The Pirates of the Caribbean Expedition is a themed retrospective inviting teams to chart a course for improvement by starting new ideas, abandoning blockers, and preserving valuable habits.

When to use this template

Use this retrospective to energize your team, encourage open sharing, and revitalise motivation—especially after turbulent sprints or when team engagement needs a lift.

How to facilitate

Introduce the pirate adventure theme, set expectations, and explain each column's purpose to get everyone in a creative mindset.

Invite each team member to silently write cards for each column: new ideas for Hoist New Sails, blockers for Sink the Curses, and valuable practices for Treasure Traditions.

Allow everyone to share their cards with the group, reading aloud or summarizing as they add them to the board.

Cluster similar cards together and facilitate a group discussion to add context, clarify intent, and explore root causes.

Guide the crew to vote on the topics most urgent, intriguing, or valuable.

Discuss the top voted items, turning discoveries into specific action items or experiments for the next voyage.

Close by celebrating the best traditions you’ll 'treasure' and noting how team contributions shape your collective journey.

Pro Tips

Lean into the theme—use pirate accents or references to break the ice and boost engagement.

Encourage storytelling when discussing traditions or blockers to surface hidden context.

Keep the pace lively but leave room for deeper discussion on recurring blockers or urgent items.

Capture action items visually and assign treasure-keepers (owners) to ensure follow-up.

FAQ

How do I keep the pirate theme from getting distracting?

Frame the theme as a light wrapper that boosts engagement, but guide conversations back to the main retrospective purpose if things drift.

What if team members are hesitant to share blockers or 'curses'?

Set a tone of psychological safety by modeling vulnerability and reminding the crew that uncovering curses is vital to improving the voyage.

How do I turn voted items into effective actions?

Collaboratively brainstorm concrete next steps for each selected card, assign clear owners, and check progress in your next retro.

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At a glance

Duration
35–50 min
Team Size
3-10 people
Columns
3 columns
Base Format
Start, Stop, Continue

Ready to get started?

Use this template to run your next retrospective

🏴‍☠️ Pirates of the Caribbean Expedition

Ahoy crew! Sail into the world of swashbuckling adventures and ghostly legends. Let’s uncover hidden treasures (ideas to start), battle sea monsters (habits to stop), and keep our loyal crew traditions (what to continue) on this thrilling retrospective journey!

Template Columns

🦜 Hoist New Sails

☠️ Sink the Curses

⚓ Treasure Traditions

About this template