Sailboat Retrospective

Actionable retrospective ideas that you can launch today.

Keeping your retros fun is vital for maintaining high team engagement in the long run and continuously improving your process. If you have come to this conclusion yourself, why not spice things up occasionally with a different retrospective format like the Sailboat retro?

It gives you the opportunity to inspect your process from the perspective of a crew sailing a boat headed toward an exotic island. 

What is a Sailboat Retrospective?

The Sailboat is a fun way of doing retrospectives by looking at your work as part of a sea journey. Imagine your team as the crew of a boat propelled by the wind and each Sprint is like a stage of the trip towards your goal of reaching the land you see ahead of you.

The topics you discuss during a Sailboat retrospective are focused on keeping the journey smooth and analyzing the problems that make it more difficult. Typically, areas of conversation during a Sailboat retro fall under one of the following categories:

  • Wind
  • Anchors
  • Life preservers
  • Rocks

The wind is what drives your boat forward and helps you reach the island. It represents what went well during the Sprint and the practices you want to continue encouraging within the team in the future. Examples of ‘wind in our sails’ usually include instances of collaboration or efficient communication among team members. 

Anchors are problems or inefficiencies during the Sprint that held you back from sailing at an optimal pace. Examples of anchors in the team process include changing priorities, a slow review process, or a redistribution of resources that stalls out the team.

Life preservers are things that helped you or could help you in the future, to avoid difficult situations or save your sprint from failing.

Rocks represent the hidden risks that endanger the boat and could prevent your team from reaching the island in the near future In a team context, examples of these instances include the presence of technical debt or a manual system that will need to be automated in the future.

The island towards which the team is moving is a representation of a predefined combination of goals that the group aims to achieve together. These goals can be both short-term or long-term.

How to Run Sailboat Retrospectives with Your Team

If you are eager to apply Sailboat retrospectives, you can get one set up very quickly either physically if you’re co-located or virtually. This format aims to help your team escape the mundane meeting routine and encourages group members to think outside the box. So, shifting from your usual retro format will be well worth it!

Sailboat retros are still retrospective meetings, after all. Consequently, you can stick to the golden rules for organizing a retrospective:

  1. Allocate a 60-90 minute time slot at a regular cadence on your team calendars
  2. Invite your team and aim for full attendance every time 
  3. Set the ground rules (e.g. no judgment, blame, or negativity) by highlighting any retrospective’s prime directive:
"Regardless of what we discover, we understand and truly believe that everyone did the best job they could, given what they knew at the time, their skills and abilities, the resources available, and the situation at hand."
--Norm Kerth, Project Retrospectives: A Handbook for Team Review

Begin by visualizing the four categories for grouping topics during the retro. Some teams draw the boat on a whiteboard and visualize the wind, anchors, rocks, and life preservers around it. During the retro, the team adds sticky notes next to or on top of the appropriate category.

For a more structured solution, draw four columns on a whiteboard for the respective categories and place tickets under each of them during the retro. 

If you are running an online retro with a remote team in ScatterSpoke, select the Sailboat retrospective template that comes ready out of the box, available in both canvas and column layout formats.

With everything in place and the team gathered (physically or virtually), tackle four questions in regards to your last Sprint:

  • What propelled us forward?
  • What delayed us?
  • What saved us from failing to complete the Sprint?
  • What could have failed us so we can prevent the danger in the future?

Each person writes their answers on separate tickets and places them under the appropriate  category. Use the topics generated to center your discussion around activities you might undertake in order to ensure that you continue practicing what is propelling your boat forward. Take some time to discuss the items under “life preservers” to bring everyone’s attention to circumstances or tools that got you out of any difficult situations that occurred during the Sprint.

It is also very important to go over the items under “rocks” and “anchors” to decide how to mitigate existing risks in the future and prevent delays going forward.

If you are unable to reach an agreement, use voting to your advantage. Assign everybody three voting points and ask them to vote for the problems with the largest negative impact (in their opinion). The items with the highest number of votes will become the focus of your improvement efforts for the next Sprint.

Based on the results of your voting, defined action items that can contribute to fixing the most significant problems as a team and close the retrospective. For greater accountability, the Team Lead can specify an owner and a due date for each action item.

Why Should You Run Sailboat Retrospectives?

The short answer is - because they are fun. The more your team enjoys your retros, the greater the value they’ll bring in the long run. In addition, the Sailboat retrospective format enables you to look outside of the box and analyze your work from an entirely different perspective.

They facilitate an environment conducive to diving deeper into your work process and talking about more than just what went well and what didn’t during a Sprint. This can prove to be a trump card for continuously improving your process.