How to prioritize

I was reviewing the 2023 roadmap of a two-pizza team with a manager yesterday. “Can you take a look at the priorities of the projects and see if they make sense?”, the manager asked. “Sure, before we do that we need to agree on the model to define priority. What is your model?”, I asked back. “Well, we can use the urgency vs. importance matrix, and prioritize high urgency, high importance project, then high importance, low urgency project, then low importance, high urgency project …”, he said. “Nice, that is a good start, using the urgency and importance dimensions to categorize our projects. But there are two more dimensions we should also consider: high leverage project and catalyst project.” “We can estimate the Return of Investment (ROI) of a project using (Value of the project)/(Cost of the project). The cost factors can include how long it needs to complete the project, how many people need to be involved, deployment cost, runtime operation cost, and ongoing maintenance cost etc. The value is from the urgency and importance matrix. Now what we are looking for are the projects with high ROI ratios, or we can call them high leverage projects, or sometimes simply low hanging fruits. High leverage projects give us the best return on the investment, the more, the earlier, the merrier. Catalyst projects are the ones that become enablers for other follow up projects. A catalyst project may take more effort for the initial launch, but once it is done it becomes a pattern for other projects to follow. The following projects are much easier with less investment because they can reuse the artifacts and learning from the catalyst project. For example, launching the first map-reduce workflow in KMS took careful design and deliberation. But once it was launched, it became a framework for all other workflows that need to scale out for heavy load. It was a catalyst project. But be mindful launching a project for the sake of launching a framework. You need to solve a real problem using the catalyst project; otherwise we might fall into the pitfalls of over engineering. A framework is grown through iterations, not front-load planning by paper generals/architects.” “The most value managers can contribute to their teams, is to decide when to do what, by who and why. The sequence of the projects matters a lot. Good roadmap plannings are connecting the dots of the projects toward one strategic direction, bad roadmap plannings are just responding to crises one after another. They go all over the directions but going nowhere.” “It’s not that the cart is too heavy to move, but for another reason: the swan is pulling up to the sky, the crawfish is dragging backward step by step, and the barracuda is pulling toward the pond. We don’t know which one is right and which is wrong. We don’t want to get to the bottom. We only know that the cart is still parked in the same place.” - A FABLE OF SWAN, BARRACUDA AND CRAWFISH