sailboat image for retrospective

Sailboat Retrospective

You know the term ‘smooth sailing’? Imagine you could apply it to all of your current projects and future sprints. Using the Sailboat Retrospective technique can help you achieve team cohesiveness using a fun, visual exercise that gets all of your team members on the same page — or should we say— boat.

What exactly is a Sailboat Retrospective?

The Sailboat technique for retrospectives is a fun, interactive, and low-key way for your team to reflect on a project. It helps team members to identify what went right, what went wrong, and what improvements and changes can be made in the future. Usually the retrospective happens immediately after the completion of a project or sprint.

This technique uses the metaphor of a sailboat heading toward shore to help teams visualize their ship (team) reaching its ultimate destination (or ultimate goals).

Let’s look at a quick breakdown of the pieces involved:

Anatomy of the Sailboat Retrospective

In a Sailboat exercise, there are traditionally five main components:

• The sailboat: The team itself (or some teams prefer to make this the project)
• The island or shore: The ultimate goal or vision for the team (where it’s headed)
• The wind (or the sails): Things that are helping the team glide along (team strengths, competitive advantages of your product, good communication, etc.)
• The anchors: things that are slowing the team or project down or delaying progress (silos, areas of weakness, etc.)
• The rocks: the risks or potential pitfalls of a project (areas of tension, bottlenecks, competition, etc.)

Some Sailboat Retrospectives incorporate other aspects that fit into their vision such as the sun, which represents things that make the team feel happy or satisfied; or, choppy waves to represent something the team feels anxious about.

Some teams even scale their sails for bigger vs. smaller problems. If you have quite a few people involved in your retrospective or you have a lot of issues and need a way to prioritize, this is an option.

Feel free to get creative and add any aspects you feel would be beneficial to your retrospective. (This can be easily done via our Sailboat Retrospective template by adding additional columns. See below.)

Why is the Sailboat Retrospective technique so effective?

The effectiveness of the Sailboat Exercise lies in its ability to use relatable metaphors to help team members easily identify important strengths and weaknesses. Because it is more of a non-pressure approach, it can help team members feel relaxed and more open to communicate without overthinking things.

This exercise is a fun way to get your team out of their day-to-day and think about the ‘big-picture’ to continually improve processes. It can also be a nice way of mixing up your retrospectives to keep them fresh and engaging.

And just because it’s fun doesn’t mean it’s not effective! The average Sailboat Retrospective normally helps to identify around 3-5 action items . That’s 3-5 new ways that your team can enhance their performance!

How to run one with your team

Ready to try your own Sailboat method retrospective?

Note: This exercise should take around 60 to 90 minutes to complete.

1. First, gather your key stakeholders

Usually, a retrospective includes the Scrum Master, Product Owner and members of the Scrum team. If there are other key stakeholders for your specific project invite them to the retrospective as well. This specific type of exercise really benefits from having different opinions and perspectives.

If your team is distributed or remote (as many are these days) you can still perform the Sailboat Exercise. Consider using a great online tool designed specifically to help distributed teams facilitate retrospectives.

2. Set some ground rules

It’s important to set the tone for how you envision your retrospective going. There are a few things that should never be included in any retrospective, and the Sailboat method is no exception. Keep your retrospective free of:

And make sure the focus is on:

• Having a growth mindset
• Being optimistic
• Being open-minded and open to constructive criticisms
• Being a psychologically-safe environment

3. Sketch your Visual

The rough sketch below is a pretty standard depiction for this type of retrospective. If you don’t want to draw your own, a simple Google search of sample Sailboat Retrospective images can help you find more examples.

Your visual should include all of the elements you’ll be discussing in order to help facilitate the exercise.

4. Set up your Template

Next, you’ll want to set up the template you’ll be using to capture your team’s thoughts. You can use a white board and post-its for this, but we’d suggest using an easy-to-build online template ( like this one ) to keep things organized.

Add all of the categories you will be discussing to your template. Then, take a few minutes to explain in detail what each category represents.

5. Brainstorming and/or discussion

Once your categories are all laid out on your template, you can either ask your team to quietly brainstorm for each one, or you can hold a group discussion. Really, this depends on the communication style of your team.

If you feel it might be better to have team members submit their feedback anonymously, they can write out their notations on post-its and you can gather them before discussion. Once you have everyone’s thoughts and additions, add them to your template.

This is the final phase of the retrospective. At this point, you and your team should identify what the biggest successes of your project were and what attributes you’d like to carry forward.

Discuss your anchors (obstacles) and brainstorm ways to overcome them. Also discuss ways to mitigate your potential risks (rocks) and how close or far you are from reaching your ultimate goals.

Once everyone is on the same page, conclude your retrospective and move forward with a plan and improved understanding of team performance!

That’s all there is to it! We hope your team enjoys this retrospective and gains some valuable insights along the way.

Happy sailing!

Sailboat retrospective template and guide

This post is also available in: German

Retrospectives are an indispensable tool for assessing past performance and identifying areas of improvement. One way of ensuring retrospectives surface true insights is by leveraging the power of visual metaphors . This is where the Sailboat Retrospective can come in handy.

Whether your agile team is co-located or presently working remotely, a sailboat retrospective is a fun and engaging retrospective technique that ensures the entire team is aligned on the larger vision while simultaneously aware of headwinds and potential threats to project success. 

In this article, we break down how to use the sailboat retrospective template in 4 simple steps in combination with Conceptboard’s collaborative, online whiteboard . 

What is a sailboat retrospective?

A sailboat retrospective is a fun retrospective template whose visual nature makes it engaging for the entire team. It comprises 4 distinct sections. 

Use template

Wind (Drivers)

This section identifies the driving force behind the team’s success. Was it a helpful colleague? A clear project roadmap? A supportive client? It’s also an opportunity to recognize team members who made significant contributions in the sprint or project. The idea should be to keep these tailwinds blowing. 

Anchors (Bottlenecks)

Anchors are the factors that held the team back. What were the blockers that slowed down progress? It could be a lack of clarity about key objectives. Or an inability to see the bigger picture. Or maybe even a lack of motivation. This section is all about introspection and identifying what could be improved in the future. 

Rocks (Threats)

Rocks are risks that can threaten the team’s future success. This section forces the team to detach themselves from the immediate present and take a longer-term view of the project. It is important to identify threats before they result in damaging     

Goals (Vision)

For teams to perform and deliver results at an optimum level, it is important that the team share a set of common goals. The idea should not be to highlight operational minutiae, but rather focus on long and short-term goals. Is the goal to be the team with the quickest time to market? Or perhaps bring build products with the highest customer satisfaction score? This is an important section that drives team alignment. 

How to use a sailboat retrospective template?

Conceptboard’s ready-made template makes it easy to dive into a sprint or project retrospective with your team. Simply click on the ‘+’ button and choose ‘insert template’ to access a large range of templates across business functions. Follow the steps below for a successful retrospective session.

• Once you have inserted the template, share the board with the rest of the team. Click on the share button on the top right and add email addresses of stakeholders.
• Set a stipulated time and have team members add their feedback as digital sticky notes . To make feedback easier to track, have each person choose a specific sticky note color.
• Discuss the feedback shared and identify actionables. Use comments or the pen tool to highlight important feedback
• Download the template as a PDF or high-res image. Given that Conceptboard is a cloud-based whiteboard tool, the boards are saved automatically. 

Agile Retrospective templates

Unlike more traditional sprint retrospectives such as the lessons learned retrospective , visual templates such as the sailboat retrospective, the hot air balloon retrospective or starfish retrospective drive engagement and help teams focus on the big picture. The simplicity of the template means that no technical knowledge is required for stakeholders to add valuable feedback.

A retrospective is also a great idea to keep the team motivated, understand frustrations and improve processes. The collaborative nature of our visual templates acts as a forcing function to get teams ideating and solving problems together. If you are looking for additional sprint retrospective ideas, we’ve rounded up 11 retrospective ideas along with their corresponding templates you can use today. 

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Sailboat Sprint Retrospective Format for Development Teams' use

People learn in all different ways. Some prefer auditory activities, while others learn better through kinetic or visual practice. This sailboat retrospective template is fitted for those who like a visual and metaphorical representation of the ideas being discussed.

How to run the Sailboat Retrospective TL;DR: 

The sailboat retrospective is a great way to create a team vision while addressing any problems that may pop up along the way. This simple agile retrospective format , also called the Pirate Ship Retrospective, involves a little artwork and a lot of discussion. It's a 4 column retrospective format, similar to the wedding retrospective and KALM , which can be very effective in giving the team a platform to come up with a vision and understand what problems or issues are impeding it.

The sailboat retrospective looks like this:

• The organizer of the retrospective draws a sailboat with an anchor, rocks, some islands, and wind.
• It’s explained that each part of the drawing represents a part of the sprint: there are certain factors that slow it down, and others that are the driving force.
• The islands represent the team’s goals and visions. Those should be written down for everyone to see.
• The team is asked to write down everything from the past sprint that slowed them down or drove them forward. Those are placed accordingly on the drawing.
• These are discussed and the team votes on the critical items to focus on.
• Then, teams can start root cause analysis and come up with solutions and outcomes.

What Is the Sailboat Retrospective?

Picture a vision board, but more dynamic and specific. It includes points of contention, future goals, causes of stagnation, risk prediction, and motivating forces - all wrapped up in a relaxing and scenic illustration of a sailboat or pirate ship at sea. 

The idea is for team members to really see their words in action. The past and the potential. 

Conceptualizing what slows the boat (the team/project) down and what blows it in the right direction is a great way to compartmentalize what processes have and haven’t been working for a smoother path to future destinations. 

When Can the Sailboat Format be Used?

The sailboat retrospective, or pirate ship retrospective, like most scrum retrospective templates , should be used directly following an iteration, so that feedback is fresh in the memory. Steps for moving forward as a unified front can then be established for upcoming projects.

A General Guideline to Using the Sailboat Retrospective Template

Either physically or virtually on a versatile retrospective platform like GoRetro , begin with an illustration of a sailboat in some water to represent the past scrum/sprint/project/team. 

Draw an anchor dropped to the seafloor, to represent what weighed the team/venture down. Towards the front of the boat, draw an island to represent the ideal destination (goals). Draw some clouds blowing wind to capture the motivating forces that propelled the team towards the 'island', and finally draw some menacing rocks just below sea level - an obstruction to the boat's path/goals. Add any other elements you'd like.

With this illustration and its metaphors explained, allow team members to add their answers to each area of the drawing. For example, in the clouds, someone could stick a note that reads 'gestures of appreciation’ as something that kept their momentum and morale up. 

Everyone can then discuss these points and get varied perspectives on those that aren't unanimous. To keep things democratic, you can vote on these controversial decisions before taking any future actions. 

By the end, the goal is to have a clear idea of what parts of the process should be repeated and what new things should be implemented for future sprints. 

How to Run A Sailboat Sprint Retrospective In GoRetro

GoRetro makes so many retrospective templates so easy to execute. Once logged in, all your team members can be invited into the dashboard and onto the chosen template. 

Team members can attach their thoughts to the virtual illustration and even take votes. The platform hosts discussion and comment threads for clear and easy participation, and even offers AI support and suggestions! 

Once a vision of future strategies and processes is formed, action tasks can be assigned with due dates. Then, the entire retrospective process will be virtually recorded for reference at any time in the future to ensure that everyone is remaining on task with all their new tools and strategies. 

Who is this Retrospective For?

The sailboat retrospective / pirate ship retrospective is for everyone who took part in the initial sprint. Each individual plays a different role in the process and has new and useful perspectives to add to the collective discussion. Leaders, partners, and valued customers could also be present.

‍ Why Is the Sailboat Retrospective Agile Format Important?

Reflecting on what edits to make for future endeavors should always be an evolving process, full of trial and error, making retrospectives incredibly important. 

This one in particular is fun, simple, and diverse for different learning/participation styles and needs. 

It's an effective way to unify the team, reminding them they are all part of the same crew, on the same boat, going in the same direction and working together. 

Retrospectives are so important for the unity and morale of the team. Putting strengths and weaknesses into perspective is a key factor in refinement strategy and group support. These meetings, whether virtual or physical, are a great place for praise, deliberation, and refocusing. 

With more and more of your workflow taking place online, trust GoRetro to get your team together online, guide effective discussions and keep every detail of the minutes forever! 

Interested in other retrospective formats?

‍ From " What Went Well " to " Starfish retrospective ", " 4Ls retrospective " and more, GoRetro's offers a wide variety of retrospective templates . Pick up the best template for your team or create your own retro board using our custom option.

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Sailboat Retrospective

Chart a new course with your agile team or start a long journey off right

What is a Sailboat retrospective?

The Sailboat retrospective template is swimming in metaphor. If you can get the whole team on board, it can be a lot of fun (okay, we’ll stop with the puns now).

The Sailboat retro is almost game-like in the way it turns obstacles into objects to sail past, and goals into tropical finish lines.

Time to take your scrum team on a journey of continuous improvement.

What are the Sailboat retrospective prompts?

Let’s breakdown the metaphorical categories of this retrospective technique. Your team are a Sailboat, you’re all on board, sailing toward the island. It could be a speedboat or a cruiser. Just make sure it’s not a mutinous pirate ship!

This is your destination, your final goal, your objective or vision. This doesn’t have to be a single thing, it can be a metric you want to hit, or a list of goals you’d like to achieve, or something even less concrete, like a state you want your team to be in. 

Example: Close 100 percent of tickets at the end of the sprint, be in a rhythm of shipping features regularly

Large stones, coral reefs, icebergs, pirates—these are things boats should generally avoid. Things in this category are the potential risks you know about and should try to steer clear of. 

Example: Last sprint there were too many super tickets causing bottlenecks! Let’s have stakeholders break them down into small tasks to keep reporting consistent

Obviously your sailboat isn’t going to get anywhere if the anchor is weighing you down. Things in this category do just that: keep you from hitting your goals. Think of things in this category as the items or issues on your team that need to be resolved to make your journey more efficient. If the rocks are external, the anchor represents internal challenges.

Example: Spring break is coming up! Have a plan to balance workload for the parents on the team who have to take time off for their kids

A sailboat can reach its destination faster with a strong wind. Things in this category help your team . They can be things you are already aware of that you know help, or things that would help if you could have them next time.

Example: A strong Q2 budget for ad spend means we can test more versions of our winning creative

Benefits of the Sailboat retrospective

The Sailboat retrospective requires a bit of imagination but it’s fundamentally a visual way of running a retrospective.  The visual imagery forces people to think outside the box, which can result in some creative solutions.

You might also notice that there’s a lot of present tense bias in some of the phrasing of a Sailboat retro, and that’s because  this template lends itself well to looking forward . Yes, the name “retrospective” does imply looking back, but some teams can benefit from running a Sailboat retro both before  and  after a project. As a facilitator, scrum master or product owner you could use it for retrospective, post-mortems, or pre-mortems!

Using the Sailboat technique as a pre-mortem works because there’s a concrete goal—everyone knows where you’re going and why—so it’s easier to focus ideas. If suggestions won’t contribute to this specific journey, they can’t be implemented.

When to do a Sailboat retrospective

Just like the Four Ls retrospective, the Sailboat template can yield a lot of data, thanks to the broad prompts. The big difference here is that the Sailboat retrospective tends to focus that data a little more thanks to the journey metaphor .

It’s also a bit like the Start Stop Continue retro in its bias toward action—you’ve got a destination in mind and you need to incorporate feedback right away if you’re going to get there . Here are few instances where a Sailboat retro could come in handy:

For long journeys

The Sailboat sprint retrospective lends itself well to looking back on large undertakings and prepping for new ones.

Maybe you migrated a portion of your company to a new platform or software and you plan to move the rest of the company next year. Having sailed this particular course before, your team will have a better map of the risks and other hazards.

So in this case, the Sailboat retro could work as a postmortem and a pre-mortem. You know the issues you faced migrating the first half of the company onto the new software, and you’ll have a better idea of what to avoid (and what could help) as you onboard everyone else.

To encourage unity

The Sailboat retrospective is also a great template to use to build team unity. By shifting the view of a simple sprint or project into an ocean-spanning journey,  team members start to work together—like a ship’s crew—to make sure the journey goes smoothly for everyone next time.

If you want to increase morale and get the whole team involved, a Sailboat retro can get all hands on deck (sorry, just one more pun). 

To have some fun

Some like the Sailboat retro just because it’s a fun way to hold an agile retrospective. Visualizing the team on a boat, steering past craggy rocks on a course to paradise—what’s not to like?

The Sailboat retro also offers the team the chance to do a bit of communal storytelling, with everyone pitching in to figure out how to make their journey successful. Plus, tying goals, hurdles, risks and responsibilities to rich imagery can make those things more memorable.

How to run a Sailboat retro with Parabol

From your dashboard select your team on the right and then hit that vibrant  Add Meeting  button.

Select Retro Meeting with the arrows, then use the dropdown to select the Sailboat  retro template.

The Icebreaker box is checked on by default. You don’t have to do one, but we recommend it. They offer a chance to break the ice and get everyone in a chatty mood for leaving useful feedback.

Hit  Start Meeting  to kick things off!

Start your retrospective with an icebreaker

If you’re doing an  icebreaker , you’ll have a random question to answer. You can refresh it if you want another option, and of course you can create your own if you want.

Reflect, group, and discuss based on the Sailboat prompts

After the Icebreaker you’ll move on to the reflect stage. This is where you brainstorm what your island, rocks, anchor and wind are. Afterwards, you’ll group themes, do dot voting and finally set action items so you can chart a bold path forward.

Discover 35+ Retrospective Templates in Parabol!

Sailboat Retrospective

Sailboat Retrospective is a fun and easy way to boost the communication of what went well and what slowed the team during current sprint. Based on the topics addressed during the retrospective, the team agrees on the improvement activities needed for future sprint.

The tropical island represents the set sprint goal they have aimed to achieve in their daily work during the sprint.

The Wind represents everything helping them to achieve the sprint goal, pushing the team's sails boat to go even faster.

The Sun represents all the things making them feel good and happy during work. As a retrospective is a time for team celebration this is a highly appreciated topic to bring up and an opportunity to bring forward kudos to your team friends.

The Anchor on the Sailing boat represents everything that is slowing us down an holding us back on the journey towards the sprint goal.

The Reef represents potential risks ahead that we see will jeopardize future sprint work.

How to use the Sailboat Retrospective

Set the stage - start the Retrospective by introducing the team of the sailboat metaphor.

Reflect and write individually - Give each team member 7 min to individually write down stickies on the board in the different areas of the sailboat canvas.

Present and discuss in pairs - Have breakout sessions with 2 (or 3) persons in each breakout room where they present their stickies to each other.

Summarize - Each pair summarize the discussion during breakout so all team members can hear what has been discussed. Opportunity to ask questions if any.

Group stickies - In case of more than one sticky with the same topics the team agrees upon grouping them together.

Voting - Time for team voting on the topic(s) that needs focus going forward. It could be topics helping the team go forward so they need continue with these to keep momentum, or topics related to what is slowing them down or potential risks coming up.

Find Actions - Based on the highest voted topic(s) the teams agree on improvement action going forward in the next sprint.

• Meetings & Workshops
• Retrospectives
• Agile Workflows
• Facilitator
• Consultants

Submit your template →

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[Full Guide] Explain the Sailboat Retrospective with Examples

6 minutes read

Every team project has multiple possible ways of moving forward. The sailboat retrospective is a tool that allows your team to evaluate the process and find out if you are on the right path. With the sailboat retro, you initiate an open conversation with all team members to uncover all the things that might stand in your way.

In this article, we will explain this agile retrospective and provide you with some sailboat retrospective examples to help you fully understand it.

What Is the Sailboat Retrospective

The magic of the sailboat retrospective is that it asks you and your team members to imagine yourselves as the crew of a boat. If you want to reach your final destination (i.e. the sunny island), you must identify the dangers and the risks. At the same time though, you have to also recognize all those things that will help you move closer to your goal.

The sailboat retro is an agile retrospective that makes the evaluation process fun by taking advantage of the above metaphor. Therefore, every member of the team can visualize the project’s goal and the route towards achieving it. With a simple sailboat retrospective template, you can immediately get started with this invaluable technique.  

What Should a Sailboat Retrospective Include

Before you are in a position to understand and utilize a sailboat retrospective template, you must first learn what each element on the visualization represents. Then, you can study various sailboat retrospective examples to see what is often included in each one of these parameters. In more detail, a sailboat retro should contain all of these elements:

The Sailboat – at the center of any sailboat retrospective there is the sailboat. As you can easily infer, this element represents the team or the team members that are working on that particular sprint. They are the ones that work on that particular project and can give you invaluable insight.

The Lighthouse or the Island – in all sailboat retrospective examples, you will find that everything moves toward the lighthouseor the island. This happens because this element represents the end goal. All the other parameters are just some tools that will allow you to reach the destination as soon as possible.

The Rocks – no sailboat retrospective template is complete without the rocks. This visual element indicates the threats and risks that you will face. In the sailboat retrospective metaphor, this means that if your boat falls into the rocks, then you run the risk of sinking. What’s even more important in this case is that you must also identify hidden risks, that aren’t visible from the beginning.

The Wind or the Sails – another thing that you will find in any sailboat retrospective template is the wind or the sails. With this element, you will be noting all the things that make your project move forward. For instance, this might be a competitive advantage you have gained or particular skills that your team members have obtained.

The Anchors – another element that you will find in a sailboat retro is the anchors. In a boat, an anchor is something that prevents it from moving either forward or backward. Therefore, this element represents everything that puts a stop to your progress. In the sailboat retrospective examples, you will see that the anchors show the bottlenecks during the process.

The Sun – the final element that a sailboat retrospective should include is the sun. Even though this is an optional element, you can add it to highlight what makes your team work. In a sailboat retro, the sun shows what makes the team members happy and what makes their collaboration effective. The positive feedback will give everyone fresh motivation to keep up the good work.

When to Use a Sailboat Retrospective

As you can see, a sailboat retrospective is a useful technique. In fact, you will benefit from using it in various stages of the project. Namely, you can apply a sailboat retrospective template in these instances:

• Upon the completion of the project – one of the main uses of a sailboat retro is to evaluate how the sprint went. This way, you can create one upon the completion of the project to see what worked well and what can be improved in the future.
• In your regular team meetings – a sailboat retrospectiveis also commonly used in regular meetings to show the project’s progress. With this tool, you can identify bottlenecks, risks, and dangers as you move forward. This way, you can eliminate these hurdles before you come across them.  
• At the beginning of a new sprint – a sailboat retrospective template will also be very useful at the beginning of a new sprint. You can use the previous sprint to showcase the bottlenecks and challenges that you faced to create a new strategy that will eliminate them.
• When the project faces some challenges – a sailboat retrospectiveis especially helpful when you seem to have hit a wall. If your project isn’t progressing as you had planned, then this technique will allow you to consult with your team members and spot what is causing the issue. This way, you will be able to find solutions that will make your boat move closer to the island.

5 Sailboat Retrospective Examples

Sailboat retrospective example – app development.

We begin our sailboat retrospective examples with one that an app development team might find useful. In this example, the team examines all the elements that make their project move forward, as well as all the potential risks.

• The Sailboat – the app development team.
• The Lighthouse– launch the app in 1 month; get numerous pre-registered users for the app.
• The Rocks – the competitor app has added a feature that might outshine our app.
• The Wind or the Sails – the marketing team’s strategy is raising the public’s hype;the new UI has got great feedback.
• The Anchors – beta users have spotted bugs; code reviewing takes longer than expected; AI gives unpredictable answers.
• The Sun – communication between remote members is effective.

Sailboat Retrospective Example – Marketing

In the following example, we will take a look at a sailboat retrospective template used by a marketing team. In this case, the team wants to increase the sales of a particular product.

• The Sailboat – the brand’s marketing team.
• The Lighthouse– increase sales by 10% in the following month.
• The Rocks – brand awareness is low; competitors have a similar product.
• The Wind or the Sails – popular influencers have agreed to promote the product; the product hashtag is getting more views on social media.
• The Anchors – ad targeting is ineffective; the management has reduced the marketing budget.
• The Sun – new team members feel welcome; the product’s reviews are positive.

Sailboat Retrospective Example – Online Sales

In the following sailboat retrospective we are going to see, we are taking a look at an example from a retail store that wants to boost its online sales. In essence, this is another sailboat retro that a marketing team might use.

• The Sailboat – the store’s marketing team.
• The Lighthouse– increase online sales by 20% by the end of the year; increase the store’s mailing list.
• The Rocks – competitors offer similar discounts; our products aren’t unique.
• The Wind or the Sails – our blog posts are getting traffic; our client loyalty program offers incentives to shop online.
• The Anchors – e-shop is still in development.
• The Sun – the percentage of return customers has increased.

Sailboat Retrospective Example – Product Design

The next sailboat retrospective example comes from a design team that aims to create new product packaging. In this case, the team members are collaborating to create a design for a physical item.

• The Sailboat – the design team.
• The Lighthouse– create a packaging that attracts clients.
• The Rocks – the new packaging might not correspond to the public’s mental image of the product; the new packaging might not be accessible to everyone; the packaging’s material might turn off eco-conscious customers.
• The Wind or the Sails – our packaging suggestion is within the brand’s budgetary limits; the labeling has received good feedback from testers.
• The Anchors – the main designer is away on sick leave.

Sailboat Retrospective Example – UX Design

The last sailboat retrospective example is that of the UX design of a new website. In this instance, the design team needs to collaborate with the development team to create a user-friendly online application.

• The Sailboat – the design team; the development team.
• The Lighthouse– create a website where users can complete the task within 1 minute.
• The Rocks – the task requires many steps; the usability of the website needs improvement.
• The Wind or the Sails – usability testing is taking place without delays; a great percentage of test users complete the task within the time limit.
• The Anchors – beta testers have given conflicting feedback; the teams have difficulty finding enough time for meetings.
• The Sun – remote communication between teams is effective.

A Ready-made Sailboat Retrospective Template

As you have seen in the above sailboat retrospective examples, this is a versatile technique that can be applied to many different projects. Therefore, adopting the sailboat retrospective agile technique will significantly help you make your sprints progress smoother than ever before.

The truth is that you can create a sailboat retro graph as simple or as complicated as you would like. However, with a ready-made sailboat retrospective template , you will have a well-designed and professional base that you can use in your meetings. In Boardmix , you will find a sailboat retrospective template with which you can immediately get started.

How to Run a Sailboat Retrospective with Template

Once you create your Boardmix account, you will gain access to many features that boost the collaboration between your team members, even if they are working remotely. Therefore, running a sailboat retrospective with this online tool can become an easy process. Here is what you need to do:

Step 1 – Go to your Boardmix workspace and click the Templates button. There, you will find the ready-made template for a sailboat retro.

Step 2 – Share the graph you have created with your team members.

Step 3 – Once they have all accessed the sailboat retrospective, Boardmix allows you to have an online meeting. Namely, you can have a video meeting or enable the chat.

Step 4 – Then, each member can contribute to the sailboat retro. Every member can add sticky notes with their thoughts and every participant will see the changes in real time.

Step 5 – Finally, once the sailboat retrospective is complete, you can save it in various file formats or create an immersive presentation. This will help you present the graph to the management or stakeholders in a professional way. If you want to complete everything online, you can share it simply via a link.

Extra Tips to Boost Your Sailboat Retrospective

As you may have already understood, a sailboat retro is a technique based on good communication. Therefore, it is important to make your team members feel comfortable to share their opinions on the sprint’s progress. Some tips that will help you are the following:

• Set some communication rules before the meeting. This way, every team member will know that their opinion will be heard and valued.
• Study sailboat retrospective examples beforehand. By doing this, you can determine which questions you must ask to uncover all underlying issues with your project.
• Keep the meeting fun and light. A sailboat retrospective usually takes place after the project’s completion. This means that there is no pressure, and you should create a pleasant environment.
• Set time limits. During the meeting, you should use timers so that each team member has the chance to state their opinion.

Wrapping Up

The sailboat retrospective is an invaluable agile technique. Start using it after each sprint to identify what works and what doesn’t to make your projects move faster and more efficiently than ever before. In Boardmix, you will find a sailboat retrospective template to take advantage of its many benefits immediately. Just try it out now!

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How to Run a Sailboat Retrospective: A Step-by-Step Guide

Explainer video

Introduction

The power of the sailboat retrospective is in the way you visualize everything from the previous sprint. You can visualize the sprint goal on the template as your focus point.

Running the sailboat retrospective, you and your team are trying to find how to get the boat to smooth sailing. Searching for risks they'll face, seeing what is working, looking for things that are slowing them down, and making sure the sailboat is heading in the right direction.

The sailboat retrospective template is one of the top agile retrospectives you can use to improve your team!

The elements of the sailboat retrospective

The retrospective consists of five elements. The sailboat, the sail, the anchor, the rocks, and the island (the focus point of the retrospective).

It gives you, as the facilitator, the perfect starting point to communicate the exercise through metaphors.

The sailboat

The sailboat represents the entire team and their processes sailing to their goal. You can use the metaphor: "Is the sailboat heading in the right direction?"

The island represents the sprint goal of your team's last sprint. This is where the team wants to go.

What is giving us wind in our sails to go to the island? What helps us move forward?

The team focuses on the good things that are happening and are helping them achieve their goals. What efforts move the team forward to their sprint goal?

What is holding us back from going to the island?

Here the team focuses on the bad things that they are doing. They'll look for impediments and issues they've faced.

What are the rocks we face when going to our island?

The rocks represent the potential risks they'll face. This part of the exercise helps them to be proactive about oncoming risks.

The benefits of the sailboat excercise

The sailboat retrospective is a great tool to see if the team is doing the right things to hit their goal. They identify risks, see what is holding them back and get to know what is working.

It brings the team members on the same page and helps improve the team's success. It gives the scrum master valuable feedback that he or she can use to help the teams focus.

As with every retrospective , it helps the team apply continuous improvement in their workflow as described in the agile manifesto .

How to run the sailboat retrospective

Facilitating sailboat retrospectives is pretty straightforward. Every good retrospective has a chronological number of exercises. This format makes it easier for the facilitator and the agile team.

We are going over the sailboat retrospective template, and I'll give you some retrospective techniques where you and your team can focus when creating actionable items.

Set ground rules for the retrospective (+- 3 min)

During a retrospective, we take our team and ourselves under the microscope. This can be an uncomfortable experience for many of us. Therefore we need to set some ground rules with the team and create an atmosphere where people feel comfortable participating.

Good ground rules

• What is said in the retrospective stays between the participants
• It is encouraged to air dirty laundry and express opinions.
• Try to focus on organizational systems and process improvements.
• It is a blame-free environment
• Encourage participation from everyone

Introduce the sailboat exercise (+- 3 min)

When the ground rules are set, we can introduce our sailboat and what we'll do during the retrospective.

Here's an example introduction:

Team, today we are doing the sailboat retrospective. We, the team are on the sailboat. We're trying to go to the island which represents our last sprint goal. [Insert sprint goal]. During our trip we've been lucky to have great wind in our sails. But we noticed that our anchor has been dragging along and slowing us down. We're going to try to raise our anchor a bit higher so we can move faster to our island. Like every sail trip, we'll face some rock along the way. This is risky business. We'll try to inspect what is risks we'll likely face so we can improve our sailboat and go smooth sailing.

The sail (+- 10 min)

The first step the team members take is the sail. Here we are going over what is working for the team. This exercise helps the team loosen up for the harder parts of the sailboat retrospective.

One retrospective technique we'll use throughout is working together alone. This means the exercises are done in silence alone. After a set period, we'll present our ideas and choose one to continue with.

Before flying straight into the sail exercise, introduce it to your team.

The first part of the sailboat retrospective is the sail. We will look what helps us move forward in our journey to our island. [Insert sprint goal] We are going to all work in silence for [Insert forseen time] when we are writing down our thoughts. Write every thought down on individual sticky notes. Afterwards we'll present our sticky notes to each other. Are there any questions?

When time passed that the team worked alone, we'll present the sticky notes to each other and put them on the sail. Keep the presentation simple, don't go deeper into the topic that is written down. Just saying out loud what is written on the sticky note is enough.

The anchor (+- 10 min)

The second step in the sailboat retrospective is the anchor. Here the team will focus on what is holding them back from reaching their target. Here we are trying to find where our process is lacking.

Here we'll use the same retrospective technique working together alone.

You can use the following template when introducing the anchor to your team.

Now that we know what helps gives us wind in the sails and helps us move forward. We'll now focus on our anchor. What is holding us back for moving forward towards [Insert sprint goal]. We are going to work again in silence alone for [Insert forseen time]. Afterwards we are not going to present the items to each other. We're just going to stick them on the lower side of the sailboat. Are there any questions?

When the time has passed, let the team put the sticky notes on the bottom side of the sailboat.

The rocks (+-10 min)

The third step in the retrospective meeting is the rocks. What rocks lie ahead of the team? After this exercise, we'll have identified risks we can be proactive about.

Again, we're working together alone. Afterward, we can stick our sticky notes on the rocks below our boat.

Here's an example introduction to the rocks:

Now that you've written down our anchors for our team, we're going to look ahead and see what risks we face for reaching [Insert sprint goal]. Again, we're woriking in silence for [Insert forseen time]. Afterward, we'll stick our sticky notes on the rocks. Are there any questions?

When the time has passed, let the team put the sticky notes on the rocks.

Vote! (+- 10 min)

We've captured a lot of insights from our team. But where do we need to put our focus? This is where we're going to vote.

There are multiple ways to vote for a focus point with your team. Here we are going to use dot-voting .

Give each team member ten votes they can use to vote on the sticky notes. They can vote on their own post-its and vote multiple times on one post-it. There are no rules.

While the team is voting, they can rearrange the post-its to make groups of related items.

Here is an example introduction to the voting part of the retrospective:

Now that we've capture all of our insights it is time to choose where we want to focus on as a team. We'll do this with our voting dots. You can vote on your own items and vote on multiple times on one item. While we are looking over our insights, rearrange the items to group them toghether if they are related. Are there any questions?

After time has passed, take the item with the most votes and put them to the side of the sailboat. Continue this step until you've created a top 3.

Brainstorming session ( +- 15 min)

We now know where the team wants to focus its efforts toward improving its processes. Now it's time to brainstorm ideas to improve future sprints.

We take the most voted issue and rephrase it to an opportunity question. We use the "How Might We" structure to create an opportunity for our anchor or risk that has been chosen.

Take the "How Might We" question you've created and put it on the top of another whiteboard or flipchart.

While we are brainstorming, everyone should work in silence again.

Here is how I would introduce the brainstorming session:

It is clear for us as a team where we want to put our efforts to improve our processes. We are going to brainstorm on [Insert "How Might We" question]. You get [Insert forseen brainstorm time] to generate ideas that we can do in the next sprint to resolve [Insert problem statement]. You are working in silence again.

When the timer goes off, the team must select the best ideas. Here you can give them five votes to vote on the best ideas.

Create actionable items (+- 10 min)

The team voted on the best idea they've found. Now it is time to take action! An idea is great, but execution is needed to improve their current process.

For an agile team, this could mean updating their definition of done. Most of the time, you'll define an experiment you'll run with the team.

• When writing an experiment, consider the following questions.
• How long will this experiment run?
• Who is going to conduct this experiment?
• What is the expected outcome of this experiment?
• When are we going to reflect on this experiment?

You can write your experiment in the following format:

What? Only allow our premium users to use the model. Who? Team Zebra When? Next sprint Expected outcome? Our premium users use the machine learning model more. Reflection date? 20/04/2023

The sailboat retrospective is a great tool to create team alignment for improving the team processes. The metaphorical way helps the facilitator and the team in the process to identify areas where they can improve, what is holding them back, and the risks they'll face.

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Sailboat Retrospective

Embark on a nautical journey with the Sailboat retrospective. This imaginative format invites teams to visualize their journey, challenges, and aspirations through the metaphor of sailing. It's not just about reflection; it's about doing so with creativity and a touch of whimsy. Perfect for teams that appreciate a break from the conventional and are eager to set sail on a sea of fresh perspectives.

When to Choose Sailboat

The Sailboat retrospective is ideal when you sense the team needs a jolt of creativity or when the usual formats seem to have lost their spark. It's especially effective for teams that benefit from visual metaphors, helping them see challenges and goals in a new light. If you're aiming to infuse some energy and imaginative thinking into your retrospective session, let the Sailboat guide your team's discussions.

Set the scene for a maritime adventure. Play some soothing island tunes and kick things off with an IceBreaker . It's all about creating a relaxed and cheerful ambiance, setting the stage for open and positive discussions. 🌺

Things helping the team

Just like the wind propels a sailboat forward, this column is about the positive forces driving your team. It's a space to acknowledge the tools, practices, or even team dynamics that are pushing you in the right direction.

Things slowing the team down

Anchors, while essential, can also hold the boat back. Here, the team can discuss what's weighing them down or preventing them from moving at the desired pace. It's about identifying obstacles and brainstorming ways to lift them.

The risks or potential pitfalls

Every sailor is wary of rocks – they represent unseen challenges. In this section, the team can discuss potential risks or challenges that might be lurking just beneath the surface, ensuring they're prepared to navigate around them.

The ultimate goal or vision

The island symbolizes the team's aspirations – the destination they're striving towards. It's a reminder of the bigger picture, the ultimate goals, and the vision that the team is working towards.

The Sailboat retrospective is more than just a feedback session; it's a creative journey. By visualizing challenges and goals in the context of a sailing adventure, teams can gain fresh insights and perspectives, making the path to continuous improvement an engaging voyage.

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Sailboat Retrospective

gather insight about the state of the team, project or company

What is a Sailboat Retrospective?

The Sailboat Retrospective is a reflection method where a team reflects on what helps them move forward (Wind) and what holds them back (Anchor). It helps the group to feel united in the same boat and reflect on the current state of a project in a visual and constructive way.

How does a Sailboat Retrospective work?

Step 1: What moves us forward?

Bring the group's attention to the area above the water where the wind moves the boat forward. Ask "What is already working well in this project?". After the time runs out, each participant reads out their post its without explaining them in length.

Step 2: What holds us back?

Turn your attention below the sailboat. The anchor represents everything that is slowing down the group on their journey. Ask "What problems and obstacles are holding us back?"

Recommendations:

• Encourage the group to create multiple post its
• Look for duplicates on the area below the sailboat
• Follow-up with Dot-Voting on the most important problems

What is a good example for a Sailboat Retrospective?

A good example for the Sailboat Retrospective is to do the method as part of a project check-in meeting. The two areas allow the team to reflect on their practices and activities in the past quarter and to get a good overview of what the team collectively values and would like to change.

Below, you see an example of what a Sailboat could look like at the end. As you can see, this provides a transparent overview of the current state of the project and what matters for the team.

Who invented a Sailboat Retrospective?

Sailboat retrospective template download, sailboat retrospective miro template.

• Click the button below, to open the Sailboat Retrospective Miro Template
• In Miro click on the name of the board in the upper-left corner, to see the board info card
• Click on the Duplicate button in the info card to add the template into your own account.

Sailboat Retrospective Mural Template

• Click the button below, to open the Sailboat Retrospective Mural Template
• In the new tab click on Create mural from template to create a new Mural board with the template in your account

Tip: You can also click "Save for later" to save the template into your account and use it in the future.

Sailboat Retrospective PDF Template

To download the Sailboat Retrospective PDF Template, simply click the button below.

Questions & Answers

More templates to try.

Sailboat Retrospective

Keeping your retros fun is vital for maintaining high team engagement in the long run and continuously improving your process. If you have come to this conclusion yourself, why not spice things up occasionally with a different retrospective format like the Sailboat retro?

It gives you the opportunity to inspect your process from the perspective of a crew sailing a boat headed toward an exotic island. 

What is a Sailboat Retrospective?

The Sailboat is a fun way of doing retrospectives by looking at your work as part of a sea journey. Imagine your team as the crew of a boat propelled by the wind and each Sprint is like a stage of the trip towards your goal of reaching the land you see ahead of you.

The topics you discuss during a Sailboat retrospective are focused on keeping the journey smooth and analyzing the problems that make it more difficult. Typically, areas of conversation during a Sailboat retro fall under one of the following categories:

• Life preservers

The wind is what drives your boat forward and helps you reach the island. It represents what went well during the Sprint and the practices you want to continue encouraging within the team in the future. Examples of ‘wind in our sails’ usually include instances of collaboration or efficient communication among team members. 

Anchors are problems or inefficiencies during the Sprint that held you back from sailing at an optimal pace. Examples of anchors in the team process include changing priorities, a slow review process, or a redistribution of resources that stalls out the team.

Life preservers are things that helped you or could help you in the future, to avoid difficult situations or save your sprint from failing.

Rocks represent the hidden risks that endanger the boat and could prevent your team from reaching the island in the near future In a team context, examples of these instances include the presence of technical debt or a manual system that will need to be automated in the future.

The island towards which the team is moving is a representation of a predefined combination of goals that the group aims to achieve together. These goals can be both short-term or long-term.

How to Run Sailboat Retrospectives with Your Team

If you are eager to apply Sailboat retrospectives, you can get one set up very quickly either physically if you’re co-located or virtually. This format aims to help your team escape the mundane meeting routine and encourages group members to think outside the box. So, shifting from your usual retro format will be well worth it!

Sailboat retros are still retrospective meetings, after all. Consequently, you can stick to the golden rules for organizing a retrospective:

• Allocate a 60-90 minute time slot at a regular cadence on your team calendars
• Invite your team and aim for full attendance every time 
• Set the ground rules (e.g. no judgment, blame, or negativity) by highlighting any retrospective’s prime directive:

"Regardless of what we discover, we understand and truly believe that everyone did the best job they could, given what they knew at the time, their skills and abilities, the resources available, and the situation at hand."

--Norm Kerth, Project Retrospectives: A Handbook for Team Review

Begin by visualizing the four categories for grouping topics during the retro. Some teams draw the boat on a whiteboard and visualize the wind, anchors, rocks, and life preservers around it. During the retro, the team adds sticky notes next to or on top of the appropriate category.

For a more structured solution, draw four columns on a whiteboard for the respective categories and place tickets under each of them during the retro. 

If you are running an online retro with a remote team in ScatterSpoke, select the Sailboat retrospective template that comes ready out of the box, available in both canvas and column layout formats.

With everything in place and the team gathered (physically or virtually), tackle four questions in regards to your last Sprint:

• What propelled us forward?
• What delayed us?
• What saved us from failing to complete the Sprint?
• What could have failed us so we can prevent the danger in the future?

Each person writes their answers on separate tickets and places them under the appropriate  category. Use the topics generated to center your discussion around activities you might undertake in order to ensure that you continue practicing what is propelling your boat forward. Take some time to discuss the items under “life preservers” to bring everyone’s attention to circumstances or tools that got you out of any difficult situations that occurred during the Sprint.

It is also very important to go over the items under “rocks” and “anchors” to decide how to mitigate existing risks in the future and prevent delays going forward.

If you are unable to reach an agreement, use voting to your advantage. Assign everybody three voting points and ask them to vote for the problems with the largest negative impact (in their opinion). The items with the highest number of votes will become the focus of your improvement efforts for the next Sprint.

Based on the results of your voting, defined action items that can contribute to fixing the most significant problems as a team and close the retrospective. For greater accountability, the Team Lead can specify an owner and a due date for each action item.

Why Should You Run Sailboat Retrospectives?

The short answer is - because they are fun. The more your team enjoys your retros, the greater the value they’ll bring in the long run. In addition, the Sailboat retrospective format enables you to look outside of the box and analyze your work from an entirely different perspective.

They facilitate an environment conducive to diving deeper into your work process and talking about more than just what went well and what didn’t during a Sprint. This can prove to be a trump card for continuously improving your process.

ScatterSpoke helps you eliminate waste in your dev process.

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Sailboat retrospective template

Reflect on a journey of completing a project from start to finish

Use the sailboat retrospective template to assess how well a project has been executed and identify areas for improvement. It allows team members to reflect on their progress and make changes as needed so that they can continue to improve their work process.

Sailboat retrospectives use a sailboat voyage as a memorable metaphor for the journey of completing a project or initiative from start to finish.

The sailboat retrospective template helps you:

• Recognize what went well in a project and why
• Identify potential risks or problems coming up in a project
• Reflect on problems faced and how to fix them
• Align with teams on a shared goals and upcoming milestones

How to use the sailboat retrospective template

1. warm up the team.

Start off the activity with an icebreaker or warmup to get the team members engaged and ready to collaborate.

2. Introduce the sailboat framework

If teams are new to this framework, introduce each section of the template and what it means.

The four basic components of a sailboat retrospective are:

• The wind in our sails (what is helping to move your project along?)
• The anchor (what is holding your project back?)
• The beacons (what outcomes are on the horizon that you're working toward?
• The barriers (what blockers are there in the way of realizing your project's goals?)

3. Start adding sticky notes individually

Start a timer for 5-10 minutes and give team members enough time to individually add sticky notes in each section of the whiteboard canvas

4. Review the sticky notes

Go by each section and review the ideas. Group common topics together to identify recurring themes.

5. Identify the top priority

Discuss and vote on the most important themes to address. What’s slowing down the team or causing the most frustration?

6. Define next steps and action items

Take the topics the team voted on and start identifying ways to fix them for future sprints in the spirit of continuous improvement.

Tips for running a sailboat retrospective meeting

• Use Mural’s private mode to allow participants to add feedback anonymously to ensure even sensitive topics get visibility
• Start a voting session with stakeholders to prioritize efforts and align the team
• Make sure to cluster related sticky notes together to help you identify trends and common themes

How to create a Sailboat retrospective template

Use mural's unique features make sailboat retrospectives a breeze.

Tags on sticky notes

Customizable labels make it easy to find, organize, and categorize your work in a mural.

Private mode

Avoid groupthink and get authentic feedback by allowing collaborators to add content privately.

Real-time collaboration

Add more productivity and engagement to meetings and calls with features to guide collaboration.

Easy sharing

There are no barriers to collaboration with the ability to safely and securely share murals with others.

Keep collaboration moving forward with a timer to structure and time-box activities.

Anonymous voting

Gain consensus and reach alignment quickly, either in real time or asynchronously.

Sailboat retrospective template frequently asked questions

What is a sailboat retrospective, how is the sailboat retrospective different from other agile or sprint retrospective methods, what are the four main questions to ask in a sailboat retrospective.

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Sailboat retrospective

Retrospective Idea – Set sail on a bon voyage with an agile and adaptive team.

What is a Sailboat retrospective?

Heard of the term “smooth sailing”? This agile retrospective technique turns your team into the crew of a sailboat travelling to its final destination:  a sunny island. It uses this metaphor to help the people reflect on the last sprint, in order to determine the best way to navigate going forward.

Imagine that your team is working together aboard a sailboat heading on a journey to your final destination. Along the way, you are propelled forward by the wind. You can be slowed or stopped by the anchor. You will have to avoid icebergs, reefs or rocks, but you have your mind set on the sunny island where your team hopes to land and celebrate. The Sailboat retrospective takes this adventurous imagery and helps you to apply it to your last sprint.

Sailboat retrospective format

Before starting the Sailboat retrospective, ask the team to imagine themselves as the crew of the sailboat. Another way to think about it is that the Sailboat is the product, project or epic that they are working on. Now, ask them to consider the following.

What is the final destination for the team? What is their goal or vision? This is where they are heading to and represents their version of success.

The Wind (or the sails)

What is pushing the team forward towards their vision? What is driving them towards the goal? It could be their own capability, support from champions, being well resourced or being motivated by a common goal.

What would slow the team down, or bring them to a complete stop? What would create drag and reduce velocity? It may be a dependency or policy. It could be a lack of process or one that is too complex. Some anchors may be necessary, and others need to be considered to see if they will be a constant drain on the team, making them less agile and achieving less progress.

What are the risks or potential pitfalls along the way? What does the team have to watch out for? There may be communication gaps, the response from competition or technical risk that could unhinge the team. Understanding what the risks are early can help the team think of ways to navigate around them or put signals in place as a warning as part of the next sprint.

What is making the team feel positive? What are the good things that can come out of this? These may be things that they look forward to and may include customer feedback, usage or improving the robustness of their infrastructure.

Some other aspects that people can include into their Sailboat Retrospective template include Choppy Waves (Things that make them feel anxious) or Calm Waves (Things that can help them experience a state of flow ).

This style of retrospective can be used when your team is having trouble completing a task. Having the ability to see what has been slowing you down and what you have achieved despite this, can be helpful in providing confidence when trying to complete a difficult task.

Suggested icebreaker questions for the Sailboat retrospective

• What is your ideal island holiday?
• Which would you rather have: a sailboat or a speedboat, and why?
• Who would you want to be your sole companion if you were stranded on an island?
• If your boat is sinking and you can only save one thing, would you rather save your gold or your pictures?

Retro Rehearsal

Invite your team to rehearse the retro referencing their life journey so far.

Then ask them:

• What has pushed them forward to reach their goal?
• What has slowed them down?
• What has made them feel better throughout the journey?

Ideas and tips for your Sailboat retrospective

• The Sailboat retrospective aims to reduce the focus on any one person. It treats the team as a team and the sailboat as the project. This is a good time to remind people that they are there to help and support each other and that the goal is to help everyone reach the final destination together. No one gets thrown overboard, and no one left behind!
• Aim for a few action items that come out of your agile retrospective that will help you course correct. While it’s good to dream and to ponder, it’s also important that the team walks away knowing that their sailboat is travelling at the right speed in the right direction, or that there is a course change that is needed.
• Fold up a ship and float it in a bowl in front of the team or camera to bring your retrospective to life!
• If you are a remote team, you can request each member to change their screen background to a place they hope to visit on their next trip.
• Utilise team health checks to measure and track your team’s happiness over time. The Team Health Check   is a specialised self-evaluation tool for agile project teams that wish to improve their collaboration in order to achieve project objectives.
• Have fun looking back. Request input from the team about each retrospective to identify a structure or activity that people enjoy so that you may conduct them more frequently. People frequently learn more effectively when they are having fun or laughing while learning.
• Using a timer, you can Timebox discussions. This will keep the conversation on track and the retrospective on course.
• A good way to conduct the sailboat retro is to discuss ways to mitigate the identified risks and to prioritise the factors that are slowing you down. It should be clear what steps can be taken to fix, avoid, mitigate or eliminate the problem.

How to run a Sailboat retrospective in TeamRetro

Start your retrospective in a click Log into TeamRetro and choose your sprint retrospective template.

Discuss the most important things first You and your team discuss the top voted ideas and can capture deep dive comments.  Presentation mode allows you to walk your team through ideas one-by-one and keep the conversation focused.

Review and create actions

Easily facilitate discussion by bringing everyone onto the same page. Create action items, assign owners and due dates that will carry through for review at the next retrospective.

Share the results Once you have finished your retro, you can share the results and actions with the team. Your retro will be stored so you can revisit them as needed.

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Project Management

Sailboat retrospective: for agile software development teams.

Engineering Team

February 1, 2024

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So much of the agile software development process is iterative. Sometimes it feels like a project never ends! But, sure enough, your team successfully crosses the finish line. Instead of simply moving on to the next project, the agile methodology requires retrospective meetings that analyze what went well and what you should change for next time. It’s all in service of fine-tuning your workflows and processes to boost team cohesion and work quality. 

Like any process on an agile team , retrospectives need structure. If you haven’t tried it yet, the sailboat retrospective technique is a true game-changer. This technique not only makes retrospectives more engaging but also provides a clear visual metaphor to help teams navigate the complexities of a project. 🛥️

Whether you’re a Scrum master , product owner, or member of an agile team, sailboat retrospectives will help you identify potential risks, celebrate what went well with the last sprint, and set goals for the next sprint. In this guide, we’ll explain what a sailboat retrospective is and offer tips for practicing retrospective techniques in ClickUp.

• What Is a Sailboat Retrospective?

The wind (or the sails)

Running a sailboat retrospective, the concept of sailboat retrospective within a scrum framework, why project managers choose the sailboat retrospective, educate your team, create a comfortable environment, embrace visual aids, manage time carefully, focus on actionable outcomes and next steps.

What Is a Sailboat Retrospective ?

Agile software development teams use sailboat retrospectives to reflect on past sprints or project phases. Retrospectives are the final agile ceremony project managers oversee to improve the quality of future projects. The goal of any retrospective is continuous improvement. After all, it’s easier to do better next time if you know what to avoid. 

While you’re free to use any retrospective technique you like, the sailboat method is different because it uses the metaphor of a sailboat on a journey. It’s less dry than other retrospective techniques and gives your Scrum team a fun way to visualize progress, challenges, and future direction. 

In a sailboat retro, you imagine the project as a sailboat moving toward a common goal. During the session, team members use sticky notes to write down their thoughts on each component of the sailboat, which you place on a whiteboard and review together. The process encourages brainstorming and open discussion, culminating in a list of helpful action items for future sprints. 

Sailboat retros might be too abstract for some teams, but many project managers like how they act as a fun icebreaker that also aligns the team on areas of improvement. It’s much more fun than staring at a wall of bland text for two hours, isn’t it?

Components of a Sailboat Retrospective

A sailboat retro is a helpful agile project management tool. Since it uses metaphor, it’s easier for teams to think critically about future sprints. During a session, your team will document their thoughts on each component of the sailboat, which you later use to map out future projects.

The goal of a sailboat retro represents the destination. Think of this as the “X” on a pirate map. Some teams refer to this as the “island” your sailboat wants to reach. The goal could be just about anything, from the end of a sprint to the completion of a major project phase. What matters is that you choose a significant milestone for the team to work toward. 🌻

The wind or sails symbolize the positive forces that move your sailboat closer to its destination. This includes all of the successes, strengths, and good conditions that had a positive impact on the last sprint or project phase. It might include things like specialized certifications, a boost in department funding, or being able to outsource some of your team’s workload. 

In a sailboat retrospective, the anchor represents challenges or obstacles slowing the team’s progress. Anchors are anything that hinders your progress, like communication issues or resource limitations. 

Rocks are potential risks or foreseeable challenges in the sailboat’s path. While you look at the anchor in the past tense, rocks look forward and require the team to proactively plan for known issues. The goal is to minimize their impact on the next sprint. Rocks could include regulatory changes or continued resource limitations.

Finally, the sun represents your team’s objectives beyond the primary goal. This element adds a layer of motivation and inspiration, focusing on the team’s long-term objectives and vision. The focus here is to identify good things that came out of the project, like an improved product or positive customer feedback. It’s important to end on this note so your team can visualize the value of their hard work.

Ready to run a sailboat retro with your entire team? The good news is you don’t have to create the visuals on your own. We might be the world’s favorite project management software, but ClickUp also includes hundreds of free templates for anything you need—including agile retrospectives. 

Simply pull up the ClickUp Sailboat template during your team meeting and you’re off to the races. Start by inviting all employees to the retrospective meeting and run through this process together: 

• Set goals: Decide on a specific destination or milestone. If you’re already set up in ClickUp, this will likely come from your ClickUp Goals
• Collect supplies: Every boat needs supplies before a long voyage, right? During this stage, you chat about the necessary resources and supplies to support your goal. That might include personnel, software licenses, and other necessary equipment
• Check the weather: Can you expect smooth seas or stormy, treacherous waters? This stage of the sailboat retro looks at potential issues in the pipeline. The ClickUp Sailboat template integrates with your ClickUp Calendar view to give you a quick snapshot of your journey so you can plan accordingly
• Build a roadmap: Goals and calendar in hand, it’s time to build a roadmap with your team. During this step, you’ll decide on timelines and visualize them with tools like the ClickUp Gantt Chart view
• Prep your boat: Any seaworthy vessel needs a thorough inspection before setting sail. In this stage of the sailboat retro, you’ll map out tasks, assignees, and any other essential elements to support your next sprint
• Set sail: Finally, your team is ready for their next big voyage. At this stage, project managers continue refining their projects, tasks, docs, and workflows for better project outcomes 

Ultimately, this fun metaphor will help you get organized, plan for future problems, and agree on a shared vision. Since this sailboat retrospective template helps bring all of your work together into one dynamic platform, implementing your sailboat retro is as easy as a few clicks. 🚣‍♀️

The sailboat retro sounds like way more fun than a typical sprint retrospective brainstorming session, but how does it fit within a Scrum framework? 

It might be more creative than other retrospectives, but the sailboat approach aligns well with Scrum principles because it’s:

• Adaptable: Sailboat retros encourage teams to reflect on past performance (wind and anchors) and anticipate future challenges (rocks), which is essential for the always-adapting nature of Scrum project management
• Collaborative: This retrospective technique promotes open communication because all team members get a say on what hindered the team and what went well. That’s a perfect fit for Scrum’s emphasis on strong teamwork
• Goal-oriented: The focus on a common goal (or the destination, if we’re following the sailboat metaphor) fits with Scrum’s focus on delivering value while meeting sprint goals

Fortunately, the sailboat retro process isn’t much different if you follow the Scrum framework:

• Conduct a sprint review: Review the outcomes and deliverables of your most recent sprint with the team
• Conduct the sailboat retrospective: Visualize the entire project with the ClickUp Sailboat template . Ask the team to write their thoughts on sticky notes for the wind, the anchor, the rocks, and the sun. Review everything together to summarize key insights and lessons learned
• Determine action items : Mobilize your insights by deciding on action items at the end of the meeting. Plug action items into ClickUp with assignees, notes, and due dates to keep the next sprint on track

Sailboat Retrospective vs. Other Retrospectives

Sailboat retrospectives are a fun, metaphorical way to do project post-mortems, but they certainly aren’t the only way to review project progress. It’s one of many potential sprint retrospective formats , each with a different approach:

• Sailboat vs. Starfish: A starfish retrospective categorizes feedback into five buckets: Start, Stop, Continue, More of, and Less of. This is a broad framework for categorizing feedback from your team, customers, and other stakeholders, which can be helpful. However, sailboat is more of a visual and metaphorical approach, making it easier for your team to engage in the retrospective
• Sailboat vs. the 4 L’s: The 4 L’s stand for Liked, Learned, Lacked, and Longed For. Like a sailboat, it focuses on individual feelings and experiences. However, a sailboat is more useful because it also looks at external factors (wind and anchor) that affect the team, giving you a more holistic view of the project environment
• Sailboat vs. Mad Sad Glad: Mad Sad Glad is a more emotion-focused retrospective that lists team members’ feelings about a project. The sailboat retrospective does account for emotions, but it primarily focuses on factors that affect the project’s progress and future risks. That’s more business-focused than, say, someone feeling sad that the project is over

The right retrospective approach depends on your goals and corporate culture. Even so, more project managers are gravitating toward sailboat retrospectives because they’re:

• Highly visual: The sailboat metaphor is easy to understand, promoting better engagement and participation
• Comprehensive: We like the sailboat retrospective because, unlike other retrospective techniques, it offers a more holistic view of projects and provides a more well-rounded analysis
• Feedback-focused: Most employees find the metaphorical, fun approach less intimidating than other retrospective methodologies. In practice, this makes people more likely to share challenges and risks they might not have shared otherwise
• Flexible: You don’t have to be on a large enterprise software development team to do a sailboat retrospective. This technique adapts to various team sizes and departments, making it a helpful tool for any agile team

Sailboat Retrospectives in Practice

At this point, we know what a sailboat retrospective is and how to run one for your team. But how do you actually implement what you learned in the sailboat retrospective? Follow these pro tips to translate your retrospective insights into tangible business results. 

Your team might say, “Huh?” if you walk into the room with a big chart with a sailboat on it. Brief your team on the sailboat retrospective method before the meeting. Always explain the metaphor at the start of the session, even if you’ve done sailboat retrospectives before. Not everyone will admit that they don’t know what’s going on, so a little refresher does wonders for understanding and participation. 

You want to encourage honest, helpful feedback, but people won’t share their honest feelings if they feel uncomfortable. Foster a safe and open atmosphere where team members feel comfortable sharing their thoughts. If you still struggle to gather candid feedback, give your team the option to share anonymous feedback instead. 

Sailboat retrospectives are highly visual, so you need some kind of visual aid going into this meeting. Whether it’s a physical whiteboard or a digital Mind Map in ClickUp , have a clear depiction of the sailboat, wind, anchors, rocks, and sun.

Retrospectives can quickly run off the rails if you don’t watch the clock. Honor everyone’s time by creating a loose agenda for the meeting that breaks down what you’ll discuss and when. If your team has a habit of going over time, assign an official timekeeper and meeting facilitator to keep everyone on task. ⏱️

Other retrospectives, like Mad Sad Glad, focus too much on feelings. Emotions are a helpful type of feedback, but they aren’t very actionable. The sailboat retrospective is useful because it emphasizes what went well while also addressing what you could do differently next time. Instead of getting too hung up on subjective assessments, focus on desired outcomes and the steps required to achieve those outcomes. That will translate into tangible change that improves the quality of future projects.

Run Better Sailboat Retrospective Meetings in ClickUp

Sailboat retros are useful for understanding how your team feels about past projects and help propel the team forward in future sprints. Executed well, they help you identify risks, eliminate future bottlenecks, and provide clear goals for your next big project.

There’s just one little problem: Most retrospective sessions happen independently of your tasks, reports, and chats. That requires flipping through multiple project management tool s, which is a recipe for confusion.

ClickUp’s all-in-one project management tool brings metrics, templates, Goals, Dashboards, tasks, and multiple views into one place—even for technical teams. See the difference for yourself: Create your ClickUp Workspace now for free .

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The Sailboat Retrospective is a fun and creative way for teams to reflect on the sprint and identify areas for improvement. It’s called “Sailboat” because the metaphor of a sailboat helps the team visualize their journey, the obstacles they faced, and the direction they want to sail towards in the future. The Sailboat or Speedboat Method for Sprint Retrospectives is an easy way to: adopt, reflect and map the team’s way forward easily, in a fun, tactile and visual way. It helps the team to reflect on what’s going well and what could be better, analyze their sails and anchors and identify opportunities for improvement or change.

The idea is that the team is on a sailboat, heading towards their goal while dealing with winds and icebergs along the way. Winds help propel the boat forward but obstacles such as pirates, rocks, and stubborn anchors represent the risks that the team might encounter that could slow them down or even stop them from getting to where they need to be.

• Boat : The Scrum team
• Sails : The things that helped us move forward (Wind, Cloud)
• Anchors : The things that held us back (Pirates, Rocks, Sharks, Icebergs, and Anchors)
• Island : The goals to be achieved
• Sun : What the team liked, the actions or attitudes that deserve thanks
• Reef : Represent future obstacles that have been identified, which the group is likely to encounter in the subsequent iterations.

Note : The original Sailboat technique doesn’t have a Sun – I added it to give them a feeling of accomplishment as most teams should understand that there are already things that work just fine. And it’s definitely worth the time to help the team to build on this base.

• Fact-based Analysis for Sprint Retrospective
• Start, Stop, and Continue Sprint Retrospective
• Glad-Sad-Mad Sprint Retrospective
• Starfish Sprint Retrospective
• Sailboat Sprint Retrospective
• Liked Learned Lacked Longed For (4Ls) Retrospective

Different Steps of Sailboat Sprint Retrospective

Step 1: set the stage – draw a sailboat.

Start by setting clear expectations for the meeting, including the purpose, goals, and agenda. Make sure everyone is aware of the retrospective’s purpose and that it is a safe space for open and honest communication.

Let the team draw a picture of a sailboat floating in the water, and fill half the space above and half below the water with the sun, anchors, wind, rocks, reef, and an island or you can simply print pictures and just attach them to the board or any available wall space. This visual representation can help the team better understand their progress.

Note : Team drawing the boat helps to act as an icebreaker and get the group participating and on the boat.

Step 2: Name the Sailboat

Decide the topic/theme of the retrospective and name the boat accordingly.

Step 3: Add mission

Ask the team to write what their mission is, what they want to achieve, and what their goal is, and add these post-it notes to the hull of the boat. The team can amend or clarify or replace 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, and new sails and anchors added.

Tips : Ask team members to share their successes and challenges during the sprint or project. This allows everyone to see what worked well and what didn’t, which can help identify areas for improvement.

Step 4: Add Sails and Anchors

Ask the team 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.

Step 5: Scale your sails and anchors

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 have stopped us from moving forward at all.

Now team should brainstorm and 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 Dot Voting. The team can compare Sails and Anchors. Is it a bigger or smaller sail/anchor than the previous one? The key here is engaging in group discussions, awareness, and consensus on what the sail/anchor is and how it impacts the team. Sticky notes may need to be clarified with extra information or split into multiple notes to score separately.

Step 6: Add ideas for +1 raising sails and/or anchors

Once all sails and anchors have been discussed and scored ask the team to capture activities and improvements to help raise sails further and raise up anchors. Ask the team 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 beside the relevant anchor or sail.

Step 7: Discuss Reef, and Sun and Plan the next steps

Remember to celebrate success and plan action items for current as well as future obstacles that have been identified during the above brainstorming.

If there are numerous suggestions for raising sails and anchors then team activities like estimation games, MoSCoW prioritization, and Dot Voting to help discuss, rank, and decide upon which improvements to take forward. Map the improvements/actions into the team backlog/future work or on a dedicated change and improvement board to help track and measure progress.

Sailboat Retrospective Example

Let’s take an example of a team that developed a mobile app during the sprint. The team was able to deliver the features on time but faced some challenges during the sprint. Here’s how they conducted the Sailboat Retrospective:

• Draw a Sailboat: The team drew a sailboat with a sail, a mast, a keel, a waterline, wind, rocks, and a shore.
• Write the Sprint Goal: The team wrote the sprint goal at the top of the sailboat: “Develop a mobile app with login, registration, and dashboard features.”
• List the Positive Factors: The team listed the positive factors that helped them during the sprint, such as good communication, pair programming, and code reviews. They wrote these on the sail and the mast, as the wind filled the sail and propelled the sailboat forward.
• List the Negative Factors: The team listed the negative factors that hindered their progress during the sprint, such as a lack of automated testing, dependency on external APIs, and unclear requirements. They wrote these on the keel and the rocks, as the obstacles that slowed down the sailboat or could cause it to crash.
• Identify the Improvement Areas: The team discussed the negative factors and identified areas for improvement.

Open-ended Questions for Sailboat Retrospective

• What makes them happy?
• What’s slowing them down?
• What’s propelling them forward? What are the gusts of wind that help our sailboat to move forward?
• Is this bigger or smaller than the last item we scaled?
• If you could cut away one anchor which would it be? How could you do that?
• If you could raise one sail to 10 which would it be? How could you do that?
• What would happen if all anchors were cut away?  what would change?
• If you could add an ‘iron sail’ (an engine!) to your sailboat what would it be?
• How can we raise this sail from a 5 to a 6?
• How can we raise this anchor from a -7 to a -6?

Sailboat or Speedboat Facilitation Tips

• First collect all the anchors, as it’s easier for most teams to organize their current problems.
• Ask the team to turn each anchor into goals, desires, or wishes and put them before the cloud to represent the gusts of wind pushing the boat forward.
• Use these “winds” to define a desirable goal you will use as a true north for the rest of the retrospective.
• Use data to help guide the retrospective discussion, such as team velocity or user feedback. Data can help provide a more objective view of the team’s performance.
• Based on the discussion, identify specific action items that the team can work on to improve. Make sure to assign ownership of these items and set clear deadlines.
• Follow up on the action items from the retrospective in the next meeting to ensure progress is being made.
• Keep the retrospective focused on finding solutions, not blaming individuals or criticizing past decisions. Maintain a positive and constructive atmosphere to encourage open communication and a sense of teamwork.

Sailboat or Speedboat Challenges & Strategies to Overcome

Sailboat Sprint Retrospectives are an important part of the Agile development process, as they allow teams to reflect on their progress and identify areas for improvement. However, there are several common challenges that teams may face during these retrospectives. Here are some of the most common challenges and tips on how to overcome them:

• Lack of Participation: In some cases, team members may be hesitant to speak up during a retrospective, which can hinder the effectiveness of the session. To overcome this, the facilitator can encourage participation by creating a safe and open environment where all team members feel comfortable sharing their thoughts and ideas. They can also try using interactive activities or icebreakers to get everyone engaged.
• Blaming and Finger-Pointing: Retrospectives can sometimes turn into a blame game, with team members pointing fingers at each other for mistakes or issues. This can lead to a negative atmosphere and prevent constructive feedback. To avoid this, the facilitator should set ground rules at the session’s beginning that encourage constructive criticism and discourage personal attacks.
• Lack of Actionable Insights: In some cases, retrospectives can feel like a waste of time if the team does not develop actionable insights they can implement in future sprints. To prevent this, the facilitator can ensure that the team focuses on identifying specific actions that they can take to improve in the next sprint. They can also assign action items to team members and set deadlines for completion.
• Dominant Voices: Sometimes, one or two team members may dominate the conversation during a retrospective, preventing others from sharing their thoughts and ideas. To prevent this, the facilitator can use round-robin or anonymous feedback to ensure that everyone has an equal opportunity to speak.
• Lack of Follow-Through: Even if the team comes up with actionable insights during the retrospective, there is a risk that they may not be implemented in future sprints. To prevent this, the facilitator can assign ownership of action items to specific team members and follow up on their progress in subsequent retrospectives.

Scrum Master Role in Facilitating Sailboat Sprint Retrospective

The Scrum Master plays a critical role in facilitating a successful Sailboat Sprint Retrospective. Here are some key responsibilities of the Scrum Master in this process:

• Creating a Safe and Open Environment: The Scrum Master needs to create a safe and open environment where team members feel comfortable sharing their thoughts and feedback. The Scrum Master should encourage open and honest communication, actively listen to the team members, and ensure that everyone has an opportunity to share their perspectives.
• Guiding the Retrospective Process: The Scrum Master should guide the retrospective process, ensuring that it stays on track and that the team is making progress towards actionable improvements. The Scrum Master should use the Sailboat metaphor to help the team identify areas of strength and improvement, and facilitate a discussion that leads to actionable items.
• Encouraging Collaborative Problem Solving: The Scrum Master should encourage the team to work collaboratively to solve problems and address issues identified during the retrospective. The Scrum Master should facilitate a discussion where the team can brainstorm potential solutions and identify concrete action items.
• Facilitating Continuous Improvement: The Scrum Master should ensure that the team is focused on continuous improvement and that the actionable items identified during the retrospective are implemented. The Scrum Master should work with the team to develop a plan to implement the changes and monitor progress towards the goals identified.
• Monitoring Team Dynamics: The Scrum Master should also monitor team dynamics during the retrospective to identify any issues that may be hindering team performance. The Scrum Master should work with the team to address these issues and promote a positive team culture.

Sprint Retrospective – Tools and Techniques: Click Here

You can read more about the Sailboat technique from Luke Hohmann's book Innovation Games. Luke also provides a free online tool to do these with distributed teams at www.innovationgames.com (choose Visual Collaboration Games).

Length of time:

Usually about 45 minutes to get through data gathering and insight generation.

Short Description:

This retrospective technique uses a sailboat as a metaphor for the team. The team identifies anchors (impediments) and wind (positive forces) and chooses an area to improve.

Either a large white board or a large piece of poster paper. Flip charts can be used, but in my experience are not quite big enough for most teams. They'll work in a pinch. Lots of sticky notes Thick markers

Preparation

Not much required, other than having the materials in place. You may wish to pre-draw the sailboat.

Introduction

The facilitator draws a large picture of a sailboat floating in the water, with about half of the space above and half below the water/boat. He/she then explains that we're going to use the sailboat as a visual metaphor for the team. On a sailboat, there are things that slow it down (anchors), and things that propel it forward (wind). Just like the sailboat, there are things that slow our team down, and things that propel it forward. The facilitator then asks the team to think of what is anchoring the team down and what is propelling it forward, and to start writing one anchor/wind per sticky note.

Gathering Data

Sometimes people will be unsure if they should gather a bunch of stickies and then come up, or just bring them up as soon as they have one. I encourage the latter. As a facilitator, just keep an eye out for the energy in the room - you may need to prompt someone to go ahead and put their items on the board. When the energy starts to die down a bit, give people a fair warning that we'll wrap this part up in a moment. Once you see that everyone is done, get ready for the next step.

Generating Insights

Ask the team to come up to the board and group sticky notes that seem related somehow. As they do it, ask them to read the sticky notes out loud. This part is a bit of a self-organizing activity, it may need a bit of facilitation to make sure that people are getting some value out of the grouping and that one person's opinion isn't dominating when creating the groups. Once the stickies are grouped, ask someone to label the groups. Typically this will result in one or a few large groups of sticky notes, which point out that there maybe a good amount of energy around addressing those items. You may ask someone to read all of the stickies at this point too, just to ensure nothing was overlooked.

Choosing what to do

Finally, you can ask team members to "dot vote" for the group or individual sticky they think should be worked on. I typically give everyone three votes, and they are allowed to use them however they please: place all votes on one sticky/group, distribute them around, or even don't use one. You can do this with drafting dots are simply everyone gets a marker and is on their honor to only place three dots. Total up the sticky/group with the most dots, and move into some root cause analysis and proposed changes to make!

The idea started from Luke Hohmann, and over the years has been modified a few times by many in the community.

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Sailboat Retrospective

Picture a sailboat headed toward a beautiful tropical island with all the drinks with umbrellas you could ever want.🍹 But as you sail to your island paradise, you want to stay wary of the obstacles in your way, like rocks or coral. And you want to harness the wind to keep your team progressing toward your end goal. Wait...obstacles, progress, and goals? Your vacation has all the makings of a great agile retrospective! In fact, a Sailboat retrospective is a useful retrospective template that can illuminate all of the things that are helping and hindering your agile team. ⛵

Use the sailboat retrospective technique when you want to…

Define your team's end goals.

Identify risks that may disrupt your path.

Identify what is slowing your team down on its journey to the end goal.

Identify what helps the team achieve its goals faster.

How to run a sailboat retrospective?

This fun retrospective exercise is all about the visual. So, before we sail off on this meeting, the facilitator sets the scene by explaining all elements of the retrospective: a sailboat heading towards an island, rocks between the sailboat and the island, gusts of wind pushing the sailboat, and an anchor hanging from the sailboat. Each of these items represents a part of the team's previous sprint. Together they will paint a full picture of your team's current sprint retrospective.

• Represents the teams’ goals and larger vision.

• Represent the potential risks the entire team may encounter while working towards their goals in future sprints.

• Represents things that are slowing team productivity and success.

• Represents ideas for improvements that may help propel the team towards your goal.

Setting the Stage

Before casting off, make sure everyone has a shared understanding of the common goal of the retrospective. Depending on the size of the team, your entire retrospective meeting has the possibility of lasting several hours. 😱 If you want to limit the time on this retrospective session, create a timebox for the entire meeting (30-60 minutes, depending on the size of the team) so the team has an idea of how much time each discussion should take.

Begin the retrospective by deciding as a team the purpose of your “mission,” keeping the end goal in mind. 🏝 At this step, the team will be expected to brainstorm and identify areas and processes that are:

⚓ Currently hindering the team

⛰️ posing risks to the team achieving the goal at hand, 🌬️  already existing team strengths that are propelling the team forward.

The facilitator should set a timebox and let participants develop their ideas and capture these as multiple notes. During the brainstorming session, the entire team should keep their valuable feedback private. 🤫 This helps prevent groupthink and ensures that team members aren't swayed by seeing the opinions of others. (Psst, we know a retrospective tool that makes this step easy...) 

Many notes will likely contain similar (or even identical) ideas. It's always great to see points of team alignment! To get the next step started, the facilitator announces the timebox (5 minutes) and encourages the participants to group notes into logical themes. This part of the exercise is intended to highlight popular and differing opinions that are in need of a discussion.

🌑 Identify the rocks: What are the things the team recognizes as potential risks to their success?

💨   identify the wind: what’s going well for your team, or, in other words, what’s putting wind in your sails, ⚓   identify the anchors: is there anything negatively anchoring your ships and blocking opportunities for improvement ‍.

Sometimes discussion topics are obvious. For example, if there are several similar notes on process improvement ideas, your team has an obvious pain point to discuss. However, sometimes it can be challenging to structure the discussion in an organized way. If this is the case, the facilitator can opt to use dot voting to prioritize the discussion based on the collective desires of the group.

Team Discussion

If dot voting was used, then the team discusses the notes in prioritized order. If not, the facilitator can choose the order of discussion. When it comes to timeboxing the discussion, you have a couple of options. You can set a period of time for the entire conversation (20-40 minutes), or you might choose to timebox the discussion of each individual topic (typically 5-10 minutes). The second approach tends to keep the conversation on topic and moving at a faster pace.  Throughout the discussion, the facilitator focuses on each part of the scene and helps the team evaluate all the anchors, wind, and rocks. For example, during the discussion, the team can strategize how to turn an anchor into a gust of wind, or eliminate as many rocks as possible. As the conversation progresses, it's imperative that the facilitator also write down any action items that come out of the discussion in order to help the team realize continuous improvement with each sprint.

This effective retrospective technique is a creative way for your team to visualize the end goal and understand what systems need to change for your team to reach all their islands. 🏝️

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Introduction to using a sailboat retrospective

Reading time: about 5 min

Sailboat retrospectives are a unique way to think about your sprints or projects and brainstorm ideas for how to reach your goals. By using this popular retrospective model, you can keep your retrospective meetings collaborative and engaging. 

What is a sailboat retrospective?

Sometimes referred to as a speedboat retrospective, a sailboat retrospective uses a metaphor to understand the Agile journey, placing various aspects of a sprint or project into perspective for your team. Sailboat retrospectives are an excellent visualization technique. By taking familiar elements of a sailing journey and comparing them to the obstacles, goals, and tools your team has, you can look back on what happened with a project and highlight areas of particular interest and emphasis. 

Elements of a sailboat retrospective

Each element serves as part of the metaphor—a sailing adventure where your team is trying to sail successfully to an island destination. Along your journey, the wind carries you forward by filling your sails and pushing your boat, but one or more anchors or rocks can get in your way and impede your progress. 

As you think about your sprint or project’s story, you may find obvious elements for each category that stand out to you. Other elements may not be so obvious or may fit a different category than you’d expect. Creating a sailboat retrospective can change your interpretation of a recent sprint and cast light on elements you weren’t previously aware of. 

Anchors represent what held your sprint back from moving forward. Anchoring your boat in place, these obstacles can be issues that cause delays, challenges you identify partway through your voyage, or impediments presented by other projects, stakeholders, or environmental conditions (such as the market). 

You may have more than one anchor that restricted your project. As you brainstorm your anchors, you could make a note of solutions that come up, but don’t focus on them until you’ve identified all of your anchors. Remember to think about:

• Anchors stall or drag your project
• How might you manage anchors?

Wind is whatever helped your team keep moving. Wind gives your project momentum and may be your advantages, helpful team members, support from stakeholders, or even the roadmap you used to guide your project along. Looking back at your previous sprint, considering what helped enable your project’s progress allows you to see what represents wind in your sailboat retrospective. 

If it’s tempting to skip over the wind section and focus on your challenges, keep in mind that this part of the retrospective is a great time to thank colleagues and recognize stakeholders. Positive recognition is encouraging for your team and creates a positive cycle that supports your project. Consider the following:

• Wind advances your project forward
• How do you guide your boat with the wind? 

For any project, threats are a strong possibility, so planning for them is appropriate risk management. Real rocks are destructive to boats and can impede the adventurer’s chances of ever reaching the island. Since rocks aren’t always visible from inside the boat, sometimes rocks show up unannounced. If sailors see rocks, they can correct their course, but it’s too late to avoid a rock if you’ve already hit it. 

Retrospective rocks are a little like that, too. Once the risk is now part of your project’s reality, your best approach might be to manage it. Anticipating rocks and avoiding them in the first place can save a lot of hassle and potential fallout. Just like real rocks tend to be in specific places (such as near land), these rocks can be more common under certain conditions. Finding out what increases the probability of hitting a rock is a valuable part of your journey. Key things to think about for rocks include:

• Rocks can damage your boat
• How can you avoid rocks with risk management and planning? 

Island/ Goal 

Everyone wants to reach the destination eventually. That’s why you’re working on the project in the first place! Successfully reaching the island represents your team’s success when they arrive at the project destination. All of the planning, navigation, mitigating risks, and looking for wind to push your boat forward culminates in finding the island. You’ll want to make sure your entire team knows what the goals and expectations are for a project. During the retrospective meeting, think about:

• The island is your goal
• Did you reach the island? 

The sun is an optional element, but it can be helpful. Sunshine can be one of the best parts of both the journey and the destination. Instead of including your kudos and positive highlights in your “wind” category, you can count these as the sun shining on your team, giving team members a chance to appreciate the work of their colleagues. Consider:

• The sun makes your team happy
• Where did the sun shine and how can you recognize it?

When to use a sailboat retrospective

Sailboat retrospectives are helpful for nearly any project and can become part of your project management process. Use a sailboat retrospective: 

• During a team meeting: With a sailboat retrospective, you can show your team important information and provide a point of discussion.
• If your project is stuck: If your project stalls and you’re not sure where to go next with it, a sailboat retrospective could help you determine how far you are from the island, if you’ve hit a rock, or if you’re dealing with anchors. 
• To inform stakeholders: Sailboat retrospectives are also a helpful technique for informing stakeholders on a project’s outcome. 
• After the project: Following the completion of your project, you can use a sailboat retrospective to review what was successful and what needs improvement next time. 

Learn more about running effective retrospective meetings.   

How Lucidspark can help 

As a virtual whiteboard, Lucidspark can be used to put together sailboat retrospectives and to review and collaborate on. Lucidspark provides a place where you can brainstorm and share your ideas visually. 

Use Lucidspark to create and review your sailboat retrospective as a team during a virtual meeting or get asynchronous feedback and comments whenever your team is online.

Create your own speedboat retrospective in Lucidspark.

About Lucidspark

Lucidspark, a cloud-based virtual whiteboard, is a core component of Lucid Software's Visual Collaboration Suite. This cutting-edge digital canvas brings teams together to brainstorm, collaborate, and consolidate collective thinking into actionable next steps—all in real time. Lucid is proud to serve top businesses around the world, including customers such as Google, GE, and NBC Universal, and 99% of the Fortune 500. Lucid partners with industry leaders, including Google, Atlassian, and Microsoft. Since its founding, Lucid has received numerous awards for its products, business, and workplace culture. For more information, visit lucidspark.com.

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Run The SailBoat Agile Exercise or Sailboat Retrospective

by Luis Gonçalves on Jun 16, 2024 9:04:15 AM

In this post, I will explain the method known as SailBoat Exercise or Sailboat Retrospective.

This exercise can be found in the book  Getting Value out of Agile Retrospectives . A book that I and Ben Linders wrote with a foreword by  Esther Derby .

Sailboat Exercise

What you can expect to get out of this technique.

From my experience, this technique is quite appreciated by teams because of its simplicity.

This exercise helps teams to define a vision of where they want to go; it helps them to identify risks during their path and allows them to identify what slows them down and what helps them to achieve their objectives.

When you would use this technique

I believe this method is quite simple and does not require any special occasion. Although, it might be interesting for situations when a retrospective is conducted with more than one team at the same time.

I had a situation, not long time ago that two teams worked together and because of their level of dependency on each other, they decided to conduct a common retrospective because of some ongoing issues.

Using the SailBoat exercise can be extremely interesting because we simply put the name of both teams on the SailBoat and we remind everyone that we are on the same SailBoat navigating in the same direction.

This technique reveals all the good things and less positive things performed by a team.

How to do it

This retrospective is quite simple. First, we draw a SailBoat, rocks, clouds, and a couple of islands like it is shown in the picture on a flip chart.

The islands represent the teams´ goals/vision. They work every day to achieve these islands. The rocks represent the risks they might encounter in their vision.

The anchor on the SailBoat is everything that is slowing them down on their journey. The clouds and the wind represent everything that is helping them to reach their goal.

Having the picture on the wall, write what the team vision is or what our goals are as a team. After that, start a brainstorming session with the team allowing them to dump their ideas within different areas.

Give them ten minutes to write their ideas. Afterward, give 5 minutes to each person to read out loud their ideas.

At this point discuss together with the team how can they continue to practice what was written on the "clouds" area. These are good ideas that help the team, and they need to continue with these ideas.

Then spend some time discussing how can the team mitigate the risks that were identified. Finally, together with the team chose the most important issue that is slowing the team down.

If you do not find an agreement within the team about the most important topic that should be tackled, you can use the vote dots.

In the end, you can define what steps can be done to fix the problem, and you can close the retrospective.

Like many other exercises, this exercise does not require a collocation of a team. You can use, for example, tools like Lino, to apply the exercise to non-collocated teams. This tool allows us to do everything that we need to run this exercise.

What do you think? Your feedback is always extremely important for me, so please leave me your comments.

An Agile Retrospective is an event that ́s held at the end of each iteration in Agile Development and it serves for the team to reflect on how to become more effective, so they can tune and adjusts its behavior accordingly.

I believe the SailBoat exercise is quite a simple Agile Retrospective Exercise and does not require any special occasion.

If you are interested in getting some extra   Agile Retrospectives   exercises, I created a blog post with dozens of  Agile Retrospectives Ideas , check them and see if you find something interesting.

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Sailboat Retrospective

• Retrospective

Whether it’s midway through a project, or at the end, a retrospective is an important part of team learning. While there are many ways of performing a retro, we’ve found that doing it in a fun way can help open up honest conversations.

Enter the ‘Sailboat Retrospective’. We’re not sure who originally came up with this idea, but we’ve got our own twist on it — complete with a shark! Using Whimsical  we help clients think through what went well and what’s on the horizon with their projects.  Click here  to access a Whimsical template that you can make a copy of to use in your own workshop.

Target group : project team

Time : 20 – 30 minutes

Material : Whimsical template

Goals : define what has gone well and could be improved

The thing to remember about this process is that the way that you carry out the planning using this canvas is as important as the outcome. Be as inclusive as possible

With that in mind, let’s identify the main areas of the template:

• LAND — what’s your destination? where are you headed? what does success look like for the project or team?
• WIND — what’s the wind in the project or team’s sails? what’s gone, or is going well? what kind of support are you getting?
• ANCHOR — what’s dragging things down? what’s slowing down the progress of the project or team? which burdens need to be addressed?
• SUN — what acts like sunlight for the project or team? what kind of recognition have you received? what is making you feel good?
• SHARK — what’s an upcoming threat to the project or team that you need to keep an eye on? what’s circling around that no-one is talking about?

Some of these can feel quite similar. For example, the difference between WIND and SUN in this retro and the difference between ANCHOR and SHARK. If it helps, consider WIND to be things internal to the project or team and SUN to be things external to it. Also, ANCHOR is about current problems, and SHARK is to do with future problems for the project or team.

To use this template, do the following:

• Create your own copy of the template and invite all members of your team to edit.
• Ensure that everyone knows how to use Jamboard by going through the basic controls.
• Spend some time ‘silent Jamboarding’ where everyone can place as many sticky notes on the template as they wish.
• When the rate of new sticky notes slows, give everyone 30 seconds longer.
• Talk about what you’ve all added to the template. Go round each person asking what they notice or would like to call attention to.

Once you’ve done all of this, it’s up to you what to do next. You could talk with the team about next steps — e.g. ‘mitigating actions’ for the ANCHOR stickies, or ‘preventative measures’ for the SHARK stickies. But don’t forget to talk as much about what is going well as what isn’t. One way to do this is to add ‘what works’ to a wiki-based handbook for new members who join the team.

Click her e to access the Sailboat retrospective template for Whimsical