Set Sail for Success: Why Your Team Needs to Try the Sailboat Retrospective

• Growth
• Team
• Toolkit
• Tool
• Retrospective

October 18, 2024

Remember when I told you about the Start Stop Continue retrospective? Well, buckle up, buttercup, because we’re about to set sail on another mind-blowing retrospective adventure. Welcome to part two of our “Make Your Team Less Dysfunctional” series: The Sailboat Retrospective.

If Start Stop Continue felt a bit too, well, structured for your free-spirited team, the Sailboat method might just float your boat. (Sorry, not sorry for the pun. There will be more.)

What the Heck is a Sailboat Retrospective?

Picture this: your team is a sailboat. Your project goals? That’s the exotic island you’re sailing towards. Now, what’s pushing you forward, and what’s holding you back?

That, my friends, is the essence of the Sailboat Retrospective. It’s like a nautical-themed therapy session for your team, minus the expensive therapist and uncomfy couch.

Here’s the breakdown:

1. The Sailboat: That’s your team (or project, if you’re feeling fancy)
2. The Island: Your ultimate goal (preferably not a deserted one)
3. The Wind: Things pushing you forward (team strengths, good communication, that one guy who always brings donuts)
4. The Anchors: Things slowing you down (bugs, miscommunication, that other guy who eats all the donuts)
5. The Rocks: Potential risks ahead (tight deadlines, budget cuts, the impending donut shortage)

Some teams even throw in extras like the sun (things that make the team happy) or choppy waves (things causing anxiety). Feel free to get creative — just don’t go overboard. (Ha! Another pun!)

Why Should You Give a Hoot?

Look, I get it. You’re thinking, “Great, another fluffy team-building exercise.” But hear me out:

1. It’s Visual: Perfect for those team members who zoned out during your last text-heavy retrospective.
2. It’s Metaphorical: Because sometimes it’s easier to admit “We’re heading for the rocks” than “Bob’s code is a disaster.”
3. It’s Comprehensive: Covers past, present, and future in one neat package.
4. It’s Collaborative: Gets everyone on the same… boat. (I warned you about the puns.)
5. It’s Actually Fun: Unlike that team-building exercise where you had to fall backwards into Karen from Accounting’s arms.

Plus, it typically identifies 3-5 actionable items. That’s 3–5 ways to make your next sprint less of a shipwreck!

How to Captain This Ship Without Sinking

Ready to embark on your maiden voyage? Here’s your treasure map:

1. Gather Your Crew: Scrum Master, Product Owner, dev team, and any other unfortunate souls crucial to your project.
2. Lay Down the Law: No blame games, no judgment, no walking the plank. This is a safe space, people.
3. Sketch Your Seascape: Draw that boat, or use a template if your artistic skills are as bad as mine.
4. Fill Your Map: Use a tool like EasyRetro (or Miro, etc.) to create columns for each element (Wind, Anchors, etc.).
5. Brainstorm or Discuss: Let your team go wild adding ideas to each category. Pro tip: If your team is shyer than a mermaid at a fish fry, consider anonymous submissions.
6. Review and Plan: Identify your biggest wins, obstacles to overcome, and risks to mitigate. Then plot your course forward!

The whole shebang should take about 60–90 minutes. That’s less time than it takes to watch “Titanic,” and hopefully with fewer tragic endings.

Real Talk: Examples to Float Your Boat

Still feeling a bit lost at sea? Here are some examples to get your creative juices flowing:

Wind (Things pushing us forward):

• Our new CI/CD pipeline is smoother than a dolphin’s back
• Team’s TypeScript skills are off the charts
• We finally fixed the coffee machine (productivity up 1000%)

Anchors (Things holding us back):

• The legacy codebase is scarier than the Kraken
• Bob and Alice’s ongoing feud over tabs vs. spaces
• That one JIRA ticket that’s older than most of our interns

Rocks (Potential risks):

• The looming deadline that’s approaching faster than a speedboat
• Potential budget cuts (goodbye, fancy ergonomic chairs)
• The possibility that our main competitor will poach our best developer (looking at you, Karen)

Drop Your Anchor Here

The Sailboat Retrospective isn’t just another corporate gimmick. It’s a powerful tool to help your team visualize where they’re at, where they’re going, and what’s helping or hindering them along the way.

So, are you ready to sail into the sunset of project success? Or will you stay anchored in the harbor of mediocrity? The choice is yours, Captain.

Next time you’re tempted to run yet another boring retrospective, remember: life’s a beach, but your retrospective doesn’t have to be.

Have you tried the Sailboat Retrospective? Did it make waves in your team dynamics? Or did it leave you feeling seasick? Drop your thoughts in the comments below. And if this post helped your team chart a course to success, consider buying me a life jacket. These puns are drowning me.

Stay tuned for the next installment in our retrospective series. Trust me, it’s going to be legen— wait for it —dary!