Method · Retrospectives

Sailboat retrospective: how to run it

Draw a boat sailing to an island: the team adds what pushes it forward (wind), what holds it back (anchors), and risks ahead (rocks) — a picture that makes a retrospective easier to talk about.

45 minutes5 stepsRetrospectives
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When it helps

Use it for a team that is tired of the same retrospective format, or when talking about problems directly is hard — the picture gives people a way to say it.

When to use something else

Skip it for a quick check-in; the drawing takes a few minutes to explain. Very literal-minded groups may prefer plain columns.

How to run it, step by step

  1. Draw the picture3 min
    • A boat, an island (the goal), wind, anchors and rocks.
  2. Name the island4 min
    • What are we sailing towards — this quarter’s goal?
  3. Add notes10 min
    • Wind: what helps us. Anchors: what slows us. Rocks: risks ahead.
  4. Discuss anchors and rocks18 min
    • Which anchor slows us most? Which rock is closest?
  5. Actions10 min
    • One anchor to cut, one rock to steer around, each with an owner.

What comes out — an example

Made up, to show the shape.

Island. Launch the mobile app by March.

Wind. A strong designer joined; customers asking for it.

Anchors. Waiting days for API changes from another team.

Rocks. App store review could delay launch.

Actions. Weekly sync with the API team (Leo); submit for review two weeks early (Mia).

Questions

What is a sailboat retrospective?

A visual retrospective using a picture of a boat: wind for what helps, anchors for what slows the team, rocks for risks and an island for the goal.

Why use a metaphor in a retrospective?

A picture can make it easier to talk about problems and keep a regular retrospective fresh.

What is the difference between anchors and rocks?

Anchors are what slow the team today; rocks are risks ahead that could cause damage if not avoided.

Can the sailboat work for a whole project, not just a sprint?

Yes. Put the project’s end goal on the island and run it at the halfway point, when there is still time to cut an anchor or steer around a rock.

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