Should I Estimate That? Complicated VS Complex Projects

SHOULD I ESTIMATE THAT?
@andreagoulet
BY ANDREA GOULET
CO-FOUNDER & CEO, CORGIBYTES
COMPLICATED VS. COMPLEX PROJECTS

@andreagoulet
We remodel
existing
software to
make it stable,
scalable, and
secure.
WHEN I  
WAS  
IN HIGH  
SCHOOL….

@andreagoulet
We remodel
existing
software to
make it stable,
scalable, and
secure.
THERE  
WAS  
THIS GUY…

@andreagouletA DECADE OR SO LATER…

@andreagoulet
“MY DREAM JOB IS CLEANING UP OTHER PEOPLE’S CODE.”
M. Scott Ford, Software Engineer

@andreagoulet
“REALLY? I THINK THERE’S A MARKET FOR THAT. LETS DO IT!”
Andrea Goulet, Marketer & Entrepreneur

OUR FIRST
PROJECT
@andreagoulet

@andreagoulet
“SOFTWARE IS REALLY HARD TO ESTIMATE.”

@andreagoulet
“DON’T WORRY. I’VE ESTIMATED HUNDREDS OF PROJECTS.  
I’VE ALWAYS DELIVERED ON TIME. ”

OUR SECOND
PROJECT
@andreagoulet

@andreagoulet
“THIS PROJECT COULD TAKE 100 HOURS OR 10,000. I CAN’T TELL.”

@andreagoulet
“I NEED YOU TO FIGURE OUT HOW TO DELIVER IT IN 100.”

OUR THIRD
PROJECT
@andreagoulet

@andreagoulet
“WE’RE OVER BUDGET AGAIN. I’M SORRY.”

@andreagoulet
“I’M STARTING TO SEE A PATTERN HERE. WHAT’S GOING ON?”

WHY ARE SOME PROJECTS
SO HARD TO ESTIMATE
@andreagoulet

WHY ARE SOME PROJECTS
SO HARD TO ESTIMATE
@andreagoulet
IMPOSSIBLE

@andreagoulet
FREDERICK WINSLOW TAYLOR
“The norm was nine feet of
steel per minute; Taylor’s
system could cut fifty.”  
 
In 1900, Taylor’s display at the
Paris World Fair “was akin to
Steve Jobs’s introducing the
first iPhone.”
Source: McChrystal, General Stanley; Collins, Tantum; Silverman, David; Fussell, Chris. Team of Teams:
New Rules of Engagement for a Complex World (pp. 36-37). Penguin Publishing Group. Kindle Edition.

@andreagoulet
SCIENTIFIC MANAGEMENT 
• discover the “one best way”
• split thinkers and doers
• micromanagement
• reduced cost 80% or more
• taught in business schools

@andreagoulet
13 years later, Henry Ford used
scientific management to
create the assembly line,
reducing the time to make a car
from days to just 93 minutes.

@andreagoulet
EFFICIENCY, which is at the
heart of scientific
management, dominated
business practices throughout
the twentieth century.

@andreagoulet
EFFICIENCY VS. RESPONSIVENESS
First Round Review: http://firstround.com/review/Responsiveness-New-Efficiency
“When we can’t predict the future, efficiency can no longer drive decisions.” - Adam Pisoni

@andreagoulet
WATERFALL VS. AGILE
First Round Review: http://firstround.com/review/Responsiveness-New-Efficiency
“When we can’t predict the future, efficiency can no longer drive decisions.” - Adam Pisoni
WATERFALL AGILE

@andreagoulet
EDWARD LORENZ
At MIT in 1961, Lorenz had been
using computers to model
weather for nearly a year. He
manually entered data,
rounding from .506127 to .506 
 
The results seemed to be “two
random weathers out of a hat.”

@andreagoulet
EDWARD LORENZ
CHAOS THEORY 
• coined the term “butterfly
effect”
• applies to “intricate dynamic
systems” such as weather,
ecoystems, and financial
markets

@andreagoulet
EDWARD LORENZ
“Interest has not been so
much in chaos itself as in the
feasibility of producing
extended-range forecasts,
particularly at the two-week
range.”
SOUND FAMILIAR?
Source: Lorenz, Edward. Our Chaotic Weather (pages 88-121). University of Washington Press, 1993.

@andreagoulet
EDWARD LORENZ
COMPLEXITY, arises from an
“intricate dynamic system”
when “small initial differences
amplify until they are no longer
small”

@andreagoulet
COMPLICATED
COMPLEX

@andreagoulet
COMPLICATED
New Rules of Engagement for a Complex World (pp. 57). Penguin Publishing Group. Kindle Edition.
COMPLEX
INPUTS
PREDICTABLE
OUTPUTS
SERIES
OF STEPS

@andreagoulet
COMPLICATED
COMPLEX
INPUTS
SERIES
OF STEPS
PREDICTABLE
OUTPUTS
DENSE  
INTERDEPENDENCIES
NON-LINEAR  
CHANGE
QUICKLY
UNPREDICTABLE

@andreagoulet
COMPLICATED
COMPLEX
THE HUNDREDS  
OF CREATIVE PROJECTS  
I’D ESTIMATED  
BEFORE JOINING  
CORGIBYTES
DENSE  
INTERDEPENDENCIES
NON-LINEAR  
CHANGE
QUICKLY
UNPREDICTABLE

@andreagoulet
COMPLICATED
COMPLEX
THE HUNDREDS  
OF CREATIVE PROJECTS  
I’D ESTIMATED  
BEFORE JOINING  
CORGIBYTES
CUSTOM LEGACY CODE  
PROJECTS WHICH HAD  
HIGH COMPLEXITY  
AND LOTS OF  
INTERDEPENDENCIES

IDENTIFYING COMPLEX
PROJECTS
@andreagoulet

@andreagoulet
“The most direct way to look
for chaos in a concrete
system…is to work with the
system itself.”
-EDWARD LORENZ

@andreagouletSource: http://arlobelshee.com/planning-with-any-hope-of-accuracy/
“Bill Hanlon (Microsoft) has data that shows estimates to
be pretty much useless as long as the story sizes are in
the roughly-linear zone. He looked at 60-ish projects that
used relative estimates. He looked at how accurate their
predictions were as compared to the actuals. Then he
reset all estimates to 1 and recomputed their velocities,
made accordant projections and compared those to
actuals. He found about a 3% variance in predictive
accuracy between full data and just using 1.”
-Arlo Belshee
EFFECTIVENESS OF ESTIMATING?

@andreagoulet
“If an engineer says they can’t
give you an estimate, it’s likely
because it’s mathematically
impossible. Chaos theory is
real. There’s no amount of
negotiating or bullying that will
change the math. ”
-ANDREA GOULET

WORKING WITH 
COMPLEX PROJECTS
@andreagoulet

@andreagoulet
TIPS FOR COMPLEX PROJECTS
MAKE ESTIMATING A VERB, NOT A NOUN.
ESTIMATING IS AN ACTIVITY YOU CONSTANTLY DO,
NOT AN ARTIFACT THAT YOU DELIVER.

@andreagoulet
FOCUS ON RUTHLESS RESPONSIVENESS.
TRANSPARENCY, EXPERIMENTATION, AND
EMPOWERMENT ARE THE KEYS TO SUCCESS.

@andreagoulet
KEEP SCOPE TINY.
PRACTICE CONTINUOUS DELIVERY, IMPROVEMENT,
DEPLOYMENT…AND ESTIMATES.

@andreagoulet
TIMEBOX ACTIVITIES.
AVOID FALLING DOWN A RABBIT HOLE. TRY
SOMETHING AND REPORT RESULTS QUICKLY.

@andreagoulet
ENGINEERING JOURNALS ARE AMAZING TOOLS.
PREDICTIONS ARE USELESS AND  
RETROSPECTIVES ARE PRICELESS.

@andreagoulet
IF THE MATH’S NOT ON YOUR SIDE, DON’T FORCE IT.
BUSINESS AND ENGINEERING TEAMS NEED TO WORK
TOGETHER AND USE THE SAME VOCABULARY.

@andreagoulet
RANGES AND CONFIDENCE VALUES CAN HELP
COMMUNICATE UNCERTAINTY.
“I’M 10% CONFIDENT I COULD GET THIS DONE IN A DAY
AND 80% CONFIDENT I COULD GET THIS DONE IN A
WEEK. I’LL KEEP YOU UPDATED ON MY PROGRESS.”

@andreagoulet
CONTACT INFO
@andreagoulet
@corgibytes
corgibytes.com
LegacyCode.Rocks

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