From Estimation Theater to Delivery Reality
Decomposing Work That Makes Business Sense
Earlier this week [Post 1] I shared how a team escaped the feature factory .
Today: what happened when they hit their next wall...
The team had learned to ask “why?”
They understood business intent. They could identify minimum impact. They knew how to think about options.
Then product asked: “Can we deliver this by next release?”
The team froze.
The Problem
They understood why now. But they still didn’t know how to answer “when?”
Product defines a business increment. Something big. Meaningful. Somewhat ambiguous.
“Can you estimate this?”
The team breaks it into user stories. Estimates in story points. Adds them up. Divides by velocity. Gives a date.
Everyone pretends this is real.
Nobody believes it.
Estimation theater.
A Different Question
I introduced a hierarchy:
Tasks build Options that create Capabilities that compose a Business Increment.
Not “estimate this increment.”
Different questions:
Can this business increment be built in the next delivery period?
Usually no.
Then: Which capabilities that make business sense can we deliver?
Then: What options do we have to stage these capabilities?
Finally: What effort does it take to build these options?
Estimate there. At the options level. Where you can actually see the work.
How It Played Out
Business increment: Improved customer onboarding.
Capabilities:
Simplified registration
Contextual guidance
Progressive disclosure
Analytics dashboard
Can we build all four in eight weeks?
Probably not.
Which ones matter most?
Registration and guidance deliver 70% of the impact.
What options for those two?
Registration:
Basic flow with email
Add social auth
Progressive profile
Guidance:
Static tooltips
Interactive walkthroughs
AI personalization
Estimate options 1 for each? Two weeks each. Four weeks total.
Fits the delivery period. Room to learn.
What Changed
Estimation became negotiation about value sequencing.
Not guessing about scope completion.
“Can we have the full onboarding improvement?”
“We can deliver simplified registration and basic guidance. That’s 70% of the business impact. The rest comes next period if this validates.”
Product makes a real decision. Based on real information.
Not a guess.
The Questions
When someone asks “can we deliver X?” - don’t estimate X.
Ask:
Can this business increment be built in the next delivery period?
Which capabilities make business sense to deliver?
What options stage these capabilities?
What effort for these options?
These questions force decomposition. Force prioritization. Force clarity.
Estimation becomes real planning.
From Theater to Reality
The team still estimates.
But they estimate options. Things they can see and understand.
When they’re wrong, they’re wrong about a two-week option. Not a three-month initiative.
They adjust. They continue.
They deliver capabilities the business can use. Not incomplete features needing “just one more sprint.”
They stopped playing theater.
Started doing real planning.
The Practice
Your next big initiative - don’t estimate it.
Ask:
What capabilities compose this?
Which matter most?
What options exist for delivering them?
Estimate the options.
Have an honest conversation about what fits.
Ship capabilities. Not story points.
Simple Agility applied to planning.
Not complicated.
Just better questions before committing to work you don’t yet understand.
Everything else is theater.