Sailboat Retrospective

Visualize team progress as a journey at sea with winds, anchors, and opportunities

The Sailboat Retrospective uses a powerful maritime metaphor to help teams reflect on their progress and challenges.

In this retrospective, the team's journey is represented by a sailboat navigating through waters. The wind represents helping forces, while anchors symbolize obstacles. Rocks represent risks ahead, and the sun represents positive elements keeping team morale high. The destination represents the team's goals.

This visual approach makes it particularly effective for teams who prefer metaphorical thinking or want to break away from traditional retrospective formats. It helps teams identify both opportunities and challenges while maintaining a clear focus on their objectives.

What is The Sailboat Retrospective

Goal

What are we working towards?

The goal represents the team's destination. Encourage participants to think about both short-term and long-term objectives. Help the team align their vision and ensure everyone understands where they're heading.

Wind

What is pushing us forward?

Wind represents positive forces helping the team move forward. Guide the discussion to identify enabling factors, resources, and practices that are working well. This helps reinforce successful behaviors and processes.

Anchor

What is holding us back?

Anchors represent impediments slowing the team down. Encourage honest discussion about obstacles while maintaining a constructive tone. Focus on identifying actionable solutions rather than just listing problems.

Rocks

What risks do we face?

Rocks represent potential future risks and challenges. Help the team think proactively about what could go wrong and develop mitigation strategies. Focus on both technical and non-technical risks.

Sun

What is making us feel good?

The sun represents positive elements boosting team morale. Encourage sharing of achievements, recognition, and positive experiences. This helps build team spirit and identifies what should be maintained or expanded.

Suggested Icebreaker Questions

  • If your current project was a type of boat, what would it be and why?
  • What's your favorite memory of being near water (ocean, lake, river)?

Ideas and Tips for Your Retrospective Meeting

  • Start by explaining the metaphor clearly and ensure everyone understands what each element represents
  • Use the visual nature of the exercise to create a collaborative diagram during the session
  • Keep a balance between discussing problems (anchors/rocks) and opportunities (wind/sun)
  • Encourage quiet team members to contribute by going around the room for each element
  • End the session by prioritizing actions based on impact and feasibility
  • Consider using breakout rooms for larger teams to ensure everyone gets a chance to contribute

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How to Run Effective Meetings with TeamRetro

Start Your Session in a Click

Log into TeamRetro and choose your template. Customise questions and the workflow to create your perfect retro for your team.

Create Your Team Easily – No Separate Accounts Needed

Invite your team in seconds via email, link, or Slack. Role based permissions and SSO options available.

Brainstorm Individually – Free From Bias

Encourage open and honest input with anonymous brainstorming. Set the mood with background music, give teams space to think independently, and keep the session flowing with built-in timers.
Grouping of ideas after brainstorming in a retrospective meeting

Smart Grouping for Faster Insights

Easily drag and drop similar ideas or let AI suggest groupings to save time. Choose between facilitator-led or participant-led grouping to match your team’s workflow.
Grouping of ideas after brainstorming in a retrospective meeting

Fair, Flexible, and Fast Voting

Keep votes private and unbiased with multiple voting options. Once voting is complete, TeamRetro automatically sorts results, helping your team focus on what matters most.
Grouping of ideas after brainstorming in a retrospective meeting

Engage, React, and Capture Key Insights

Walk your team through ideas one by one with Presentation Mode. Stay in sync, spark real-time discussions, and capture feedback with comments, live reactions, and polls—all in one place.

Grouping of ideas after brainstorming in a retrospective meeting

Turn Ideas Into Action

Propose next steps with team buy-in, get AI-powered action suggestions, and keep everything in one place. Committed actions sync to your personal dashboard and integrate with your workflow tools—keeping you on track.

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Save, Share, and Stay on Track

Get quick AI-powered summaries, add facilitator notes, and store retrospectives in your library for easy access. Schedule your next session and track published actions to keep your team accountable at the next retro.

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Turn Team Data into Actionable Insights

Uncover trends, common themes, and key engagement metrics at a glance. Track sentiment shifts, analyze conversations, and monitor completed actions to drive continuous improvement.