JO’s Newsletter 📰

Hello, and welcome to the retro newsletter. This week's Poll is: Which aspect of retrospectives would you like to dive deeper into? Today is a deep dive into the Sailboat retro and how to use it.

What's in this newsletter

• 🗳️Poll - get involved in what you want to see

• Mastering the Sailboat Retrospective: A Deep Dive …

  • 1. What is the Sailboat Retrospective?

  • 2. How and When to Use the Sailboat Retrospective

  • 3. Tips for Making the Sailboat Retrospective Impa …

• TickTok tip of the week ⏩

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🗳️Poll - get involved in what you want to see

Mastering the Sailboat Retrospective: A Deep Dive ⛵️

1. What is the Sailboat Retrospective?

The Sailboat Retrospective is a visual, metaphor-driven activity that can be used in the Gather Data phase of a retrospective. It helps teams reflect on their progress by visualizing a sprint or iteration as a sailboat's journey toward a goal. The exercise involves identifying factors that help the team move forward (wind), obstacles or risks that slow them down (anchors), potential dangers on the horizon (rocks), and the end goal (the island).

Key elements include:

• Wind: The wind that moves us forward

• Stars: The Stars that light the way

• Anchors: The Anchors that weigh us down

• Sharks: The sharks up ahead ready to bite us

• Treasure: The treasure you are sailing toward.

Why it’s useful:
This exercise encourages team members to reflect visually and conceptually, which can lead to richer discussions, especially around obstacles and risks that might not surface in a traditional retrospective.

2. How and When to Use the Sailboat Retrospective

When to use it:

• Mid-project retrospectives: To assess how the team is progressing toward a milestone and what risks may need attention before proceeding.

• End-of-sprint retrospectives: To highlight lessons learned and focus on continuous improvement before starting the next cycle.

• After major changes (e.g., new team members or tech stack changes): To understand how the team dynamics have shifted.

How to run the exercise:

1. Set the stage: Get all the voices in the room and remind everyone of the retrospective's purpose and outcomes.

2. Gather Data: Share the metaphor with the team and draw it on a whiteboard or use a remote tool. (Here is a nice Miro template.) Give the team the opportunity to write sticky notes for each of the topics. 7 - 10 minutes timebox. Once everyone has their sticky notes, add them to the board. If you are using a remote tool, then just add the sticky notes while you go.

   • Wind: The wind that moves us forward

   • Stars: The Stars that light the way

   • Anchors: The Anchors that weigh us down

   • Sharks: The sharks up ahead ready to bite us

   • Treasure: The treasure you are sailing toward.

3. Generate Insights: After collecting everyone’s input, check for any confusing or unclear sticky notes. Then, group similar ideas together. Ask a few questions of the team. What do they notice about the data? What is surprising? What exceptions do they see? Then, based on some of the deeper insights you have gathered, decide which groups to talk about in which order. You probably won’t have time for all the sticky notes or all the ideas, so make sure you are choosing the most important topics for the team. Facilitate a discussion about each of these. Make sure to timebox this discussion and leave time for deciding what to do.

4. Decide what to Do: Focus on actionable takeaways from the discussion—how can you remove anchors? Avoid the rocks? Capitalize on the wind? As you discuss the insights, start looking for ideas about what to do. Get the team to make notes on these as you go. Once the discussion on generating insights is over, you should have high-level ideas about what the team wants to do. Get the team to vote for 1 or 2 that will get actioned in the next sprint. Don’t choose too many, or none will happen. Spend some time going into details of what to do, and ensure each action is assigned to a volunteer.

5. Close: Thank everyone for their time. Ask for feedback on the retrospective or have everyone write an appreciation for someone on the team.

3. Tips for Making the Sailboat Retrospective Impactful

Encourage diverse input : 😃 
Encourage every team member to participate. Request that people add at least 1 sticky per category. Quiet voices often surface critical risks (rocks) or identify opportunities (wind) that others might overlook.

Use visuals effectively : 👁️‍🗨️ 
If you're working in person, a large, colorful diagram can make the exercise more engaging. For remote teams, tools like Miro or MURAL offer templates for creating interactive sailboat retrospectives. Here is one for Miro.

Follow-up on anchors and rocks: 🪨
Find a way to visualise your action items; some teams add them to the Product backlog, some teams create an improvement board, and some teams have an awesome board. Find a way to visualise these and then you can easily follow up.

Adapt the metaphor 🚀 :
Modify the sailboat metaphor to fit your team’s unique situation. For example, if you’re working on a technical project, you might adapt the exercise to something more relevant to your context, like a racing car or spacecraft.

Final Thought:
The Sailboat Retrospective can be a powerful metaphor for helping a team think differently about their work. You can also make it more focused. For example, use the sailboat to discuss technical practices or even a specific backlog item.

TickTok tip of the week ⏩

For more on Nancy Kline and Thinking environments go here 

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Next Issue

In the next newsletter, I will consider the poll results and base my newsletter on what you want to learn about. Feel free to contact me at [email protected] and share what you want me to discuss or ask for help with specific scenarios.