Run a sailboat retro in 30 minutes

The sailboat retro usually takes 45 minutes or more. Here’s a version that fits in half an hour without losing what makes it work.

What you need

A board with four zones: wind (what pushed us forward), anchors (what held us back), rocks (risks ahead) and an island (where we want to get to). Use our free sailboat retrospective template, or draw it on a whiteboard.

The 30-minute plan

1. Set the scene 2 min

   Name the period you’re looking back on, walk through the four zones once, and say it’s about the work, not people.

2. Write alone 6 min

   Everyone writes in silence, one thought per note, in the zone where it belongs. Silence matters: it stops the first speaker setting the tone.

3. Read and group 7 min

   Read the wind first, then the anchors and rocks. Stack notes that say the same thing. No solutions yet.

4. Vote 5 min

   Everyone votes for the anchors and rocks that matter most. Take the top two.

5. Actions 8 min

   For each, write the very next step and who owns it: “When ___ happens, I’ll ___.” One owner per action.

6. Wrap up 2 min

   Each owner says their action out loud. Book the next retro and start it by checking these.

What to cut, and what not to

To save time, skip the pre-mortem on the rocks and keep the vote short. Don’t cut the silent writing: it’s the step that gets the quiet people’s notes on the board, and it’s why the retro is worth having.

Doing it remotely

In Stetley Board the timer runs on the server and moves the room on at the end of each step, notes stay blurred until the reveal, and an anonymous session keeps notes free of names for good. Try a board without signing up.

The sailboat retrospective template · More from the journal

Published 1 November 2026.