Turn Your Failed Sprint into a Success: The "Worst Idea" Retrospective

Turn Your Failed Sprint into a Success: The "Worst Idea" Retrospective

As you begin to run your first Retrospectives, you will discover how the collective work of your team is, uncovering their key strengths and pinpointing areas for improvement. This step-by-step approach will help your team reach important goals faster, progressing towards crucial milestones and improving your business outcomes, including the quality of your products or services.

At this point, adopting the Agile methodology seems easier than you initially thought, as your colleagues will now fully understand the steps to plan, work and review each work cycle. To your surprise, everyone is more willing to participate during the Retrospective sessions, sharing their feedback and asking all the right questions.

So why do you feel you haven't gotten the most out of Agile Retrospectives yet? What is missing?

The answer can be complex. Although the Retrospective techniques are easy to follow, their difficulty lies in their simplicity; you must be very attentive to details to discover where you are failing.

Some common errors that most of us come across at least once are:

  • Lack of clear leadership.
  • Imposing techniques that don't suit the team or project.
  • Difficulty in integrating team members’ suggestions properly.
  • Ambiguous action items that prove ineffective.
  • Failure to follow-up on agreed tasks.
  • Allowing discussions to stray off-topic.

Fortunately, with the appropriate tools and a little bit of patience, these errors can be recognized and resolved. Let's explore ways to enhance the effectiveness of your Retrospective sessions consistently.

The Importance of a Well-done Retrospective####

As you have adopted Agile, you will know that Retrospectives are a fundamental ceremony for improving your sprints. Identifying areas in teamwork that require review is vital to implement corrective measures, evaluations, and optimization actions.

Achieving a successful Retrospective goes beyond merely following the steps and actively participating; it means being critical of one's own performance, committing to challenging tasks, engaging in self-directed learning, and maintaining a proactive outlook that prioritizes the team's well-being and progress. Knowing some techniques is insufficient; you must fully embrace the Agile Mindset.

Having the wrong mindset is one of the most common issues that makes newly adopted Retrospectives less valuable because it leads to ineffective conclusions and actions to improve sprints.

After all, it is much easier to mind your own business or look disapprovingly at the mistakes of others than to analyze the situation and find out what went wrong, especially if there is no positive relationship between team members. These ideas usually come from a more traditional organization where communication and relationships are more vertical, and it is necessary to be more individualistic.

This problem can be worsened by a lack of experience and using techniques that don't motivate team members to participate.

But don’t worry; there is a solution. What if we told you that, in order to get better, you need to start by understanding how to mess up your next sprint?

A Good Retrospective Checklist####

Let's not jump straight to the worst-case scenarios that could impact your sprint. Instead, let's start by making sure you have everything needed to run a good Retrospective:

Good retrospective checklist

  • A communication tool for your remote team.
  • A specialized tool to run your Retrospectives.
  • A task-tracking tool to monitor assigned tasks.
  • Ensuring that your team knows how to use these tools.
  • Team members are familiar with one another.
  • There is a foundation of trust and effective communication.
  • Maintain transparency throughout the process.
  • Colleagues possess the ability to both give and receive feedback.
Good Practices######
  • You start your Retrospectives with an ice-breaker.
  • You experiment with different Retrospectives techniques to maintain interest.
  • You allow everyone to talk but keep the conversation focused.
  • You assign each task to a person and define delivery dates.
  • You maintain daily communication with your colleagues and ask them about their status.
  • You keep track of tasks and let your team know when they are completed.

If you have checked that all the items mentioned above are covered, it’s now time to address the feeling of inefficiency you may still be experiencing during your Retrospectives.

Let's brace ourselves to contemplate the worst-case scenarios.

Fail Your Next Sprint####

What is this about? It's a reverse psychology trick that helps teams adopt the Agile mindset: an inverted Retrospective technique.

Suppose, as a team, you still need help identifying the areas of opportunity or defining the specific actions to improve the work. But what would happen if you change the perspective? Instead of focusing on positive outcomes, explore the worst-case scenarios that could potentially derail progress and hinder task completion. Create the worst sprint.

It’s important to note that this technique is not about falling into an Agile anti-pattern or imagining fictional catastrophic scenarios rather, it encourages an honest examination of genuine concerns and potential threats based on past experiences or current project dynamics.

Although this technique may seem somewhat negative, it offers several benefits:

  • Short-term problems are corrected, which improves the performance of the team.
  • Latent concerns are shared among the members, which enhances their communication.
  • Improves work confidence by proactively addressing and avoiding potential disasters.
  • Promotes optimism, which helps adopt a more positive and productive mindset.
The "Worst Idea" Technique#####
Step 1: Set the stage######

After the ice-breaker, introduce the technique and clarify the objectives you want to achieve.

Instead of using any of the traditional Retrospective questions, we will define specific areas where tasks are challenging, assigning each a column. You can use our fully customizable Agile Retros app (available for Jira, Confluence, monday.com, and Trello) to facilitate this step.

Select the topics for discussion as a team or, if you are having a hard time deciding, begin with our suggestions and change them or add more in future Retrospectives:

  1. Tools
  2. Processes
  3. People

Failed sprint

Step 2: Gather data######

Based on the chosen topics, generate ideas that address potential threats, problems, errors, and other sensitive or negative situations that could impact the successful delivery of value in the upcoming sprint.

For example:


  • Too many technologies that fail to integrate together or become repetitive.
  • The tools used by the team don't cover the needs of the project.


  • Not updating the dashboard with the corresponding progress.
  • Misestimating features.
  • Changing priorities at the last minute and not properly discussing them with the team.


  • Slow review and approval of completed work.
  • Not sharing implemented changes and information with the team.
  • Team members not communicating with others as questions arise.
Step 3: Generate insights######

To define which ideas will be worked on, we will proceed to vote in three stages:

  1. Select the idea that would be the most problematic and that poses the most significant risk.
  2. Choose the idea that is most likely to occur or is already happening among the previously identified risky ideas.
  3. If there are still numerous ideas remaining, prioritize the ones that would significantly impact the tasks within the sprint.
Step 4: Decide what to do######

The select ideas are the tasks that require immediate attention to prevent any negative impact on the next Sprint. The actions defined at the end of the Retrospective must be specific to avoid and solve those problems.

Remember always to assign someone responsible for each task. If your Retrospectives tool is integrated with your process management platform, exporting each action as a task and setting a due date becomes more convenient. This allows for easy tracking and monitoring of the tasks.

Step 5: Close the Retrospective######

Once this process is finished, thank your team for their willingness to try this new technique and ask them how they felt about it and what results they hope to obtain by the end of the next Sprint.

To Summarize...#####

This technique is particularly beneficial for teams new to Agile as it enhances analytical skills, promotes teamwork, and gradually reduces risks and errors. It helps the team focus on positive opportunities rather than negative situations, ultimately fostering the adoption of the Agile mindset. When combined with the Retrospective's do's and don'ts, this technique will accelerate your mastery of the subject.

When you're ready to explore other ideas, consider reading "5 Creative Retrospective Techniques to Master Continuous Improvement" for further inspiration. Embrace the opportunity to try new approaches and continue learning and growing!

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