Every company I have joined in the last decade has been proud of its roadmap. Most of them shouldn't have been.
The roadmap, as it is practised in most product organisations, is not a plan. It is a piece of comfort literature. It exists to make the board feel there is a plan, to make the CEO feel there is a plan, and, above all, to make the operators feel there is a plan. It performs the ritual of planning without the discomfort of it.
What the artefact actually does
A well-made roadmap does three useful things: it sequences bets, it names owners, and it declares what the organisation will not do this quarter. Almost every roadmap I have seen accomplishes exactly one of those — usually the first, and even then only nominally.
The other two require actual conversation. Naming an owner means someone in the room accepts they will be the one to answer for the outcome. Declaring what will not happen means telling a stakeholder — often a senior one — that their favourite thing is losing this cycle. Neither of those is photogenic. Neither survives contact with quarterly PowerPoint.
A roadmap the whole room agrees with is a roadmap that made nobody uncomfortable. Which usually means it also made no decisions.
What replaces it
Cadence. Not a document — a rhythm. A short list of named bets, each with an owner, a hypothesis, a decision date, and a shutdown criterion written before the work begins. Reviewed on a defensible cycle. Postmortemed with the room present.
The point of the cadence is not the artefact it produces. The artefact will be embarrassing at first. The point is the practice: the same room, on the same rhythm, learning to name the bets and defend them out loud. Six cycles in, that practice is the operating system. The document is a byproduct.
The first thing to try
Pick one bet on the current roadmap. Write the shutdown criterion for it — the specific evidence that would tell the team to stop. If no one in the room can write that sentence, the bet is not a bet; it is a wish with a Gantt chart. That is not a failure of planning. It is the beginning of it.
The full essay continues in the working library. Reader-list subscribers get early access when it publishes.