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How to conduct the Sailboat retrospective

If you want to break the routine and perform a substantial retrospective activity, the Sailboat is the perfect option to have in your Agile toolbox.

In “Agile retrospectives: making good teams great,” Esther Derby, Diana Larsen, and Ken Schwaber say that an Agile retrospective can be referred to as “heartbeat” retrospective — part of the regular rhythm and lifeblood of the project team. Listening to a heartbeat or taking a pulse gives indicators about the health of a person, and iteration retrospectives diagnose the health of the team.

When you are holding retrospectives iteration after iteration, especially when the iterations are short, one or two week increments, teams get bored when the same activities or approaches to discussion show up week after week.

How to break this monotony caused by the repetition of the same retrospective activity?

The last thing you might associate software development with would be with the thought of the open ocean. The sailboat retrospective excels at making the team think about the goals of the project, the factors that are slowing them down, and the risks that could arrive without any notice.

If you want to break the routine and perform a substantial retrospective activity, the sailboat is the perfect option to have in your Agile toolbox.

What is the Sailboat retrospective?

Imagine your team on a sailboat trying to reach an island. The island is your team’s objective, and the wind is all the things that help your team achieve its goals. The anchor is what is slowing down the boat, and the iceberg represents what could stop their journey.

How to set up this activity

For this exercise, we won’t use a matrix to collect comments. Instead, we will use the illustration below to symbolize five different aspects to discuss the past and future sprints.

💡 Drawing this exercise with your team can be a good icebreaker before starting the meeting. It will also help to understand how this meeting will be conducted.

Sailboat retrospective drawing with the Island, the Iceberg, the Sailboat, the Anchor and the Wind.

1. The island

On the left, draw the island. The island is a visualization of your team’s goals. It is the purpose of their journey.

2. The boat

On the right, draw a ship that represents your team. You can add the name of your team on it, or use your team’s logo to make your team members feel more engaged.

3. The wind in your sails

Illustrate the wind that is pushing the boat’s sail. Explain to the team that the wind symbolizes everything that helps them reach their goals.

4. The anchor

Draw an anchor that is in the ocean and attached to the boat. The anchor stands for anything that is slowing the team down.

5. The iceberg

Last but not least, draw an iceberg in the ocean. The iceberg is a symbol of the risks that the team could encounter in the future.

How to conduct the Sailboat activity


You will ask everyone to write down what their goals are for the completion of the sprint. These goals are your starting point. Starting this activity by the end will help your team members think about how they “navigate” to the end of the project. After a few minutes, you will invite each person to present their goals and paste them on the island.

Repeat this process for each step (the wind, the anchor and the iceberg). Remember to give your team members a short description of every element you drew so they will know what you expect from them. You can group similar comments to facilitate the voting step.

Discuss, vote and create an action plan

When your team members have exposed all their comments, proceed to the dot voting phase. Allow five votes per participant. Discuss the most voted topics with your team to create action items. As usual, assign owners to these items, and provide a short and clear description so everyone can understand how to resolve their action items.

It is an excellent practice to add these action items to a public board.

Takeaways of the Sailboat retrospective

This exercise is excellent for getting an overview of how everyone feels and your team’s strengths and weaknesses. As a scrum master, you will be aware of the potential risks your team could face.


You can adapt this framework to build a specific themed activity. For example, if your team is a fan of Star Wars, you can substitute the Boat with a Spaceship (X-Wing or the Millenium Falcon). The Island can be the Rebellion base; the Iceberg will be an Imperial fleet. The Engine of your ship can replace the Wind, and a damaged Wing or Asteroids can replace the Anchor.

A Rebellion base, a X-Wing, Asteroids and the Imperial Fleet.

Adapting retrospective activities to your team is vital to make these moments fun, engaging, and productive.

I hope this article helped you perform the Sailboat retrospective. You can find this retrospective template on Neatro. Give it a try, and feel free to reach out to me if you want to share some feedback about the app!