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Software Estimation Without Guessing: Effective Planning in an Imperfect World


Cover image for Software Estimation Without Guessing

Software Estimation Without Guessing

Effective Planning in an Imperfect World


Developers hate estimation, and most managers fear disappointment with the results, but there is hope for both. You’ll have to give up some widely held misconceptions: let go of the notion that “an estimate is an estimate,” and estimate for your particular need. Realize that estimates have a limited shelf-life, and re-estimate frequently as needed. When reality differs from your estimate, don’t lament; mine that disappointment for the gold that can be the longer-term jackpot. We’ll show you how.

Customer Reviews

I hate estimating and I’m all too familiar with the anti-patterns. I was surprised
by how much I liked this book. An easy read on why, when, how, and how not to
estimate, with pragmatic advice both for the art of estimation itself and for handling
the human behaviors that invariably surround it.

- Liz Keogh

Director, Lunivore Limited

When I first started reading this book, I knew it was providing a good framework
for software estimation. I have recommended to my boss that we buy copies for
all of our senior developers who are responsible for both creating project estimation
and vetting estimations, since it provides a common language for discussing those
estimations as well as helping improve our estimations.

- Josef Finsel

Senior Developer,, Mt Mediabox

This book is about different aspects of the estimation process. While it won’t teach
you how to estimate more accurately, it does the more important stuff: explain
how our estimates can be used effectively, and what to do when they aren’t.

- Gil Zilberfeld

Agile Consultant

We all estimate at work. George’s book offers helpful advice on when to use which
kind of estimation, regardless of the kind of work and the size of the company.
Read this book to apply these approaches in your context.

- Johanna Rothman

Author and Consultant, Rothman Consulting Group, Inc.

This is not so much a how-to-do-estimates book, but a how-to-think-aboutestimation
book (though it does have how-to guidance as well).

The book focuses on why people need estimates, and how that affects how one
might approach any particular estimate. Context, as always, matters. If you use
estimates or are asked to give estimates, this book will be valuable to you.

- Esther Derby

President, Esther Derby Associates, Inc.

See All Reviews

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What You Need

No software needed, just your past experience and concern for the outcomes.


Contents & Extracts

  • Introduction
    • Benefit of Headlights
    • Beyond Story Points and Planning Poker
    • Definitions
    • Who This Book Is For
    • Goal of This Book
    • What’s in This Book
    • Conventions Used
    • Now It’s Your Turn
  • Starting Something New
    • When You’re Asked to Estimate Something New
    • Case: Developing a Fixed-Price Bid
    • Case: Is This Worth Starting?
    • Case: Can We Make This Work?
    • Case: What Should We Budget?
    • Case: Which of These Should We Choose?
    • Case: A Mixture of Questions
    • Stepping Back for a Broader View
    • Now It’s Your Turn
  • Comparison-Based Estimation
    • Comparison to Past Experience
    • Memory vs. Recorded Data
    • Aspects to Compare
    • Gestalt Estimation
    • Decomposition
    • Estimating the Unknown
    • Stepping Back for a Broader View
    • Now It’s Your Turn
  • Decomposition for Estimation
    • Which Way to Slice?
    • Decomposing by Phase
    • Decomposing by Implementation
    • Decomposing by Functionality
    • User Stories
    • Decomposition Decisions
    • A Large Number of Small Parts
    • A Small Number of Large Parts
    • Affinity Estimation
    • Ordering the Parts
    • Multi-Level Decomposition
    • Comparing Big Items with Small Ones
    • Decomposition Gotchas
    • Stepping Back for a Broader View
    • Now It’s Your Turn
  • Checking Progress
    • Getting Things Done
    • Detecting Progress
    • What to Measure
    • Visualizing Progress
    • Showing Value for the Money
    • Efficiency and Effectiveness
    • Optimization
    • Are We Going Fast Enough? excerpt
    • Pushing Our Limits
    • Situational Awareness
    • Stepping Back for a Broader View
    • Now It’s Your Turn
  • Model-Based Estimation
    • Modeling the Size
    • Modeling the Rate
    • Unavoidable Subjectivity
    • The Linear Model Approach
    • Advanced Linear Model Techniques
    • The Parametric Model Approach
    • The Stochastic Model Approach
    • Comparison-Model Hybrid
    • Stepping Back for a Broader View
    • Now It’s Your Turn
  • Estimating Milestones
  • When Estimates and Actuals Differ
    • Driving Up Costs
    • Salvaging the Situation
    • Learning from the Situation
    • Stepping Back for a Broader View
    • Now It’s Your Turn
  • Planning for Incorrect Predictions
    • Seeking Out Information
    • Setting Traps for Information
    • Avoid Traps for the Unwary
    • Stepping Back for a Broader View
    • Now It’s Your Turn
  • When People Clash
    • It Starts So Innocently
    • How It Goes Wrong
    • Understanding Human Behavior
    • Imagine a Better Situation
    • Retraining Ourselves
    • Tools for Better Understanding
    • Stepping Back for a Broader View
    • Now It’s Your Turn
    • Conclusion


George Dinwiddie is a software development consultant and coach who has helped a wide variety of people in a wide array of organizations and situations. He has studied both technical and human aspects of software development and has decades of experience in hardware and software engineering. His eclectic background extends well beyond software development, and he uses that knowledge and his personal experience with estimation to facilitate improvements in technical, organizational, and social realms.

Upcoming Author Events

  • 2020-07-21: George Dinwiddie
    Getting Value From Estimates in an Agile Context -- People say software development estimates are hard to make, and always wrong. Estimation triggers conflict, and breeds a lot of pain. Surprisingly, estimates are more valuable for Agile software develo (Agile 2020, Orlando FL)