I despise most roadmaps. They require tons of alignment meetings. Everyone has a different prediction for the future. Everyone wants their pet project funded. Roadmaps end up either too short sighted or overly ambitions. And at the end of it, they often become useless the moment they’re finished. 

I like to practice anti-fragile roadmapping, inspired by Nicholas Nassim Taleb’s book. In a nutshell, 75% of the roadmap should have a very low risk of NOT having an impact. These are sure bets with lots of optionality and minimal pain when pivots or changes come up. 

The other 25%  should be high risk but massive impact potential. This doesn’t always mean bigger or longer projects. It just means there is a massive opportunity to change the course of a project, organization, or strategy. These things typically have the highest risk of missing the mark and a fixed, inflexible investment, so they should represent a smaller percentage of effort.

The exact split is not as important as the concept. Roadmaps need a balance of low and high risk bets, and those high risk bets better have an outsized potential for impact. 

The key to doing this well is two parts. First, an aligned definition of impact and risk. Everyone needs to be on the same page about how to calculate impact and risk, and those metrics needs to be applied uniformly. Second, a strong mechanism for learning. The goal is to get better and better at assessing risk and impact over time.