|Doing a road map can be a tricky thing. There are plenty of constraints and dependencies to consider:
I find that pair programming is by far the fastest way of traversing the decision tree. Basically, if you are a Product Owner, construct the road map together with another person. Lay out the plan that best meets the constraints and business goals and let the other question the options. (Of course, don’t forget to switch).
Altogether, it helps you check the different options and prepare arguments. You will be better prepared when meeting the stakeholders. For when you do, there is always something uncertain waiting for you.