Down the Rabbit Hole Retrospective

Down the Rabbit Hole retrospective format

The Rabbit Hole

What curious problem or surprise should we explore?

This topic is about identifying the issue, event, or surprising outcome that deserves a deeper look. Encourage the team to name the things that made them go 'that's odd' or that keep coming back. Keep prompts open and non-judgmental so people surface genuine curiosities rather than easy targets. Aim to land on one or two compelling rabbit holes worth following.

Falling Deeper

Why did it happen? Keep asking why beneath the surface.

Here the team descends through the layers using repeated 'why' questions, much like the 5 Whys technique. Push past the first comfortable answer and keep going until you reach a meaningful root cause. Encourage people to challenge assumptions and follow the chain of cause and effect rather than stopping at symptoms.

Wonderland

What did we discover along the way, good or bad?

This topic captures the insights, patterns, and surprises uncovered during the deep dive. Some discoveries may be uncomfortable truths, others might be hidden strengths worth celebrating. Help the team articulate what they now understand that they didn't before, and how it reshapes their view of the problem.

Finding the Way Out

How do we act on what we found and climb back up?

This is where exploration turns into action. Convert the root causes and discoveries into concrete, owned next steps with clear accountability. Encourage the team to prioritise a small number of high-impact actions rather than trying to fix everything at once, and assign owners and timelines.

When to use this retrospective

• When a recurring problem keeps resurfacing despite previous fixes and you need to understand the true root cause.
• When the team tends to stop at surface-level symptoms and you want to encourage deeper, curiosity-driven analysis.
• When you want a more playful, engaging alternative to a standard root cause analysis session.
• When a surprising outcome — good or bad — warrants a thorough exploration before deciding on action.

Suggested icebreaker questions

• If you could follow any white rabbit into a mystery, what would you most want to discover?
• What's one thing you were endlessly curious about as a child?

Ideas and tips for your retrospective meeting

• Lean into the Wonderland theme to keep things light, but make sure each rabbit hole leads to a genuine root cause and not just a fun tangent.
• Use the '5 Whys' mindset in the Falling Deeper stage — keep asking why until you hit something actionable rather than stopping at the first plausible answer.
• Focus on one or two rabbit holes rather than trying to explore everything; depth beats breadth in this format.
• Keep the conversation blameless by focusing on systems and processes rather than individuals.
• Timebox each stage so the team doesn't get lost in the rabbit hole and always makes it back out with clear actions.
• Capture discoveries even if they don't lead to immediate action — they may reveal valuable patterns over time.

Frequently asked questions