Sailboat Retrospective

• When the team needs to align on a goal before discussing problems.
• Planning for an upcoming release or quarter.
• Visual, engaging retros for teams bored of column formats.

Purpose: Identify what drives the team forward, what holds it back, and what risks lie ahead.

• 🏝️ Island

  Our destination — what does success look like?

• 🌬️ Wind

  What's helping us make progress?

• ⚓ Anchor

  What's slowing us down?

• 🪨 Rocks

  What risks could threaten us ahead?

1. 1

   Define the destination · 3 min

   Agree on the island: the goal or definition of success. One or two cards is plenty.

2. 2

   Silent brainstorming · 6 min

   Keep the room quiet so everyone thinks on their own first. Remind people one idea per card.

3. 3

   Share & group observations · 8 min

   Ask each person to briefly read their cards. Clarify, don't debate. Move duplicates next to each other or into the right column.

4. 4

   Vote · 4 min

   Everyone spends their votes on what matters most. Totals stay hidden until you move on.

5. 5

   Explore obstacles & risks · 9 min

   Focus on the top anchors and rocks. For each, ask: can we remove it, reduce it, or prepare for it?

6. 6

   Agree on actions · 5 min

   Leave with one anchor to address and one rock to mitigate.

Notes a software team might write:

Expected outcome: One obstacle to address, one risk to mitigate, and a shared understanding of the team's goal.

• Spend real time on the island — teams often disagree on the destination.
• Rocks are future risks; anchors are happening now.

Each prompt is a column on a shared board. Everyone writes silently, then the team groups notes, votes with hidden totals, discusses the top cards and turns them into actions with owners.

Each stage comes with instructions for the facilitator and the participants and a suggested timer you can adjust. Teammates join with a link and their name; no account needed.