An article on our blog, Introduction to Strategic Roadmapping, introduced the concept of strategic roadmapping. The next question that naturally follows is, “How do we get started with roadmapping?” The best — and easiest — way to start a roadmapping process is to hold workshops to educate your organization on process fundamentals and roadmapping best practices. Once a foundational understanding is established among stakeholders, you can automate the roadmapping process with software to provide structure and efficiency. For example, the software will aid you in creating basic templates for process deliverables and help standardize your roadmapping approach. It can “force” team members to start thinking about future markets, products and technologies in a structured way. With software, you'll be able to implement best practice elements in your deliverables and process from the get-go. The templates enable team members to focus on key information, and they provide a level of control over gathered information that you wouldn't have in free-form Microsoft ® Word documents or PowerPoint ® slides. Lastly, software will enable you to build and maintain roadmaps much more efficiently than is possible using a manual approach. 
Start Small Rather than introducing roadmapping enterprise-wide immediately, you can start with a more gradual approach. Begin in the area where you have the most urgent business need. Clearly define which decisions you want your roadmaps to address and which value streams you want to focus on. This approach will help you to tie your process closely to those value streams and derive maximum benefit from your efforts.
Start Simple Your roadmaps don't need to be complex at the beginning. Instead, focus on what you already know, such as where your products are headed and which specific needs your customers have in the short term. Collate that information into a roadmap. Later, you can create a more complete, end-to-end roadmap by incorporating long-term customer or market trends. Don't let an initial lack of long-term market knowledge prevent you from getting started with a short-term roadmap now!
Source: Strategic Product Roadmapping: How to Develop Plans that Work
