sailboat in agile

Run The SailBoat Agile Exercise or Sailboat Retrospective

This exercise can be found in the book  Getting Value out of Agile Retrospectives . A book that was written by me and  Ben Linders  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.

"Starfish exercise" or "Starfish Retrospective"

The world cafe - agile retrospective technique, similar blog posts.

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The Instant Retrospective

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Project Management

Sailboat retrospective: for agile software development teams.

Sarah Burner

ClickUp Contributor

February 1, 2024

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)

The sun , 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 tools, 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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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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Retrospective: The Sailboat

• June 2, 2022
• No Comments

The sailboat retrospective

The sailboat retrospective is a good format to use when you want to reflect on your progress towards a specific goal. This goal can be product- or process related.

The Icebreaker

For this template, we selected a fun icebreaker: share a picture of meme that explains the last iteration to you. You shouldn’t go into too much detail during the icebreaker, as the intention is just to get everybody engaged and participating in the retrospective. But, you can ask the participants to share a few words about the picture or meme that they shared, to get some more insights and make it interactive.

The retrospective format

The sailboat retrospective consists of two rounds:

• “Our destination”: what’s our goal? This should be the main theme for the retrospective. What are we striving for? As mentioned above, this can be something related to the product that you are building, or it can be something related to the way of working within the team.
• “Helping us”: what is currently helping us on our road to achieving this goal? What should we keep doing?
• “Holding us back”: what is currently holding us back, slowing us down, or preventing us to reach our goal?
• “Obstacles”: what risks do we see in the future, that could prevent us from reaching the goal? Something that we see happening, but is not yet happening to us today.

After explaining the stages to your team, give everybody a few minutes to write down their thoughts on a post-it. After this, you can do a quick dot voting session to determine the most important one(s) and start with a discussion on those.

First discuss all the post-its in the “Destination” category and come to a conclusion of the goal of the team before discussing the other stages. It’s important that everything you are discussing in the “Helping us”, “Holding us back” and “Obstacles” categories are related to the overall goal that you are trying to achieve as a team.

While having the discussion on a topic, always focus on what’s within the control of the team. Don’t focus too much on external people or factors, but mainly on the things that are within the control of the team to identify improvement actions that the team is able to take. You want to have 1 – 2 action items at the end of the retrospective that you can implement in the next iteration(s). Remember: you will not always have big live changing action items in each retrospective. That’s also not the intention. A small action that brings a small improvements is already very good. Try to improve a little each sprint instead of trying to bring big changes at once.

About last retrospective...

A crucial part of the retrospective is to reflect on the outcome of the previous one! Teams often forget to do this, but it is very important as it gives the team the confirmation that the action items are actually important… And that we want to make sure we improve! There is a section on the top of the template where you can refer to the action items of the last retrospective. Go over them, see how you are doing in regards to them, and decide what to do next.

Rate your retro!

At the very end of the retrospective, I ask the team to quickly rate their retrospective with focus on: 

• Did we have a good discussion? Did we speak openly, and respect each others opinion?
• Do we have valuable action items? And, are we confident that we will do them in the next sprint?

We also use a feedback wall where team members can share their feedback on the retrospective. As the facilitator, you can encorporate this feedback into the next retrospective session.

Other things about the format

On the very top of the format, you can see 2 elements:

• Action items / experiments: this is the place where you would write down the action items during the retrospective. This makes it easy to summarize them at the end of the session.
• Idea for the next retrospective: I always like to foresee an area where people can give feedback or give input for the next retrospective. This can be feedback on the current format, ideas for a new format, tips, general feedback… Anything that can help us make the next retrospective even better! I would not make it required for people to give input in this, make them feel free to give input when they come up with something.

Download the template (for free)

You can download the Miro template for free below:

If you don’t have a premium version of Miro, you can also download the picture at the top of the screen and create the board in Google Drawings .

Tom Abrahams

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A Step by Step Guide to Retrospective Sailing with videos, examples, tips & templates

Retrospective Sailing Game Guide, Video & Examples

Click on the speech bubble to speak to Agile Bee your Smart Agile Coach and Guide

Retrospective Sailboat Guide & Video

Retrospective Sailing is a great game for teams to play who wish to reflect collectively and identify improvements. This page includes video guides, short and long written step by step guides, agile sailboat templates, tips, examples and all you need to successfully run your retrospective.

click on the speech bubble and ask Agile Bee to Play Retro Sailing!

Retrospective Sailing is a great game for teams to play who wish to reflect collectively and identify improvements. This page includes video guides, short and long written step by step guides, agile sailboat templates, tips, examples and all you need to successfully run your retrospective. If you are interested in coaching and training for your team, contact us to organise a free retrospective to design your own custom sessions.

Upcoming Workshops

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Retrospective Sailing Game

Retrospective Facilitation

If you are looking for a remote facilitator for your retrospective please do get in touch

Formats available

• Facilitated online team session
• 45-90 minute conference workshop
• Half Day Retrospective workshop for teams
• Retrospective Day

Workshops and Sessions can be facilitated remotely connecting individually or as a group.

If you are interested in a Being Agile Programme for your team, we offer a Retrospective session as part of designing your custom agile programme

Being Agile : Retrospective Sailing is one of the most popular games teams adopt to reflect and map their way forward easily, in a fun, tactile and visual way.  It can be used for many purposes where you want to review what’s going well, what could go better, and ensure you are responding regularly to the shifting horizon your organisation and teams face. 

Retrospective Sailing Short Guide

1. Draw Boat 2. Name your boat/ agree topic 3. Mission? 4. Add Sails – what’s going well? 5. Add Anchors – what could be better? 6. Scale Sails 1 to 10 7. Scale Anchors -1 to -10 8. +1 actions to raise sails/anchors 9. Agree actions to take forward

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

The game is a combination of coaching and agile tools, methods and approaches created and refined over the years working with teams to visualise information and develop ways to help teams to improve their agility.  There are other great variations of this game too created by others, all games that empower teams to reflect and move forward positively are great news for building an agile culture, and great sign that the approach works well for many teams.

Sailboat Retrospective Full Guide

Find out more : read : Being Agile in Business

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

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

Agile Retrospective Sailing Game – Overview

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

Retrospective Sailing — an agile reflection game

A hands on workshop facilitating a practical retrospective game.

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

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

Retrospective Sailing Full Guide – being agile

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

Step 1 – Draw Your Boat

Updated Slide Template 07/22

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

TIP – It’s valuable not to give the team a template boat but let them draw their own, this gives ownership and buy in to the activity, it also helps to create a safe creative space for the team to be open and all contribute. Drawing the boat helps to act as an icebreaker and get all of the group participating and on the boat.  Encourage all members of the group to pick up a pen and add to the picture. Encourage the addition of extra features to their picture, sunshine, fish, sharks or icebergs, ask gently if the additions represent anything particular or just doodling for fun.

Running your retro remotely?

The sailboat metaphor works equally well to help facilitate a team discussion online, you can use a shared whiteboard tool like Miro, create a template in a shared document or use the metaphor in a slack chat.

Slide Template

Download Slide Template

Use this template in google slides to group edit the boat as part of a remote meeting. https://beingagile.co.uk/wp-content/uploads/2020/10/RetroSailingTemplateGoogleSlides.pptx

Step 2 – Name the boat

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

Ask teams to name their boat themselves, it can be a practical name or a fun one, the key is conversation to agree the theme/topic of the retrospective. Fun names like Boaty McBoatface often come up, a sign of a playful (perhaps a little chaotic) group.  Name can indicate the mood and position of the team currently, it can be whatever your team agree on. If you have a boat called Titanic, be cautious they have literally drawn a sinking ship, you will need your best facilitation skills handy, most of the time it’s not the final option, and filed as a joke opting for an alternative (but it’s an early flare to be aware of). Even for teams facing great challenges the game can be a positive way to find a way forward and more positive outlook and help avoid mutany!

The name can tell you a lot about how the topic of the retrospective is going! Techtanic – a sinking ship!

Step 3 – Add your mission to the hull of your boat

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

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

Goal established – GROW

Step 4 – Add Sails and Anchors

Ask the teams again using post it notes to add sails and anchors to their boat, make sure everyone has post its and a pen.

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

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

Sometimes things can be sails and anchors, for example it could have good outcomes and bad, if this is the case ask for them to clarify this on separate notes.   Encourage all members of the team to write and add notes.  Ask the group to review the sails and anchors they have added, group them as appropriate. Encourage members to add duplicates even if the note is already there, there could be different angles (perspectives) and also multiple inclusion shows that it is possibly a larger sail or larger anchor, for example if everyone writes ‘team’ on a post it that creates a larger sail naturally. This can give a visual cue when grouping notes as to which are key topics and themes for the team.

Step 5 – Scale your sails and anchors

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

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

Reality Mapped – GROW

Step 6 – Add ideas for +1 raising sails and anchors

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

The key here is that we look for small incremental improvements that can be made, remembering we want to take an agile approach to becoming more agile.  Ask groups to think of small actions that would raise one of the sails, or anchors on the boat by just one point, raise an anchor from a -6 to a -5, or raise a sail from a 2 to a 3. Capture ideas for improvements on post it notes and place them besides the relevant anchor or sail, or in a cloud or a map representing ideas/instructions for making their ship ‘go faster’.  Encourage the team to be imaginative with their ideas, get everyone to add their suggestions and then discuss.

The idea here is that the team then have actionable improvements that can be added to their work backlog and schedule them into future sprints of work as improvement activities alongside their day to day activities. This encourages Continuous Improvement in the team as well as time to regularly reflect, celebrate successes and flag up challenges.

Find out more about the agile canvas and download your copy here

Options identified – GROW

If there are numerous suggestions for raising sails and anchors then team activities like estimation games, MoSCoW prioritisation, 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.

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

Way Forward Agreed – GROW

Remind the team that it is not the aim to make everything a +10, this would unbalance the boat! Ideally we would like to raise our anchors, but be mindful that some anchors sometimes offer stability, and most sails don’t need to be 10/10 (perfect) to be effective. Often if we have one area which increases another might decrease and counteract it and unforeseen outcomes may occur.

Revisit your boat and review it as an ongoing retrospective tool, encourage the team to use boats to reflect on other topics and areas, put your boat on the wall to remind the team of their mission and purpose.

• 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 sail boat 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?

Tips and Formatting

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

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

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

Participant Numbers : can be used with individuals and small teams, for larger groups break into multiple boats with 6-8 people per boat. For groups with multiple boats, multiple topics can be covered and participants can choose a topic, or rotate to contribute to each boat. Include a gallery walk. It is an ideal game to photograph and circulate/share following the session.

Sailboat Retrospective Workshop Video and Example Gallery

Below are examples of sailboats created at conferences and events with group participants.  The workshop works well at conferences to review the conference or the theme of the conference as participants are all familiar with the topic.  If you would like to run this workshop at your conference or our help facilitating this with your team please do get in touch Retrospective Sailing – Agile Workshop – Agile on the Beach 2017 from Belinda Waldock

Sailboat Retrospective Workshop – Video

You can also find a guide to Sailboat Retrospective game by watching this video, and the gallery of example boats below.  Overview starts at 5min 50secs in

Retrospective Sailing Examples Gallery

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The origin of retrospective sailing and the sailboat game.

The game originated at Agile on the Beach Innovation Games workshop in 2012 – I was attending the Innovation Games Training Day with Jeff Brantley of Enthiosys and we were playing various games. The day aimed for us to learn about Innovation Games, how to facilitate them, and review how they could be applied to high growth small and medium size businesses in Cornwall as part of the EU growth programme we were working on. Its still one of my all time favourite Agile on the Beach workshops, and there have been a few!

One of the games we played was the Speedboat game. When we came to play the game I decided to draw a sail boat instead and build on the game, play with the ideas and thoughts spurring in my mind!

1 – Anchors are not something I associate with speed boats! I immediately found myself reacting to the idea and felt a need to improve/adjust it! We were in Falmouth, Cornwall, a tall ship seemed more fitting! Plus a sailboat felt like a more creative and fun thing to draw. I wasnt sure taking a game about speedboats would really fit the culture of businesses in Cornwall, a sailboat just seemed to be more appropriate!

2 – I loved the idea of the game but looking at just the negatives didn’t sit well with me as a solutions focused coach! It reminded me of SWOT analysis games, so often we identify all the issues, but then there is no step to look at how we improve them, for example in SWOT one powerful question is “do we have any strengths to mitigate against threats”. Similarly in the game there was the action of reflection to identify the Anchors, but no clear mission for the boat, and no clear facilitation for learning and improvement. The game was great, but it inspired me to play with the idea of a Sailboat and developing my own game to use with clients.

3 – If I drew a sail boat I could map what was holding us back, but also what was taking us forward. Plus I was studying coaching tools including Scaling and Grow , marrying the idea of a boat with sails and anchors, then scaling them and looking at how we could raise them by a point fit together really well.

A brilliant opportunity for iteration and innovation to improve and develop the game for use with cornish businesses. Innovating innovation games!

And Retrospective sailing was born!

In the workshop I played about with the idea, and immediately began using it with clients to help them reflect and identify improvements and opportunities to mitigate problems. Every one loved it, and still do!

This is one of the early boats facilitated with a team. The team was growing fast, the business had grown significantly and the teams were working to update and evolve their ways of working to manage the growth and ensure that business could continue to scale.

I love the intern post it note and the addition by the team of the word crucial! Centre sail and a +9, he finished his intern on a high! Before the game he told me he has no idea if he had been useful or not and was very nervous about adding it!

The +1 improvements to raise their sails and anchors were added to the back log of their change and improvement board. After seeing the server downtime report created the server got an immediate upgrade, making their boat go much faster and smoother!

They then went on to build a pirate ship aimed at breaking into a new market, showing how adaptable the game can be for reviewing and reflecting on any mission, goal, or scenario a team would like to explore.

The differentiator of this game compared to others I have seen is that this includes scaling of the sails and anchors and the identification of actionable outcomes. It ensures that we not only reflect but we identify key actions and outcomes that help ensure that we are on course and any adjustments we need to make to our sails and anchors are captured to be acted upon as improvements.  It is important to reflect on the Goal and current Reality, but it is also vital to ensure we identify Options to improve and agree a Way forward to ensure we gain maximum value. (GROW model – see my book for more details on GROW!).

I have played the game with individuals, small teams (upto 8 per boat is ideal) and groups of over 100 at conferences, yes, we created a small fleet! It has been tried, tested, and has evolved over the past 8 or so years with a wide array of teams, topics and settings and everyone always really enjoys it. The game is almost entirely self facilitated by the team themselves and encourages them to take responsibility and action.

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

Enjoy being agile!

Belinda @belindawaldock

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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

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.

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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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.

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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 | Enhance your retro meeting with AgileBox

Welcome to the world of Agile retrospectives and the innovative Sailboat Retrospective. In this journey of reflection and improvement, your Agile team becomes a crew on a sailboat navigating the seas of project development. Just as sailors gather on a ship’s deck to review their voyage, your team comes together to discuss how your project journey has been.

About the Sailboat Retrospective

Benefits of using sailboat retrospective, ideal scenarios and contexts for sailboat retrospectives, teams and projects that can benefit most from this format, agilebox introduction, setting up and preparing for a sailboat retrospective, superficial feedback , imbalance in focus , lack of action items , failure to prioritize , inadequate follow-up .

Imagine your Agile team is like a ship on a journey through the vast sea of project development. The Sailboat Retrospective is a special kind of meeting where your team reflects on its recent journey. Just like sailors gather on a ship’s deck to review their voyage, your team comes together to discuss how things went during the project.

The name “Sailboat Retrospective” is fitting because it represents the idea that your project is on a journey, just like a sailboat, and you want to adjust your sails to reach your destination.

The elements of the Sailboat Retrospective are as follows:

• Wind: The wind represents the things that are helping the team to move forward. This could include things like the team’s strengths, their resources, and their positive attitude.
• Sails: The sails represent the things that the team is doing to achieve its goals. This could include things like the team’s processes, their tools, and their communication.
• Anchor: The anchor represents the things that are slowing the team down. This could include things like bottlenecks, problems with communication, or conflicts within the team.
• Obstacles: The obstacles represent the challenges that the team is facing. This could include things like deadlines, budget constraints, or technical problems.
• Island: The island represents the team’s destination or its goals.

Some of the benefits of using the Sailboat Retrospective are:

• It helps teams visualize their project progress and challenges using a simple and engaging metaphor.
• It encourages teams to celebrate their achievements and appreciate what helped them move forward.
• It enables teams to identify and address the factors that slowed them down or hindered their progress.
• It helps teams anticipate and mitigate potential risks or obstacles that may affect their future performance.
• It fosters a positive and constructive feedback culture among team members.

The Sailboat Retrospective is better than other templates because:

• It is more fun and creative than traditional retrospective techniques, which can increase team motivation and participation.
• It is more flexible and adaptable to different project contexts and team preferences, as it can be customized with different questions and scenarios.
• It is more comprehensive and holistic than other retrospective techniques, as it covers both past and future aspects of the project.

When to use Sailboat Retrospective

• Regular Sprint Retrospectives: Sailboat Retrospectives work well for Agile teams conducting regular sprint retrospectives. It adds a creative and engaging touch to these routine meetings.
• Team Bonding and Creative Exploration: Use the Sailboat Retrospective when you want your team to bond and think creatively. It’s particularly effective in fostering a positive team spirit.
• Projects with Both Challenges and Successes: When your project journey involves both positive aspects (the wind) and challenges (the anchors), Sailboat is ideal. It helps balance the discussion of these aspects.
• Seeking Fresh Perspectives: If your team has been using traditional retrospective formats for a while and is looking for a fresh perspective, the Sailboat Retrospective can inject new energy into the process.
• Creative Teams: Teams that thrive on creativity, like design or innovation teams, can benefit significantly. Sailboat retrospectives resonate with their creative thinking processes.
• Teams with Diverse Skill Sets: Cross-functional teams with members from various backgrounds can use Sailboat Retrospectives to bring their unique perspectives together.
• Projects with Complex Dynamics: Projects with intricate dynamics, where multiple factors influence success or failure, find Sailboat Retrospectives valuable for dissecting these complexities.
• Teams Struggling with Engagement: If your retrospectives have been lacking engagement, Sailboat Retrospectives can reignite team interest due to their fun and interactive nature.

Running a retrospective with the Sailboat template with AgileBox

AgileBox is a set of tools designed to help Agile teams plan and manage their projects more effectively. It provides a range of features such as planning poker, retrospectives, and daily stand-up meeting tools. AgileBox is an add-on for Jira that enhances the Jira experience for Agile teams.

AgileBox Retrospectives is designed to help Jira teams have productive, meaningful conversations about their work. It enables teams to reflect on successes, identify areas of improvement, and develop action plans for the future. AgileBox Retrospectives allows teams to capture feedback, insights, and ideas in an easy-to-use, visual way.

Besides 8 different available retrospective templates, AgileBox doesn’t support the Sailboat template yet. But with the custom retrospective template, this is not a problem! Users can easily add the Sailboat retrospective to AgileBox within several steps.

Follow the instructions video to add the Custom retrospective templates to your retro meeting:

For the Sailboat retrospective, we suggest the given details: 

• Template title: The Sailboat Retrospective
• Description: The team imagines themselves as the crew of a sailboat sailing towards their destination. They then identify the different factors that are helping them to move forward (wind, sails, crew), the factors that are slowing them down (anchor, obstacles), and the things that they need to do to reach their destination (navigate, adjust sails, work together).

Learn how to facilitate the retrospective meeting with AgileBox here: Agile Retrospective Explanation | How to do it with AgileBox

Common pitfalls when using the Saiboat template

To have successful Sailboat retrospectives, it’s essential to be aware of these pitfalls and take proactive steps to address them. Some of them are: 

Team members may provide shallow or vague comments without delving deep into the actual issues or strengths, leading to incomplete insights.

→ Encourage team members to explore the root causes of issues by asking “Why?” multiple times. This technique encourages deeper thinking and uncovers underlying problems, resulting in more meaningful feedback.

Sometimes, teams may emphasize either the positive aspects (winds) or the negative aspects (anchors) excessively, neglecting the need for a balanced view.

→ Set a timer for each phase of the Sailboat Retrospective (winds, anchors, island) to ensure that the team spends roughly equal time discussing each aspect. This helps maintain balance in the discussion.

Identifying problems and strengths is essential, but failing to convert these insights into actionable items and strategies for improvement can hinder progress.

→ At the end of the retrospective, have the team collectively create a clear action plan. 

Teams may struggle to prioritize the identified issues, leading to difficulty in addressing the most critical concerns effectively.

→ After identifying issues, give each team member a certain number of “dots” (e.g., stickers or virtual tokens) to vote on the issues they believe are most critical. 

Even when action items are established, some teams may not follow up on them properly, resulting in unresolved issues in subsequent retrospectives.

→ Implement a tracking system, whether it’s a shared document, task management tool, or a user story mapping tool like ProductGo .

As you embark on your Agile retrospective journey with the Sailboat template, remember that it’s not just a meeting; it’s a creative voyage of self-discovery and improvement. By visualizing your project as a sailboat journey, you gain unique insights into what’s driving your progress and what’s holding you back.

So, adjust your sails, set your course, and embrace the Sailboat Retrospective as a powerful tool to enhance your retrospective meetings with AgileBox. Bon voyage to your Agile journey!

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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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Sailboating: How This Agile Activity Can Help You Spark Innovation

UI/UX Design

Working Agile

When developing a digital product, the classic process involved documenting requirements, designing solutions, and building and testing in a waterfall approach. Then Agile came around and changed everything, decreasing the time it took to deliver working software and reducing the need for front-loaded documentation.

By working in ‘sprints’, development teams can focus on core requirements to build a product, while allowing for the ups and downs that come with developing complex technology. An added bonus is that clients can deliver feedback after sprints rather than at the end of the ‘completed’ project.

Agile is a system of working, but it’s also a mindset based on promoting better interaction between the people involved in the project, the flexibility to change things when required, and focusing on working, functional product over bureaucracy. It’s a flexible way of working - hence the name ‘agile’, but it also encourages the concept of taking stock after a sprint to see what worked and what didn’t.

This is often called an Agile retrospective. These are exercises performed after a sprint or project to determine efficiency and spot problems or issues so a team can avoid them in the future. It also ties into a Lean methodology in that a retrospective helps cut future waste.

One of the most powerful forms of retrospectives comes in the form of the ‘sailboat exercise’.

What is the Agile Sailboat?

If you’re planning to work in an Agile system, or working with an agency that utilises Agile methodology (hint hint, it’s us), then you’ll probably encounter the term sailboating.

Even if you’re NOT an agile organisation, the sailboating exercise can still be a great way to help rethink your projects and prioritise the production journey. It’s a visual metaphor and an exercise that focuses on the team and future direction.

A sailboat workshop involves two main processes: the team writing down answers to a few questions and then mapping these answers against the ‘sailboat’ metaphor.

You can use a digital board such as Miro for this, or Sticky notes will do the trick if you’re doing it in person. Ask your team the following questions (adjusting based on whether you’re running this as a sprint exercise or at an operational level.)

At operational level:

What’s moving us forward?

What are our goals?

What’s holding us back?

What’s not gone so well?

For sprint exercises:

What risks did the sprint/project face?

What delayed the sprint?

What propelled the sprint forward?

The Sailboat in action at a KOMODO Innovation Workshop.

Once your team have created their answers as Sticky Notes, ask them to stick them to a graphic you’ve drawn or printed that includes the following elements:

A boat - this is your team/project.

An island - this is the goal you’re working towards. It can be the specific features designed in a sprint or a more operational-level goal.

Wind in your sails : what propels your team/project forward.

Rocks : the risks your project faces in the future as it reaches the goal.

Anchor : the problems and challenges which delayed the sprint/project.

Once the team has had a chance to place their sticky notes, go through as a group and see if you agree on the placements. Then see if there’s a common theme being suggested by multiple people as a delay.

Just like you would in an Agile sprint, you can use this information to pivot and enact change. For example, if there’s an anchor problem holding your team back, prioritise a way to remove it. Outlining the ‘rock’ or future risk also helps you spot potential obstacles that should be dealt with before they become a problem and ‘sink’ the ship.

The sailboat exercise is great because it’s a visual metaphor that is easy to understand. It aligns the team and quite literally puts everyone in the same boat. For an agency/client relationship, sailboating also helps both sides of the relationship feel they are aligned and heading in the right direction.

While the Sailboat method is so often used in a retrospective fashion, we believe it has great value as an onboarding process for new projects and why it features as the first activity in our innovation workshop process.

Sailboat as a prospective tool

The sailboat system can also be used at the beginning of a project to help map out your strengths and weaknesses.

Demand for your product.

What your user’s needs are.

What solutions are most important in terms of priority.

We’ve written about this sort of thinking many times - but it’s so important we thought we’d mention it again here in the context of the Sailboat exercise. You can’t, for example, just go into a planning session with ‘general ideas’ of what your customers want. Instead, you need to do research and ensure that your product can solve a genuine need . Otherwise, it’s all based on guesswork.

Once you know enough about your users, you can use Sailboat to plan the overall product or project. This time, you’d define the elements as:

Rocks : what risks does the product face in terms of competitors, technical issues, user error?

Island : what functional requirements are most important - they should be positioned closer to the ‘shore’ to create priorities.

Anchor : what issues could delay the project. Think of factors like stakeholder intervention, poor client/agency communication etc.

Wind/sail: what can contribute towards the product being completed to the right timeframe?

While you might not have the same retrospective analysis to assign actual, tangible things that went wrong for your rocks etc. The sailboat is still a good way to map out a project at the beginning to get your team on the same page.

Remember that the sailboat as a concept is not really that important. It could be many different visual metaphors - all of them just have to share a way to map goals, threats and success factors.

By completing these exercises either at the start of a project or as a retroactive after a sprint as intended, you’ll be putting your team on the right track and creating a more collaborative process both internally and, if working with an agency, externally too.

The sailboat is just one Agile exercise we love. If you choose to work with KOMODO for your digital product development, we’ll lend our workshopping expertise to your project journey to help ensure the product is as functional and successful as it can be. Get in touch if you’d like to know more .

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Setting your Agile Course with the Sail Boat Futurespective

• Post author: Ben Linders
• Post published: February 28, 2017
• Post category: All (English/Nederlands) / English Articles
• Post comments: 4 Comments

A futurespective exercise helps agile teams to find ways to reach their goals . The team comes together to agree upon their way of working and define actions to reach their goal.

The sail boat futurespective is based on the sailboat exercise described in Getting Value out of Agile Retrospectives . You use the exercise to define a shared goal and explore how to get there:

You can use a sail boat retrospective exercise with a team to agree upon the team goal and to explore what is needed to reach that goal. This metaphor exercise includes “wind” to collect things that can help you to reach the goal, and an “anchor” to discuss things that might slow you down.

How to do the exercise

You start by discussing the goal that your team want to reach. Try to be as concrete as possible. Make the goal visible so that team members can image how it will look, and draw it in the upper right corner of a blank flip over sheet or whiteboard. For instance, if it’s a product then draw how it looks. If it’s how you want the team to be, visualize it in some way. Make a drawing how for example “the best team”or the “first team to deliver xxx  looks, and try to be specific what “best” means.

To go on a journey towards your goal, prepare by drawing a boat in the lower left corner, an anchor at the end of the boat, wind at the top, and rocks at the bottom of your sheet.

As the goal is clear now team members can start imagining how they got there. Put yourself in the future and come up with different ways of how you reached this goal. Think about the kind of things you did that helped you, write them on a sticky note and put it on the wind. Think about problems that you had along the way, make a sticky note and put it on the rocks. Brainstorm to come up with as many things as possible.

Now it’s time to go back to today. Team members brainstorm about things like the skills and qualities that they have, the means that are available for the team, anything is there to help them do their job successfully. Write down every single thing that pops up on a separate sticky note and put it on the boat. Also think about things that are hindering the team and making things difficult, write each one on a sticky note and put it on the anchor.

Now you have a drawing of the journey towards your goal. There’s the goal that you need to reach, the ups (wind) and downs (rocks) that were there along the way and all things that are there already to to start traveling (boat) or which are holding you back (anchor). You may want to take a picture of this to remember it, you can even do a short celebration with a cup of coffee or a beer for the great work that you’ve done!

But we’re not there yet. Now it’s time to start working towards actions. The team gathers around the board, look at the sticky notes, and starts clustering them on a new blank sheet. Team members work together to assemble related sticky notes and cluster them at a place on the blank sheet. It doesn’t matter if cards are on the wind or boat, or on the rock or anchor, if they are about the same (or similar) thing then put them together. Give each cluster a short headline to describe what’s in there.

As a new team that’s starting up you can’t do everything immediatly. So it’s time to prioritize. The team members will vote for the cluster(s) that they think is most important, the issue(s) that needs to be addressed now. I often use dot voting for this, where each team member get’s a number of dots that they can put on one or more clusters. Usually 3-5 dots per person works best. It’s allowed (and encouraged) to put more dots on the same cluster, people should pick what matters most and vote for that.

When the voting is done, count the dots that each cluster received. Discuss the cluster that received most dots. Team members start thinking of actions that are needed now to solve the issue. Write each action on a sticky note and put it close to the cluster that they belong to. Depending on the number of actions you might need to do additional voting on the actions  to agree upon the vital few actions that the team will do in their first iteration/sprint.

If you have room for more actions in your first iteration then team members can look at the next cluster with most points and come up with actions. Don’t define too many actions, as you won’t be able to do them anyway. Sometimes it’s better to take a fresh look at the clusters and define actions after a couple of iterations. You might need to do a new dot voting as priorities can change along the way.

Exercises for Agile Retrospectives

The sail boat futurespective is a great exercise that helps you to set your agile course and start sailing. I recommend this exercise to teams which are starting up and trying to figure out how to do their work in a good way.

This exercise is available in the the Retrospective Exercise Toolbox , a free of charge agile and lean tool that helps you to do Valuable Agile Retrospectives .

The book  Getting Value out of Agile Retrospectives  from Luis Gonçalves and Ben Linders provides many different retrospective exercises that you can use to design effective retrospectives for continuous sustainable improvement.

A book that I highly recommend for anyone who works with teams is Liftoff by Diana Larsen and Ainsley Nies. It provides lot’s of ideas to form agile / Scrum / Kanban teams and get them started.

Related posts, news, workshops, conferences, and books:

Ben Linders

This post has 4 comments.

This post uses gray text on a white background. It is difficult to read, especially if a user has any vision disability. The contrast between foreground and background is only 3.11. WCAG 2.1 requires it to be at least 4.5. Why not make this site more inclusive by upgrading the font color to black, or at least closer to black?

Thanks Jonathan for pointing this out. I’ve set font color to black, is this Better?

Fabulous!!! Thank you!

You’re welcome 🙂

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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.

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The Sailboat Exercise

An unconference approach to running productive team retreats.

I thoroughly enjoy planning and facilitating team retreats. When done well, they are a rejuvenating time for team members to reflect on the previous few months, to plan what’s coming next, and to just straight up have some fun together.

As a manager, I’ve found these retreats essential in keeping a team aligned and empowered to take ownership of what they’re building together. Even in Covid times – when the idea of getting together in-person seems quaint – taking time off from "normal work" to connect with your team in a less formal setting can still be quite valuable.

I’ve experimented with different approaches to running these retreats, but one exercise that has become essential is the “Sailboat Exercise”*:

At its core, the Sailboat Exercise is a brainstorming process for garnering honest feedback from employees about the state of the team / product / company. As such, it can be used independently of team retreats. That said, I’ve found it particularly effective in such a setting because it’s a fun, low pressure exercise at a time when folks are in a mindset to candidly assess the state of things — i.e. they’re removed from the stresses of their normal day jobs, and able to come up for air to think more holistically.

In fact, I’ve found it to be such a good exercise for divining the zeitgeist of the team — what’s been good/bad/indifferent and where should we head next? — that I use it to kick off the retreat, with its outcome driving the topics to be discussed during the rest of the event.

In this way, it essentially becomes a tool for running a team retreat as an unconference (i.e. a participant-driven conference), but with enough structure in place to achieve the goals of 1) clear-eyed retrospection, and 2) forward-thinking planning.

For those wanting to try out the Sailboat Exercise, the steps are as follows:

• Draw the sailboat scene on a whiteboard (have some fun with it!), being sure to include the following visual elements: the wind in the boat’s sails, the anchor dragging behind it, the hidden rocks beneath the surface ahead, and the island beyond that.
• Ask the team to write as many ideas as they can possibly think of, 1 per sticky note, for each of the four groups, where:
• Wind = the things that are propelling the team forward (e.g. inherent team strengths, competitive advantages of what you’re building, solid processes, etc.)
• Anchor = the things that are slowing the team down (e.g. gaps in the team, competitive weaknesses, subject areas to invest in, etc.)
• Rocks = the things that aren’t currently being considered at the moment, but are risk points for the team going forward (e.g. areas of tension, bottlenecks around scaling, lurking competition, etc.)
• Island = the things that the team should be aspiring to (e.g. short term objectives, medium term goals, long term mission, etc.)

3. Let the team members independently brainstorm these ideas for 20–30 minutes, encouraging them to not overthink it. At the end of the brainstorming process, have them affix each sticky note to the whiteboard near its appropriate visual element. People are often inclined to avoid affixing a sticky note that duplicates one already on the board, but it’s important to help the group fight that urge since it’s actually quite useful to see which topics were brought up by multiple team members.

4. At this point, the facilitator’s job becomes to organize the stickies on the board so that similar ones are physically connected (see image below). This can be done with the full group’s participation, or with just 1 or 2 others while the rest of the group mingles. Either way, it’s useful for the facilitator to have at least some help in order to group these sticky notes together into thematic topics.

5. Once grouped, the facilitator asks each team member to assign a total of 5 votes to whichever topics that they personally would like the group to discuss while at the retreat. I’ve found that five votes seems to be the right number for most situations, and that the fastest way to enable the voting is to let each person write their own tally marks:

6. The most popular topics become the basis for the set of follow-up sessions during the rest of the retreat. The scheduling of which topics to discuss when can be outlined at this point, or left fluid as the retreat unfolds. As facilitator, your goal is to help the team cover as many of the highest ranked topics as possible while ensuring that the group is energized going into a given session at a particular time. If they don’t seem ready for a discussion because they need a break, some food, a lighter topic, etc. it’s best to delay or forgo the conversation rather than plow ahead.

7. Whenever possible, I look for others on the team to facilitate and/or drive the conversation during a particular session, only speaking up myself when necessary to move the discussion along, or to alleviate any buildup of tension.

8. At the end of our time together, we run a retrospective on the retreat as a whole — what did people like/dislike, and what might we do differently next time. This includes feedback on the Sailboat Exercise itself, as well as the topics that were brought up / discussed. As part of this retrospective, I make sure to thank everyone for their time, energy, and input. I also outline a few actionable steps we’ll be doing as we come out of the retreat because it’s important to a) ensure that team members have felt heard, and b) carry the positive momentum and energy from the event back into the workplace.

That’s it! The Sailboat Exercise has been a crucial tool in my manager tool belt largely because it’s simple to run and consistently produces great results.

I was recently asked by a fellow technologist what advice I had for creating a highly productive team. I said that, amidst a dizzying number of variables, the underlying foundation is almost always that each member of that team feels empowered — to share their opinions, to take on responsibilities, and to be a tangible part of contributing to something larger than themselves. It’s a cliched answer, of course, but as with most cliches, the devil is in the details; accomplishing this goal requires constant nurturing through thoughtful intent, communication, and processes.

In my experience, the Sailboat Exercise has been a great concrete tool for showing, not just telling, team members that they are central to the process of steering the ship.

* Note: I was introduced to this idea by friend and former colleague, Christopher Atkins . He had seen a few folks in the agile community using a version of it for sprint retrospectives, and we decided to experiment with the idea of leveraging it to run our next team retreat. It turned out to be a highly successful experiment, and I’ve since run the process numerous times / adapted it a bit as I’ve learned what works and what doesn’t. It’s worth noting that in doing research for this post, I discovered that the original inspiration for this type of process was a “Speed Boat Exercise” developed by Luke Hohmann .

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