Sailboat

group size: 2-10 | Time: 1 hour | difficulty: Easy



The Sailboat is a Retrospective format that is great for a team that wants to create an overview of their surrounding. Primarily the sailboat retro is divided in four parts: Goals, Help, Risk, Hindering – these could be extended by topics such as: The Crew and Learnings.

  • Goal(s): which outcome is your team working towards? Note here that the goal is to focus on outcome not output. It is often easy for teams to say “I’m going to deliver my application XYZ or the requested marketing campaign”. This is an output! Try to question your team in such a manner that they look at the overall goal and vision of the team.
  • Help: Who or what is supporting your team in achieving their goal(s)? Here you can think of other teams, proactive stakeholder, a stimulating environment, particular software. Goal here is to appreciate what is already there and also find out how to use those channels to your advantage.
  • Risk(s): What obstacles might result in not achieving your goal(s)? Currently it is probably smooth sailing for your team. No major issues, no big stresses. But what could become a big issue? Or which stakeholder might change his mind? Is software going to be decommissioned? Getting those possible issues to the service gives your team opportunity to adapt up front and change course if needed.
  • Hindering: What is slowing down your team in being the best? This might sound like a really big question… and it is! But that shouldn’t hold you back on asking it. Sometimes it is good to aim for the stairs, but it is also completely fine to take a small step. What makes your work life easier?
  • Bonus | The Crew: Who is our ideal crew? The boat in the middle doesn’t have a particular name nevertheless a boat is only as efficient as its crew. Reflecting together on who is on the boat might gain insights in skills that are present or missing. Who is the captain? Who is an amazing watch and who is our mechanical engineer? Make it fun and determine where and how everyone could accelerate the journey.
  • Bonus | Learnings: Which route did we take? No journey comes without its obstacles. A nice topic to reflect on with each other is how you got to your destination so far. Which repairs did you have to do? How often did we have to change course? Looking back at the journey so far can yield more insights for the future!

Performing the Sailboat retrospective

  1. Always start your retrospective with a Check-in. Since this is a more lengthy retrospective I would advice a short opening question, a quick this-or-that or a happiness checker. See my Check-in page for more ideas
  2. Give the team 5 minutes to fill in the board! It is ofcourse most fun to do this together in office and put post-its on a wall. In a hybrid way use a collaboration tool such as Mural or Miro to create a nice template. A whiteboard in for instance Teams could also do but keep in mind to not make it to complicated, this will take away from the brain capacity of the team.
  3. Go over the topics one by one. No indeed this is no rocket-science. I can make it if you want… but lets keep it simple. As facilitator you have one important task: TIME. As you can imagine by this point we’re already 10-15 minutes in the retrospective. which leaves 40 minutes to also wrap up and give everyone time to get a drink before the next meeting. Therefore be a TIME KEEPER! [TIP 1] Since we’re looking at the big picture of the team there might be topics to big to discuss here. put those topics to the PARKING – this is a fictional place where you decide to move topics which are important but not now! [TIP 2] you can guide the team by looking at what is put up and combine if possible certain topics. This will safe you some time and can also bring people together and see coherency in the stories. [TIP 3] Note down important insights or action points. In this way you can give a short recap at the end and take the actions into your next sprint or to the attention of others
  4. Wrap up and look ahead (5-10 min). We started our journey to achieve our goal – getting to our dream island. What have we discussed and what needs to be improved? After recapping (shortly) about the list go back to the goal and vision. This is why we come to work every day. Lets keep this in mind and have fun on our journey!

A retrospective is fun for everyone! choose the format that works for you and you and your team will leave the room with more energy than when you arrived.

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