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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, leadership and strategy expert 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 Model, a practical framework for anticipating threats, diagnosing vulnerabilities, and taking action before the stakes get high.
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.
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.
Chapter 1. Cobra Snakes, License Plates, and a Celebrity’s Estate
Chapter 2. The Confidence Trap
Chapter 3. The Anatomy of a Decision
Chapter 4. The Premortem: A Counterintuitive Approach
Chapter 5. The Problem With the Postmortem
Chapter 6. Failure as a Strategic Tool: The Power of “What If”
Chapter 7. Frozen in Film: When Success Stops You From Seeing What’s Next
Chapter 8. The RISK Framework
Chapter 9. Camping Chaos: A Premortem in Action
Chapter 10. Recognize the Threats
Chapter 11. Imagine the Disaster
Chapter 12. Solve for Vulnerabilities
Chapter 13. Kickstart the Solutions
Chapter 14. Building a Culture of Premortems
Chapter 15. Avoiding Premortem Pitfalls
Chapter 16. The Fine Line Between Preparation and Paralysis
Chapter 17. Your Next Decision Starts Now