“Stories” Don’t Tell a Story: Good Sprint Planning Uses Milestones

Chuck Groom argues that engineering teams lose sight of end value when sprint planning focuses solely on story backlogs rather than milestones (near-term goals). The core problem is that stories are only a 'crude approximation' of work needed and teams 'lose sight of the forest for the trees' when churning through tasks without connecting to company roadmap. Traditional story-focused planning creates projects left in 'almost-done' states because it overlooks 'glue' steps and final release polish—like 'frantically assembling Lego blocks in hopes they'll add up by March.' The solution shifts focus from 'we will do THIS WORK' to 'we want to do THIS THING, so that's why we think we should do THIS WORK,' making milestones units of delivered value that can be explained simply to internal and external stakeholders. The milestone management approach uses living documents with bullet points describing intended value, related projects, and specific tasks, with sprint planning beginning with milestone discussions before building supporting story boards. Engineering leaders will learn that when people focus on goals and see tasks as 'directional and partial' rather than 'absolute and complete,' they become empowered to deliver value instead of just doing work.