Sailboat retrospective
The sailboat retrospective is the one format here that looks forward as much as back. The boat is the team, the island is where it's going, the wind pushes it there, the anchors hold it back, and the rocks are what could sink it. That last column is the reason to use it: it's the only common retro format with a place to put a risk that hasn't happened yet.
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The columns
Wind
What's pushing the team forward: momentum, help, tooling, anything making the work easier.
Ask: What's carrying us along?
Wind: the new CI pipeline cut review turnaround in half
Anchors
What's slowing the team down right now. Present, active drag.
Ask: What's holding us back?
Anchors: three separate approval steps before a release
Rocks
Risks ahead that haven't hit yet. The column no other format has.
Ask: What could sink us that hasn't yet?
Rocks: only one person can deploy the payments service
Island
Where the team is trying to get to. Write it first. Everything else is relative to it.
Ask: What are we actually aiming at?
Island: ship self-serve onboarding by end of quarter
What a filled-in board looks like
A seven person team at the start of a quarter, planning self-serve onboarding, running 50 minutes.
Wind
Wind: the new CI pipeline cut review turnaround in half
Wind: design has the flows ready two weeks ahead of us
Wind: we did the auth work last quarter and it has held
Anchors
Anchors: three separate approval steps before a release
Anchors: the signup form still lives in the marketing site repo
Anchors: nobody reviews PRs in the first week of a sprint
Rocks
Rocks: only one person can deploy the payments service
Rocks: the trial logic assumes a sales-assisted signup and nobody has checked what self-serve does to it
Rocks: the identity provider contract is up for renewal in March
Island
Island: ship self-serve onboarding by the end of the quarter
Island: a new customer reaches a working account without talking to anyone
What grouping surfaced
- The island took ten minutes, because two people thought self-serve meant no sales contact at all and two thought it meant sales later. That was the most valuable ten minutes of the session.
- Two rocks were the same rock: things that only work because one particular person knows about them.
What they left with
- Jo runs a deploy of the payments service with somebody else driving, before the end of the month.
- Kit checks what the trial logic does on a self-serve signup and reports back at the next planning session.
When to use it
- Start of a quarter, project kickoff, or planning a big piece of work
- Teams that need to talk about risk without a formal risk review
- Retros where the goal itself is unclear or contested
- Groups that engage better with a visual metaphor than a table
When not to: It's a poor fit for a routine sprint retro where the goal is obvious and unchanged. If the island is the same every fortnight, the column stops earning its place.
A variation on Luke Hohmann's 'Speed Boat' innovation game, widened from a pure obstacle exercise into a full retrospective by adding the island and the wind.
Running it
- 01Set the stage and draw the metaphor: boat, island, wind, anchors, rocks.5 min
- 02Fill the island first, together. If the team disagrees here, that's the retro.5 min
- 03Silent writing into wind, anchors and rocks.10 min
- 04Reveal and group.10 min
- 05Actions for the top anchors; owners and dates for the top rocks.15 min
Facilitation notes
Do the island first and do it out loud. A team that can't agree where it's sailing has found its most important problem.
Rocks need an owner and a date, not a discussion. A risk everyone acknowledges and nobody owns is still a risk.
Anchors are present tense, rocks are future tense. Keeping that line clean stops the two columns collapsing into one.
Variations
Speed Boat
The original game this format came from: the boat and the anchors, nothing else. Half an hour, one question, and a ranked list of what is slowing the team down. Reach for it when the goal is not in question and you only want the drag.
Add a sun and a storm
The sun is what the team is optimistic about, the storm is the weather it cannot control: a reorganisation, a hiring freeze, a market shift. Separating the storm from the anchors stops the team writing actions against things no action will reach.
Run it as a pre-mortem
Island and rocks only, before the work starts rather than after. Ask the team to imagine the quarter has failed and to write why. It gets the same risks onto the board as the full format and takes twenty minutes.
Reach for a different format when
The goal has not changed and what you want is a short retro that produces process actions.
Start / Stop / Continue retrospective →
Something went badly wrong and the team needs to talk about it before it can plan forward.
Mad / Sad / Glad retrospective →
Common questions
›What is a sailboat retrospective?
A retrospective format using a sailing metaphor: the island is the goal, the wind is what's helping, the anchors are what's slowing the team down, and the rocks are risks ahead that haven't caused problems yet.
›What's the difference between anchors and rocks?
Anchors are slowing you down now. Rocks are hazards that haven't hit yet. Keeping them separate is the point of the format. Most retro formats have nowhere to put a future risk.
›When should you run a sailboat retrospective?
At the start of a quarter or project, or any time the team needs to talk about goals and risk together. It's less useful for a routine sprint where the goal hasn't changed.
›Is a sailboat retrospective the same as a speedboat retrospective?
Speed Boat is the original and narrower exercise: the boat and the anchors, asking only what slows the team down. The sailboat adds the island, the wind and the rocks, which turns an obstacle game into a full retrospective that also looks forward.
›Do you need to draw the boat?
No. The drawing helps a room that engages better with a picture than a table, but the format works as four columns. What actually matters is filling the island first, because every other column is written relative to it.
›How long does a sailboat retrospective take?
About 45 minutes, of which the first five go on the island. Budget more if the team has never agreed the goal out loud, because that conversation is the one worth having and it will not fit in five minutes.
Other formats
Start / Stop / Continue
Good / Bad / Start / Stop
Mad / Sad / Glad
Liked / Learned / Lacked / Longed for
Run a Sailboat retro now
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