Wishlists with a Gantt chart glued on

Most AI roadmaps we see are 14 features with a velocity assumption. The fix is not better estimation. The fix is cutting 13 of them. We show the exact heuristic we use, and the three questions that shake loose the one that compounds.

The pattern we keep seeing

A team comes to us with a roadmap. It has 14 items. Each item has a T-shirt size. The sizes add up to “about two quarters.” The team has four engineers. The math checks out if you squint.

Here is what actually happens: item 1 takes six weeks instead of two. Item 2 gets blocked on a vendor decision. Items 3 through 14 never ship. The board asks what happened. The answer is always the same: “we underestimated.”

No. You over-scoped.

The three questions

When we see a roadmap like this, we ask three questions:

1. Which of these compounds? Not “which is important” — they are all important, that is why they are on the roadmap. Which one, if you ship it and nothing else, makes the next thing easier to build? That is your only item.

2. What is the smallest version that teaches you something? Not an MVP in the startup sense. A version small enough that you can ship it, measure it, and learn whether the full version is even worth building. If you cannot describe this version in one sentence, you are not ready to build it.

3. What happens if you never build the other 13? Usually the answer is “nothing, because we were never going to build them anyway.” Sometimes the answer is “we lose a customer.” That is useful information. But it does not mean you should build 14 things. It means you should pick differently.

The heuristic

One feature per quarter. Two if the team is large and the features are independent. Anything more is a wishlist with a Gantt chart glued on.

tl;dr

The pattern. AI teams commit to 14 roadmap items per quarter with T-shirt-size estimates that assume everything goes smoothly, item 1 takes three times as long as planned, and items 3 through 14 never ship. The fix. Ask which single item compounds — which one, if shipped alone, makes the next thing easier to build — and treat everything else as optional until that one is done. The outcome. You ship one thing that actually works and compounds, instead of fourteen things that are perpetually 80% done.