Sailboat retrospective template

Wind, anchors, rocks, and the island — one picture of what moves the team and what holds it back.

The sailboat retrospective draws the team as a boat on a journey. The island is where you are trying to get to, the wind is everything pushing you towards it, the anchors are what slow you down, and the rocks are the hazards ahead that have not hit you yet. Everyone writes cards into the four areas, and the picture does the work: strengths, drag, and risk end up on one board instead of in three separate conversations.

The rocks column is what sets it apart. Went Well / To Improve and its relatives only look backwards, while the sailboat asks the team to name what is coming — which makes it a strong fit before a launch, midway through a long project, or any time people privately suspect trouble ahead. The metaphor is also gentle enough for mixed rooms: "an anchor" lands softer than "this hand-off is broken".

Timebox

45–60 minutes

Team size

3–15 people

Cadence

Every few sprints, at project milestones, or before a launch

The Sailboat board

Island

Where are we actually trying to get to? What does arriving look like?

  • A checkout that converts as well on mobile as on desktop
  • Releases boring enough that nobody stays late for them
  • The legacy service switched off, not just bypassed
  • A new engineer from first day to first deploy inside a week
  • Billing support tickets down to single digits per week

Wind

What is pushing us forward? What should we do more of?

  • Feature flags let us ship half-finished work safely
  • The one-day review SLA has held for six weeks straight
  • Two people can deploy every service now, not one
  • Design joins refinement, so tickets arrive unambiguous
  • Stakeholders see real work on Fridays and stopped asking for status

Anchors

What is slowing us down? What drags on every single sprint?

  • The 22-minute build, so nobody pushes small changes
  • Three approvers required for config-only changes
  • Flaky tests we rerun instead of fixing
  • Tickets arriving without acceptance criteria
  • Two of us split across another project, unaccounted for in planning

Rocks

What is ahead that could hurt us? What are we sailing towards?

  • The vendor contract renews in six weeks and nobody owns it
  • Our only database expert is on leave during the migration
  • The compliance deadline lands the same week as the launch
  • Staging has drifted from production, so the rehearsal will prove nothing
  • Traffic triples in November and we have never load-tested this path

How to run a Sailboat retrospective

  1. 1

    Draw the boat (5 min)

    Explain the four areas: island = the goal, wind = what pushes us forward, anchors = what holds us back, rocks = hazards ahead. Name the period under review and the destination out loud, or the cards will describe four different journeys.

  2. 2

    Agree on the island first (7 min)

    Collect and read the island cards before anything else. If the team disagrees about the destination, that disagreement is the retrospective — there is no point debating anchors while half the room is rowing somewhere else.

  3. 3

    Silent writing (8–10 min)

    Everyone fills wind, anchors, and rocks privately with cards hidden. Ask for specifics: "the Tuesday approval step", not "process".

  4. 4

    Reveal and cluster (7 min)

    Reveal all cards at once and group them. Watch for the same item appearing as both wind and anchor — a practice that helps some people and blocks others is usually the most productive discussion on the board.

  5. 5

    Vote across the whole board (3 min)

    Four or five votes each, spent anywhere. Anchors and rocks will compete, and letting them compete is the point: you are choosing between removing drag now and avoiding a hazard later.

  6. 6

    Cut anchors, chart around rocks (15–20 min)

    For the top anchors, agree what gets removed or changed and who owns it. For the top rocks, agree a mitigation or a named early-warning signal somebody watches. Give the strongest wind card one decision too: what protects it.

Sailboat retrospective examples for engineering teams

Wind

  • Trunk-based development with flags on anything risky
  • Runbooks written before a service takes traffic
  • Pairing on the payment path — three people know it now

Anchors

  • Manual release steps that take an hour and one specific person
  • A test suite slow enough that people push in batches
  • Tech-debt tickets that never survive prioritisation

Rocks

  • The framework version we are on loses support in March
  • One unowned service handles 40% of traffic
  • The next hire starts with onboarding docs six months stale

Sailboat examples for a project or milestone review

At a milestone the island is worth rewriting, not restating. Teams drift: the goal agreed at kick-off is often not the goal the work has been serving for the last two months, and the sailboat surfaces that in the first ten minutes.

Island

  • Customers self-serve the migration without contacting support
  • One codebase, not two running in parallel
  • The team owns the whole flow, including the alerts

Wind

  • The weekly stakeholder demo killed three bad assumptions early
  • A written decision log meant no call got relitigated
  • Support joined refinement and rewrote the macros in time

Rocks

  • The old system has no switch-off date, so both will run forever
  • The integration partner has not confirmed their timeline
  • Peak season starts before the last batch is migrated

Sailboat examples for non-technical and mixed teams

The format needs no agile vocabulary, which is why marketing, support, ops, and leadership groups pick it up quickly — and why it works with stakeholders in the room.

Wind

  • The shared campaign calendar ended the double bookings
  • Weekly 15-minute check-in replaced four escalation threads
  • New hires shadow calls in week one and ramp faster

Anchors

  • Approvals sit in one inbox and wait for the weekly review
  • Three tools hold the same customer list, none authoritative
  • Reporting is copied by hand into a deck every Monday

Rocks

  • Two people cover the whole rota and both booked December leave
  • The pricing change lands with no support briefing planned
  • Our biggest account renews in eight weeks with no owner

Best for

  • Teams that need to talk about risks ahead, not only problems behind
  • Milestone and project reviews where the goal itself needs restating
  • Mixed or non-technical groups — the metaphor needs no agile vocabulary
  • Retros that have gone stale on the same three columns every sprint

Facilitation tips

Start with the island, not the wind

Most facilitators go straight to wind and anchors and leave the island as decoration. Reversing the order catches misalignment about the goal, which is the most expensive kind, and it makes every other card easier to judge — "does this move us to the island?" becomes an answerable question.

Every rock leaves with an owner or a signal

A rock with no mitigation and nobody watching for it is a rumour on a whiteboard. Each risk that survives the vote gets either something the team does now, or a specific signal somebody checks: a date, a metric, a person to ask.

Do not let anchors become a blame list

Anchors are practices, constraints, and dependencies. When a card names a person, ask what that person is being asked to do that turns them into a bottleneck — the answer is almost always a process card in disguise.

Skip the artwork if it costs you time

The metaphor works from four labelled columns; the picture is optional. Fifteen minutes spent drawing a boat on a digital board is fifteen minutes not spent deciding anything.

Variations

Speedboat

The ancestor of the format, from Luke Hohmann’s Innovation Games: the team lists only the anchors slowing the boat and estimates what each one costs. Sharper when the destination is already agreed and you only need the drag list.

Sun and clouds

Some boards add a sun for what the team is grateful for and clouds for uncertainty outside its control. Worth adding when morale, rather than process, is the thing that needs discussing.

Hot air balloon

The same four roles in a different picture: hot air lifts, sandbags weigh down, storms are the risks, and the landing site is the goal. Swap to it when the team has run the sailboat five times and stopped reading the labels.

Sailboat futurespective

Point the boat at work that has not started: the island is the launch, the wind is what will help, the rocks are what is waiting. The futurespective guide covers the forward-looking version in more depth.

Frequently asked questions

What is a sailboat retrospective?+

It is a visual retrospective format where the team is drawn as a boat sailing towards an island. Participants add cards for the island (the goal), the wind (what pushes them forward), the anchors (what holds them back), and the rocks (risks ahead), then vote on which anchors to remove and which rocks to mitigate.

What do the island, wind, anchors, and rocks mean?+

The island is the goal or vision the team is heading for. The wind is everything helping it get there — practices, tools, people worth protecting. The anchors are what slows the team down. The rocks are hazards that have not caused damage yet but are visible ahead, which is the part most retrospective formats never ask about.

How is the sailboat different from the speedboat retrospective?+

The speedboat asks only about anchors: what is slowing the product or team down, and how much each drag costs. The sailboat keeps the anchors and adds the island, wind, and rocks, so one session covers the goal, the strengths, the drag, and the risks. Use the speedboat when the destination is settled and you want a focused list of what to remove.

How long does a sailboat retrospective take?+

Plan 45–60 minutes for a team of up to 12: 5 minutes to set up, 7 minutes to agree on the island, 10 minutes of silent writing, 7 minutes to cluster, 3 minutes to vote, and 15–20 minutes to decide on anchors and rocks. Four areas produce more cards than three columns, so it needs more clustering time than Start Stop Continue.

Where does the sailboat retrospective come from?+

It grew out of Luke Hohmann’s Speedboat game from Innovation Games (2006), which asked participants to name the anchors slowing a product down. Agile facilitators added the island, wind, and rocks to turn it into a full retrospective, and the sailboat is now one of the most widely used visual formats.

Run Sailboat online in FocusRetro

Start a blank board, name the columns Island / Wind / Anchors / Rocks, and invite the team with a link — then run the phases with timers, hidden cards, and blind voting. Free plan available at focusretro.com.

Start a board free

No credit card required

Related guides

Futurespective template

A retrospective run before the work starts: imagine the outcome, then work backwards.

Release retrospective template

The retro for a whole release: timeline first, then the three things that change before the next one.

How to run a sprint retrospective (step-by-step guide)

A step-by-step sprint retrospective guide: the 5-phase agenda, exact timings for a 60-minute session, facilitation tactics, remote tips, and common failure modes.

What is a retrospective? The complete guide for teams

A retrospective is a recurring team meeting for inspecting how you work and deciding what to change. Learn the formats, agenda, timings, and mistakes to avoid.

Retrospective timebox calculator

How long Sailboat should run for your sprint length and team size, split across the five phases.

Icebreaker and check-in questions

Openers for the first two minutes of a Sailboat session, sorted by situation.