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Sailboat Retrospective

Whether it’s midway through a project, or at the end, a retrospective is an important part of team learning. While there are many ways of performing a retro, we’ve found that doing it in a fun way can help open up honest conversations.


Enter the ‘Sailboat Retrospective’. We’re not sure who originally came up with this idea, but we’ve got our own twist on it — complete with a shark! Using Whimsical we help clients think through what went well and what’s on the horizon with their projects. Click here to access a Whimsical template that you can make a copy of to use in your own workshop.

Target group: project team

Time: 20 – 30 minutes

Material: Whimsical template

Goals: define what has gone well and could be improved

The thing to remember about this process is that the way that you carry out the planning using this canvas is as important as the outcome. Be as inclusive as possible

With that in mind, let’s identify the main areas of the template:

  • LAND — what’s your destination? where are you headed? what does success look like for the project or team?
  • WIND — what’s the wind in the project or team’s sails? what’s gone, or is going well? what kind of support are you getting?
  • ANCHOR — what’s dragging things down? what’s slowing down the progress of the project or team? which burdens need to be addressed?
  • SUN — what acts like sunlight for the project or team? what kind of recognition have you received? what is making you feel good?
  • SHARK — what’s an upcoming threat to the project or team that you need to keep an eye on? what’s circling around that no-one is talking about?
Sailboat with wind, sun, land, anchor, and shark represented as icons

Some of these can feel quite similar. For example, the difference between WIND and SUN in this retro and the difference between ANCHOR and SHARK. If it helps, consider WIND to be things internal to the project or team and SUN to be things external to it. Also, ANCHOR is about current problems, and SHARK is to do with future problems for the project or team.

To use this template, do the following:

  1. Create your own copy of the template and invite all members of your team to edit.
  2. Ensure that everyone knows how to use Jamboard by going through the basic controls.
  3. Spend some time ‘silent Jamboarding’ where everyone can place as many sticky notes on the template as they wish.
  4. When the rate of new sticky notes slows, give everyone 30 seconds longer.
  5. Talk about what you’ve all added to the template. Go round each person asking what they notice or would like to call attention to.
Example of completed retro template

Once you’ve done all of this, it’s up to you what to do next. You could talk with the team about next steps — e.g. ‘mitigating actions’ for the ANCHOR stickies, or ‘preventative measures’ for the SHARK stickies. But don’t forget to talk as much about what is going well as what isn’t. One way to do this is to add ‘what works’ to a wiki-based handbook for new members who join the team.

Click here to access the Sailboat retrospective template for Whimsical

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