Collaboration

Sailboat Retrospective

Use the sailboat metaphor to run a team retrospective. Visualize what helps (wind), hinders (anchor), defines goals (island), and threatens (rocks). It's an accessible way to discuss project status and team performance.

Duration
45 mins
Group Size
4-10
Category
Collaboration
Difficulty
Easy
The goals of this exercise are to reflect on team performance, identify obstacles and aids using a visual metaphor, create actionable improvements, and build alignment on challenges and goals.

  • Completed sailboat retrospective.

  • Identified key anchors and winds.

  • Action plan created.

This visual metaphor makes difficult conversations easier, especially for teams new to retrospectives. The drawing doesn't need to be perfect. Consider adding a SUN element for "things going well" to balance the discussion. Some teams add SHARKS for external threats or TREASURE for unexpected wins. Start with the positive (wind/sun) to set a constructive tone. When discussing anchors, focus on solutions, not blame. The rocks discussion should lead to risk mitigation plans. Regular use (monthly/quarterly) shows progress over time. Take a photo for comparison in the next retrospective. I've found that sometimes the 'rocks' category is difficult for teams - be prepared to prompt them with examples.

  1. Setup & Drawing (5 minutes): Draw a large sailboat on a whiteboard or flip chart. Include the island (goal), wind (helps), anchor (hinders), and rocks (risks). Distribute sticky notes to participants.

  2. Individual Reflection (10 minutes): Each participant writes sticky notes for each category (wind, anchor, rocks, island). Encourage multiple notes per category. Focus on specific, constructive, and actionable items. Work silently.

  3. Posting & Grouping (12 minutes): Participants post their notes in the relevant areas of the drawing. Read the notes aloud while posting (optional). Group similar notes together to identify themes. No discussion yet, just organizing.

  4. Discussion (15 minutes): Discuss each category, starting with WIND (positive momentum). Then move to ANCHOR (challenges), ROCKS (risks), and confirm the ISLAND (shared goal). Identify the most critical items in each area. Ensure everyone's perspective is heard.

  5. Action Planning (3 minutes): Select the top 2-3 items to address. Assign owners for each action. Set a timeline for addressing anchors and plan how to amplify the winds. Document actions and commitments.

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For Facilitators

  • Review participant profiles and expectations
  • Prepare all materials and supplies
  • Test technology and room setup

For Participants

  • Complete pre-session survey
  • Review background materials
  • Prepare examples or case studies

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  • Large whiteboard or flip chart paper

  • Markers

  • Sticky notes (multiple colors)

  • Pens

  • Sailboat visual reference (optional)

  • Dot stickers (optional, for voting)

  • Action planning template (optional)

  • Camera (optional, for documentation)

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  • Facilitator Guide (PDF)
  • Participant Workbook Template
  • Presentation Slides
  • Printable Materials

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