This is a "how to" book for the next generation of CIOs, CTOs, and other leaders who work in and with technology. It includes practical tips, case-studies, and personal insights from Singapore's first CIO. It also has guest chapters on the Future of Work, the Future of Money, and Lessons from the current Covid-19 crisis. The book is divided into six parts: management of legacy information and telecommunications technology (ICT) issues, information overload, motivation and mentoring, change management, fostering innovation, and the future (of money, work and AI). It will have a foreword written by Dr Tan Chin Nam, the father of civil computerization in Singapore.