My answer, originally published on Quora.
Q: What is the best way to visually present a product roadmap to executive stakeholders?
What are some effectively ways to communicate a product roadmap to executives clearly and concisely?
My facetious answer is to use powerpoint with lots of superfluous animation and images of guys in business suits jumping over hurdles and charts.
My real answer - based on years of experience in giving and witnessing Roadmap presentations - is to construct a Powerpoint that answers the questions in the order that the executives are likely to think of them.
I use an approach called the Minto Pyramid Principle for this (see What is "The Minto Pyramid Principle," and how do I use it?. I've found it works great for Roadmap presentations, and really any presentation.
For a Roadmap preso, the first question in the mind of the viewer, and executive stakeholder, is probably "What's on the roadmap?". So, show a summary slide with the releases for the next 1-5 years, the theme & major features for each.
After seeing that, the next question they have is probably "OK, but WHY is this the roadmap?" Explain your high-level thinking as to what you're directionally aiming at, and a bit of the logic as to the phasing.
After that, the next questions that naturally pop into the viewer's head might be "OK, but why this direction and not that other direction?" and you explain why the other direction is not as attractive as the one you're pursuing.
After you've finished exploring WHY this specific direction for the overall roadmap, the next questions the viewers might have are about each release:why THIS release plan?, what's the timing of the release (and how at-risk is it)?, why these features? what position will the company be in after this release? You'll know the exact questions when you think of the specific people you are presenting to.