This is now my second year having to come up with a roadmap for what we call 'release', so while I'm not old hat, I am definitely learning and getting a little better! One of the fun aspects of this is looking at the 'how you go about roadmapping', as in, if you are starting from scratch or not, what are the exercises you can go through to help you develop a plan for the coming year? We're fortunate enough to have a CTO who pushes things like value proposition design ( pain-gain diagrams ), and encourages us to really think through what it is we are trying to do - plus takes the time to guide us himself. Last year's roadmap started with a fresh canvas and the question 'if you could only work on one thing, what would it be?'. This was to help focus my scattered brain, and I found it a great starting point. As I am also a visual person, draw.io was used extensively to sketch out my thoughts ( also used my whiteboard, but draw.io is portable ).