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 of 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 and prevention services, making those more accessible and easy to use for the fund’s 4.2 million customers.
Designing, building and scaling a complex program like Live Better involves tens of thousands of choices – big and small. Many are intertwined and interdependent. This is an example of a project 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, the organisations doesn’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 write this book because I kept seeing the same pattern: talented leaders and well-resourced organisations making avoidable mistakes on the decisions that mattered most. Not because they lacked intelligence 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 was ever going to write a book, it would be 100% content – 0% filler. 100% beer – 0% froth. Densely packed with insights, grounded in real-world practice, and practical enough to use on Monday morning. You’ll be the judge of whether I succeeded.