The value comes from the conversation and the decisions that follow.

Facilitation tips

Why retrospective variety matters

Teams run retrospectives regularly. Repeating the same questions and format can make the session predictable: participants return to familiar answers instead of examining the work again. This is also why experienced practitioners recommend rotating retrospective techniques to keep conversations fresh.

Change the angle when the current format has become stale. A Sailboat Retrospective can refresh a team that usually uses direct columns, and later another metaphor or question set may be more useful in turn.

Choose variety with purpose, though. A new picture can't repair missing trust, defensive leadership, or repeated failure to complete retrospective actions. The facilitator still needs to create safety, guide a useful discussion, and close the feedback loop.

Common mistakes

Spending too much time on the picture

A polished sailboat is unnecessary. Use a clear image, explain the symbols, and move quickly into reflection.

Treating every obstacle as an anchor

Separate current drag from future danger. This distinction helps the team decide whether to remove an active blocker or prepare for a risk.

Leaving the destination vague

Wind, anchors, and rocks only make sense in relation to a journey. Define the scope and destination before collecting ideas.

Discussing too early

Let participants generate cards before the group debates them. Once a debate starts, later contributors write toward it.

Stopping with a decorative board

A full sailboat is a starting point. The retrospective still needs clarification, prioritization, and action.

Voting without understanding

A quick vote on unclear cards creates a ranking without shared meaning. Clarify and group first.

Reusing Sailboat every time

Even a creative format becomes routine through repetition. Keep several retrospective approaches available and match them to the purpose of the session.

Variations

Destination-first Sailboat

Clarify the Island first. Then ask what provides Wind, what creates Anchors, and which Rocks lie ahead. This works well when the team has lost sight of its goal.

Wind-first Sailboat

Begin with strengths and helpful conditions before discussing blockers and risks. This can create a constructive tone for a group that tends to focus immediately on problems.

Sequential Sailboat

Reveal one prompt at a time. Sequential collection helps participants concentrate and lets the facilitator allocate different amounts of time to each question.

Pre-mortem Sailboat

Use the activity before a project or difficult phase. Define the destination, identify expected support, anticipate drag, and map risks before they happen.

Simple Speed Boat

Use the narrower form associated with Luke Hohmann's original Speed Boat Innovation Game. Focus only on the boat and the anchors holding it back. This variation works when the main purpose is to understand and prioritize sources of frustration.

Tools and setup

You can run a Sailboat Retrospective on any shared surface that can hold the visual scene and participant contributions. The setup should make the four prompts clear and leave enough room to group or move cards during the debrief.

Low-tech and general-purpose tools

For an in-person session, draw the boat, Island, Wind, Anchors, and Rocks on a whiteboard or large sheet of paper. Use one sticky note per observation. A rough drawing is enough.

For remote or hybrid groups, use a shared document, slides, a generic online whiteboard, or another collaborative board. Prepare the four areas before the session and decide whether participants will see every prompt at once or move through them sequentially.

The low-tech version works well for collection and discussion. Larger groups may need more support for reorganizing contributions, changing the review perspective, and running a fair vote.

Using Stormz

The Stormz Sailboat Retrospective preset provides four guided areas:

• What gives us wind?
• What anchors are slowing us down?
• What rocks should we watch for?
• What island are we trying to reach?

Participants add one observation per card in the Metaphor view. The visual surface supports collection, while the same cards can be reviewed differently afterward.

The facilitator can switch to the Kanban view or Table for a more structured review. Cards can also be grouped by participant, explored through the Word Cloud view, or shown in random order when the group needs to reduce ordering bias.

Voting is optional and starts as a separate facilitation step. Once a voting session exists, the facilitator can choose Random order before participants prioritize the cards.

This flexibility supports the principle behind the whole activity: collect with the view that stimulates reflection, then debrief with the view that best supports the next conversation.

FAQ

Sources and further reading

• Speed Boat, Luke Hohmann explains the original customer-understanding game, its anchors, facilitation process, and prioritization approach.
• Sailboat, Agile Retrospective Resource Wiki documents the retrospective adaptation, community evolution, grouping, and voting flow.
• 9 retrospective techniques that won't bore your team to tears, Atlassian discusses Sailboat alongside other formats and the value of keeping retrospectives fresh.
• The Lazy Netflix B: An Ethnographic Study on the Use of Humour and Visual Metaphors in Teaching Graphic Facilitation, Heidi Hautopp is a peer-reviewed study of humour and visual metaphors in graphic-facilitation teaching. Yes, that is really the paper's title.
• Conceptual similarity and visual metaphor, Lagerwerf, Van Mulken, and Lagerwerf examines how people interpret visual metaphors compared with more literal visual relationships.