Delivering in Bets

Defining a delivery strategy can be challenging. Teams often underestimate risk, fail to explicitly state assumptions, and don’t involve the delivery team early in the process. Chris introduced the concept of delivering in bets to several clients. In this approach, each delivery is treated as a series of bets with different odds and risks, and each bet is matched with a corresponding confidence level. For higher-risk bets, teams can improve their chances of success by placing smaller, incremental bets. Delivering in bets keeps teams outcome-focused, allows them to view decisions as a portfolio, and helps communicate the expected timeframe for results. Across multiple clients, adopting this mindset shifted perspectives and improved delivery performance.

In this session, Chris demonstrated how using bets reshaped the way clients approached delivery. He showed how familiar tools like Story Mapping and Monte Carlo Forecasting enhanced results and discussed methods for defining and sizing releases. Participants left with a practical, new approach for identifying, planning, and forecasting delivery outcomes.