Sailboat retrospective Blog Feature

Sailboat Retrospective: For Agile Software Development Teams

So much of the agile software development process is iterative. Sometimes it feels like a project never ends! But, sure enough, your team successfully crosses the finish line. Instead of simply moving on to the next project, the agile methodology requires retrospective meetings that analyze what went well and what you should change for next time. It’s all in service of fine-tuning your workflows and processes to boost team cohesion and work quality. 

Like any process on an agile team, retrospectives need structure. If you haven’t tried it yet, the sailboat retrospective technique is a true game-changer. This technique not only makes retrospectives more engaging but also provides a clear visual metaphor to help teams navigate the complexities of a project. 🛥️

Whether you’re a Scrum master, product owner, or member of an agile team, sailboat retrospectives will help you identify potential risks, celebrate what went well with the last sprint, and set goals for the next sprint. In this guide, we’ll explain what a sailboat retrospective is and offer tips for practicing retrospective techniques in ClickUp.

What Is a Sailboat Retrospective?

Agile software development teams use sailboat retrospectives to reflect on past sprints or project phases. Retrospectives are the final agile ceremony project managers oversee to improve the quality of future projects. The goal of any retrospective is continuous improvement. After all, it’s easier to do better next time if you know what to avoid. 

While you’re free to use any retrospective technique you like, the sailboat method is different because it uses the metaphor of a sailboat on a journey. It’s less dry than other retrospective techniques and gives your Scrum team a fun way to visualize progress, challenges, and future direction. 

In a sailboat retro, you imagine the project as a sailboat moving toward a common goal. During the session, team members use sticky notes to write down their thoughts on each component of the sailboat, which you place on a whiteboard and review together. The process encourages brainstorming and open discussion, culminating in a list of helpful action items for future sprints. 

Sailboat retros might be too abstract for some teams, but many project managers like how they act as a fun icebreaker that also aligns the team on areas of improvement. It’s much more fun than staring at a wall of bland text for two hours, isn’t it?

Components of a Sailboat Retrospective

A sailboat retro is a helpful agile project management tool. Since it uses metaphor, it’s easier for teams to think critically about future sprints. During a session, your team will document their thoughts on each component of the sailboat, which you later use to map out future projects.

The goal

Sailboat retrospective: ClickUp's Dashboard
The highly customizable ClickUp Dashboard can help you break down goals, tasks, agile points, and project statuses

The goal of a sailboat retro represents the destination. Think of this as the “X” on a pirate map. Some teams refer to this as the “island” your sailboat wants to reach. The goal could be just about anything, from the end of a sprint to the completion of a major project phase. What matters is that you choose a significant milestone for the team to work toward. 🌻

The wind (or the sails)

The wind or sails symbolize the positive forces that move your sailboat closer to its destination. This includes all of the successes, strengths, and good conditions that had a positive impact on the last sprint or project phase. It might include things like specialized certifications, a boost in department funding, or being able to outsource some of your team’s workload. 

The anchor

In a sailboat retrospective, the anchor represents challenges or obstacles slowing the team’s progress. Anchors are anything that hinders your progress, like communication issues or resource limitations. 

The rocks

Rocks are potential risks or foreseeable challenges in the sailboat’s path. While you look at the anchor in the past tense, rocks look forward and require the team to proactively plan for known issues. The goal is to minimize their impact on the next sprint. Rocks could include regulatory changes or continued resource limitations.

The sun 

Finally, the sun represents your team’s objectives beyond the primary goal. This element adds a layer of motivation and inspiration, focusing on the team’s long-term objectives and vision. The focus here is to identify good things that came out of the project, like an improved product or positive customer feedback. It’s important to end on this note so your team can visualize the value of their hard work.

Running a Sailboat Retrospective

The ClickUp Sailboat template
The ClickUp Sailboat template is a retrospective strategy that helps the team identify factors that affected the sprint goal such as challenges that were encountered, future risks foreseen, and motivations

Ready to run a sailboat retro with your entire team? The good news is you don’t have to create the visuals on your own. We might be the world’s favorite project management software, but ClickUp also includes hundreds of free templates for anything you need—including agile retrospectives. 

Simply pull up the ClickUp Sailboat template during your team meeting and you’re off to the races. Start by inviting all employees to the retrospective meeting and run through this process together: 

  1. Set goals: Decide on a specific destination or milestone. If you’re already set up in ClickUp, this will likely come from your ClickUp Goals
  2. Collect supplies: Every boat needs supplies before a long voyage, right? During this stage, you chat about the necessary resources and supplies to support your goal. That might include personnel, software licenses, and other necessary equipment
  3. Check the weather: Can you expect smooth seas or stormy, treacherous waters? This stage of the sailboat retro looks at potential issues in the pipeline. The ClickUp Sailboat template integrates with your ClickUp Calendar view to give you a quick snapshot of your journey so you can plan accordingly
  4. Build a roadmap: Goals and calendar in hand, it’s time to build a roadmap with your team. During this step, you’ll decide on timelines and visualize them with tools like the ClickUp Gantt Chart view
  5. Prep your boat: Any seaworthy vessel needs a thorough inspection before setting sail. In this stage of the sailboat retro, you’ll map out tasks, assignees, and any other essential elements to support your next sprint
  6. Set sail: Finally, your team is ready for their next big voyage. At this stage, project managers continue refining their projects, tasks, docs, and workflows for better project outcomes 

Ultimately, this fun metaphor will help you get organized, plan for future problems, and agree on a shared vision. Since this sailboat retrospective template helps bring all of your work together into one dynamic platform, implementing your sailboat retro is as easy as a few clicks. 🚣‍♀️

The Concept of Sailboat Retrospective Within a Scrum Framework

The sailboat retro sounds like way more fun than a typical sprint retrospective brainstorming session, but how does it fit within a Scrum framework? 

It might be more creative than other retrospectives, but the sailboat approach aligns well with Scrum principles because it’s:

  • Adaptable: Sailboat retros encourage teams to reflect on past performance (wind and anchors) and anticipate future challenges (rocks), which is essential for the always-adapting nature of Scrum project management
  • Collaborative: This retrospective technique promotes open communication because all team members get a say on what hindered the team and what went well. That’s a perfect fit for Scrum’s emphasis on strong teamwork
  • Goal-oriented: The focus on a common goal (or the destination, if we’re following the sailboat metaphor) fits with Scrum’s focus on delivering value while meeting sprint goals

Fortunately, the sailboat retro process isn’t much different if you follow the Scrum framework:

  1. Conduct a sprint review: Review the outcomes and deliverables of your most recent sprint with the team
  2. Conduct the sailboat retrospective: Visualize the entire project with the ClickUp Sailboat template. Ask the team to write their thoughts on sticky notes for the wind, the anchor, the rocks, and the sun. Review everything together to summarize key insights and lessons learned
  3. Determine action items: Mobilize your insights by deciding on action items at the end of the meeting. Plug action items into ClickUp with assignees, notes, and due dates to keep the next sprint on track

Sailboat Retrospective vs. Other Retrospectives

Sailboat retrospectives are a fun, metaphorical way to do project post-mortems, but they certainly aren’t the only way to review project progress. It’s one of many potential sprint retrospective formats, each with a different approach:

  • Sailboat vs. Starfish: A starfish retrospective categorizes feedback into five buckets: Start, Stop, Continue, More of, and Less of. This is a broad framework for categorizing feedback from your team, customers, and other stakeholders, which can be helpful. However, sailboat is more of a visual and metaphorical approach, making it easier for your team to engage in the retrospective
  • Sailboat vs. the 4 L’s: The 4 L’s stand for Liked, Learned, Lacked, and Longed For. Like a sailboat, it focuses on individual feelings and experiences. However, a sailboat is more useful because it also looks at external factors (wind and anchor) that affect the team, giving you a more holistic view of the project environment
  • Sailboat vs. Mad Sad Glad: Mad Sad Glad is a more emotion-focused retrospective that lists team members’ feelings about a project. The sailboat retrospective does account for emotions, but it primarily focuses on factors that affect the project’s progress and future risks. That’s more business-focused than, say, someone feeling sad that the project is over

Why project managers choose the sailboat retrospective

The right retrospective approach depends on your goals and corporate culture. Even so, more project managers are gravitating toward sailboat retrospectives because they’re:

  • Highly visual: The sailboat metaphor is easy to understand, promoting better engagement and participation
  • Comprehensive: We like the sailboat retrospective because, unlike other retrospective techniques, it offers a more holistic view of projects and provides a more well-rounded analysis
  • Feedback-focused: Most employees find the metaphorical, fun approach less intimidating than other retrospective methodologies. In practice, this makes people more likely to share challenges and risks they might not have shared otherwise
  • Flexible: You don’t have to be on a large enterprise software development team to do a sailboat retrospective. This technique adapts to various team sizes and departments, making it a helpful tool for any agile team

Sailboat Retrospectives in Practice

At this point, we know what a sailboat retrospective is and how to run one for your team. But how do you actually implement what you learned in the sailboat retrospective? Follow these pro tips to translate your retrospective insights into tangible business results. 

Educate your team

Your team might say, “Huh?” if you walk into the room with a big chart with a sailboat on it. Brief your team on the sailboat retrospective method before the meeting. Always explain the metaphor at the start of the session, even if you’ve done sailboat retrospectives before. Not everyone will admit that they don’t know what’s going on, so a little refresher does wonders for understanding and participation. 

Create a comfortable environment

You want to encourage honest, helpful feedback, but people won’t share their honest feelings if they feel uncomfortable. Foster a safe and open atmosphere where team members feel comfortable sharing their thoughts. If you still struggle to gather candid feedback, give your team the option to share anonymous feedback instead. 

Embrace visual aids

Sailboat retrospective: organizing ClickUp's Mind Map
Plan and organize your sailboat retrospective in ClickUp Mind Maps for the ultimate visual outline

Sailboat retrospectives are highly visual, so you need some kind of visual aid going into this meeting. Whether it’s a physical whiteboard or a digital Mind Map in ClickUp, have a clear depiction of the sailboat, wind, anchors, rocks, and sun.

Manage time carefully

Retrospectives can quickly run off the rails if you don’t watch the clock. Honor everyone’s time by creating a loose agenda for the meeting that breaks down what you’ll discuss and when. If your team has a habit of going over time, assign an official timekeeper and meeting facilitator to keep everyone on task. ⏱️

Focus on actionable outcomes and next steps

Assigning users and tasks in ClickUp Whiteboard
Turn your sailboat retrospective into tasks with an assignee and due date in just a few clicks on ClickUp

Other retrospectives, like Mad Sad Glad, focus too much on feelings. Emotions are a helpful type of feedback, but they aren’t very actionable. The sailboat retrospective is useful because it emphasizes what went well while also addressing what you could do differently next time. Instead of getting too hung up on subjective assessments, focus on desired outcomes and the steps required to achieve those outcomes. That will translate into tangible change that improves the quality of future projects.

Run Better Sailboat Retrospective Meetings in ClickUp

Different ClickUp views
ClickUp’s 15+ views provide organizations with a wall-to-wall solution for every team

Sailboat retros are useful for understanding how your team feels about past projects and help propel the team forward in future sprints. Executed well, they help you identify risks, eliminate future bottlenecks, and provide clear goals for your next big project.

There’s just one little problem: Most retrospective sessions happen independently of your tasks, reports, and chats. That requires flipping through multiple project management tools, which is a recipe for confusion.

ClickUp’s all-in-one project management tool brings metrics, templates, Goals, Dashboards, tasks, and multiple views into one place—even for technical teams. See the difference for yourself: Create your ClickUp Workspace now for free.

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