If you had two options, one that gave you an 88% chance of success and another that gave you about 50%, which one would you choose? Would you be surprised to know that teams and individuals routinely make choices that only give them a 50% probability of success? Are you trying to coach teams to use better decision-making models and watching them stick temporarily before they revert to old behaviours? In this talk, we will discuss why some coaching lessons and innovative approaches take hold while others don’t. We will explore lessons we can learn from the research in the field of Behavioral Economics. We will draw parallels with sports including Basketball and High-Jump to dig into reasons some proven practices are abandoned for inferior alternatives while others catch on. We will also look at real-life example of a failing Agile Transformation that was turned around by leveraging lessons from behavioural economics. We will also discuss how the lessons from these examples can be used to enhance coaching practices and create a culture of learning.