blog details

Sailboat Retrospective

The Sailboat retrospective is a well-known and well-used retro - and for good reason. It’s easy to grasp, visually interesting and can be applied to just about any team or situation to reflect on their team journey.

You’ll present the team with an image of a boat sailing to a paradise island, with forces helping it along as well as holding it back. The team can then reflect on their own journey and contribute their thoughts towards this visualisation. The common themes become clear and you can easily help steer them towards ownership of their grande voyage.

Tools Required

  • 30-90 minutes depending on team size
  • Whiteboard or flipchart
  • Whiteboard pen or marker
  • Post-its
  • Pens for each of your team


  1. On your whiteboard or flipchart, draw a boat sailing across the sea towards a paradise island. Add in a gust of wind behind the sails (helping the boat along), an anchor trailing behind the boat (slowing the boat down) and finally some rocks beneath the waterline, between the boat and the island (a potential obstacle).
  2. Explain that the sailboat represents the team on their journey, and the paradise island represents the teams end goal. This should be an easy start, but ask the team to jot down on post-its what they believe is their end goal.
  3. Next, explain that the wind blowing the sails towards the island represents all the good stuff that’s helping the team along. Leave it open to interpretation and ask them to write their thoughts on post-its and stick them on the gust of wind.
  4. Next, the anchor represents things that are slowing the team down. Ask them to note these things and stick them onto the anchor below the boat.
  5. Finally, the rocks hiding under the water represent future risks or potential obstacles. Ask the team to think about what these might be, then write them down on post-its and stick them over the rocks.
  6. Now your scene will be covered in post-its. Time to delve into some discussion - start with the ‘paradise island’ and begin to group the post-its into any obvious themes, clarifying meaning as you go and encouraging discussion until the team are happy their contributions have been heard. Repeat this step for each element of the scene (wind, anchor and rocks).
  7. Finally, you can draw some conclusion to the discussion and bring the team towards action to help them on their journey. We’ll cover that in takeaways - but first, let’s look at some challenging questions that can really help the team get clarity on their situation.

Challenging Questions

Asking questions may be helpful to get the team to unpack some of the more complex issues that have been raised, or they may be directed at members of the group who’ve had less of a chance to speak. Here are some easy examples:“What is the real challenge here?”Great for getting straight to the root of a discussion, especially if the team are going round in circles over a theme.“Is there anything else here that we haven’t covered?”Helps make sure everyone has contributed. Also good for moving a repetitive conversation along.“What advice would you give to another team in this situation?”Enables the team to step out of the picture and look in with a fresh perspective. Helps draw out positive learnings.“Has anyone got a different view on this?”Gives those who maybe don’t agree with the current conversation an opportunity to speak up.“Is there anyone who hasn’t spoken on this theme yet that would like to contribute?”Offers opportunity for the quieter members of the team to speak.


Getting actions from the sailboat retrospective shouldn’t be the goal, but learnings will crop up quite naturally. Once the sailboat scene has been fully discussed, and you’ve asked those challenging questions, you can finish by asking:

“What one action could we take away that would make the biggest difference in moving us faster towards our paradise island?”

It may be doubling down on something good that’s helping them along, or it may be dealing with something that’s dragging them back, or it could even be tackling a future obstacle before it becomes a current problem.Try and stick to one action only: get clarity on what the action is, what will it look like when it’s done, when will it be done by and who’s going to ensure it happens.It’s important that you let the team come up with their own actions and take responsibility for them. A great coach brings awareness and prompts responsibility; this way, the team will feel like they own their actions and are far more likely to follow through.

join our newsletter

If you have any questions or need help, please contact with Brutzai

get started