Purpose

The Sailboat Retrospective uses a visual metaphor to help teams reflect on what propels them forward (wind), what holds them back (anchors), what risks lie ahead (rocks), and what goals they are sailing toward (island). It encourages balanced reflection by covering strengths, obstacles, risks, and aspirations in a single exercise.

At a glance

• Group size: 3–12 people
• Duration: 30 minutes
• Difficulty: Beginner
• Facilitation style: Semi-structured
• Setting: Both / Remote-friendly

How to run

1. Draw a sailboat on a whiteboard or shared canvas with four zones: island (goals), wind (tailwinds / what helps), anchors (what slows us down), and rocks (risks ahead).
2. Give participants 5 minutes to silently write sticky notes for each zone.
3. Have each person place and briefly explain their notes (10 minutes).
4. Cluster similar items and discuss themes (10 minutes).
5. Vote on the top 1–2 items to act on and agree on owners and deadlines (5 minutes).

Materials needed

• Whiteboard or digital board (Miro, Mural, FigJam)
• Sticky notes and markers
• Timer
• Dot-vote stickers or digital voting

Pitfalls & common mistakes

• Skipping the rocks zone: teams tend to focus on wind and anchors and forget to discuss upcoming risks.
• Letting one person dominate the debrief — enforce equal airtime.
• Not converting insights into concrete action items with owners.

Inclusion & accessibility

• Use colour-blind-friendly sticky note colours or label zones with text, not colour alone.
• Allow anonymous posting so quieter team members can contribute freely.
• Provide a digital option for remote or mobility-impaired participants.

Variations

• Anchors and Wind: remove the island to focus purely on speed vs. drag.
• Catamaran: use two boats to compare two teams or two sprints.
• Pirate Ship: add a treasure zone for unexpected wins.

When NOT to use this

• When the team needs a deep root-cause analysis — use Five Whys or Fishbone instead.
• Immediately after a major incident where emotions are raw; start with a safety check first.

Source & further reading

• Innovation Games by Luke Hohmann (original Anchors and Wind concept).
• Retromat (retromat.org) for variations.