The document discusses the challenges of estimating software projects that have high complexity due to factors like interdependencies between components and nonlinear changes. It notes that for such complex projects, predictions are very difficult or impossible due to chaotic dynamics. The document provides tips for managing complex projects, such as focusing on continuous delivery and responsiveness over efficiency, keeping scope small, and using ranges/confidence values when estimating to communicate uncertainty.

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

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

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

4. @andreagouletA DECADE OR SO LATER…

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

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

7. @andreagoulet

8. OUR FIRST
PROJECT
@andreagoulet

9. @andreagoulet
“SOFTWARE IS REALLY HARD TO ESTIMATE.”
M. Scott Ford, Software Engineer

10. @andreagoulet
“DON’T WORRY. I’VE ESTIMATED HUNDREDS OF PROJECTS.
I’VE ALWAYS DELIVERED ON TIME. ”
Andrea Goulet, Marketer & Entrepreneur

11. OUR SECOND
PROJECT
@andreagoulet

12. @andreagoulet
“THIS PROJECT COULD TAKE 100 HOURS OR 10,000. I CAN’T TELL.”
M. Scott Ford, Software Engineer

13. @andreagoulet
“I NEED YOU TO FIGURE OUT HOW TO DELIVER IT IN 100.”
Andrea Goulet, Marketer & Entrepreneur

14. OUR THIRD
PROJECT
@andreagoulet

15. @andreagoulet
“WE’RE OVER BUDGET AGAIN. I’M SORRY.”
M. Scott Ford, Software Engineer

16. @andreagoulet
“I’M STARTING TO SEE A PATTERN HERE. WHAT’S GOING ON?”
Andrea Goulet, Marketer & Entrepreneur

17. WHY ARE SOME PROJECTS
SO HARD TO ESTIMATE
@andreagoulet

18. WHY ARE SOME PROJECTS
SO HARD TO ESTIMATE
@andreagoulet
IMPOSSIBLE

19. @andreagoulet

20. @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.

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

22. @andreagoulet
FREDERICK WINSLOW TAYLOR
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.
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.

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

24. @andreagoulet

25. @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

26. @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

27. @andreagoulet

28. @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.”
Source: McChrystal, General Stanley; Collins, Tantum; Silverman, David; Fussell, Chris. Team of Teams:
New Rules of Engagement for a Complex World (pp. 55-56). Penguin Publishing Group. Kindle Edition.

29. @andreagoulet
EDWARD LORENZ
Source: McChrystal, General Stanley; Collins, Tantum; Silverman, David; Fussell, Chris. Team of Teams:
New Rules of Engagement for a Complex World (pp. 55-56). Penguin Publishing Group. Kindle Edition.
CHAOS THEORY
• coined the term “butterfly
effect”
• applies to “intricate dynamic
systems” such as weather,
ecoystems, and financial
markets

30. @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.

31. @andreagoulet
EDWARD LORENZ
COMPLEXITY, arises from an
“intricate dynamic system”
when “small initial differences
amplify until they are no longer
small”
Source: Lorenz, Edward. Our Chaotic Weather (pages 88-121). University of Washington Press, 1993.

32. @andreagoulet
COMPLICATED
Source: McChrystal, General Stanley; Collins, Tantum; Silverman, David; Fussell, Chris. Team of Teams:
New Rules of Engagement for a Complex World (pp. 55-56). Penguin Publishing Group. Kindle Edition.
COMPLEX

33. @andreagoulet
COMPLICATED
Source: McChrystal, General Stanley; Collins, Tantum; Silverman, David; Fussell, Chris. Team of Teams:
New Rules of Engagement for a Complex World (pp. 57). Penguin Publishing Group. Kindle Edition.
COMPLEX
INPUTS
PREDICTABLE
OUTPUTS
SERIES
OF STEPS

34. @andreagoulet
COMPLICATED
Source: McChrystal, General Stanley; Collins, Tantum; Silverman, David; Fussell, Chris. Team of Teams:
New Rules of Engagement for a Complex World (pp. 57). Penguin Publishing Group. Kindle Edition.
COMPLEX
INPUTS
SERIES
OF STEPS
PREDICTABLE
OUTPUTS
DENSE
INTERDEPENDENCIES
NON-LINEAR
CHANGE
QUICKLY
UNPREDICTABLE

35. @andreagoulet
COMPLICATED
Source: McChrystal, General Stanley; Collins, Tantum; Silverman, David; Fussell, Chris. Team of Teams:
New Rules of Engagement for a Complex World (pp. 57). Penguin Publishing Group. Kindle Edition.
COMPLEX
THE HUNDREDS
OF CREATIVE PROJECTS
I’D ESTIMATED
BEFORE JOINING
CORGIBYTES
DENSE
INTERDEPENDENCIES
NON-LINEAR
CHANGE
QUICKLY
UNPREDICTABLE

36. @andreagoulet
COMPLICATED
Source: McChrystal, General Stanley; Collins, Tantum; Silverman, David; Fussell, Chris. Team of Teams:
New Rules of Engagement for a Complex World (pp. 57). Penguin Publishing Group. Kindle Edition.
COMPLEX
THE HUNDREDS
OF CREATIVE PROJECTS
I’D ESTIMATED
BEFORE JOINING
CORGIBYTES
CUSTOM LEGACY CODE
PROJECTS WHICH HAD
HIGH COMPLEXITY
AND LOTS OF
INTERDEPENDENCIES

37. IDENTIFYING COMPLEX
PROJECTS
@andreagoulet

38. @andreagoulet
“The most direct way to look
for chaos in a concrete
system…is to work with the
system itself.”
-EDWARD LORENZ
Source: Lorenz, Edward. Our Chaotic Weather (pages 88-121). University of Washington Press, 1993.

39. @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?

40. @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

41. WORKING WITH
COMPLEX PROJECTS
@andreagoulet

42. @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.

43. @andreagoulet
TIPS FOR COMPLEX PROJECTS
FOCUS ON RUTHLESS RESPONSIVENESS.
TRANSPARENCY, EXPERIMENTATION, AND
EMPOWERMENT ARE THE KEYS TO SUCCESS.

44. @andreagoulet
TIPS FOR COMPLEX PROJECTS
KEEP SCOPE TINY.
PRACTICE CONTINUOUS DELIVERY, IMPROVEMENT,
DEPLOYMENT…AND ESTIMATES.

45. @andreagoulet
TIPS FOR COMPLEX PROJECTS
TIMEBOX ACTIVITIES.
AVOID FALLING DOWN A RABBIT HOLE. TRY
SOMETHING AND REPORT RESULTS QUICKLY.

46. @andreagoulet
TIPS FOR COMPLEX PROJECTS
ENGINEERING JOURNALS ARE AMAZING TOOLS.
PREDICTIONS ARE USELESS AND
RETROSPECTIVES ARE PRICELESS.

47. @andreagoulet
TIPS FOR COMPLEX PROJECTS
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.

48. @andreagoulet
TIPS FOR COMPLEX PROJECTS
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.”

49. @andreagoulet
QUESTIONS?

50. @andreagoulet
CONTACT INFO
@andreagoulet
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