Retro format 04 of 27
Sailboat retrospective
Draw a boat heading to an island: wind pushes it, anchors slow it, rocks are risks ahead.
- 45–60 min
- 2 to 20 people
- Great remote
Good for
A team that has lost sight of its goal or keeps hitting the same blockers. The picture makes it easy to talk about risks.
Also called: Sailboat retrospective
Facilitator tip
Agree the island first. If the team can't name the goal, that is the most useful thing you'll learn all hour.
The Sailboat board, drawn out.
4 areas: Island (goal), Wind (helps us), Anchors (slow us), Rocks (risks ahead). Draw the picture on your whiteboard before the retro. Here's what a software team might put in each.
1Island (goal)
Ship the new checkout by end of Q1
2Wind (helps us)
New CI runners cut builds to 6 minutes
3Anchors (slow us)
Two days waiting on platform review
4Rocks (risks ahead)
Postgres upgrade lands in launch week
How to run a Sailboat retrospective.
About 60 minutes as written. Change the length in the agenda builder below and every step scales with it.
- 1
Check in
5 min
Say why you're here and that the retro is about the system, not people. Go through last retro's action items: done, in progress, or dropped on purpose.
- 2
Set the island
3 min
Write the team's goal for the next month or quarter on the island. Agree it before anything else.
- 3
Write silently
8 min
Everyone adds notes to wind, anchors and rocks.
- 4
Read out
10 min
Each person places and reads their notes.
- 5
Group and dot-vote
5 min
Cluster notes that say the same thing and name each cluster. Everyone gets three votes. Sort by votes.
- 6
Discuss anchors and rocks
14 min
Which anchor could we cut this sprint? Which rock needs a plan before we reach it?
- 7
Agree action items
10 min
Pick one to three actions from the top topics. Each gets one owner and a due date, and goes into the next sprint's backlog, not only the retro notes.
- 8
Close
5 min
Read the actions and owners back. Ask everyone to rate the retro 1 to 5 (return on time invested) and change one thing next time if the scores are low.
Prompts to put on the board.
Read one out when the writing stalls, or paste them next to the columns.
- What is pushing us toward the goal right now?
- What is slowing us down: tech debt, waiting on another team, too many meetings?
- What risks do you see coming in the next few sprints: a migration, a holiday, a key person away?
- Is the island still the right goal?
Your Sailboat agenda, timed to your slot.
Fill in the team and the time. Copy the agenda into Confluence, Notion or Google Docs as formatted text, or grab the Markdown.
Length
- 0:00–0:05Check in · 5 min
- 0:05–0:08Set the island · 3 min
- 0:08–0:16Write silently · 8 min
- 0:16–0:26Read out · 10 min
- 0:26–0:31Group and dot-vote · 5 min
- 0:31–0:45Discuss anchors and rocks · 14 min
- 0:45–0:55Agree action items · 10 min
- 0:55–1:00Close · 5 min
Payments team Sprint 14 retro: Sailboat
Length: 60 min
Draw a boat heading to an island: wind pushes it, anchors slow it, rocks are risks ahead. A team that has lost sight of its goal or keeps hitting the same blockers. The picture makes it easy to talk about risks.
Agenda
| Time | Step | Min |
|---|---|---|
| 0:00–0:05 | Check in | 5 |
| 0:05–0:08 | Set the island | 3 |
| 0:08–0:16 | Write silently | 8 |
| 0:16–0:26 | Read out | 10 |
| 0:26–0:31 | Group and dot-vote | 5 |
| 0:31–0:45 | Discuss anchors and rocks | 14 |
| 0:45–0:55 | Agree action items | 10 |
| 0:55–1:00 | Close | 5 |
How to run each step
- Check in (5 min). Say why you're here and that the retro is about the system, not people. Go through last retro's action items: done, in progress, or dropped on purpose.
- Set the island (3 min). Write the team's goal for the next month or quarter on the island. Agree it before anything else.
- Write silently (8 min). Everyone adds notes to wind, anchors and rocks.
- Read out (10 min). Each person places and reads their notes.
- Group and dot-vote (5 min). Cluster notes that say the same thing and name each cluster. Everyone gets three votes. Sort by votes.
- Discuss anchors and rocks (14 min). Which anchor could we cut this sprint? Which rock needs a plan before we reach it?
- Agree action items (10 min). Pick one to three actions from the top topics. Each gets one owner and a due date, and goes into the next sprint's backlog, not only the retro notes.
- Close (5 min). Read the actions and owners back. Ask everyone to rate the retro 1 to 5 (return on time invested) and change one thing next time if the scores are low.
Board
- Island (goal)
- Wind (helps us)
- Anchors (slow us)
- Rocks (risks ahead)
Prompts
- What is pushing us toward the goal right now?
- What is slowing us down: tech debt, waiting on another team, too many meetings?
- What risks do you see coming in the next few sprints: a migration, a holiday, a key person away?
- Is the island still the right goal?
Last retro's action items
| Action | Owner | Status |
|---|---|---|
Action items
| Action | Owner | Due |
|---|---|---|
Copy pastes as formatted text into Google Docs, Notion or Confluence. Markdown is for GitHub, Jira or Slack.
Try next, when this one gets stale.
- 01
Start Stop Continue
- 30–60 min
- 2 to 20
- Great remote
- 07
Lean Coffee
- 30–55 min
- 2 to 10
- Great remote
- 10
Speedboat
- 30–50 min
- 2 to 20
- Great remote
Book the retro on a day the whole team is in.
A retro with two people out hears half the sprint, and its actions have no owners. Forgot shows sprints, holidays and time off on one board, so you can see who's out on retro day before you send the invite.
Sailboat retrospective questions
What is a Sailboat retrospective?
Draw a boat heading to an island: wind pushes it, anchors slow it, rocks are risks ahead. A team that has lost sight of its goal or keeps hitting the same blockers. The picture makes it easy to talk about risks.
How long does a Sailboat retro take?
45 minutes at the shortest, and about 60 minutes as written here. The agenda builder on this page stretches or squeezes each step to fit your slot.
Can you run Sailboat remotely?
Yes, it works well on a video call. Set up the board on a shared whiteboard before the call, give everyone silent writing time with cameras optional, and use anonymous dot-voting.
What goes on a Sailboat board?
4 areas: Island (goal), Wind (helps us), Anchors (slow us), Rocks (risks ahead). For example, from a software team: Island (goal): “Ship the new checkout by end of Q1”; Wind (helps us): “New CI runners cut builds to 6 minutes”; Anchors (slow us): “Two days waiting on platform review”; Rocks (risks ahead): “Postgres upgrade lands in launch week”.
What team size is Sailboat for?
2 to 20 people. With more people, split into groups for the writing and discussion, then bring the top topics back together.
What can I run instead of Sailboat?
Start Stop Continue, Lean Coffee, Speedboat. They suit similar sprints from a different angle. Rotate formats every two to four sprints so the retro doesn't go stale.