How to not shoot yourself in the foot with estimation

How to not
shoot
yourself in
the foot with
estimation
neil_killickNeil Killick, 2017, All Rights Reserved

Business wants predictability…
+ Bang for buck
+ Responsiveness to change
+ Speed of delivery
+ High quality

Neil Killick, 2017, All Rights Reserved
Traditional…
• Build a plan up front
• Keep changes to a minimum
• Plenty of time for course
correction
• Functional teams/estimation/
milestones
• Project Manager steers
“Agile”…
• Cross-functional teams/
estimation
• Little time for course correction
• Unclear objectives
• Unclear milestones
• Frequent change
• Frequent prioritisation
Potential to shoot yourself in the footFAIR HIGH
neil_killick

"Scrum employs an iterative,
incremental approach to
optimize predictability and
control risk.”
~ The Scrum Guide

Incorporating feedback as we go 
Not knowing exactly what we’re doing,
in sequence, throughout the project 
Welcoming change, making it easy, and
incorporating it
Do these things make us unpredictable?

Empirical
predictability
Understand how long we have to
do what we need to do 
Create/update the plan 
Monitor progress through working
software and other metrics and
observations 
Deterministic
predictability
Determine how long it will take to
do what we need to do 
Put the answer in a plan 
Keep asking how long is left to
deliver the plan 
Stick to the plan

1
Become predictably
good at delivering

Predictability is improved by behaving
and delivering more predictably, not
by making predictions

2
Be transparent —
share your process and
your progress

10
Empirical predictability
Working software
every 2 weeks or so 
Collaborative review
with customers of where we’re at, and
what we should do next — better than
“status reporting” 
Mitigating risks and impediments 
by testing assumptions, managing/
reducing dependencies
neil_killick

3
Find out what type of
estimate is required

• What will we get, and when? 
• Which is quicker/smaller, A or B? (for ROI purposes) 
• When will we get X (feature)? 
• How much will be done by Y (date)? 
• Will X/everything be done by Y? 
• Can we deliver X/everything for the time/money
available? 
• Are you going to deliver maximum bang for buck?
Do you have a plan?
What are we
actually
estimating?

Sales
What features can we sell to (potential) customers?
Marketing
When can we start our campaign?
What features can we talk about at the next roadshow?
Project and program managers
When will Jane/Team A become available for other projects?
When will we need Jane? (our shared UX specialist)

4
Incorporate appropriate
levels of uncertainty

Part of estimate — call out risks/
assumptions/issues/dependencies
• How stable is the team? Losing/gaining members?
• Are all team members 100% committed to the project?
• How predictable is the team’s throughput/velocity of
PLANNED work?
• Is there a predictable level of UNPLANNED work?
• What are our technical/schedule/people dependencies?

Don’t give a precise date when a
set of scope will be delivered
Don’t say a precise set of scope
will be delivered on a given date
— use confidence levels and shades of grey

5
Take into account
poor/no prioritisation
— and agility

Remember - We are in a different paradigm

6
Estimate options for
solving problems, not
specific solutions

We control time rather than predict it
in iterative development
• Minimum effort to solve problem, then iterate 
• Iterative/incremental is a different paradigm 
• Let’s discuss this, and align expectations

Problem
We need to be able to contact
dormant customers by email
Solution 1 (~6-8 weeks)
Build an automated customer email system,
integrated with MailChimp
Solution 2 (~2-3 days)
Send manual email with no integration

7
Revisit estimates regularly
and frequently

8
Estimate cycle times,
not effort

9
Use data
(yesterday’s weather)

RELEASE 1
HIGH CONFIDENCE
LOW
CONFIDENCE
MAY 30th
MAR APR MAY JUN
THROUGHPUT FORECASTING
INCORPORATING VARIANCE,
CONFIDENCE AND UNCERTAINTY
Milestone falls in
our pessimistic
forecast range, so
we have fairly
high confidence
neil_killick

RELEASE 1
(added scope)
HIGH CONFIDENCE
LOW
CONFIDENCE
MAR APR MAY JUN
MAY 30th
Milestone falls in our optimistic
forecast range, so we have lower
confidence - project needs
steering to stay “on track”
neil_killick

RELEASE 1
HIGH CONFIDENCE
LOW
CONFIDENCE
MAY 1st
(earlier date)
MAR APR MAY JUN
Milestone again falls
in our optimistic
forecast range, so we
need steering to stay
“on track”
neil_killick

RELEASE 1
(even more added scope)
HIGH CONFIDENCE
LOW
CONFIDENCE
MAR APR MAY JUN
MAY 30th
Milestone falls outside even our optimistic
forecast range, so we need to reduce scope
or push out date
neil_killick

Summary
• Become empirically predictable — good at delivering, and know
when you plan/review/release
• Be transparent — share your process and your progress
• Know what type of estimate is needed
• Incorporate uncertainty
• Account for poor/no prioritisation — and agility
• Estimate problems and options, not specific solutions
• Revisit estimates regularly and frequently
• Estimate cycle time, not effort
• Use data (yesterday’s weather)

Thank you!
Any questions?

How to not shoot yourself in the foot with estimation

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