I’m coaching an estimation session as I write this.  I haven’t been to one of these in a while, and I’m taken by how much more quickly we run through the stories AND how much more tightly grouped the blind estimates are.

In the beginning, you could read fear in the faces of the team.  Estimates would range from tiny to huge; depending on who you asked and what perspectives and experiences each member brought to the room.

I tried to convince them, to calm them, to ease them, but in the end…

Nothing worked but a blind leap into the unknown.

And the only thing that makes that leap less terrifying is…your team.

Let’s revisit the problem of bigness.  The reason why large organizations are unable to move as quickly as small enterprise is because we value low value things.  In this case, there are two (related) ‘things’ that we cling to:  Certainty, and Safety.

The reason why our estimation session now happens so much more quickly, so easily, and with more consensus and confidence, is because they’ve simply done it a few times.  And nothing bad happened.   Or if something bad did happen, it was relatively small and became a retrospective item – something the team could absorb and work on solving together.

The converse – being paralyzed by fear and discussing minor details to the nth degree – cost us time and actually created more rework and errors.

Lesson learned – to conquer uncertainy, just jump.  Live at the edge of your ability, the edge of your fear, and count on a team to back you up.

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