One of the hardest things for any algorithmic leader is knowing when do nothing at all. This is not an entirely new dilemma. Test pilots in the early days of the space program, struggled with the idea of not having manual controls - even when their own interventions led to deadly mistakes. So just when do humans make good decisions? To get to the bottom of that, I chatted with Jason Collins, a behavioral economist, who has written extensively on these ideas at the Behavioral Scientist, and currently runs the data science team at a major financial regulator. He previously co-led PwC Australia's behavioral economics practice.

The Life Insurance industry is a fascinating case study in the challenges, and the potential rewards of digital transformation. Traditional insurance carriers have been largely slow to transform themselves, with many policies hosted on a multitude of legacy platforms. But change is coming, in the form of new types of insurance companies, like Haven Life, a spin-off from MassMutual, which uses AI and machine learning to radically reimagine the customer experience. To learn more about this complex industry, I had coffee with Gautam Thakkar, who is the CEO of se2, a company that builds platforms for 21st century insurance carriers.

Mark van Rijmenam is one of the world’s foremost experts on the Blockchain, and its potential impact on the future of the firm. Named as one of the top 10 global big data influencers by Onalytica, he is the author of the book 'Think Bigger – Developing a Successful Big Data Strategy for Your Business'. His latest book is titled 'Blockchain: How a Revolutionary Technology will Improve Business and Society'. After reading some of his research papers, I was fascinated to have a coffee with him and talk about algorithms, smart contracts and what decentralized autonomous organisations might mean for tomorrow’s leadership teams.

Rusty Young has spent his life living, and writing about things that most of us would feel uncomfortable thinking about, let alone actually experiencing. Strangely enough, he and I first met at law school many years ago. But while after graduation, I left to join the digital industry, he travelled to South America where he met Thomas McFadden, a convicted English drug trafficker who ran tours inside Bolivia's famous San Pedro Prison, and ended writing about his story in his first bestselling book, ‘Marching Powder’. Rusty was then recruited as a Program Director of the US government's Anti-Kidnapping Program in Colombia, after which he released a new novel about Colombia's child soldiers called 'Colombiano’, and a documentary on the drug trade called ‘Wildlands’. Catching up with him in Sydney, we spoke about the global drug trade, how Cartels design their technology stack, and the economics of the world’s strangest prison.

Vince Frost is a world renown designer, author, creative impresario, and one of the most brilliant thinkers on human centered design that I know. He is the founder and Executive Creative Director of Frost*collective, Sydney. We met almost a decade ago, when I approached him to design my first book, ‘Futuretainment’ which was published by Phaidon. His inspired work on that book led to a design award by the Art Director’s Club in New York. Before starting Frost* Design, Vince was the youngest Associate Director at Pentagram. In 2004, he relocated to Sydney and, as Executive Creative Director of Frost*collective, has lead a wide range of projects for clients such as Deutsche Bank, Qantas, Frasers Property and the Sydney Opera House. His latest book is called, ‘Design Your Life’, and is well worth a read. Vince dropped around to my beach pad in Bondi for a coffee, and we took the time to chat about the future of design, and how everyone, even business leaders, could benefit from thinking more like designers.