eXtreme Estimates – Facilitator’s Guide

A long due manual, here is the facilitator’s guide to eXtreme Estimates, a workshop we designed from scratch in 2011 with a few Octo colleagues, as our teams we growing very frustrated with typical agile estimate technique existing at the time (=poker planning).
I refined the practice over probably a hundreds of sessions across time and continents, but here is the original description for reference, still standing:

Workshop Overview

What is eXtreme Estimates?

A collaborative estimation technique that allows teams to:

• Estimate everything at once rather than item by item
• Iterate on confidence through group discussion
• Build shared understanding through conversation

Core Principles

1. Global System Thinking – View the entire backlog holistically
2. Facilitation as Conversation – Everyone talks, contradictions are explored
3. Questions & Learning – Continuous improvement through variations

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The eXtreme Estimates System

Step 1: Place Cards

• Lay out all items to be estimated
• Move quickly (FAST approach)
• Initial placement based on gut feeling

Step 2: Improve Through Iteration

• Shake until stable – Keep adjusting positions until consensus emerges
• Use concrete criteria:
  • Concrete indicators – Tangible measures of complexity
  • Proxy indicators – “How complex is it to test when it is done?”
• Continue iterations until the team reaches stability

Step 3: Choose Yardsticks

• Select 2 reference items per category
• These become anchors for relative sizing
• Ensure yardsticks are well-understood by all

Step 4: Talk Numbers

• Apply numerical values using a scale
• Discuss and align on final estimates

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Facilitation Guidelines

Creating the Right Environment

• Facilitate like a conversation
  • Encourage everyone to speak
  • Create space for contradictions and debate
  • Keep energy flowing

Reading the Room

• Observe body posture to gauge confidence:
  • Leaning forward = engaged and confident
  • Arms crossed = skeptical or uncertain
  • Standing back = low confidence

Checking the progress

• Hand vote for confidence check (you can repeat it over time)
  • 1 = Random (no confidence)
  • 2 = Not random, but not reliable
  • 3 = It’s OK, but a lot will change if we give it a second look
  • 4 = We will probably find that a lot of these are exact
  • 5 = It’s quite relevant for the project/release

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Talking Numbers – Practical Tips

Choose Your Scale

Pick a gross scale that works for your team:

• Fibonacci: 3, 5, 8, 13, 21…
• Exponential: 2, 4, 8, 16…

Key Questions to Ask

• For each category:
  • What’s the minimum complexity/effort?
  • What’s the maximum complexity/effort?
• For total calculation:
  • What’s our velocity prediction?
  • What assumptions are we making?

Language Tips

• Say “prediction” instead of “estimates”
• Reference: Johanna Rothman – “Predict the Unpredictable”
• Always report any assumptions made during estimation

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Best Practices

Do’s

• Keep energy high and pace quick
• Encourage open discussion
• Make criteria visible to all
• Document assumptions
• Celebrate reaching consensus

Don’ts

• Don’t get stuck on perfect accuracy
• Avoid lengthy debates on single items
• Don’t skip the confidence check
• Never force consensus

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Workshop Materials Needed – easy to adapt to virtual

• Index cards or sticky notes for all backlog items – this one is 90% of your preparation time
• Large wall or table space for card placement
• Markers for writing
• Timer for keeping pace
• Scale reference chart visible to all

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For questions or coaching, reach out from the contact form