Snakes and Ladders Retrospective

A gamified approach to identify risks and opportunities in your project journey

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.

What is The Snakes and Ladders Retrospective

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.

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

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How to Run Effective Meetings with TeamRetro

Start Your Session in a Click

Log into TeamRetro and choose your template. Customise questions and the workflow to create your perfect retro for your team.

Create Your Team Easily – No Separate Accounts Needed

Invite your team in seconds via email, link, or Slack. Role based permissions and SSO options available.

Brainstorm Individually – Free From Bias

Encourage open and honest input with anonymous brainstorming. Set the mood with background music, give teams space to think independently, and keep the session flowing with built-in timers.
Grouping of ideas after brainstorming in a retrospective meeting

Smart Grouping for Faster Insights

Easily drag and drop similar ideas or let AI suggest groupings to save time. Choose between facilitator-led or participant-led grouping to match your team’s workflow.
Grouping of ideas after brainstorming in a retrospective meeting

Fair, Flexible, and Fast Voting

Keep votes private and unbiased with multiple voting options. Once voting is complete, TeamRetro automatically sorts results, helping your team focus on what matters most.
Grouping of ideas after brainstorming in a retrospective meeting

Engage, React, and Capture Key Insights

Walk your team through ideas one by one with Presentation Mode. Stay in sync, spark real-time discussions, and capture feedback with comments, live reactions, and polls—all in one place.

Grouping of ideas after brainstorming in a retrospective meeting

Turn Ideas Into Action

Propose next steps with team buy-in, get AI-powered action suggestions, and keep everything in one place. Committed actions sync to your personal dashboard and integrate with your workflow tools—keeping you on track.

Grouping of ideas after brainstorming in a retrospective meeting

Save, Share, and Stay on Track

Get quick AI-powered summaries, add facilitator notes, and store retrospectives in your library for easy access. Schedule your next session and track published actions to keep your team accountable at the next retro.

Grouping of ideas after brainstorming in a retrospective meeting

Turn Team Data into Actionable Insights

Uncover trends, common themes, and key engagement metrics at a glance. Track sentiment shifts, analyze conversations, and monitor completed actions to drive continuous improvement.