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Sailboat Retrospective Meeting Template

The sailboat retrospective is a framework & metaphor to reflect and align the end of a sprint

Created by Brennan 👋

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Sailboat Retrospective Meeting Template

Walkthrough

How to run a Sailboat Retrospective Meeting

The ⛡️ Sailboat Retro is a collaborative and fun way to reflect on the sprint with the whole team. Based on your discussion you not only leave with a better reflection on what just happened, but also how to make it better next sprint.


Introduce the metaphor of the ⛡️

The Sailboat Retro can't work unless everyone understands how the metaphor helps you reflect on the journey you're on. Here's a handy guide, but I recommend adding some of your personality when sharing the mythos to your team.

⛡️ Sailboat = That’s the team.
🏝 The Island = The sprint's goals.
🌬 Wind = What helped you to achieve the sprint goal, pushing the boat faster?
β˜€οΈ Sun = What were you glad happened during the sprint? Things to appreciate.
βš“οΈ Anchor = What slowed us down or held us back?
πŸͺ¨ Rock/Reef = What potential risks do we see ahead of us?


Reflect, Write, Post

With the metaphor out of the way, give everyone your team time to write down their answers/thoughts for discussion section. Time for individual brainstorming and reflecting is critical for the team to raise things that are important to them.

You should collect these discrete thoughts in a collaborative way for several reasons:

  1. The more individuals see others participating the more likely they will too.
  2. Reading others thoughts can spur and inspire thoughts of others.
  3. At this point the more information you collect, the better.

Give your team 5-10mins depending on how much activity is going on.


Share and discuss

With content populated, have each individual present their submissions. If your team is large consider breaking out into smaller groups and doing the same thing to save time. Then only present a summarized topics pertinent to the whole group afterwards.

In either scenario consider this a safe time for them to share what's going in their head. It'll be your job to moderate the discussion, questions, and tangents that can arise during this. Read more about psychological safety here if interested.


Document the Reflection

Some discussions will be different views at the topic. Merge, clean, and organize your list as you go. Get confirmation from the group as you do. It's recommended to assign someone on your team to this role so there can be a moderator and a note taker without having one person attempt to do both.

For the remaining points, document the groups reflection as a summary for those who weren't able to attend.


Find Next Steps

At the end recap the ideas, learnings, and reflections. If there are next steps coming from any of these points this is your chance to capture those and confirm who is going to be responsible for following through on getting things done.




How to run a Sailboat Retro Meeting in Hypercontext

After setting up the meeting in Hypercontext, and introducing the concept to your team. When the retro starts, have everyone open the application together. The agenda should be split up into several sections: The 🏝️ Island , 🌬️ Wind, β˜€οΈ Sun, βš“ Anchor, πŸͺ¨ Rocks, and Wrap Up)

Start the meeting at 🏝️ The Island. Use 5 mins or so to remind the team of the sprint goals you set. If needed feel free to get inspired by the goals listed in our OKR library

Once you've done that, give your team 10 mins to add their content to the other sections. They should add each separate thought as a separate "Item" for discussion later. If they want they can add more detail in a "description" or they can just leave it as a short item title for now. Hypercontext allows your team to see all the action in real time so the activity will spur more activity.

Drag and drop the items within the sections to get a starting order for discussion. Then either
a) follow the order you set, discuss, and move to the next point.
b) allow each individual to discuss all of their points before moving to the next person.

Document and summarize the discussion under each item's SUMMARY field. If there are next steps, document those under the NEXT STEPS of each item.

Finally, during the wrap up. Confirm the notes, next steps, and plan for the next week.

About this template

The ⛡️ Sailboat Retro is a collaborative and fun way to reflect on the sprint with the whole team. Based on your discussion you not only leave with a better reflection on what just happened, but also how to make it better next sprint. Read more about how to run this meeting

Updated Mar 16, 2022

Sailboat Retrospective Meeting FAQs

How long should a sailboat retrospective meeting be?

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You should initially set your sailboat retrospective meetings for 1-2 hours with your team. If you prepare and share an agenda in advance you're likely to get through more faster.

How often should you have sailboat retrospective meetings?

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Most sailboat retrospective meetings tend to occur bi-weekly. As you go through a few iterations of them you may need to increase or decrease the frequency.

How do you structure a sailboat retrospective meeting?

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You should think about deviding the meeting into 6 sections: 🌬 Wind - What helped us achieve our goals?, ☀ The Sun - What made you feel good/happy during work?, ⚓ Anchors - What slowed us down or held us back?, :rock: The Rocks - What potential risks do we see ahead of us?, 🏝 The Island, Wrap Up. Then adding the following sailboat retrospective meeting topics, where appropriate:

  • Sun Example: When the bug popped up we all solved it together. Made me feel like we're a great team.
  • Anchor Example: We didn't confirm our plans with all stakeholders before starting work. This made us underestimate what was involved and means we need to start again.
  • Wind Example: When we updated our framework there were a few new functions that allow us to do more, faster.
  • Rock Example: We have a critical team member who is going on mat. leave in the coming weeks. We need to plan around that.
  • Reminder of Sprint Goals (If needed: https://hypercontext.com/goal-examples)
  • Review all next steps

What should you discuss during a sailboat retrospective meeting?

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6 great things to discuss in your Sailboat Retrospective Meeting:

  • Sun Example: When the bug popped up we all solved it together. Made me feel like we're a great team.
  • Anchor Example: We didn't confirm our plans with all stakeholders before starting work. This made us underestimate what was involved and means we need to start again.
  • Wind Example: When we updated our framework there were a few new functions that allow us to do more, faster.
  • Rock Example: We have a critical team member who is going on mat. leave in the coming weeks. We need to plan around that.
  • Reminder of Sprint Goals (If needed: https://hypercontext.com/goal-examples)
  • Review all next steps

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About the Author

Brennan 👋

Brennan McEachran is the CEO and Co-Founder of Hypercontext, a suite of tools to help leaders and their teams streamline objectives, meetings and morale into one workflow. He has spent more than a decade in the leadership and employee engagement space building apps to create better relationships between managers and their teams.

Follow him on twitter.