How to run an effective Sailboat Retrospective meeting

Learn the ins and outs of conducting a successful Sailboat Retrospective meeting. Discover the sailboat model's benefits, tips, and methods to encourage effective team retrospectives.

Team on a boat sailing toward an island.

We're diving deep into the Sailboat Retrospective technique—a creative and effective approach to help your team assess what's working and what needs improvement.

What is a Sailboat Retrospective?

The Sailboat Retrospective is an innovative team meeting framework that uses maritime symbols to evaluate what's aiding and impeding your project's progress. By understanding each component of the metaphor, your team can identify actionable steps to move forward effectively. The five components of a Sailboat Retrospective are as follows:

  • Sailboat: Representing your team or project, the sailboat is the core element. Think of each part of the boat as different facets of your team.
  • Wind: Wind represents the positive forces that propel your boat forward. This symbolizes best practices, team strengths, and opportunities that are currently pushing your project towards success.
  • Anchor: The anchor represents the challenges, bottlenecks, or obstacles holding you back. Identifying these allows the team to understand what needs to be addressed to move forward.
  • Island: Symbolizing your project's goals or objectives, the island is what you're aiming to reach. It serves as a visual reminder of the team’s collective destination.
  • Ocean: Sometimes included, the ocean symbolizes the external market conditions or project environment. It's the context in which your 'sailboat' has to operate, filled with both challenges and opportunities.

This approach offers a creative spin compared to more traditional techniques like Start-Stop-Continue or 4 Ls (Liked, Learned, Lacked, Longed for).

Sailboat retrospective meeting templates

Benefits of Sailboat Retrospective

If you're considering giving the Sailboat Retrospective a try, here are some of the main benefits that you can expect:

Team engagement

Traditional retrospectives serve their purpose well but can sometimes feel routine. The Sailboat Retrospective adds a touch of creativity that energizes these crucial team meetings. By using the metaphor of navigating a sailboat, the atmosphere of the meeting naturally becomes more engaging. Team members often find this imaginative setting encouraging, which increases active participation.

Holistic understanding

The beauty of the Sailboat Retrospective lies in its balance. It encourages a holistic view of your project, allowing you to identify both obstacles (anchors) and positive influences (winds). The island and sometimes the ocean are also part of the equation, providing context for goals and external influences. The end result? A comprehensive understanding that leaves no stone—or in this case, sea shell—unturned.


By the end of a Sailboat Retrospective meeting, your team will not only identify the positive and negative influences on your project, but you'll also walk away with a list of actionable steps. In essence, this format provides a concrete pathway to navigate your project more effectively towards its goals.

So, if you're looking for a method that combines engagement, a comprehensive viewpoint, and a focus on action, the Sailboat Retrospective could be your next great team meeting strategy. Ready to embark on a productive journey?

How to plan an effective Sailboat Retrospective?

Now that we have established what the main benefits of the Sailboat Retrospective are, we can look at the best way to implement this technique:

Preparation is half the battle: Before you start, gather the essentials. You'll need Post-its, markers, and a whiteboard. For remote teams, Craft offers a digital template for a Sailboat Retrospective which is perfect for getting started. A digital board like Miro could also do the trick.

Agenda matters: Clearly outline the objectives. Whether you're seeking to address bottlenecks or boost productivity, make it known.

Time is of the essence: A good Sailboat Retrospective needs at least 60 minutes. Ensure everyone's availability during this time to encourage full participation.

Steps to implement

1. Set the stage: Begin by drawing a visual representation. Sketch a sailboat in the center, some anchors below it, wind clouds on either side, and an island in the distance representing your team's goal. If you are working remotely, the Craft Sailboat Retrospective template is already set up with visual representations. By creating this visual metaphor, you establish the framework for the retrospective.

2. Brainstorm: Now, allow your team-members to give their input. If you are doing this retrospective in person then Post-It notes are recommended; this step is also very simple remotely as team members can all put their thoughts into a shared digital space.  Ask them to write down what they consider to be winds (factors aiding the project) and anchors (factors hindering progress). Encourage everyone to be as specific as possible; the more detailed the input, the more meaningful the discussion that follows.

3. Group & discuss: For in person retrospectives, begin grouping the Post-Its by similarity. This will help in analyzing patterns and areas that require attention. If you are using the Craft template then everyone will have already input their comments into the relevant sections. Then, open the floor for discussion. Allow team members to explain why they placed certain items where they did and what those items mean to the team and the project.

4. Action plan: After the discussion, it's time to switch into action mode. Prioritize notes and comments based on urgency, impact, or any other criteria the team agrees upon. Discuss how to harness the winds effectively and how to remove or mitigate the anchors. Finally, create an action plan outlining the steps needed to resolve the issues and move forward with your project in an effective manner.

Useful tips for organizing your Sailboat Retrospective

1. Be inclusive: The Sailboat Retrospective is a space for each and every team member to express themselves. Methods like round-robin or silent brainstorming can help make this possible. In a round-robin, each person takes turns sharing their thoughts, ensuring that everyone is heard. Silent brainstorming gives people a few minutes to jot down their ideas independently before discussing them collectively. The aim is to create a participative atmosphere where all opinions are equally valued.

2. Effective moderation: It's essential for a facilitator to manage the discussion to ensure it stays on track. The facilitator should aim to guide the discussion without monopolizing it. Use timers if necessary to allocate time for each agenda item and employ techniques to refocus the group if the conversation strays too far from the main topic. The facilitator’s role is crucial in maintaining a focused and effective dialogue.

3. Prioritize: Given that there will likely be multiple challenges and opportunities identified, it's impractical to think you could address them all simultaneously. A simple voting system can be a useful tool here. Each team member gets a certain number of votes (often three) to place on the issues they find most pressing. This way, the team gains a clear sense of direction, allowing you to tackle the most critical issues right away.


The Sailboat Retrospective can bring fresh energy to your team's reflective and collaborative processes. Far from being a mere 'feel-good' exercise, this technique is a strategic tool will help you team navigate towards your project goals more effectively.

The Sailboat Retrospective is essentially about charting the best course for your team's journey. It balances the need for introspection and action, giving everyone a clear sense of direction and purpose. The visual metaphor of the sailboat makes abstract concepts more relatable, therefore enhancing comprehension and participation among team members. Using this approach can improve your team's engagement and understanding while providing an effective plan of action.

So, as you look to the future of your project, consider adopting the Sailboat Retrospective. It's a methodology that not only identifies where you are but also points you in the direction you want to go. Are you ready to set sail towards project success?