A Cone Roadmap is a roadmap that takes uncertainty into account by mapping the roadmap on three tracks: Best case, projected case, worst case. At a glance, this allows anyone to see the range in which a milestone might be achieved. Which supports more realistic and agile planning.
Step 1: Map out the best case
Ask yourself "How would the roadmap look like, when everything goes well?". Given your answer, add the milestones to the top track that represents the best case for the roadmap. Where you place the milestones should be optimistic, but at the same time realistic and achievable.
Step 2: Map out the worst case
Ask yourself "How would the roadmap look like, when everything goes wrong?". Especially think about how long it might take to achieve a milestone. Now duplicate and place the same milestones on the bottom track to represent the worst case scenario.
Step 3: Map out the projected case
Given the best and worst case of the roadmap, you can now see a range for when each milestone might be achieved. As the last step, duplicate each milestone one last time and place it in the middle of the range. When you are done with all milestones, this creates an average between the two extremes and gives you the projected case.
In the example below, you can see a Cone Roadmap for a fictional marketing team across 12 months. In the best case, the last milestone of the roadmap would already be achieved by mid October. In the worst case, the roadmap would stretch out until the end of December. (Hopefully no one needs to work on Christmas!)
In the middle, you can see the projected case, witch is the average between the two extremes of each milestones. By using colors for the sticky notes, it's easy to identify each milestone across the three tracks.