Agile Rituals
Start free

Sailboat retrospective template

A visual metaphor: what pushes you forward, what holds you back, and what risks lie ahead.

Start a Sailboat retroFree. No account needed. Share the link and your team joins.

The columns and what to ask

  • Wind

    What is pushing us toward our goal?

  • Anchor

    What is holding us back or slowing us down?

  • Rocks

    What risks could sink us if we don't watch them?

  • Island (Goal)

    Where are we heading? What does success look like?

Best for

  • Planning a release, quarter or project, not only looking back
  • Teams that find abstract discussion hard. The metaphor makes it concrete.
  • Surfacing risks early, before they become incidents

Skip it when

  • The team has no shared goal yet. Agree the destination first, or the Island column stays empty.
  • You only have a short slot. Four columns and a metaphor need time to set up.

How to run it in 60 minutes

Sized for a team of up to eight. Add time for larger groups.

  1. 1

    Set the stage and name the island · 10 min

    Agree on the goal (a release, a quarter, a milestone) and write it in the Island column. Everyone should be sailing to the same place.

  2. 2

    Write cards · 10 min

    Everyone adds cards to Wind, Anchor and Rocks silently.

  3. 3

    Read and group · 10 min

    Read the cards, cluster them and vote for the anchors and rocks that matter most.

  4. 4

    Discuss · 20 min

    Take the top anchors first (current problems), then the top rocks (future risks). For each, ask what would remove it or reduce it.

  5. 5

    Commit to actions · 10 min

    Turn the top anchors into actions and the top rocks into mitigations or a watch list, each with an owner.

Facilitation tips

  • Write the goal in the Island column first and read it aloud. Without it the other columns have no reference point.
  • Anchors are problems you have now. Rocks are problems you might have. Give every rock an owner who watches it.
  • Use Wind to decide what to do more of, not just to feel good.
  • Keep the board and revisit it partway through the project. It doubles as a lightweight risk register.

Questions

What is a sailboat retrospective?
A retrospective built on a metaphor: wind moves the boat toward the island (your goal), an anchor holds it back, and rocks are hidden risks. Cards go in each area.
Is it only for looking back?
No. It works well at the start or middle of a project to plan around risks, which is where it differs from most retrospective formats.

Run it with your team now

Your board opens with these columns. Votes, timers and anonymous cards are built in.

Start a Sailboat retro

Other retrospective formats

See all 6 templates