I really like Matthew Ström’s concept of Responsive Roadmaps that “visualize the process of turning uncertainty and complexity into outcomes and output.” He presents this as an antidote to all the things that are wrong with traditional roadmaps:

Traditional project roadmaps are right about our knowledge in a moment of time. They are good records of our beliefs about the correct sequence and magnitude of our work. But these roadmaps are wrong about the reality of work, and almost every roadmap I’ve ever used goes out the window as soon as the work starts. No battle plan ever survives contact with the enemy.

Responsive roadmaps are right about the nature of work: it is full of uncertainty and subject to change. They are wrong about what we’ll be doing in the future; the farther out we look, the less accurate a responsive roadmap is. That tradeoff affords us time to focus in the present on delivering at the highest level of quality.

He goes into much practical detail on how to create, maintain, and use responsive roadmaps.