Managing the Unknown
How to Lead When the Rules Don’t Exist
Most project management books are written for predictable environments. This one is not.
Managing the Unknown tackles the question that every leader faces eventually: what do you do when the old playbook doesn’t apply? Whether you’re navigating a tech disruption, a new venture, or a high-stakes transformation, this book gives you a framework for making decisions when certainty is off the table.
What the Book Is About
The authors introduce a new model for project management in uncertain environments—where outcomes can’t be predicted, variables change constantly, and traditional Gantt charts fall apart. Rather than forcing control on chaos, this book teaches you to classify the type of uncertainty you're facing and adapt your management style accordingly.
It breaks uncertainty into four types—variation, foreseen uncertainty, unforeseen uncertainty, and chaos—and offers strategies to deal with each. The central message: you can’t eliminate the unknown, but you can prepare for it, design around it, and even lead through it.
Why This Book Mattered to Me
In fast-changing environments—especially legal tech and innovation—uncertainty isn’t the exception. It’s the operating environment.
This book helped me stop pretending everything could be managed like a fixed-scope case or contract. It taught me how to embrace ambiguity while still moving forward with discipline.
One of the most valuable shifts was from “plan-and-execute” to “sense-and-respond.” That applies whether I’m launching something new at Fennemore, navigating a leadership transition, or advising clients in dynamic industries. The tools in this book helped me make better decisions—not by removing risk, but by managing it more intelligently.
Key Takeaways
Not all uncertainty is the same. Understanding what kind you’re dealing with is the first step to managing it.
Flexibility is not failure. Adaptive project structures often outperform rigid plans in high-change environments.
You don’t manage uncertainty with certainty. You manage it with mindset, structure, and constant learning.
Who Should Read This
This is essential reading for anyone managing complex projects, launching new initiatives, or leading in fast-moving industries. It’s especially valuable for innovation teams, legal ops professionals, and execs trying to scale new ideas without clear precedent.
If you’ve ever felt like the ground was shifting under your plans—this book helps you lead anyway.
Final Thought
Managing the Unknown doesn’t give you a perfect plan. It gives you something better: a way to stay effective when nothing goes according to plan.
It helped me lead more confidently through ambiguity—and that’s a superpower in today’s world.