Start

What things should we start?

Weekly knowledge sharing sessions to spread expertise across the team
Regular check-ins with stakeholders to ensure alignment
Using a shared documentation system for better knowledge retention
Snakes

What pitfalls should we be aware of?

Dependencies on external teams causing unexpected delays
Technical debt accumulating in legacy systems
Unclear requirements leading to rework
Ladders

What will help take us to the next level?

Adopting new automation tools to speed up deployment
Building stronger relationships with other departments
Implementing more efficient code review processes
Finish

What do we expect at the end?

Reduced deployment time by 50% through improved automation
Zero critical bugs in production for three consecutive sprints
Complete migration to the new architecture by Q4

What is the Snakes and Ladders Retrospective?

The Snakes and Ladders retrospective transforms the classic board game concept into a powerful project reflection tool. Drawing inspiration from the traditional game of advancement and setbacks, this format helps teams visualize their journey toward their goals. Participants identify potential shortcuts (ladders) that can accelerate progress and pitfalls (snakes) that might slow them down. This creates a strategic map of opportunities and risks, allowing teams to plan their path forward more effectively. This retrospective format is particularly effective for project planning and risk assessment, as it encourages teams to think both optimistically and critically about their journey. It helps create a balanced view of challenges and opportunities while maintaining an engaging, game-like atmosphere.

Snakes and Ladders Retrospective Format

Start

What things should we start?

Begin by establishing the current state and immediate opportunities. Encourage participants to think about new initiatives or changes that could benefit the team. Focus on actionable items that can be implemented in the near future.

Snakes

What pitfalls should we be aware of?

Guide the team in identifying potential risks and challenges that could impede progress. Encourage honest discussion about both technical and interpersonal challenges, while maintaining a solution-oriented mindset.

Ladders

What will help take us to the next level?

Focus on identifying accelerators and opportunities that can help the team progress faster. Look for both quick wins and strategic advantages that can be leveraged for long-term success.

Finish

What do we expect at the end?

Help the team envision their desired outcomes and success criteria. Encourage specific, measurable goals while maintaining aspirational thinking about what's possible.

When to use this retrospective

  • When planning a new project or initiative to identify potential risks and opportunities early
  • During project milestones to assess progress and adjust strategy
  • When the team needs to break out of a rut and think creatively about solutions
  • For teams that respond well to gamified approaches to problem-solving

Suggested icebreaker questions

  • What was your favorite board game as a child and why?
  • If you could instantly master one skill that would help our team, what would it be?

Ideas and tips for your retrospective meeting

  • Keep the game metaphor light and fun, but ensure discussions remain focused on actionable insights
  • Encourage participants to think about both short-term and long-term implications of each snake and ladder
  • Use voting or prioritization to identify the most critical snakes to address and the most valuable ladders to pursue
  • Consider creating a visual board to track progress on addressing identified snakes and leveraging ladders
  • Balance the discussion between risks and opportunities to maintain a positive outlook
  • Follow up on previous retrospective items to ensure continuity and progress

New to retrospectives? Read our guide on how to run a retrospective →