Most software estimation is wasteful. After 30 years as an engineering manager, CTO, and CTO coach, I've learned that teams spend countless hours estimating work that never informs actual decisions. This book challenges conventional wisdom and provides a framework for when estimation matters—and when it doesn't.

Written for CTOs, VPs of Engineering, and engineering managers, this guide tackles the real problems you face: CEOs demanding impossible timelines, marketing getting unlimited budget while engineering fights for resources, and teams losing credibility when "estimates" become unmovable commitments.

 You'll learn:

 - The five valid reasons to estimate (and why everything else is waste)

 - Why software estimation is fractal, and what that means for your planning

 - How to stand your ground when executives pressure you for unrealistic dates

 - The "Four Goal Model" that replaces single-number targets with actionable ranges

 - How to reframe engineering from a cost center to a profit center

 - Practical techniques: effort vs. duration, maintaining error margins, and sprint planning that actually works

Drawing from decades of hands-on experience and coaching dozens of CTOs, this book delivers immediately actionable frameworks without academic theory or estimation theater. If you're tired of estimation exercises that waste time and destroy trust, this guide shows you a better way.