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Sailboat Retrospective

Picture a sailboat headed toward a beautiful tropical island with all the drinks with umbrellas you could ever want.🍹 But as you sailed to your Island paradise you would want to stay wary of the obstacles in your way, like rocks or coral. And you would harness the wind to keep your team progressing toward your end goal. Wait...Obstacles, progress, and goals? Your vacation has all the makings of a great retrospective! In fact, a Sailboat retrospective is a useful tool that can illuminate all of the things that are helping and hindering your team and develops clear improvement activities in a fun and visual way.⛵

Use the sailboat retrospective when you want to…

Define the end goals.

Identify risks that may disrupt your path.

Identify what is slowing your team down on its journey to the end goal.

Identify what helps the team achieve their goals faster.

How it works

Step One: Prepare the exercise
This retrospective technique is all about the visual. So, before we sail off on this quick retrospective, the facilitator sets our scene by projecting an image of a sailboat heading towards an island, rocks between the sailboat and the island, clouds (wind) behind the sailboat, and an anchor hanging from the sailboat. Each of these items represents a part of the team's last sprint. Together they will create a full picture for your team’s retrospective.  

  • The Island
  • Represents the teams’ goals.
  • The Rocks
  • Represent the potential risks the team may encounter while working towards their goals.
  • The anchor
  • Represents things that are slowing the team down.
  • The Wind
  • Represents things that may help propel the team towards your goal.

    Setting the Stage

    Before casting off, make sure everyone has a shared understanding of the functions and goals of the retrospective. Depending on the size and ideas of the team, this retrospective has the possibility of lasting several hours. 😱  If you want to limit the time on this retrospective activity, create a timebox for the entire meeting (30-60 minutes, depending on the size of the team) so the team has an idea of how much time each discussion should take.


    Begin the retrospective by naming the boat to match the topic of the retrospective and decide as a team the purpose of your “mission,” keeping the end goal in mind. 🏝
    At this step, the team will be expected to brainstorm and identify areas and processes that are:

    • ⚓. Currently hindering the team
    • ⛰️. May pose risks to the team achieving the goal at hand
    • 🌬️  And things that are helping to propel the team forward

    Give participants 5 minutes to develop their ideas and capture these as multiple notes.

    While brainstorming, participants should keep their ideas private. 🤫 This helps prevent groupthink and ensures that team members aren’t swayed by seeing the opinions of others. (Psst, we know a digital tool that makes this step easy.)


    Many notes will likely contain similar (or even identical) ideas. It’s always great to see when your team has some points of alignment! To get the next step started, the facilitator announces the timebox (5 minutes) and encourages the participants to group notes into logical themes. This part of the exercise is intended to highlight popular opinions as well as differing opinions that are in need of a discussion.

    • 🌑. Identify the rocks: What are the things the team recognizes as potential risks to their success?
    • 💨  Identify the wind: What’s going well for your team, or, in other words, what’s putting wind in your sails? 😉
    • ⚓  Identify the anchors: Is there anything negatively anchoring your ships and preventing your team from moving forward?

    Dot Voting (optional)

    Sometimes discussion topics are obvious. If there are several similar notes on the rocks, your team has an obvious pain point to discuss. However, sometimes it can be challenging to structure the discussion in an organized way. If this is the case, the facilitator can opt to use dot voting to prioritize the discussion based on the collective desires of the group.

    Team Discussion

    If dot voting was used, then the team discusses the notes in prioritized order. If not, the facilitator can choose the order of discussion. When it comes to timeboxing the discussion, you have a couple of options, you can timebox the entire discussion (20-40 minutes) or you might choose to timebox the conversation of each individual topic (typically 5 or 10 minutes). The second approach tends to keep the conversation on topic and moving at a faster pace.

    Through the discussion, the facilitator focuses on each part of the scene and help the team evaluate all the ideas paired with the anchors, wind, and rocks. For example, during the discussion, the team can strategize how to turn an anchor into a gust of wind, eliminate as many rocks as possible, or encourage more processes that symbolize wind. As the conversation progresses, it’s imperative that the facilitator also write down any action items that come out of each discussion topic in order to help the team realize continuous improvement with each sprint.

    This technique is a creative way for your team to visualize the end goal, understand what could help your team get to the goal faster, and what systems need to change for your team to reach all their islands. 🏝️

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