Sailboat Retrospective Template
The Sailboat retrospective is a creative and visual format that helps teams reflect on their sprint by imagining their project as a boat journey. It’s a powerful metaphor-based exercise that makes it easier to talk about blockers, risks, momentum, and goals — especially in a team that prefers visual thinking.
This template invites your team to reflect on:
Wind: What’s pushing us forward?
Anchors: What’s holding us back?
Rocks: What risks are ahead?
Island: Where are we trying to go?
This template is available through our Atlassian app SprintRetro (link coming soon).
Why this template?
The Sailboat retro is great for uncovering how the team feels about their direction, speed, and obstacles. It’s especially useful after high-pressure sprints, when you want to assess both momentum and risk — or when retros have become too repetitive or dry.
It’s visual, metaphor-driven, and ideal for getting deeper insights from your team in a non-threatening way.
And, as always, it comes with a built-in Actions column and visibility of open items from past retros in SprintRetro — so you’re not just sailing aimlessly.
Template structure
The Sailboat retrospective includes four metaphor-based columns:
💨 Wind
These are the things that are propelling the team forward. Maybe it’s great collaboration, automation improvements, or high morale. This column captures momentum and positive drivers.
⚓ Anchors
What’s slowing the team down or dragging behind? These could be technical debt, unclear processes, or lack of support. Anchors identify what’s making the journey harder than it should be.
🪨 Rocks
These represent upcoming risks or threats on the horizon. Is there a dependency that might cause trouble? A looming deadline? This is the team’s chance to call out what could go wrong.
🏝 Island
This is your goal or vision — what the team is aiming for. It could be the sprint goal, a feature release, or simply “a smoother workflow.” It helps align everyone on what success looks like.
📝 Actions
The Actions column in SprintRetro ties everything together. Your team can turn feedback into next steps — and even track unresolved actions from previous retros.
Progress isn’t just visual — it’s real and trackable.
How to run the session
Set the scene
Introduce the sailboat metaphor: your team is on a boat, moving toward a goal (the island), with wind in your sails and some anchors holding you back. Help the team get into that mindset.Add reflections
Encourage team members to fill in each area. Silent writing followed by discussion works well. You can vote, comment, and sort to prioritize the most important insights.Identify risks and goals
Spend time talking about Rocks and Island. It’s easy to skip these, but they’re key to surfacing potential derailments or unclear goals.Translate into actions
Capture clear, doable next steps in the Actions column. Decide what to fix, improve, or double down on — and track open items over time.
Try this template in SprintRetro
Our free Sailboat retrospective template is available inside the SprintRetro Atlassian app. It’s a powerful way to visualize your sprint’s journey, surface blockers, and align your team around a common goal.