[Layvier]

Ever since I worked in multi stage stochastic optimization I think of strategies in terms of decisions at each nodes of a tree of scenarios. Basically you want to optimize on the long term objective function, and take decisions at the optimal time based on the cost of indecision and the estimated benefits of having more information. Having probabilities associated to each branching in the tree of scenario also makes it have baked in risk management. This is not so easy to apply in practice but it is worth doing and allows having a much longer horizon: else how could you make a strategy with decisions in 6 months not being dependent on the results of the decisions you take now ? As another comment pointed out, the main goal of product roadmap is communication, strategy is something else. In this case the roadmap could be the most likely path to take in the scenario/decision tree, with diminishing confidence over time based on the probabilities observed.

Multi stage stochastic optimization is often used in finance/trading (e.g. portfolio optimization), I highly recommend to check it out.