Notes
Tuesday, December 09, 2025

Why Most Product Roadmaps Fail (And the One Question That Fixes Them)

Most product roadmaps are lies. You know the kind I mean.

They look like colorful Gantt charts. They have specific dates for features six months out. They give your sales team certainty and your engineering team anxiety. And by Q3, they are almost entirely irrelevant.

The problem isn't that we're bad at predicting the future (though we are). The problem is that we treat roadmaps as a delivery schedule instead of a strategic narrative.

The Commitment Trap

When you present a roadmap as a list of features with dates, stakeholders hear "promiscuous commitment." They hear that you will build X by date Y.

But in product, discovery happens continuously. We learn new things. If you learn that Feature A won't actually solve the user's problem, but it's on the roadmap for November, you're trapped. You build it anyway to "keep your promise."

That is the definition of a Feature Factory. You are shipping code, but you aren't creating value.

The Fix: One Magic Question

You can fix this dynamic without burning bridges. You just need to change the conversation from "When" to "Why."

For every single item on your roadmap, ask this:

"What needs to be true for this to be the right thing to build?"

This question forces the roadmap back into the realm of strategy. It exposes the underlying assumptions.

How to use it tomorrow:

  • In planning meetings: Instead of fighting about dates, list the assumptions. "For the Referral Program to work, we assume users actually love the product enough to share it. Is that true yet?"
  • In stakeholder updates: Stop reporting on "% complete." Start reporting on confidence. "We are high confidence on the checkout flow, but low confidence on the new dashboard widgets."
  • In your own head: Use it to kill "zombie features"—the ones that stay on the roadmap just because someone asked for them six months ago.

A good roadmap doesn't tell people what you are doing on Tuesday, November 14th. It tells them the story of how you are going to win.

If you can't answer what needs to be true for a feature to succeed, it doesn't belong on a roadmap. It belongs in the trash.

Sources & Further Reading: