Sailboat Retrospective – Rocks (risks), Wind (pushing), Anchor (holding back), Island (goal)

Wouldn’t you love it if your everyday work would feel like a day on a sailing boat? I definitely would, but unfortunately we can’t promise you the stars (or the ocean days) by asking you to try out agile retrospective techniques. Still the Sailboat Retrospective is a great way to improve your agile collaboration and by using it you can definitely ease the waves on your way to success as a team. 

The Sailboat Retrospective contains four different categories that are used to discuss different elements of your agile collaboration. 

These are called Rocks, Wind, Anchor and Island. Everything you need for the perfect day on a boat, right?

These four stand for different things which can possibly occur throughout a sprint: Rocks (risks), Wind (pushing), Anchor (holding back) and Island (goal). The Sailboat itself represents the team.

So, the question is, how can you reach the desired island by implementing the Sailboat Retrospective?

What is the Sailboat Retrospective?

The Sailboat Retrospective is an agile retrospective technique which aims to define a vision where a team wants to go and the possible assistance and problems that may arise. Teams often appreciate this agile retrospective technique because it’s simple and clear. 

In order to carry it out you need a flip chart, pens and sticky notes. If you’re not good at drawing you can use pictures as well.

You draw a sailboat, clouds, rocks, an anchor and an island on the flip chart and explain to your team which item represents which category. Afterwards the team members are asked to label sticky notes with topics that they want to discuss in each of the categories. You should set a timebox of about five minutes for it. In the end you can use dot-voting to decide which topics you want to discuss more intensively. 

As you can see, it is fairly easy to do this. To give you a more detailed insight into what the different categories mean, we’ll provide you with examples on questions that can be asked.

Questions to open up a Sailboat Retrospective 

Sailboat Retrospective – Rocks (risks)

Rocks in the Sailboat Retrospective represent the risks and potential problems that occurred throughout the last sprint. To initiate the train of thought you can ask questions like: 

  • What problems did we need to solve?
  • What hindered our workflow?
  • What made us feel insecure?
  • Or if you want to do it in a more metaphorical way: Which rocks did we have to avoid?

By reflecting this you can avoid risks in the next sprint and work more smoothly and solution oriented. 

Sailboat Retrospective – Wind (pushing)

As probably everyone knows, a sailboat needs wind to sail. This can be seen as a metaphor for teams: What makes a team go forward? In this agile retrospective technique the wind can be seen as all the pushing factors that make your team work efficiently. 

To figure out what those factors are for your fellow members, ask them questions like:

  • What makes us perform in the best possible way?
  • What motivates us?
  • What propels us forward to reach our goals?

By identifying the pushing and positive factors of your agile collaboration you’ll learn to reflect your working behaviours more intensively and get an awareness of how you can work optimally. That’s how you can integrate your best practices in your agile collaboration.

By the way: If you like this retro format, you can open it directly in the team development tool Echometer:

This is what it looks like to open a retrospective in the Echometer tool: Click on the button and invite your team – no login required 🙂 As you can see, it even gives you the option to choose from more retrospective ideas.

Sailboat Retrospective – Anchor (holding back)

This category contains factors that were holding you back in your last sprint. What’s the difference to Rocks (risks)? Aspects in your collaboration that are holding you back are different to risks and therefore need to be looked at separately. This is because they aren’t things that potentially harm your collaboration but are slowing you down or keep you from trying out new ways of work.

  • What is holding us back?
  • What did we always want to do but didn’t dare to?
  • Which aspects of our daily work are slowing us down?

It is important to carefully reflect your last sprint and try to find out at which point you could have worked faster/ better/ more smoothly. It is relevant to discuss those things because realizing what potential anchors are will help you improve your work. This will lead to efficient work and satisfied colleagues. 

Sailboat Retrospective – Island (goals)

Where do you want to go with your sailboat? To the island! In my opinion this category is the most important one. This is because setting goals is an essential part of efficient und fulfilling work. By defining what your goals are you can work out explicitly what you want and are going to do to reach those goals. You have to keep a few things in mind while defining those goals. Goals need to be specific, terminated and measurable in order to be motivating and effective. 

It’s good if you keep the SMART-Formula in mind while setting those goals. SMART is an acronym and stands for




All these attributes are essential since teams need to have a personal interest in reaching those goals (accepted), they need to know what they gotta do (specific), they want to be able to find out if they reached their goal (measurable), they need a timetable (terminated) and they need to be able to reach those goals (realistic). 

Defining your goals helps you identifying the Rocks (risks), Wind (pushing) and Anchor (holding back) because you can specifically measure what helped and hindered you to reach your goals during your last sprint.

Once again, in case this is interesting: You can find many more fun retrospective ideas in the Echometer retrospective tool. Feel free to have a look (no login required):

Summary: Sailboat Retrospective

This agile retrospective technique is a little more metaphoric than other agile retrospective techniques (see our articles about 4L Retrospectives, The “Mad, Sad, Glad” Retro Format and the Starfish Retrospective). 

This may seem a little weird to you at first but it often helps people to wrap their mind around past events and look at them from a different perspective. 
Sailboat Retrospectives are an efficient agile retrospective technique which can help your team to gather detailed information on the events of your last sprint and define specific goals for upcoming sprints. Nevertheless, there are still more possibilities to create retrospectives in order to look at recent events from different perspectives. If you want to gain further insight in other agile retrospective techniques you should check out our articles about 4L Retrospectives and the “Start, Stop, Continue” Retro.

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