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Sailboat Retrospective

The sailboat in the image serves as a metaphor for the team; they identify the anchors that slow them down, the winds that speed them up, and the rocks that risk their future. The island ahead of them is a representation for their goals and mission which they must strive to reach. Adjusting the sails is a way of navigating all of these components in order to be successful. This technique encourages the team to become proactive and think about all possible scenarios.
What is the wind pushing our sails that make us go fast
What anchors are holding us back
What rocks are ahead of us that risk our future
What is our ideal island destination
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Sailboat Retrospective: A Fun and Effective Reflection Tool

The Sailboat retrospective technique is a creative and low-stress way for a team to reflect on a project. It allows team members to identify what went well, what went wrong, and what improvements can be made in the future. This technique usually takes place immediately after the completion of a project or sprint.

Anatomy of the Sailboat Retrospective

A Sailboat retrospective typically has five main components:

  • The sailboat: the team or project
  • The island or shore: the ultimate goal or vision
  • The wind (sails): the strengths and positive aspects of the team or project
  • The anchors: the obstacles that slow down progress
  • The rocks: the risks or potential pitfalls of the project

Some teams add additional aspects such as the sun to represent things that make the team happy, or choppy waves to represent areas of anxiety. Teams can customize the retrospective to fit their specific needs.

Why Sailboat Retrospective Works

The Sailboat retrospective is effective because it uses relatable metaphors to help team members identify their strengths and weaknesses. The non-threatening approach allows team members to communicate more freely and openly. This fun exercise helps the team think about the big picture and improve their processes. The average Sailboat retrospective leads to the identification of 3-5 action items for improvement.

How to Run a Sailboat Retrospective

A Sailboat retrospective should take about 60 to 90 minutes to complete. Here's how to run one with your team:

  1. Gather key stakeholders
  2. Set ground rules for a positive and open environment
  3. Sketch a visual of the sailboat and its components
  4. Set up a template to capture team feedback
  5. Brainstorm or hold a group discussion to gather feedback
  6. Review the feedback and conclude the retrospective with a plan for improvement.


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