Digital transformation is sometimes limited by business inertia (old ways of working on the business side). More specifically, it limits our ability to plan and execute market iterations of products and hurts business results in the process. Business inertia also limits the ability of board members to appreciate complexity when assessing digital transformation plans. This talk describes the problem and suggests ways to overcome it. I delivered it at an event for ThoughtWorks' clients in 2019. The recommendations in this talk have since evolved into a comprehensive method called "Business Retrospectives". A related challenge is that of Measurement Debt.