Milestones aren’t just dates—they’re value-prop signals

“Plans are useless, but planning is invaluable.”
Eisenhower said it. Product teams would be wise to embrace his wisdom.

We’ve worked with countless organizations that had beautiful roadmaps—slides that looked like art. But when we dug in, the milestones were built around the wrong things: tech releases, stakeholder promises, internal headcount timelines. The stuff that looks good in QBRs but means little to your users.

Most roadmaps are overbuilt and under-aligned

The core problem? Many roadmaps are made in isolation, then pushed onto the teams expected to deliver them. They get passed down like orders instead of being built up through insight and shared authorship.

When that happens, even your most capable teams end up executing someone else’s plan. They might deliver the roadmap, but they don’t own the outcomes, and that disconnect shows up in everything from morale to market performance.

We’ve seen this misalignment up close:

• Delivery teams “taking orders” from a document they didn’t help shape.
• Milestones get tied to feature checklists, not user value.
• Teams are stuck defending a five-year roadmap that no longer reflects reality.

A milestone is a signal. Make sure it means something.

In a purposeful roadmap, milestones should be value-prop inflection points.

Each one should represent a validated step forward for your users and your business. It should be easy to say why it matters, who it serves, and what it unlocks.

Think of them like lighthouses—clear signals everyone can navigate toward, not just dots on a Gantt chart. When your roadmap reflects shared understanding, it becomes more than a schedule. It becomes a story the whole org can follow and understand.

And like the product itself, your roadmap starts as a sketch—a rough outline that sharpens with input. You start with the fat marker version. Then you refine it with the people who will bring it to life: product, design, engineering, users, and executives.

That’s how you de-risk bold bets and build alignment early.

👇 Coming soon

In Part 3, we’ll explore how execution becomes sustainable when strategy is co-owned, not handed down. The best teams we’ve worked with don’t just follow a plan. They help build it. And because of that, they deliver on it—again and again.