Sailboat Retrospective Explained: A Creative Approach to Agile Reflection
- Michelle M
- Jul 27
- 5 min read
In Agile project management retrospectives are a powerful tool that empower teams to reflect, learn, and improve continuously. Among the many retrospective formats, the Sailboat Retrospective stands out as a creative and visually engaging technique. Unlike traditional retrospectives that follow a rigid structure, the Sailboat Retrospective uses a metaphorical approach to make team reflection more intuitive and fun.
Whether you're new to Agile or a seasoned Scrum Master looking for a fresh retrospective idea, the Sailboat Retrospective can bring a refreshing perspective to team discussions. It encourages participants to visualize their journey, identify potential risks, recognize driving forces, and celebrate achievements all while aligning efforts toward a common destination.
This blog will explore what a Sailboat Retrospective is, how it works, when to use it, its benefits, how to run one step by step, and tips for making the most of this exercise.
Understanding the Sailboat Retrospective Metaphor
The Sailboat Retrospective uses a metaphor where your team is a sailboat sailing toward an island your goal. Along the way, the boat encounters various elements that impact its journey. These elements form the core categories of the retrospective:
The Island: Represents the team's goals or vision. What are you working toward?
The Sail: Represents the driving forces pushing you forward things that went well.
The Anchor: Represents things that are holding the team back impediments or blockers.
The Rocks: Represent hidden risks or potential problems that might derail your project.
The Wind: Represents enablers team behaviors, tools, or practices that help you move faster.
By breaking down a sprint or project into these metaphorical elements, teams can discuss not just what happened but why and how they can navigate more effectively in the future.
When to Use a Sailboat Retrospective
The Sailboat Retrospective is versatile and can be used:
At the end of a Sprint in Scrum or Iteration in Kanban.
After completing a project milestone or release cycle.
During team reset or strategy planning sessions.
With new Agile teams who benefit from visual metaphors.
In remote or hybrid settings using online whiteboards like Miro, MURAL, or FigJam.
It works especially well when the team needs a break from more analytical or repetitive retrospective formats like Start/Stop/Continue or 4Ls (Liked, Learned, Lacked, Longed For). The visual nature of the Sailboat makes it easier to generate insights in a creative way.
How to Run a Sailboat Retrospective
Here’s a step-by-step breakdown of how to run a successful Sailboat Retrospective session:
Step 1: Prepare the Canvas
Create a simple drawing or digital board of a sailboat on water, sailing toward an island. The drawing should include:
Island on the horizon (Goal)
Sail above the boat (What moved us forward?)
Anchor below the boat (What slowed us down?)
Rocks underwater or near the boat (What risks do we see?)
Wind pushing the sailboat (Enablers or strengths)
Use sticky notes, icons, or markers so that each participant can interact with the canvas.
Step 2: Set the Stage
Explain the metaphor to the team. Make sure everyone understands what each element represents. For example:
“The Island is where we want to go. The wind helps us move. The sail captures the wind. The anchor holds us back. The rocks are dangers we might not have noticed yet.”
Set a psychologically safe environment by reminding everyone that the goal is improvement, not blame.
Step 3: Collect Inputs
Ask team members to brainstorm and contribute to each area using sticky notes (physical or digital). Give 5–10 minutes per section or allow freeform contributions.
Island – What is our shared goal?
Sail – What helped us progress? (e.g., teamwork, good communication, tools)
Anchor – What held us back? (e.g., unclear requirements, bottlenecks)
Rocks – What risks do we foresee? (e.g., changing scope, dependencies)
Wind – What strengths or enablers should we amplify?
Encourage honesty, creativity, and reflection.
Step 4: Group and Discuss
Once everyone has added their thoughts, group similar items together. Facilitate a discussion around each area:
What patterns do we notice?
What’s surprising?
Are we aligned on the goals (Island)?
Which anchors are within our control?
Which winds can we catch better?
Which rocks need proactive action?
Use dot voting if necessary to prioritize which issues to discuss in depth.
Step 5: Define Action Items
The ultimate purpose of a retrospective is to improve future work. Take the most critical insights and convert them into clear, actionable items. Assign owners and define timelines.
Examples:
“Schedule a mid-sprint check-in to reduce blockers.”
“Create a risk board for better visibility.”
“Automate manual testing to reduce delays.”
Don’t overload the team. Focus on 1–3 key improvements.
Step 6: Close and Reflect
Thank the team for their honesty and insights. Ask them:
What did they think of the Sailboat format?
Was it more helpful than past retrospectives?
Do they feel heard and aligned?
You might even consider doing a retro of the retro!
Benefits of the Sailboat Retrospective
Using the Sailboat metaphor offers several advantages:
1. Increased Engagement
The visual and storytelling nature of the exercise makes it more engaging than plain text-based formats.
2. Encourages Creativity
It helps team members think outside the box and view problems and opportunities differently.
3. Promotes Psychological Safety
The metaphorical framing allows participants to raise concerns indirectly, which is helpful in sensitive situations.
4. Improves Team Alignment
It aligns everyone on the shared vision (the Island) and uncovers whether everyone sees the same destination.
5. Adaptable to Any Team or Project
From software development to marketing teams, this format can be customized for different projects and team dynamics.
Pro Tips for Facilitators
Customize the Metaphor – You can adapt the sailboat image to a rocket ship, hot air balloon, or racecar depending on your team’s interests.
Keep it Time-Boxed – Aim for 60–90 minutes. Breakout rooms help with larger groups.
Use Fun Tools – Online platforms like Miro, MURAL, and Jamboard make the experience interactive.
Rotate Roles – Let different team members facilitate to encourage ownership and growth.
Follow Up – Review action items in the next sprint review or planning session.
Variations of the Sailboat Retrospective
Once your team gets used to this format, try these tweaks:
Stormy Weather – Add storm clouds to represent external forces affecting the project (e.g., market changes).
Treasure Chest – Add a section for “wins” or “lessons learned.”
Multiple Islands – Use if the team has multiple goals or stakeholder expectations.
When Not to Use It
While versatile, the Sailboat Retrospective may not be the best fit if:
Your team prefers highly structured, non-metaphorical discussions.
You’re dealing with highly technical blockers that need root cause analysis.
Time is limited, and a quicker retro format is required.
In those cases, consider formats like the 5 Whys, Fishbone Diagrams, or Mad/Sad/Glad.
Conclusion
The Sailboat Retrospective is more than a fun drawing it's a powerful team alignment tool wrapped in metaphor. It helps Agile teams navigate the choppy waters of software development or project execution with clarity, collaboration, and purpose.
By reflecting on what drives us forward, what holds us back, and what lies hidden beneath the surface, teams can make better-informed decisions and foster a culture of continuous improvement.
If your retrospectives are starting to feel routine or mechanical, setting sail with the Sailboat Retrospective may be just the wind your team needs.
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