Facilitation · 45-60 minutes

Sailboat Retrospective

The Sailboat is a visual metaphor-based retrospective technique designed to help teams identify forces that propel them forward and obstacles that hold them back. By using the imagery of a sailboat, teams can collaboratively surface insights and prioritize improvements in a low-friction, engaging format.

When to use Sailboat Retrospective

This framework is most effective during Agile retrospectives, project post-mortems, or team alignment sessions where a holistic view of team dynamics and environmental factors is required.

How Sailboat Retrospective works

Facilitators can integrate this framework into the 'Reflect' or 'Review' stage of a learning cycle or project sprint. It serves as a structured bridge between raw data collection and concrete action planning, utilizing visual thinking to categorize team sentiment.

Phases of Sailboat Retrospective

  1. Preparation: The facilitator draws the sailboat picture: wind (what pushes us forward), anchors (what holds us back), rocks (risks ahead) and an island (the goal). Prepare sticky notes and a timebox.
  2. Introduction & Metaphor Setup: The facilitator explains the picture and the meaning of each element, and sets the goal or island so the team knows what it is sailing towards.
  3. Data Gathering: Team members silently write notes for the wind, anchors and rocks and place them on the picture. The facilitator keeps time and encourages one idea per note.
  4. Insight Generation & Grouping: The team reads the notes aloud, clusters similar items and discusses what they reveal. The facilitator helps name the clusters and draws out causes.
  5. Prioritization (Dot Voting): Participants dot-vote on the anchors or risks they most want to address. The facilitator orders the clusters by votes.
  6. Action Planning: For the top items, the team agrees concrete improvement actions with owners, such as cutting an anchor or steering past a rock. Actions are reviewed at the next retrospective.

Key principles

  • Metaphorical Thinking: Using 'wind' and 'anchors' to lower defensive barriers.
  • Self-Organization: Allowing the team to group and label their own data points.
  • Democratic Prioritization: Using dot voting to ensure the team focuses on the most impactful issues.
  • Visual Collaboration: Creating a shared mental model through a central workspace.

Best for

  • Agile Team Retrospectives
  • Project Debriefs
  • Continuous Improvement Workshops

Considerations

  • Requires sufficient physical or digital canvas space for all participants to contribute simultaneously.
  • Facilitators must monitor energy levels and prompt participation if data gathering stalls.
  • The grouping phase requires active facilitation to ensure dominant voices do not override the collective consensus.

Attribution & sources

Developed by Luke Hohmann, originally featured in 'Innovation Games'.

Primary source

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