The Sailboat Retrospective Template

Looking for an engaging way to reflect on your team's journey and chart a course for success? The Sailboat retrospective uses nautical metaphors to create a powerful visual framework for identifying what's propelling your team forward and what's holding you back.

What Is The Sailboat Retrospective?

The Sailboat retrospective transforms your team into seafarers on a voyage toward their goals. This popular agile retrospective format uses a compelling nautical metaphor where your team is aboard a vessel navigating through both calm and challenging waters.

The template consists of four key metaphorical elements:

• Goal/Island: The destination your team is sailing toward
• Wind: Positive forces pushing your team forward
• Rocks: Potential risks and obstacles ahead
• Anchor: Factors holding your team back or slowing progress

This versatile template works equally well as a retrospective for completed sprints or as a "futurespective" when planning upcoming work or projects.

Benefits & When to Use

Use the Sailboat retrospective when:

• You want to break out of standard retrospective formats and engage your team with a visual metaphor
• Your team needs to balance reflection on past performance with planning for future challenges
• You're starting a new project and want to identify potential obstacles early
• Team morale needs a boost through a more creative and engaging format

The Sailboat template is particularly effective for remote development teams as it provides clear visual cues that help structure conversation and ensure everyone contributes across all areas.

How to Run a Sailboat Retrospective Session

Time needed: 60-75 minutes

1. Introduction (5 minutes)

   • Explain the sailboat metaphor and what each section represents
   • Clarify that this is both backward and forward-looking

2. Define the Goal (10 minutes)

   • Have team members add sticky notes describing what they believe is the team's goal or vision
   • Place these on the island
   • Group similar notes and discuss to align on the destination you're sailing toward

3. Individual Reflection (10 minutes)

   • Ask team members to add sticky notes to all four sections:
     • Goal/Island: What are we working towards?
     • Wind: What is pushing us forward?
     • Rocks: What risks do we face?
     • Anchor: What is holding us back?

4. Group Discussion (15 minutes)

   • Take turns revealing and discussing each area
   • Group similar items together
   • Use reactions to show agreement or disagreement with specific points

5. Prioritization (10 minutes)

   • Vote on the most important items in each category
   • Focus on identifying patterns across categories

6. Action Planning (15 minutes)

   • Based on the prioritized items, brainstorm specific actions to:
     • Harness more wind (leverage positive forces)
     • Navigate around rocks (mitigate risks)
     • Lift the anchor (remove impediments)
   • Add these to the Actions section

7. Assign Ownership (5 minutes)

   • Determine who will be responsible for each action item
   • Set timeframes for completion

Tips for a Successful Sailboat Session

• Balance the metaphor: While the sailing theme is engaging, don't let it overshadow the actual retrospective work. Keep discussions focused on real team dynamics.

• Highlight the interconnections: Help the team see how elements in different categories relate to each other. For example, how addressing an anchor might help you better navigate around rocks.

• Use prompting questions if teams get stuck:

  • "What external factors are accelerating our progress that we should leverage more?"
  • "Which team practices or habits are holding us back most significantly?"
  • "What unseen obstacles might we encounter in the coming weeks?"

• Visual highlighting: Use Metro Retro's participant highlighting feature (click on a team member's icon) to see who contributed which notes, ensuring everyone participates.

• Look for patterns: Pay special attention when similar themes appear across multiple categories – these often indicate systemic issues that need addressing.

Remember that the goal isn't just to identify what's working and what isn't, but to chart a clear course forward with actionable steps your team can begin implementing immediately after the session.