I’ve spent over two decades making, influencing, and occasionally getting wrong the kinds of decisions that shape businesses. From structuring deals across ten time zones at a global energy trader, to leading strategy engagements at the top tier management consulting firm, to running a customer health division at Australia’s leading health insurer — the thread running through my career has been a fascination with how consequential choices get made, and why they so often go South.
The Story Behind the Book
I had a privilege leading the design, launch, and scale-up of Live Better — Australia’s largest and most integrated health-focused rewards program, with over a million active users, 25+ major partner brands, 3,500+ partner locations, and ~$50 million of annualised rewards redemptions.
This program helped transform the relationships with fund’s customers and turn what was a traditional health insurance app into a leading digital health platform with millions of monthly logins. We’ve also digitised and integrated a wide portfolio of telehealth, prevention and homecare services, creating an ecosystem that is accessible and easy to use for the fund’s 4.2 million customers.
Designing, building and scaling a complex program like Live Better and integrating health services into an ecosystem involves tens of thousands of choices – big and small. Many are intertwined and interdependent. This are the examples of what I call projects with infinite degrees of freedom.
Were all the decisions we made perfect? Some were brilliant. Some I’d rather “undo”. But nonetheless the program was still immensely successful. As I illustrate in the book, organisations don’t need to make every choice perfect. To succeed, it’s often sufficient to make the consequential calls right more often than not.
In my 20+ years of experience, the decisions that mattered most were rarely the big, obvious, board-level calls. They were the ones hiding in the middle of the pyramid — an interpretation of a regulatory clause that nearly killed a business model, a platform fork that nobody noticed until it was too late, a minor scope omission could have led to a disaster in operations. These experiences, and the scars they left, became the foundation of this book.
I decided to put it all in writing because I kept seeing the same pattern: talented leaders and well-resourced organisations making avoidable mistakes on the most important decisions. Not because they lacked competence or data, but because they lacked a framework and discipline for identifying which decisions deserved extreme care and a method for getting those right. This book is a humble attempt to help leaders nail the decisions that shape success.
The other promise I made myself was that if I ever write a book, it will be 100% content – 0% filler. 100% beer – 0% froth. I did my best to walk the talk by densely packing it with insights, grounding it in real-world practice, and keeping practical enough to apply on Monday morning. You’ll be the judge of whether I succeeded.