Retrospective Sailboat Guide & Video

Formats available

  • 45-90 minute conference workshop
  • Half Day Retrospective workshop for teams
  • Retrospective Day

Being Agile : Retrospective Sailing is one of the most popular games teams adopt to reflect and map their way forward easily, in a fun, tactile and visual way.  It can be used for many purposes where you want to review what’s going well, what could go better, and ensure you are responding regularly to the changing seas and horizons your businesses and team face.  The game is a combination of coaching and agile tools, methods and approaches created and refined over the years working with teams to visualise information and develop ways to help teams to improve their agility.  There are other great variations of this game too created by others, all games that empower teams to reflect and move forward positively are great news for building an agile culture, and great sign that the approach works well for many teams.

This article is a collation of materials that will help you and your team to play Retrospective Sailing, it includes a step by step guide, Slides, a Video of a workshop in action, and examples of boats that have been created that I am able to share in the public domain.

The differentiator of this game compared to others is that this ensures that we not only reflect but we identify key actions and outcomes that help ensure that we are on course and any adjustments we need to make to our sails and anchors are captured to be acted upon as improvements.  It is important to not just plot the goal and current reality, but also the options and way forwards (GROW model – see my book for more details on GROW!).

I hope you find this guide useful, if you adopt and like this variety of Retrospective Sailing then please share it more widely, a credit is always appreciated, photos of boats by email and social media even more so! @belindawaldock or @beingagile

Enjoy being agile!


Sailboat Retrospective Guide

Find out more : read : Being Agile in Business

Agile retrospectives are a great practice for helping teams to reflect on what’s going well and what could be better, analyse their sails and anchors and identify opportunities for improvement or change.

Retrospectives within teams helps to encourage self organisation, management and improvement.

Agile Retrospective Sailing Game – Overview

Put the wind back in the sails of your team, raise the anchors holding you back. Try out the Agile Retrospective Sailing game with your teams today, you’ll need something to draw a boat on, some post it notes and pens.

Retrospective Sailing — an agile reflection game

A hands on workshop facilitating a practical retrospective game.

Retrospective Sailing is a game you can play as an individual in any role, as part of a development team, or, with clients and customers to help understand how your journey is fairing. This game will give you a new and fun way to run a retrospective to help to gain your bearings, identify what’s putting the wind in your sails, the anchors holding you back, and discover hidden treasure.

You’ll plot your mission and map a way forward that raises those anchors and catches the tide and a fair wind. Try it with your teams for some constructive fun, practical outcomes, and a useful tool for reviewing and finding a smooth course.

Retrospective Sailing Guide – being agile

For the exercise teams need a large sheet of paper, I like A0 (or whiteboard or similar) on which they can draw a boat and stick post it notes to.  Each member of the group will need post its and pens.  2 colours of post it notes are ideal, one for sails / anchors and one for improvements.

Step 1 – Get the group to draw a boat, a blue wavy line about 2/3 down the page is a good starting point.  Teams should be free to design the style of their own boats with 3 requirements – it should have a body – a hull, sails and an anchor.   Ideally have coloured markers, so the teams can get creative, it could be a yacht, a viking ship, a container ship, a cruise ship, pirate ship.  Allow the team at least 5 minutes to draw their boat and encourage them to add any extras to the picture too.  These can often indicate the mood of the team, good and bad metaphors – eg, sunshine, fish, sharks, icebergs, lightning bolts, stormy seas, flags, kraken, I have seen many props added!

TIP – It’s important not to give the team a template boat but let them draw their own, this gives ownership and buy in to the activity, drawing the boat also helps to act as an icebreaker and get all of the group participating and on the boat.  Encourage all members of the group to pick up a pen and add to the picture.

Step 2 –Name the boat – ask teams to name their boat, Boaty Mc Boatface often comes up of course, a sign of a playful group, again encourage the team to choose their own name and add it to the boat.  A name can indicate again the mood and position of the team currently, a boat called Titanic is a concern, they have literally drawn a sinking ship!

Step 3 – Add the mission, ensure every member of the group has post it notes and a sharpie – ideally all the same colour notes, save the other colour for later!   There is no one ‘scribe’ in this game, all participants can contribute!  Ask members of the group to think about what their boat represents, the topic or theme, this could be a project, an event, a product, the team, any topic.  Ask them to put onto post its what their mission is, what they want to achieve, and what is their goal, add these post it notes to the hull of the boat.  If more than one member of the group has the same thing, still add it to the boat, multiple notes show this mission is a shared one, and most likely important, group these together and discuss.

At any point should a member of the group wish to they can add another note to the mission, these often are identified when the team begin to talk about their sails and anchors next, equally post it notes can always be removed or amended, clarified or replaced as the game continues.  The boat can be saved and revisited as part of sprint reviews, where sails and anchors can be reviewed, rescored, removed, new sails and anchors added.

Step 4 – Add Sails and Anchors – ask the teams again using post it notes to add sails and anchors to their boat.

Sails represent things going well, what’s good, and what is putting the wind into their sails.

Anchors are the things that could be going better, the anchors holding them back and limiting progress.

Sometimes things can be sails and anchors, for example it could have good outcomes and bad, if this is the case ask for them to clarify this on separate notes.   Encourage all members of the team to write and add notes.  Ask the group to review the sails and anchors they have added, group them as appropriate.

Step 5 – Scale your sails and anchors – next ask the teams to scale their sales and anchors, their sails from +1  to + 10, is it a +1 or 2, a nice but relatively small in value sail, or a main sail that’s providing huge momentum, a +9 or +10.  The anchors from -1, a minor impediment, or -10 this anchor has stopped us moving forward at all.

Teams should discuss each note, seek to clarify the meaning of the note and then decide as a group where on the scale it should be.  Teams can vote by writing on post it notes, or using their fingers to all show their vote at the same time, once the team have discussed and scored one of two sails and anchors, the time to score others should decrease significantly and can be done using a higher or lower group voting approach.  Is it a bigger or smaller sail/anchor than the previous.

Step 6 – Once all sails and anchors have been discussed and scored, give each member of the team another colour post it note, again make sure everyone has notes so that they can add to the boat themselves.  This second colour is for capturing activities and improvements to help raise sails further, and raise up anchors.

The key here is that we look for small incremental improvements that can be made, remembering we want to take an agile approach to becoming more agile.  Ask groups to think of small actions that would raise one of the sails, or anchors on the boat by just one point, raise an anchor from a -6 to a -5, or raise a sail from a 2 to a 3.

Capture ideas for improvements on post it notes and place them besides the relevant anchor or sail, or in a cloud or a map representing ideas/instructions for making their ship ‘go faster’.  The idea here is that the team then have actionable improvements that can be added to their work backlog and schedule them into future sprints of work as improvement activities alongside their day to day activities.

Encourage the group to discuss these actions individually, the goal, the current state, the desired impact, any blocks to implementing it and how this can be actioned.  A person maybe allocated to the task, and an estimate of how big the task is, how long it will take and when it can be completed.  New tasks or activities may be identified too which can be discussed, or an improvement may need to be broken down further.

A great question to ask teams at the end of the session is what would happen to their boat if they cut away all their anchors.  Where would they be in 2 0r 6 weeks time, what would change?


Tips and Formatting

If there is more than one group in the room, its great to share content that has been added to the boats, and feedback regularly throughout the exercise, or at the end of the activity.

Timing, at pace this game can be run in 40 minutes on a theme that the team are already familiar with, with very good results, in effect the lack of time does encourage participants to write down what comes to mind without too much thought, scores are honest, decisions are made quickly, teamwork is encouraged.  The downside is that there is less time for groups to discuss and gain a shared understanding.    The exercise can also run for an afternoon, with 40 minutes for each section of the exercise, or anywhere in between, depending on the size and complexity of the chosen topic.

The game can be used for many themes and topics for review.  It can also be used as a great ideation tool where we are looking for ideas to put wind in our sails, or to map our activity, such as a pirate ship with the goal of breaking your product into a new market!


Powerful questions

using the sailing analogy you can ask a variety of powerful questions to help the team to reflect and plan their way forward

for example:

how do we make the boat go faster?

what would happen if we cut all the anchors?



Sailboat Retrospective – Slides, Video and Example Gallery

Below are examples of sailboats created at conferences and events with group participants.  The workshop works well at conferences to review the conference its self, or the theme of the conference as participants are all familiar with the topic.  If you would like to run this workshop at your conference or our help facilitating this with your team please do get in touch

 for updates to the game

created and developed by Belinda Waldock

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