What Is a Sailboat Retrospective?
A sailboat retrospective is a creative and visual project management tool that helps Agile teams reflect on their progress, challenges, and goals using the metaphor of a sailboat journey. By exploring elements like wind, anchors, rocks, and the island, teams can surface what’s helping, what’s hindering, and what risks lie ahead. This format encourages open, honest dialogue and collaborative problem-solving in a relaxed, non-judgmental setting.
Key Components of a Sailboat Retrospective
🏝️ The Island – The Goal or Vision
The island represents the destination the team is trying to reach. It could be the successful completion of a sprint, a product launch, improved team performance, or any objective you’ve been working toward.
💨 The Wind – What’s Helping Us Move Forward
The wind symbolizes the things that are pushing the team toward their goal. These are the positive forces—the team’s strengths, helpful tools, supportive communication, good collaboration, or anything else that’s going well.
⚓ The Anchors – What’s Holding Us Back
The anchors represent what’s slowing the team down or making the journey harder. These could be inefficient processes, lack of clarity, distractions, bottlenecks, or even team dynamics that need attention.
🪨 The Rocks – Risks or Potential Threats
The rocks are hidden dangers that might not be causing problems right now, but could cause trouble if left unchecked. These are future risks—things the team is worried about or sees as possible blockers.
🌊 The Currents – External Forces (Optional)
Some teams also use currents to represent outside influences—factors that are beyond the team’s control but still impact their work. These could include organizational changes, client decisions, market shifts, or tools provided by other departments.
How to Run a Sailboat Retrospective
Here’s how to run a sailboat retrospective effectively:
Step 1: Prepare the Space and Tools
Before the sailboat activity begins, decide how you’ll run the retrospective—in person or virtually.
- In-person: Use a whiteboard or flip chart to draw the sailboat scene (island, boat, wind, anchors, rocks).
- Remote: Use an online whiteboard tool like Creately, which has ready-to-use sailboat retrospective templates.
You’ll also need:
- Sticky notes (physical or virtual)
- Markers or digital pens
- A timer to keep things on track
- A calm, focused environment
Tip: Invite all relevant team members, and ensure everyone knows the session is a safe space—free of judgment or blame.
Step 2: Set the Stage
Start the session by welcoming everyone and having the sailboat retrospective explained, along with its purpose. Let the team know this is about reflection, learning, and improvement—not pointing fingers.
Then, introduce the sailboat metaphor:
“Imagine we’re all on a retro sailboat, sailing toward our goal. Let’s explore what’s pushing us forward, what’s slowing us down, what risks we might face, and where we’re headed.”
Briefly explain the components:
- Island = goal
- Wind = what’s helping
- Anchors = what’s slowing us
- Rocks = risks
- Currents (optional) = outside forces
This framing helps people think more clearly and creatively.
Step 3: Create or Show the Sailboat Visual
If you haven’t done it already, display the sailboat illustration—either drawn live or shared via a template on an online whiteboard tool like Creately. Make sure it includes all the key elements.
Encourage the team to visualize themselves as the crew of this sailboat working toward a shared goal.
Tip: Add a touch of creativity—color-coded notes, emojis, or light humor—to make it more engaging.
Step 4: Brainstorm and Add Input
Now comes the core of the retrospective—getting input from the team.
Give everyone a few minutes to reflect individually. Ask them to write down their thoughts for each area of the sailboat.
Questions you can use:
- 💨 Wind: “What’s helping us move forward?”
- ⚓ Anchors: “What’s holding us back?”
- 🪨 Rocks: “What risks or obstacles are ahead?”
- 🏝️ Island: “What is our current goal?”
- 🌊 Currents (optional): “What outside forces are influencing us?”
Each person adds their notes to the board—either silently or one by one.
Tip: Encourage honesty and don’t rush this part. The best insights often come when people feel heard.
Step 5: Group, Discuss, and Reflect
Once the notes are in place, review them together as a team.
- Group similar ideas to identify themes.
- Ask clarifying questions.
- Dig into why certain anchors or risks exist.
- Highlight recurring strengths (wind) to preserve and grow them.
Keep the tone constructive and collaborative. The goal is shared understanding, not debate.
Tip: Guide the discussion gently. If tensions rise, remind the team to focus on outcomes, not blame.
Step 6: Identify Action Items
Now that you’ve explored what’s happening, move toward solutions.
Ask:
- “What can we change to reduce or remove these anchors?”
- “How can we protect against the rocks we’ve spotted?”
- “What should we continue doing to harness the wind?”
Prioritize ideas and agree on a few clear, actionable steps. Assign owners and set deadlines so the actions actually stick.
Tip: Keep it practical—two or three well-defined improvements are better than a long list that never gets done.
Step 7: Close the Session
Wrap up with a quick recap:
- Thank the team for their openness.
- Summarize the key themes and action items.
- Ask for quick feedback on the retrospective itself—what worked well, what could be better.
Some teams like to end with a one-word check-out, a mood emoji, or a confidence vote on the upcoming sprint.
Example: “Let’s go around and share one word about how you’re feeling after this session.”
Sailboat Retrospective Templates
To help you get started quickly, we’ve put together a collection of ready-to-use sailboat retrospective templates. Whether you’re running your first session or looking to simplify your next one, these templates are designed to save time and guide meaningful conversations. You can customize them to suit your team’s style, and use them online or during in-person sessions.
Pick a template, share it with your team, and start reflecting with clarity and purpose.
Sailboat Retrospective AI Template
Blank Sailboat Template
Sailboat Retrospective Example
Sailboat Exercise Template
Sailboat Sprint Retrospective Template
Retrospective Generator Template
Icebreaker Questions for the Sailboat Retrospective
Here are some thoughtful and fun options you can choose from:
Project-Focused Icebreakers
- “If this sprint was a type of weather, what would it be and why?”
- “What was your proudest moment from this sprint?”
- “What’s one thing you wish we had done differently?”
- “If you could rename this sprint like a movie title, what would you call it?”
- “What’s one word to describe how you felt during the last sprint?”
Sailboat-Themed Icebreakers
- “If our team were a boat, what kind would it be today—speedboat, cruise ship, canoe, or lifeboat?”
- “What’s one thing you’d pack for our team journey to the island?”
- “If you were steering the boat right now, what course would you set?”
- “What kind of sea do you think we’re sailing through—calm, choppy, or stormy?”
Team Bonding Icebreakers
- “What’s one small win (work or personal) you’ve had this week?”
- “What’s something you appreciate about someone on the team?”
- “What’s one thing you learned recently—at work or outside of work?”
- “If we had a team mascot, what should it be and why?”
Quick One-Word Starters
- “In one word, how are you feeling today?”
- “Describe the sprint in one emoji.”
- “Pick one word to describe our team right now.”
Tips for Using Icebreakers Well
- Keep it optional – Let people pass if they’re not comfortable answering.
- Keep it light – Don’t start with anything too deep or heavy.
- Match the energy – Choose questions that feel right for your team’s mood and culture.
- Join in – As a facilitator or Scrum Master, answer first to break the ice yourself.
Conducting Your Sailboat Retrospective with Creately
Running a sailboat retrospective is easy and more fun with Creately, a tool made for teams working together—whether you’re in the same room or far apart. Creately gives you ready-made sailboat retrospective templates with all the important parts like the island, wind, anchors, and rocks. You can start quickly and customize the board to fit your team. With Creately AI, the smart assistant, you can create boards from simple instructions, get helpful questions, and turn team ideas into clear action points—saving time and effort.
Everyone can join in at the same time, adding notes, comments, and votes, making sure every voice is heard. Creately also connects your retrospective to other work tools like Jira and Slack, keeping everything organized in one place. You can add extra notes for context, share the board safely, export results, and use presentation mode to show your findings clearly. All of this helps your team reflect better and move forward together.
References
Silva, P.A. (2020). The Sailboat Exercise as a Method for User Understanding and Requirements Gathering. [online] Available at: https://www.researchgate.net/publication/342354794_The_Sailboat_Exercise.
Matthies, C., Dobrigkeit, F. and Ernst, A. (2019). Counteracting Agile Retrospective Problems with Retrospective Activities. Communications in Computer and Information Science, pp.532–545. doi:https://doi.org/10.1007/978-3-030-28005-5_41.
The sailboat retrospective is guided by four key questions, each tied to a part of the sailboat metaphor: These questions help the team reflect on progress, blockers, and potential challenges in a structured but creative way. Use a sailboat retrospective when you want to encourage open reflection and team alignment. It works best:FAQs About the Sailboat Retrospective
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