Help Your Team Reflect and Improve

Help Your Team Reflect and Improve

So you’re about to kick off a crucial project and eager to learn from past mistakes. Enter, the Sailboat Retrospective - a fun way to set your new project up for success by reflecting on the drivers and blockers of the last one.

Set up the template in your favorite virtual whiteboarding tool (you can find one in the deep-dive section), schedule 60 minutes, and run your team through the following phases:

🏝️ The Tropical Island: Where are you headed?

Start the session by reflecting with your team on how close they got to the destination in their last project or sprint. Ask them:

• What was the outcome we hoped for? • What did we accomplish? • What didn’t we?

This is a useful icebreaker to set the context and get people thinking about what helped and hindered them on their journey.

⛵ The Wind: What’s moving us forward?

What things felt like wind in your team’s sails? Ask your team to write down 3 things that helped move things forward.

For example, for the dev team, it might be the fast turnaround on bugs reported.

⚓ The Anchor: What’s holding us back?

What are the weights that are slowing your team down? Brainstorm things that got in the way of reaching the goal.

For example, for a customer support team, it might have been a lack of triage process for dealing with the large number of support tickets.

☀️ The Sun: What made us feel good?

What made the work enjoyable for your team? For example, for the design team, it might be getting to interview inspiring customers and the collaborative spirit.

This is an important part of the Sailboat Retro as celebrating wins can help keep your team engaged with their work and feel rewarded for their efforts!

🦈 The Reef: What risks lie ahead?

What obstacles lie ahead in the way of your team’s next destination? Encourage your team to bring up risks and concerns they have about your upcoming goals.

For example, the lack of quality documentation of your sales team’s processes is blocking new hires from onboarding at a faster pace.

Categorize

Start clustering similar issues and ideas together.

It’s often quicker and more effective to do this silently again as you avoid too much debate or having the loudest voices dominate. Simply move stickies around without speaking until there seems to be a general consensus.

Prioritize

You can’t do everything at once so have your team prioritize which risks and problems they want to address first in order of importance.

Give everyone five color dots, which they can use to vote on whole groups or individual issues. They can put all their votes on one, or spread them out more evenly.

Find owners to each problem area

Once everyone has voted, list the top 2-3 issues and find volunteers to own them (or whoever seems most qualified eager to work on it).

They will now be the ones responsible for follow-up sessions regarding those issues / problems.

Bon voyage! 🐚

Congratulations! You’re now ready for a smoother journey to your next tropical island! Just don’t forget that as well avoiding reefs and removing anchors, be sure to take care of your crew. After all, it’s not just about the destination, but the journey too!