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Imagine the Worst to Prepare for the Best
If you want to be ready for what’s ahead, start by picturing everything going wrong.
In The Upside of Downside Thinking, Matthew Confer reveals a simple but transformative truth: The most powerful strategic advantage isn’t luck, speed, or even innovation; it’s foresight. By deliberately imagining failure before it happens, leaders can uncover blind spots, stress-test strategies, and build plans that bend without breaking.
Drawing on unforgettable stories from history, psychology, and business—including famous examples from Blockbuster and Kodak to NASA and Netflix—Confer shows why some organizations thrive under pressure while others crumble. At the heart of the book is the RISK framework, a practical premortem approach for anticipating threats, diagnosing vulnerabilities, and taking corrective action when necessary.
This book is perfect for busy business leaders and anyone who wants to lead with confidence, minimize costly mistakes, and turn risk into resilience. Whether you’re leading a team, launching a product, or navigating a personal decision, you’ll learn how to
- Spot the hidden flaws in your best-laid plans.
- Challenge overconfidence and groupthink.
- Build a culture that plans for failure without fear.
Most people analyze failure after it happens. The best decision makers consider the downside early. The upside? You’ll be ready for anything.
“If you’re not regularly asking, ‘What could go wrong?’ you’re not being optimistic—you’re being reckless. The Upside of Downside Thinking is the wake-up call every leader needs. Seeing all sides of things makes us better prepared to succeed and is one of the most positive and productive things we can do, and Matthew Confer makes that case in a way you won’t forget.” —Lisa Bodell, CEO, FutureThink; Author, Why Simple Wins and Kill the Company
“If you coach, lead, or develop others, this book gives you a practical way to uncover hidden risks early—and turn them into a real advantage.” —Jay Moore, Senior Advisor, ICEO; Former CLO, General Electric
“We live in a time of uncertainty, change, and disruptive innovation. In The Upside of Downside Thinking, Matthew Confer challenges you to examine how to navigate uncertainty with respect for the downside of any conversation about change. A must-read for learning, education, business, and talent leaders!” —Elliott Masie, Chair, MASIE Learning Foundation
“By considering the worst-case scenarios in advance, you build a more resilient team whose members trust one another. This book takes the fear out of failure and translates it into practical steps to help you and your team succeed in any task.” —Jennifer Alesia, Managing Partner, Rockstar Learning and Development
“What a wonderful, enjoyable, and educational read. In this book, Matthew Confer shows leaders how to turn uncertainty into smarter decisions. The Upside of Downside Thinking describes how good decisions can be made with savvy and smarts. The book provides leaders with practical tools to anticipate failure, stress-test their thinking, and make stronger choices. If you aspire to leadership or are leading others, you need to read this book cover to cover.” —Karl M. Kapp, EdD, Professor of Instructional Technology, Commonwealth University
“The Upside of Downside Thinking is a phenomenal blend of approachable psychology, real-world examples, and practical tools for approaching failure and decision making in a surprisingly new way. Most organizations could benefit from the premortems Matthew Confer outlines in the book.” —Megan Galloway, Founder and CEO, Everleader
“The workplace isn’t slowing down, and neither are the decisions it demands of us. The Upside of Downside Thinking provides a practical decision-making approach for anyone who wants to think clearly and stay at the edge of work.” —Al Dea, Founder, The Edge of Work
“I’ve known Matthew Confer for years, and The Upside of Downside Thinking reads exactly like a conversation with him. He has a rare gift for turning complicated ideas about decision making into something you can use the next day at work. If you’ve ever been quietly certain about a decision that fell apart anyway, this book is for you. It will change how you think about the ones still ahead.” —Sean Stowers, CEO and Chief Learning Officer, WeLearn Learning Services
As chief strategy officer at Abilitie, Matthew Confer has worked with organizations across six continents to strengthen their leadership capability through experiential learning. His TEDx Talk, “Before You Decide: 3 Steps to Better Decision Making,” has been viewed more than 1.5 million times. As the host of the Learn to Lead podcast, Confer explores leadership lessons from world-class thinkers, founders, and change makers. The Upside of Downside Thinking is his first book. It grew from a simple idea he’s tested in boardrooms, classrooms, and his own life: If you want to make better decisions, first imagine what could go wrong, and then plan for it. Confer lives in Austin, Texas.
Introduction. Cobra Snakes, License Plates, and a Celebrity’s Estate
Part 1. How and Why We Make Decisions
Chapter 1. The Confidence Trap
Chapter 2. The Anatomy of a Decision
Chapter 3. The Premortem: A Counterintuitive Approach
Chapter 4. The Problem With the Postmortem
Chapter 5. Failure as a Strategic Tool: The Power of “What If”
Chapter 6. Frozen in Film: When Success Stops You
From Seeing What’s Next
Part 2. The Premortem
Chapter 7. The RISK Framework
Chapter 8. Camping Chaos: A Premortem in Action
Chapter 9. Recognize the Threats
Chapter 10. Imagine the Disaster
Chapter 11. Solve for Vulnerabilities
Chapter 12. Kickstart the Solutions
Part 3. Real-World Application
Chapter 13. Building a Culture of Premortems
Chapter 14. Avoiding Premortem Pitfalls
Chapter 15. The Fine Line Between Preparation and Paralysis
Chapter 16. Your Next Decision Starts Now